She spent seventeen years in corporate, all of it in insurance, and made VP. Then she took a bigger VP role that required moving her whole family from Southern California to Arizona during the pandemic. House to sell, house to buy, a dog, and her mom, who lives with them. She landed in mid-June when it was a hundred and fifteen degrees.

The job was great, until it wasn't.

She describes the feeling the way a lot of us would recognize. Not burnout exactly. More like wearing a suit that kinda fits. Day by day you notice the fit is off, and then one day you have to take it off or lose your mind.

She joined the Escapee Collective in October of 2024, gave herself until the end of 2025 to decide, gave notice in July, and walked out in December. Two or three months before her pension vested. On paper, a terrible decision. She'll tell you she had no choice.

Then she made it harder. Insurance is a small world, and the easy path out is referrals and consulting gigs inside the industry you came from. She left the industry too. Which meant starting over with about three hundred LinkedIn connections, more than half of them in a business she was never going back to.

What she says about that period is the part I keep thinking about. Being excellent in corporate doesn't mean you know how to talk about your work. Her reputation was built inside the walls of one office and one industry, and none of it came with her.

The back half is her actual craft, and it's good. Her idea of building a neighborhood instead of an audience is the best framing I've heard on LinkedIn, and I'm stealing it. Not finding your ICP and bombarding them. Building a street where some people hire you, some people refer you, and some people are just people you talk to.

ABOUT THE GUEST

Hana Kim is a personal brand strategist who works with solopreneurs and founders. Before going solo in December 2025, she spent seventeen years in B2B marketing in the insurance industry, finishing as a VP. She started out as a freelance writer and editor, went to law school, and practiced as an attorney before moving into corporate. She is intentionally a solo operator and has no plans to build an agency.

LinkedIn: https://www.linkedin.com/in/hanakim/

She also has no content pillars, on purpose, and she'll explain why.

In this episode:

• Seventeen years in one industry, and the VP job that required moving states
• Why she doesn't call it burnout
• Falling out of favor, and how it's never one big thing
• The pension she walked away from
• Interviewing for a C-suite role and realizing she didn't want it
• Why the SVP math stopped making sense
• Leaving the industry, not just the job
• Rebuilding a network from three hundred connections, most of them dead
• The post that went semi-viral and brought the first client
• Year zero, and the seven or eight offers nobody remembers
• Building a neighborhood instead of chasing an ICP
• Why she has no content pillars
• Deciding what you don't want to be known for
• The rented land problem, and why she's planning her exit from social

THE NEIGHBORHOOD, ASSEMBLED

Hana's core idea, pulled into one place.

The wrong model: find your ICP, connect with your ICP, bombard your ICP with information until they like you enough to hire you.

The right model: a neighborhood. Not everyone on your street is a customer. Some are people you chat with. Some will refer you to the person who needs what you do. The value of the street isn't that everybody on it buys from you.

What that changes in practice:

• You talk to people who will never hire you, on purpose.
• You stop optimizing every post for conversion.
• You control what you can control, which is how you show up, because the algorithm is not yours.
• You decide what you want people to say about you when you're not in the room, and then you stay on brand even in the throwaway posts.
• You pick what you don't want to be known for, and you walk away from content that works but points the wrong direction.

And the one that takes the pressure off: nobody remembers your early offers, and nobody remembers your failed ones. Hana tested seven or eight in her first year and can't recall what was in most of them.

TIMESTAMPS

Taken from the raw transcript. Shift for cold open and sting.

• 00:01 — Welcome
• 00:46 — English degree, law school, attorney, caregiving break, seventeen years in corporate
• 01:40 — Joined the Escapee Collective in October 2024, and the deadline she set herself
• 02:56 — Why she wouldn't call it burnout
• 03:00 — The VP opportunity, and what it cost
• 03:30 — Uprooting the family to Arizona during the pandemic
• 04:30 — Sunday scaries, and thinking everyone had them
• 05:09 — Landing in mid-June at a hundred and fifteen degrees
• 05:20 — Finding Brett on LinkedIn, and "corporate gave up on you"
• 05:40 — Falling out of favor, and how it's never one big thing
• 06:00 — The process of elimination: the job, the company, or the work itself
• 06:45 — The pension she left on the table
• 06:56 — Brett on purgatory and the Geoff Curtis episode
• 08:18 — A suit that kinda fits
• 09:02 — A long notice period, and leaving before next year's projects
• 09:30 — Walking away from the industry, not just the company
• 10:00 — Turning fifty. "Too old. Maybe tired is the word."
• 11:36 — Caregiving and what corporate flexibility actually means
• 13:16 — Interviewing for a C-suite job and not wanting it
• 13:53 — The SVP math: a lot more responsibility for a little more money
• 14:40 — Six months of experiments
• 15:00 — Being excellent in corporate doesn't mean you can talk about your work
• 15:22 — A reputation built inside one office
• 16:00 — Three hundred connections, and starting LinkedIn over
• 16:46 — Build quietly, or build somewhere your peers won't look
• 18:57 — The post that went semi-viral
• 20:16 — The first contract and the first inbound client
• 21:00 — Brett on what happened when he got polished
• 21:47 — Solo on purpose, and saying no to an agency
• 22:30 — Sustainable, and where your energy goes
• 24:00 — Not building a light version of your corporate career
• 24:30 — Year zero
• 24:54 — When AI told her the target audience was "marketers who want revenue"
• 26:00 — High functioning lazy, and the world-class lollygagger
• 26:48 — There is no one path
• 27:48 — The neighborhood
• 28:34 — ICP bombardment versus actual neighbors
• 29:19 — LinkedIn's identity crisis
• 29:56 — Control what you can control
• 30:14 — Why she has no content pillars
• 30:24 — The content that worked, and why she dropped it
• 31:08 — Hana asking Brett if he was walking away from the Escapee brand
• 31:31 — Brett on how AI quietly boxed him in
• 32:19 — Nobody remembers your failed offers
• 33:18 — Building in public, intentionally
• 33:51 — Deciding what not to be known for
• 35:42 — Brett on optimizing the next thirty years
• 37:05 — Separate the money from the mission
• 37:36 — Get offline. Chamber of commerce. Actual neighbors.
• 39:20 — The rented land problem
• 39:30 — Why she's investing in her own site
• 40:03 — Locked out of LinkedIn, with no way back in
• 40:30 — The guy who walked into office parks and left with three engagements
• 41:28 — Business owners don't care about your label, they care about the problem
• 42:08 — Where to find Hana

LINKS:

Questions or guest ideas? bt@bretttrainor.com

Episode Overview:

Janet Tanguay got spitballed by her own colleagues in a corporate training for going off script. She lasted four days in her next job. Now she helps people build the life they actually want, and she has the most practical approach to it I've come across.

Janet Tanguay is a serial entrepreneur who has run a record label and an art business, and now runs Hammock Way of Life, helping people and companies get clear on what they actually want through vision boarding. She's the author of Hammock Way of Life: Leaping Toward Joy, part memoir and part business book, available in print and audio.

GUEST LINKS

https://www.linkedin.com/in/jazzyjan/

https://hammockwayoflife.com/

In this episode:

• The spitball training, and the ten years she stayed anyway
• Four days in banking and the sweater vest that ended it
• The boss who told her at a book signing that she almost made him quit
• Why the questions stop after enough years inside
• Finding the work by accident at a chamber of commerce
• The five whys, and why the fifth one is the real answer
• Three values as the filter for everything you say no to
• How to actually build a board, and the words to keep off it
• What she does with people who have four ideas at once
• Vision boarding inside companies, and what it turns up

THE METHOD, ASSEMBLED

Janet laid this out across the whole conversation. Here it is in one place.

1. Run the five whys. Start with one question. "Why do I want to leave?" Answer it, then ask why again, five times. The fifth answer is usually the real one.

2. Pick three values. Start with a list of ten, cut to five, then three. These become your North Star. When something lands in front of you, you check it against the three, and that's how you say no to things that look good but aren't yours.

3. Build the board around one center. Put the single most important thing in the middle. Cluster everything else around it. If you scatter it, your dreams come out scattered.

4. Get specific. Numbers, timelines, how many people, how much money. "I want to be rich" isn't a goal, it's a mood.

5. Watch your words. Nothing with a double meaning. Janet's examples: "nailed it," "crushed it," "a family affair." These things manifest in ways you didn't intend. She put a Buddha in the center of a board because she wanted more yoga and more stillness, and ended up sent to China to the largest Buddha temple in the country.

6. If you have four ideas, make four boards. Then talk through each one out loud with somebody. The one where your eyes light up is the one. Janet says it happens every time.

7. Take the free step. Not the big step. The free one. Go to the open house. Test drive the car. Send one email. She almost didn't test drive a car because she assumed she couldn't afford it, then drove it off the lot.

8. For a business, use the business model canvas as the board. Revenue streams, resources, partners, value proposition. Same exercise, different frame.

Questions or guest ideas? bt@bretttrainor.com

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Welcome, and where the company name came from
• 01:35 — The spitball training
• 02:33 — Ten years in anyway, then done
• 03:11 — Four days in banking
• 03:29 — Day two: all the ways you could be killed on the job
• 03:46 — The sweater vest, in the parking lot, at ninety nine degrees
• 04:33 — The old boss who showed up at her book signing
• 04:50 — The four column form nobody could explain
• 05:30 — What happens when you stop asking why
• 06:36 — No plan, and what came next
• 06:48 — The chamber of commerce, and finding the work by accident
• 07:47 — Why lenders squash dreams, and why she wanted a room where they couldn't
• 08:11 — Your life experience qualifies you for more than you think
• 08:46 — The ski instructor is only a few lessons ahead
• 09:26 — Getting past the fear of judgment
• 11:14 — Breaking the rut while you're still in it
• 12:05 — The book, and what's in it
• 15:47 — The five whys
• 16:00 — Three values, and how to get to them
• 16:30 — Using the three to say no
• 18:00 — Asking other people how they see you
• 19:25 — Clearing the old stuff out
• 19:54 — Cutting the negative people, and how easy it turned out to be
• 20:55 — The gossip in the office, and the woman who ended it with one sentence
• 22:34 — Asking for a sign, and the fish sign
• 23:50 — Why she asked for eagles
• 25:35 — How to actually build a board
• 26:43 — Numbers, timelines, and specificity
• 27:00 — The words to keep off your board
• 27:40 — The Buddha, and the trip to China
• 28:00 — Using the business model canvas for a company
• 29:30 — Brett's half marathon, and day eleven of 75 Hard
• 30:20 — It isn't about thinking anymore. It's about feeling.
• 30:45 — "That's coming to me now"
• 31:31 — What does joy actually feel like
• 32:29 — Small steps that break the pattern
• 33:27 — Connecting dots across 370 conversations
• 34:07 — Why AI won't connect those dots for you
• 35:22 — Take the free step. The open house. The test drive.
• 36:53 — Four ideas, four boards, and watching which one lights you up
• 38:25 — What happens when you run this inside a company

• • 40:49 — Where to find Janet

Hans Weygoldt had everything on paper. Good money, job security, the family business, the life that looks right from the outside. And he was empty.

He spent ten years trying to leave. Every time he sat down to build the plan, his mind went blank. As he puts it, the more he thought about it, the more self-doubt showed up, so the planning itself was digging the hole deeper.

When he finally went, it took about a second. Something changed at work, he said that's it, and gave notice with no plan B at all. He didn't even tell his wife until days later, halfway to Maine on a camping trip. She was shocked, then she smiled.

His only regret is that he waited so long.

Getting to that point went through some hard ground. A decade of substance abuse while managing in the corporate world, driven by a void he couldn't name. A trip to Peru that broke the addiction but left the guilt behind. And eventually breathwork, which is now what he does for other people.

Two ideas in here I haven't been able to put down.

The first is his split on pressure. External pressure eventually crushes you. Pressure you build from the inside is something you can expand through. He spent a career trying to meet expectations other people set for him. Now he sets them himself, and sets them higher than anyone else ever did.

The second is from a mentor of his, and it's the best thing said in this episode: it takes a lot of curiosity to find out who you are, and then a lot of courage to be that way.

This one pairs with the Geoff Curtis conversation from earlier this week more than I expected. Two guys, completely different paths, both landing on the same thing: the planning is usually the avoidance.

In this episode:

• Golden handcuffs, and the beliefs underneath them
• The decade of substance abuse nobody at work knew about
• Peru, and what broke the pattern
• What actually happens in a breathwork session
• Why the planning kept him stuck for ten years
• External expectations versus the ones you set yourself
• Trust as a practice, not a feeling
• Why he never told his wife until after he'd quit
• Skydiving, piano, and a master's degree at this stage of life

ABOUT THE GUEST

Hans Weygoldt is a breathwork facilitator and emergence coach. He spent years in a family business before leaving with no plan, and now works with people on breaking the patterns underneath addiction, emotional suppression, and self-sabotage. He runs in-person group sessions and one-on-one sessions online, and is pursuing a master's in consciousness-based leadership and coaching.

• LinkedIn: https://www.linkedin.com/in/hans-andreas-weygoldt-151777356/
• Facebook: Hans Weygoldt

THE IDEAS WORTH KEEPING

The plan B was the trap. Ten years of trying to engineer an exit produced nothing but more self-doubt. He left without one and figured it out after.

External pressure crushes, internal pressure expands. The same force, two completely different outcomes depending on who's applying it.

Trying to be strong made him weak. The mask cost more than it protected.

Trust is the first principle. In a session and out of it. He says breathwork reflects life, and learning to trust the process on a mat taught him to trust it everywhere else.

Curiosity first, then courage. Finding out who you are is the curious part. Being that person in public is the hard part.

What you think of me is none of my business. Not original to him, but it's the line that got him on camera after a lifetime of avoiding it.

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Welcome, and how Hans describes what he does now
• 02:07 — The family business, the money, and the empty feeling
• 03:34 — Golden handcuffs, and the beliefs formed in childhood
• 05:28 — Peru, and how he found breathwork
• 06:13 — First session in 2018, out of the job a year later
• 06:59 — Questioning everything he believed about himself
• 08:41 — Awareness as an ongoing practice, not a destination
• 10:44 — The decade of substance abuse while managing in corporate
• 11:09 — The void he was trying to fill
• 12:46 — The first session: "I cannot keep this up any longer"
• 13:20 — An hour gone, and no inner dialogue
• 14:42 — What actually happens in a session
• 16:28 — The physiology, in his words
• 17:04 — In person versus online, and which suits who
• 19:40 — Why Gen X never invests in itself
• 20:09 — How many sessions, and why integration matters more
• 21:34 — Fear of judgment, failure, and criticism
• 22:02 — "You'd never have seen me on a podcast"
• 23:11 — External expectations versus internal ones
• 23:40 — External pressure crushes. Internal pressure expands.
• 24:05 — First generation college and the path that gets installed
• 26:16 — The mask, and how trying to be strong made him weak
• 27:47 — Ten years of trying to quit
• 28:30 — Why the plan B was making it worse
• 29:00 — Trust as the first principle of breathwork
• 31:03 — The relief after, and his only regret
• 31:40 — Telling his wife on the road to Maine
• 32:20 — The year he spent with his kids
• 34:42 — Skydiving, piano, and going back for a master's
• 37:37 — Boredom, curiosity, and what lit the fire
• 38:00 — Curiosity to find out who you are, courage to be that way
• 38:23 — Approaching a session with childlike curiosity
• 40:00 — It's the most fulfilling work he's done, and it's hard
• 41:30 — Where to find Hans

LINKS

Connect with Hans — LinkedIn or Facebook, both under Hans Weygoldt

Mentioned: The Ultimate Journey: The Mystery of Life and Death by Stanislav Grof, and Grof's work on holotropic breathwork

Get the letters — Letters from a Corporate Escapee:https://bretttrainor.substack.com/

The Escapee Collective: https://theescapeecollective.com/

Questions or guest ideas? bt@bretttrainor.com

HASHTAGS / KEYWORDS

breathwork, emergence coaching, golden handcuffs, leaving corporate, patterns, emotional suppression, self sabotage, GenX transition, personal development, holotropic breathwork, consciousness

Geoff Curtis spent nearly thirty years building a career in healthcare communications. Title, expertise, platform, the whole thing. Then the company was acquired, his role went redundant, and all of it disappeared at once. What followed wasn't a reinvention arc. It was the discovery that he'd spent his adult life using work to avoid feeling anything.

He picked purgatory on purpose. As he puts it, words like transition imply progress, and he wasn't making any.

The other choice that makes this book different: most people write about this from the far side, after they've figured it out. Geoff is writing from inside it. Three years out and still working through it. There's no five step plan in here, and some readers are frustrated by that. I think it's the reason the book works.

The idea I keep coming back to is his separation of three things we tend to mash together. Livelihood, identity, and self-worth. Livelihood puts food on the table. That's all it has to be. The trouble starts when livelihood quietly becomes identity, and identity becomes self-worth. Then losing the job isn't a financial event, it's an existential one.

We also got into something that isn't in the book. Four weeks before we talked, Geoff did the Hoffman Process. Eight days, completely unplugged, thirty nine strangers, fifteen hours of prep work and days running 7:15 in the morning to 9:30 at night, all aimed at understanding which of your behavior patterns you inherited from your parents. He says he wishes he'd written the book afterward.

Fair warning, this one is heavier than most. Depression, grief, his father's death, and a lot of honesty about patterns neither of us is done with.

In this episode:

• Why he chose purgatory over transition
• Livelihood versus identity versus self-worth
• Thirty years of running on external validation
• Running as emotional suppression, and how to tell it from progress
• New metrics for happiness, and why the old ones keep coming back
• Investing in yourself, therapy, and the Hoffman Process
• Why people doubt themselves inside corporate, not just outside it
• The imposter syndrome nobody on his team ever mentioned to each other
• Everything is a choice, and why we only price the downside

ABOUT THE GUEST

Geoff Curtis spent nearly thirty years in healthcare communications before an acquisition made his role redundant. He's the author of Embracing Your Own Purgatory, written from inside the transition rather than after it, and he now runs a nonprofit he built with his wife that works with college students.

LINKS

The book: Embracing Your Own Purgatory — Amazon, Barnes & Noble, and anywhere books are sold

Author site: https://geoffreycurtis.com/)

LinkedIn: https://www.linkedin.com/in/geoffreycurtis/

THE IDEAS WORTH KEEPING

Livelihood is not identity is not self-worth. Three things, and we let them fuse. "Livelihood puts food on the table. If you don't make the livelihood the identity, then you're good."

Transition implies progress. Purgatory doesn't. That's why he picked the harder word.

Running versus progressing. Both are fine, but you have to evaluate the ending. Why did you leave? Bored, burned out, actually moving toward something? Skip that and you rinse and repeat for thirty years.

Closer to right than quick. The nonprofit took two and a half years instead of the five months his old metrics demanded. That gap is where the real work happened.

Realism as a Trojan horse. Geoff's admission that he uses "I'm a realist" to smuggle in negativity is the sharpest self-observation in the episode.

You're not your patterns. The Hoffman framing: you absorb your parents' patterns as a kid to stay close to them, rebel against them as a teenager, then repeat them under stress for the rest of your life until somebody shows you where they came from.

The conversation nobody has. Geoff and a former direct report both had imposter syndrome the whole time and never said a word. "I always thought you had it together, and I wanted to make sure you thought I had it together."

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Why this book landed differently
• 01:31 — Why he chose the word purgatory
• 02:46 — Not brave enough to say we're unfinished
• 02:51 — Brett: I think I was in purgatory while still employed
• 03:53 — His wife knew it was going to hit him before he did
• 05:08 — Identity, self-worth, and what work was really providing
• 05:49 — Thirty years of running on external validation
• 06:48 — Why there's no path out in the book, only questions
• 08:30 — Livelihood is not identity is not self-worth
• 09:35 — Separate the money from the mission
• 10:49 — The college senior who wants success and fun
• 12:36 — First generation college, and the expectations that come with it
• 13:49 — Running when things get uncomfortable
• 14:25 — Evaluate the ending, or you'll repeat it
• 15:45 — Running as emotional suppression, and his father
• 16:35 — Love the process and eventually the process loves you
• 17:30 — Three years out, and building new metrics for happiness
• 18:57 — The old metrics never fully stop flashing back
• 20:00 — Brett talked his way back into a full time job because it was comfortable
• 21:18 — Geoff turns it around: how much was external pressure?
• 22:58 — What changes when you finally become value driven
• 24:20 — Following energy as a compass
• 25:17 — Why the nonprofit took two and a half years, and why that was right
• 26:52 — First dollar out versus being methodical
• 29:41 — Why you'd be a better leader now than you were then
• 30:25 — Gen X and the refusal to invest in ourselves
• 31:25 — The Hoffman Process, eight days unplugged
• 33:06 — The patterns you inherited and repeat under stress
• 35:44 — Getting comfortable being uncomfortable
• 36:58 — Doing the uncomfortable thing, and how the podcast started
• 37:41 — The nonprofit as his uncomfortable thing
• 40:17 — People are doubting themselves inside corporate now
• 41:50 — The imposter syndrome nobody admitted to each other
• 43:00 — Everything is a choice, and we only price the downside
• 44:15 — Negativity as an inherited pattern
• 46:15 — The quarterly business review Brett runs with his wife
• 48:11 — Why most of the book's feedback is coming from men

QUOTES

"Words like transition mean progress. In purgatory, there's a lot less progress." — Geoff

"We're too focused on being finished, and not brave enough to say that we're unfinished." — Geoff

"Livelihood puts food on the table. If you don't make the livelihood the identity, then you're good." — Geoff

"We're tying how we feel to what somebody else thinks about us. That's an interesting psychological juxtaposition when you sit down to think about it." — Geoff

"Things don't need to be quick anymore. They need to be closer to right than quick." — Geoff

"I use my realism to mask my negativity. It's almost a Trojan horse." — Geoff

"He said, I always thought you had it together, and I wanted to make sure that you thought I had it together." — Geoff, on imposter syndrome with a former direct report

"I convinced them to hire me full time. In hindsight it made no sense. But it was comfortable." — Brett

"You're not being let go because you don't have the skills. Drop you into any situation and you know more than ninety five percent of the people in the room." — Brett

Questions or guest ideas

Quick version if you missed it. UGC is user generated content. Brands pay you to make short videos, and instead of posting them yourself, they use the footage in their own ads. No followers required. No production setup. Megan's been doing it four years and has taught more than 16,000 Gen X and Boomers how to do it, including her mom.

Her origin story is the part I keep thinking about. She was on a call trying to sell a footwear brand on hiring her, mentioned her mom in passing, and the brand got noticeably more excited about her mom than about her. Nobody that age was doing this. So she went and built the thing that didn't exist.

I keep coming back to UGC because I've been hunting low friction, high value income, and this one lands at the top of the list every single time. You're not applying for a job. You're not competing against five hundred other applicants. You already own the equipment.

We got into the money, and Megan gives real numbers instead of vague ones. What a beginner should charge. What the performance-based deals actually pay and why she turns them down. What her students are making, from a few hundred a month up to one who cleared twenty-two thousand last month.

Also worth your time: brands are now writing "no AI content" directly into their creative briefs. Megan's read is that the flood of AI has made real human video more valuable, not less. Her phrase for the moment is a trust recession, and it's the most useful thing said in the whole episode.

In this episode:

• What UGC actually is, and why followers don't matter
• The brand call that accidentally started her business
• Why brands are banning AI content in their briefs
• What to charge when you're brand new
• Performance-based deals and why she passes on them
• What her students actually earn, at every level
• Where the Amazon Influencer program fits, and where it doesn't
• Why she quit TikTok Shop
• Local businesses, and trading content for services
• How to find the right person at a brand

HOW TO ACTUALLY START, ASSEMBLED

Megan walked through this across the conversation. Here it is in order.

1. Go look at UGC videos on TikTok or Instagram so you know what you're making. It isn't for everyone and it's better to find that out in ten minutes than ten weeks.
2. Make three or four videos using products already in your house. Megan's first two were cat treats. Basic editing. Nothing fancy.
3. Put them in a portfolio. Canva works. Any simple site works. Brands need proof you can make content, same as any other business.
4. Pick a lane to get hired. Either join the creator platforms, or pitch brands directly. Megan pitches.
5. Start local or start small. Local service businesses, gyms, spas, a fencing company. Many have real marketing budgets and have never worked with a creator. Gifted or traded work counts here.
6. To reach a bigger brand, DM their customer service account and ask who handles content partnerships. They want a quick answer they can check off, and they'll usually give you the name.
7. Treat pitching as volume. Megan's rule of thumb is that roughly one in fifty says yes, and a no often just means not right now.
8. Then chase repeat clients. That's where the margin is, because you stop relearning a new brand every time.

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Why Megan's back
• 01:10 — What UGC is, and the 16,000 students
• 02:13 — Why Brett keeps coming back to low friction income
• 03:13 — Why so many people freeze before they start
• 04:24 — She saw it on TikTok while working a corporate job
• 05:00 — Out of that job in fourteen months
• 05:32 — The footwear call where they got excited about her mom
• 06:33 — Nobody that age was doing this
• 07:01 — Why corporate trained us to overthink it
• 08:37 — Who am I to teach this, and why two steps ahead is enough
• 09:26 — A detour into other low friction businesses
• 10:18 — What AI is doing to this market
• 10:37 — Brands writing "no AI content" into the brief
• 11:55 — The trust recession
• 12:32 — Is it too late to start?
• 13:10 — Why it's an ongoing need and not a trend
• 14:18 — What to charge when you're brand new
• 15:00 — Performance based deals, and the math on them
• 16:42 — Why Megan turns those down
• 17:11 — Brett butchering a brand name on camera, and the brand not caring
• 18:24 — The part-timers, and what a summer looks like
• 19:00 — Replacing corporate income
• 19:45 — The student who made $22,000 last month
• 20:48 — Why repeat clients change the economics
• 21:52 — Where the Amazon Influencer program fits
• 23:29 — Income stacking and double dipping
• 24:45 — Why she quit TikTok Shop
• 27:11 — How to start, step one
• 28:39 — Cat treats, and your first videos
• 29:30 — Platforms versus pitching
• 30:27 — Big brands versus local businesses
• 32:00 — Why local wins give you momentum
• 33:13 — What the first fifty dollars does to your head
• 33:20 — Trading content for services
• 34:38 — How to find the right contact at a brand
• 35:30 — Pitching as a volume game
• 36:41 — Getting a fence stained in exchange for content
• 38:30 — The fears that stop people, and why none of them hold
• 40:03 — Belief, action, and the first dollar
• 41:09 — Where to find Megan

QUOTES

"I happened to mention my mom, and they got way more excited about my mom than me." — Megan

"We're all in a trust recession. We don't know what's real and we don't know what's fake. So the more real and raw, the better." — Megan

"Brands are literally writing no AI content into the brief. I've seen it several times just in the past couple of weeks." — Megan

"She's in her fifties, functional medicine, lab coat. She made twenty-two thousand dollars last month." — Megan

"A brand paid me fifty bucks. I'm now a content creator. That carries through everything else." — Megan

"It's a volume game. For every fifty that say no, one's probably going to say yes." — Megan

"We're not saving lives here. This is not brain surgery. Don't take it so seriously." — Megan

"You probably spend a lot of time on social media consuming content, when you could be creating it and getting paid." — Megan

"You're not applying for a job. You're not competing against five hundred other people." — Brett

LINKS

Megan Collier TikTok, Instagram, and YouTube: @megan_ugc Instagram DM is the best place for a specific question.

Megan's UGC course — https://stan.store/affiliates/bd030aba-a9a1-4f50-9073-45cc67b073f1

Mentioned in the episode Creator platforms Megan named: Insense, Billo, Cohley, and others. Confirm exact spellings with Megan before publishing, the audio is unclear on a couple. Email lookup: hunter.io AI pitching service she mentioned: confirm the name with Megan.

Questions or episode ideas? bt@bretttrainor.com

UGC, user generated content, side income, GenX side hustle, content creation, brand deals, making money outside corporate, no followers needed, creator economy, low friction income

She was a grief counselor before she was a coach, which is why she talks about layoffs differently than anyone else I know. We opened on the Oracle news, because the math on it is ugly. Twenty years in, fifty or sixty hour weeks, and what shows up is an automated email at 6 a.m. that doesn't say thank you.

Her point stuck with me: you spend a career radiating loyalty outward, and at the very end, when it matters most, you don't get any of it back.

Then we get into the trap almost nobody sees coming. You leave, you go independent, and because you're wired for comfort and you just absorbed six losses at once, you rebuild the exact role you escaped. Director of sales, but fractional. Same work, same frustrations, now with no benefits. As Shelley put it, you built the same box you just got out of, and you can't figure out how you ended up back inside it.

I did a version of this myself. I had a good contract gig that paid well doing work I liked. Instead of building on it, I talked the company into hiring me full time, because the title felt safer. I was miserable within months.

The back half is her method for getting unstuck, and it's the opposite of what most people do. You don't sit down and list your skills. You don't mine your performance reviews. When you've just been laid off, you are the least qualified person in your own life to describe how good you are, because you're operating from doubt.

So you go gather evidence instead.

In this episode:

• Why the coldness of a modern layoff lands harder than people admit
• Identity, job titles, and the shorthand you lose
• The comfort trap, and why rebuilding the old job is a normal human response, not a failure
• The physical toll nobody talks about
• Why performance reviews are useless for this
• How to ask people who know you what you're like at your best
• Turning what comes back into five words, and using them as a filter
• The portfolio approach when one opportunity only delivers part of what you need
• The guilt of not being busy, and why you were never productive nine hours a day anyway

THE EXERCISE, ASSEMBLED

We covered this across the conversation but never laid it out in one piece. Here it is.

1. Pick five to ten people who know you well and who you genuinely trust. Mix of personal and professional. The trust part matters more than the title.
2. Ask one question: "Can you describe what I'm like when I'm operating at my best?"
3. Let them go long. Most people won't give you adjectives, they'll tell you a story about a specific time you showed up. Those stories are the useful part.
4. Read all of it together. If you find yourself doubting it, notice what that means. You'd be calling people who love you liars.
5. Synthesize it down to five words that describe how you show up at your best.
6. Use the five as a filter. For any opportunity, job or client or project, ask whether it not only allows but requires you to show up that way. If it only hits three, go find the other two somewhere else in your life.

ABOUT THE GUEST

Shelley McIntyre is a coach for Gen X professionals in transition, and a former grief counselor, which is where a lot of her perspective on identity loss comes from. She hosts Burn the Map, a podcast built around short episodes, and works with clients on figuring out who they are outside a job title.

• Podcast: Burn the Map
• Site: https://burnthemapcoaching.com
• LinkedIn: https://www.linkedin.com/in/shelley-mcintyre/

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Welcome back, and why her first episode still gets downloads
• 01:00 — The Oracle layoffs, and the severance math
• 02:08 — Getting numb to the coldness of it
• 02:40 — You radiate loyalty your whole career and don't get it back
• 03:41 — The 6 a.m. automated email that doesn't say thank you
• 04:22 — Why identity and job title get intertwined
• 05:08 — "I'm a VP of marketing" as shorthand for who you are
• 06:11 — Title, industry, company. The trifecta.
• 07:18 — The trap: going independent and rebuilding the same role
• 08:16 — "I built the same box I just escaped"
• 09:29 — Brett talked his way back into a full time job and hated it
• 10:26 — We are wired for comfort, and that's not a character flaw
• 11:38 — The losses stack up all at once
• 12:17 — Remembering who you are underneath all of it
• 14:02 — Why skills lists and performance reviews don't work here
• 14:58 — When the doubt spreads to things you were always good at
• 15:50 — The physical toll: illness, accidents, the hospital
• 16:32 — Usefulness, and being told you're not needed
• 17:25 — You're not the most qualified person to say how great you are
• 18:23 — Becoming a detective of your best self
• 19:16 — Why corporate feedback is performative
• 20:00 — What actually happens when you ask
• 21:07 — "Let me tell you a story"
• 23:00 — The surprise birthday party nobody would have predicted
• 24:00 — If you don't believe it, you're calling them liars
• 24:51 — What to do with it: five words
• 26:08 — Using the five as a filter for every opportunity
• 27:00 — But what if nobody has anything good to say?
• 28:19 — The portfolio: when one thing only delivers three of five
• 29:01 — Separate the mission from the money
• 29:55 — "What do you do for fun?" "Fun?"
• 32:15 — What if you could do something you're good at and it's fun
• 33:11 — Ideas need space. You can't rest and be busy at the same time.
• 34:38 — Nine hours in the chair, maybe four of real work
• 35:41 — It nets out the same. You're just doing it on your terms.
• 36:33 — A walk in the park beats a useless meeting
• 40:00 — The former client who'd never go back
• 40:28 — Take a part-time job and watch all your time disappear
• 40:43 — The real hourly math on a hundred thousand dollar salary
• 43:03 — Burn the Map, and where to find Shelley

KEY QUOTES

"You're radiating this love and loyalty out throughout your career, and then you don't get it back. At the very end, when it matters the absolute most, you don't get it back." — Shelley

"I have built the same box for myself that I just escaped. And how is it that I'm back inside of it?" — Shelley

"You're not actually the most qualified person to talk about how great you are. Because you're in a world of doubt." — Shelley

"If you don't believe that, then you're calling these people liars and you're out of integrity." — Shelley

"You can't rest and be busy at the same time. It doesn't work." — Shelley

"You might have been in the chair for nine hours a day, but you did not do productive work for nine hours a day. So why are we beating ourselves up when we're being equally productive? We're just doing it on our terms." — Shelley

"Instead of going to a useless meeting, what if you could go for a walk in the park?" — Shelley

"I had a good contract gig. Instead of building off of that, I convinced the company to bring me back full time, because it was the title and it was more comfortable. I was absolutely miserable." — Brett

I'd been repeating that exact line for years and never once dug into it.

So this episode is two things. Why people still say entrepreneurship isn't for everyone, and why I think it's true about something almost nobody is actually doing.

When people hear "entrepreneur" they picture the same movie. Raise money, hire a team, sign a lease, bet the house. That version is brutal and it isn't for most people, me included. But in 2023 roughly 117,000 one-person businesses cleared a million dollars in revenue. No employees. No payroll. Nobody to manage.

The four myths I go after:

1. You need a business plan
2. You need a website, a brand, an LLC, a logo
3. You need to be a salesperson
4. It's risky

That last one is backwards. Your corporate job is one customer providing one hundred percent of your income, and they can end it for reasons that have nothing to do with how good you are. Attach a W-2 to it and we call it stability.

The second half is the part I didn't get into in the LinkedIn article: finding clients is closer to a job search than to building a company. I've had seven or eight corporate roles and seven of them came from a referral or somebody in my network. Not one came from a blind posting. That's the same channel that brings in solo work.

I also walk through how I'd structure a first offer. Good, better, best, and why people almost always take the middle one.

In this episode:

• Where the stereotype came from, and why it was true about a different thing
• The four myths, one at a time
• Why corporate politics skills don't transfer, and why that's good news
• Your job is one customer with one hundred percent concentration
• The interview and the discovery call are the same conversation
• Good, better, best, and pricing your first engagement
• Owning your own calendar, which took me longer than I want to admit

TIMESTAMPS

• 00:00 — The LinkedIn article, and what this episode adds to it
• 01:30 — The TikTok comment that started it
• 01:55 — I'd been saying the same line for years
• 02:20 — Hundreds worked with, thousands talked to, and almost none were prototypical entrepreneurs
• 03:00 — Where the stereotype came from
• 03:45 — 117,000 one-person businesses over a million in revenue
• 04:10 — Stop thinking customers. Think micro jobs.
• 04:25 — Myth 1: you need a business plan
• 04:41 — Myth 2: you need a website, a brand, an LLC
• 05:15 — Myth 3: you need to be a salesperson
• 05:50 — Why corporate politics skills don't help you out here
• 06:20 — Myth 4: it's risky
• 07:15 — Your corporate job is your one customer
• 08:00 — What a diversified solo practice actually looks like
• 08:30 — If it takes six months to find your next customer, you're running it wrong
• 08:50 — Put a tenth of your job hunt effort into finding clients
• 09:55 — Finding clients looks a lot like looking for a job
• 10:25 — Seven of my eight roles came from referrals. None from a posting.
• 11:00 — Think of it as mini job applications
• 11:36 — The interview process, walked through step by step
• 12:15 — Same conversation, but with a business owner
• 12:45 — Good, better, best
• 13:35 — They take the middle option nine times out of ten
• 14:20 — Nobody's judging you
• 14:55 — You'll probably underprice the first one. It doesn't matter.
• 15:30 — You'll work fewer hours than you do now
• 15:50 — Owning your own calendar, and why it took me so long
• 16:11 — Don't feel guilty when you're not busy
• 16:40 — The few who go back, and why they go back with a plan
• 17:20 — Reallocate some of those job hunting hours
• 17:45 — It's relationships, not postings
• 18:15 — Don't chase shiny objects. Pick one or two.
• 18:30 — Maybe the word itself is the problem
• 19:00 — Corporate ends either way. Take control.

Key Quotes

"Seven of my eight corporate roles came from a referral or somebody in my network. I honestly can't think of a single job I got from a blind posting."

"Your corporate job is one customer. One revenue stream. If that customer goes away, you've got nothing."

"One bad quarter, or even a good one with a new VP, and you're gone."

"If it takes you six months to find your next customer, you're not running that business very well."

"Put a tenth of the effort you put into a job hunt into finding problems to solve, and you'd have more customers than you'd know what to do with."

"The people who got ahead in corporate because they knew how to play the games, that doesn't work out here. These people just want their problem solved."

"Nobody's judging you except you."

"Corporate's going to end whether you choose it or not. You might as well take control."

LINKS

Questions, or an episode idea? bt@bretttrainor.com

He didn't have a plan. He took a couple months, picked up some contract work to hold him over, and then a light bulb went off: if he could find enough of these, he might never need a full-time job again.

Four years later he's got a practice serving independent consultants and a book, The Expert's Privilege, that I told him he should have written before I left corporate.

The core idea is three stacked pieces:

1. You've built real, transferable expertise over your decades in corporate.
2. That expertise has been inefficiently deployed inside the corporate machine.
3. You can deploy it far better on your own.

His metaphor for point two is the one that stuck with me. Imagine running a cruise line with a hundred ships and fifty of them permanently tied up in port. That's what corporate does with what you know.

We also get into the stuff nobody tells you. Why hourly pricing punishes you for being good. What happens when a client pigeonholes you before you open your mouth. How he figured out which part of his own service people actually valued, and then sold only that. And the thing I keep running into with Gen Xers: deeply experienced people who sit down, look at twenty-five years of work, and say "I don't know what I know."

In this episode:

• Two layoffs, and the one that changed his mind about going back
• Client zero, and why hourly was the wrong model
• Getting pigeonholed as "a writer" and the pricing that comes with it
• The coach question that triggered his pivot: do you actually like doing this work?
• Writing daily for two years before there was a book
• Why he deliberately left AI out of the book
• The Expert's Privilege, defined
• Intellectual headshots, and how asking former clients one question reshaped his business
• Investing in yourself when corporate always paid for it before

TIMESTAMPS

• 00:00 — Intro
• 01:43 — Two layoffs, and why he didn't want another corporate role
• 03:26 — Why almost nobody who gets out wants to go back
• 04:32 — He didn't know solo consulting was even an option
• 06:43 — What the work actually was: executive ghostwriting and content strategy
• 08:22 — Client zero, and the first lesson about hourly rates
• 09:18 — Project fees, and putting guardrails on your availability
• 10:44 — Getting pigeonholed as "a writer" before the conversation starts
• 12:14 — When the business model started breaking
• 13:11 — The coach's question: do you actually like doing this work?
• 13:41 — The pivot to serving independent consultants
• 14:59 — Brett's own winding path out of corporate
• 15:53 — The three-tier offer, and why clients almost always pick the middle
• 16:50 — Helping people map their lane while they're still employed
• 17:47 — "I never gave serious thought that I could take the reins myself"
• 20:18 — Building authority from zero, and writing daily for two years
• 21:44 — You turn around and there's a library there
• 22:34 — The self-doubt going into the book
• 23:10 — Not the book. A book. Your first book.
• 26:11 — Brett's stuck manuscript problem
• 26:33 — The North Star workshop and the parachute metaphor
• 27:44 — Why he left AI out on purpose
• 30:04 — The Expert's Privilege, the three stacked ideas
• 30:53 — A hundred ships and fifty of them tied up in port
• 32:10 — In the corner four months ago, desperate for his brain today
• 34:00 — Most businesses need level one help, not level three
• 36:28 — "I don't know what I know," and why that trap is so common
• 37:34 — Start with the problem, not with yourself
• 38:48 — Need-to-solve versus nice-to-solve
• 39:26 — Brett on chasing energy as the compass
• 40:31 — Intellectual headshots, and the one question that created them
• 42:08 — Saying no, and the add-on that killed Brett's margin
• 43:18 — Investing in yourself when corporate always covered it
• 45:39 — Laid off tomorrow: square one, or a head start?
• 48:05 — You're a business with one client. Is that a good deal?
• 49:28 — Where to find Wes and the book

QUOTES

"I wasn't angry. I just didn't have the energy to attach myself to someone else's mission again, just for it to get taken away in a couple of years." — Wes

"Imagine you had a cruise line with a hundred ships and fifty of them were tied up in port permanently. That's how we are in corporate." — Wes

"I was that person four months ago that was getting put in the corner. And here, in a different context, they're desperate to know what I know." — Wes

"If you're good at something, an hourly rate doesn't do you any favors." — Wes

"Don't think of it as the book. Think of it as a book. Even easier, your first book." — Wes, on the advice that unstuck him

"I don't know what I know. I've done so many things that I feel like I can't do any of them." — Wes, on what he hears constantly

"Think of your current job like you're a small business owner with one client. Is that a good deal for you?" — Brett

"If you were laid off tomorrow, do you want to start from square one, or do you want to feel like you had a head start?" — Wes

ABOUT THE GUEST

Wes Wheless is the author of The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo (July 2026). After two layoffs, including one from the tech education company Reforge, he built an independent practice helping solo consultants pull their expertise out of their heads and turn it into visual frameworks, something he calls intellectual headshots. He now also works with people still inside corporate who want to map and pressure-test a consulting lane before they need one.

LINKS

The book The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo https://theexpertsprivilege.com/ Amazon: https://www.amazon.com/Experts-Privilege-Self-Deployment-Leaving-Corporate/dp/1788464028

Wes's site and services https://bio.site/weswheless

Wes on LinkedIn — https://www.linkedin.com/in/wwheless/

The Collective https://trp-collective.circle.so

Questions or guest ideas? bt@bretttrainor.com

Three things are colliding at once.

Corporate is chaos. It's not your age, it's your expense. Somebody can do half your job for half the price, and that's who gets picked. Getting laid off is one thing. Getting back in is the real problem. Look around your own network if you don't believe me.

The savings math. The generation before us had pensions. We got a 401k and a how-to video. Roughly half of Gen X has nothing put away, and the typical household isn't close to what 30 years actually costs.

Longevity. This is the good news. If you take care of yourself there's a real chance you're looking at 30 or 40 more years, healthy and active.

Put those three together and it doesn't add up.

I'm not doing this to scare anybody. It's not a prediction, it's already happening. But there are two ways to react. You can treat it as a sunset and ride it out. Or you can treat it as the start of a second adult lifetime, which is the way I'm choosing to look at it.

The back half of this episode is the part that matters: you already have everything you need to generate income on your own. The skills, the experience, the problem solving. What's in the way is unlearning what corporate taught you, and the fact that we make making money way more complicated than it needs to be.

In this episode:

• Why it's your expense, not your age
• The musical chairs problem, and why the chairs aren't coming back
• Pensions versus the 401k handoff
• What 30 or 40 more years actually costs
• Why gig work is the wrong answer
• Low friction, high margin income, and what that actually looks like
• Why the first dollar outside corporate changes everything

TIMESTAMPS

• 00:00 — Welcome, and why I'm zooming out this week
• 01:20 — Naming it: Gen X has a math problem
• 01:42 — Two ways to react: sunset, or jumpstart
• 02:05 — Musical chairs, and why they're pulling five at a time
• 02:25 — Part 1: It's not your age, it's your expense
• 03:40 — Getting laid off isn't the problem. Getting back in is.
• 04:20 — The professional athlete parallel
• 04:46 — Part 2: How prepared are we, really
• 05:05 — They got pensions. We got a how-to video.
• 06:00 — The savings numbers nobody wants to look at
• 07:05 — How few of us actually have a pension
• 07:45 — Part 3: Longevity, and why it's genuinely good news
• 08:45 — Putting all three together
• 09:15 — This isn't a prediction. It's happening now.
• 09:55 — The good news: you already have what you need
• 10:30 — Seventeen income streams, and why I'm not special
• 11:05 — Why it's not Uber and it's not DoorDash
• 11:45 — The real blocker: unlearning corporate
• 12:45 — Low friction, high margin income
• 13:40 — Go sell that first dollar
• 14:05 — Don't bet on another 20 years in corporate
• 14:45 — The opportunity sitting in your own backyard
• 15:05 — Don't replace your job with a worse version of it
• 16:00 — What changed inside the community
• 16:25 — Nobody's judging you (my TikTok debut says hi)
• 17:35 — The better you are, the more at risk you are
• 18:20 — What the 20-somethings figured out that we didn't
• 18:45 — How to reach me

LINKS AND CTA

The Collective Now focused entirely on the thing most people are stuck on: making money outside of corporate. A group of Gen Xers figuring it out together. https://trp-collective.circle.so

Everything else https://BrettTrainor.com

Questions or episode ideas? Email me: bt@bretttrainor.com

If the show's useful to you, hit follow wherever you listen.

GenX, laid off over 50, ageism at work, corporate layoffs, retirement math, 401k, longevity, second act, making money outside corporate, career change over 50, side income, Gen X retirement crisis

At the time I thought this was about one thing: replacing my income. Six years, 350 episodes, and a whole lot of experiments later, I've figured out it was never really about the money.

This is the first solo episode under the new name, and I wanted to start by sharing the nine things I've learned on this quest so far. Not a playbook. Not a system. Just the stuff that turned out to be true, whether you're still in corporate, recently laid off, or already out and still trying to piece it together.

I don't have it all figured out. I'm a lot closer to where I want to be than I was six years ago, and I'm bringing you along for the rest of it.

The nine:

1. I wasn't running from corporate. I was running toward control.

2. Time is the currency. Grinding is just rationalizing giving it away.

3. Without your health, none of the time means much.

4. We overcomplicate everything. Especially making money.

5. Stop building your life around a job. Fund the life you want instead.

6. Stop asking permission. Nobody's coming.

7. Action beats planning. Every time.

8. Doing less is the whole skill.

9. It comes down to four buckets: relationships, health, purpose, and fun.

The Collective Now focused on the thing most people are actually stuck on: making money outside of corporate. https://trp-collective.circle.so/checkout/the-time-rich-project-collective

Got a question, or know a Gen Xer doing something interesting? Email me: bt@bretttrainor.com

If you're getting something out of the show, hit follow or subscribe wherever you're listening. Still moves the needle.

TIMESTAMPS

Estimated from the transcript. Spot-check against the final cut, and shift everything by the length of your cold open plus sting.

• 00:00 — Six years in, and why I'm doing this podcast with more intention

• 01:55 — #1: I wasn't running from corporate, I was running toward control

• 03:00 — #2: Time is the currency (and the 90-minute commute that broke me)

• 05:05 — #3: Prioritize your health now, not later

• 06:00 — #4: We overcomplicate everything, especially making money

• 07:30 — #5: Stop building your life around work, fund the life instead

• 09:10 — #6: Stop asking for permission

• 10:25 — #7: Action beats planning, every single time

• 11:30 — #8: Doing less is the whole skill

• 13:55 — #9: The four buckets (relationships, health, purpose, fun)

• 17:50 — Quick recap of all nine

• 19:20 — There is no one path. Don't follow somebody else's plan.

• 20:05 — What's changed inside The Collective

• 21:05 — How to reach me

After six years of building life beyond the default corporate playbook, thousands of conversations with Gen Xers, entrepreneurs, and experts, and features in Fortune, Fast Company, Forbes, Harvard Business Review, and Inc., Brett Trainor is still on the quest to build his ideal life—and he shares what he learns along the way.

Part personal journal, part practical guide, and part curious conversation, this is a candid, lightly produced show about stripping away the noise, rejecting unnecessary grind, and seeing more of what is possible.

Brett is a deconstructor, explorer, dot connector, and self-admitted high-functioning lazy person. Through solo episodes and unfiltered conversations with Gen Xers, founders, creators, and experts, he explores the decisions, habits, tools, tradeoffs, and ideas that can help you build a life you actually want to live.

The conversations span the areas that make life worth living: money, mind and body, purpose, connections, possibility, and fun.

There is no singular path. No hustle theater. No permission required. Just better questions, useful ideas, and real examples that help you see what is possible—and ask:

Why not me?

This is the episode that ties the whole thing together: what a time rich life actually is, and why control of your time, not your income, is the key to the life you want.

My first year out of corporate, I chased one thing: replace the paycheck and then some. I did it. And I wasn't much happier. This is the story of what I was actually missing, and the simple framework that fixed it.

In this episode:

• What a time rich life really is, and why money isn't part of it

• The four areas that actually move your happiness: connections, health, purpose, fun

• The "50 hours back" question that reframes everything

• The calendar mistake I made that was worse than corporate

• Define, Fund, Live: the three moves to get there

• Low-friction income: funding your life in the fewest hours

If corporate has you trading every hour for a paycheck, this is your blueprint for taking the hours back.

CHAPTERS / TIMESTAMPS

00:00 — What this episode answers, and why it matters 02:18 — Kicked out: I chased the money and wasn't happier 03:30 — What a time rich life actually is 04:44 — The "50 hours back" question 05:30 — The four areas: Connections and Health 07:07 — Purpose, and why "escape" was the wrong word 08:20 — Fun, and my two non-negotiable time blocks 09:24 — What control actually looks like (golf Friday, granddaughter over) 10:49 — Why it all comes down to time 12:00 — We overcomplicate making money 13:16 — The calendar problem, and losing the guilt 14:30 — Time blocking, and the 30-minute disaster (thanks Glaveski + Shirley) 15:38 — Learning to say no 17:52 — The four areas as your monthly barometer 19:20 — Money is a tool, not the goal (thanks Diana Alt) 20:03 — The framework: Define it, Fund it, Live it 22:24 — Funding the life: from fractional to low-friction income 25:00 — Two things you can do today

LINKS & RESOURCES

Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes

The Time Rich Collective (connect with Gen Xers on the same path) → https://trp-collective.circle.so/checkout/the-time-rich-project-collective

Website → https://timerichproject.life

Mentioned in this episode:

• Steve Glaveski, author of Time Rich — earlier TRP episode

• Paul Shirley, The Art of Focused Work — earlier TRP episode

• Diana Alt on separating mission from money — recent TRP guest episode

• The "15 ways I've made money outside corporate" episode → https://youtu.be/p5rxv-f1M7k

Listen / subscribe:

• Spotify → https://open.spotify.com/show/5UQSv8iKydo8E2cevuIAB5

• Apple Podcasts → https://podcasts.apple.com/us/podcast/the-time-rich-project-formerly-the-corporate-escapee/id1469405998

• Newsletter → https://trpnewsletter.beehiiv.com/

This one is all mechanics. If you're 45+ and trying to make your first dollar outside corporate, or just want to stop betting everything on one paycheck, this is the playbook.

In this episode:

• Your real number: why you think in cash flow now, not salary, and why it's lower than you'd guess

• Why one boss is the riskiest bet you can make

• Separating mission from money so you fund the life without burning out

• 15 ways I've actually made money since leaving corporate, from higher-effort work to low-friction income anyone can start

• Three live examples with real numbers: the guy negotiating car deals, a wedding-dress business I built in 4 hours for $10, and the Amazon Influencer Program

• A simple four-part filter to score any idea: pay, demand, ease, repeatability

Watch the version with slides on YouTube, or grab the deck from the resources below.

Money is solvable. Time is the thing you can't get back. Stop trading so much of it.

THE 15 WAYS (quick reference)

Higher-effort income (monetize your corporate experience — great cornerstone accounts, but more hours):

1. Fractional leadership

2. Consulting (project-based)

3. Solo consulting

4. Advisory

5. Business development (setting meetings for brands in your network)

6. Reselling services for smaller brands

7. Affiliate sales

Audience-based (helps to have a following): 8. Sponsored posts 9. Paid community 10. Speaking 11. Paid content / brand sponsorships

Low-friction income (anyone can start, small audience or none): 12. Paid workshops 13. Coaching (business, career, or a hobby — you just have to be a step ahead) 14. Facilitating webinars 15. User-generated content (UGC)

Bonus area to dig into: AI services for business owners.

THE FILTER (score each idea 1–10)

• Pay — how much per hour?

• Demand — is this a need-to-solve problem, not a nice-to-solve one?

• Ease — how fast and simple to deliver?

• Repeatability — can you do it again and again?

LINKS & RESOURCES

Watch this episode with the slides on YouTube → https://youtu.be/p5rxv-f1M7k

Download the deck (the 15 ways + the filter) → https://stan.store/thecorporateescapee

Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes

The Time Rich Collective (connect with Gen Xers on the same path) → [COMMUNITY LINK — drop in]

Website → https://timerichproject.life

Mentioned in this episode:

• Unveiled + Unboxed (the wedding-dress project) → https://unveiledunboxed.com

• Megan's UGC course for Gen X and Boomers → https://stan.store/affiliates/bd030aba-a9a1-4f50-9073-45cc67b073f1

• Tommy / Deliver (car-buying negotiation service)

• Wall Street Journal, "The Rise of Million-Dollar Companies With Just One Employee" → https://www.wsj.com/tech/ai/the-rise-of-million-dollar-companies-with-just-one-employee-f36a77c1

• Amazon Influencer Program

CHAPTERS / TIMESTAMPS

00:00 — Making money outside corporate at 45+ 01:00 — The real blocker: we overcomplicate it 02:20 — The five things this episode covers 02:50 — 1. Stop thinking salary, start thinking cash flow 04:00 — No pension, and becoming a high-functioning lazy person 05:00 — 2. Why one boss is the riskiest bet 06:45 — 3. Separate mission from money (thanks, Diana Alt) 07:50 — 4. The 15 ways I've made money (deck on YouTube) 08:30 — What low-friction income actually means 09:00 — Higher-effort: fractional, consulting, advisory, reselling 11:20 — For the record: I've spent $0 on marketing 11:40 — Audience-based: sponsored posts, community, speaking 12:20 — Low-friction anyone can start: workshops and coaching 15:00 — UGC: my favorite way to start 15:40 — The solo-business boom (WSJ) 16:10 — Solve one simple problem, not all of them 16:40 — AI services for business owners 18:30 — Example 1: Tommy negotiates car deals 20:30 — Example 2: the wedding-dress business I built in 4 hours 24:30 — Example 3: the Amazon Influencer Program 26:30 — The filter: pay, demand, ease, repeatability 27:50 — Don't chase shiny objects 28:40 — Money is solvable

Here's the part nobody says out loud: when corporate moves on from you, it usually isn't because your talent slipped. You just got too expensive. Gen X is the first generation facing this without a pension to catch us, and we're going to outlive the old retirement math by decades.

So this episode borrows from the people who have been managing forced career transitions for 50 years: professional athletes. What do they lose when the game ends, and what can we take from their playbook?

In this episode:

• The four things you lose when corporate retires you: identity, community, structure, and money

• Why "you got too expensive" is not the same as "you're done"

• The three-part transition: design the life you want, fund it, then live it

• The four areas to rebuild around: relationships, mind and body, purpose, and fun

• Separating mission from money so you don't burn out chasing the wrong one

• Becoming a high-functioning lazy person: funding your life in the fewest hours possible

You've got another 30 good years, and 20-plus years of experience the athletes don't have. This is the sunrise, not the sunset. Let's build the plan.

LINKS & RESOURCES

Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes

The Time Rich Collective (connect with Gen Xers on the same path) →

Website → https://timerichproject.life

Mentioned in this episode: https://trp-collective.circle.so/checkout/the-time-rich-project-collective

• Paul Shirley (former pro basketball player and author) — earlier TRP episode

• Diana Alt — "separate mission from money" (recent TRP guest episode)

ABOUT THE SHOW

The Time Rich Project is for Gen Xers who paid their dues and are ready to write the next chapter. It's about taking back control of your time and funding the life you want in the fewest hours possible, so the rest of your time is yours. Real stories, real mechanics, no hustle. Hosted by Brett Trainor.

CHAPTERS / TIMESTAMPS

00:00 — The parallel nobody talks about: pro athletes and corporate 00:50 — You didn't get worse, you got too expensive 01:30 — The first generation without a pension (and outliving retirement) 02:45 — The four things you lose when corporate retires you 02:55 — 1. Identity: who are you without the title? 03:40 — 2. Community: everyone misses the locker room 04:50 — 3. Structure: owning your calendar, and my time-blocking mistake 06:45 — Why it's called Time Rich 07:30 — 4. Money: funding the lifestyle instead of chasing a paycheck 09:00 — Turn the faucet up or down: your first dollar out 10:00 — Start with what you know, then go wider (UGC, AI, small services) 10:50 — Separate mission from money (thanks, Diana Alt) 11:50 — The pyramid: from C-suite to everyone else 13:40 — What we have that athletes don't: 20+ years of experience 14:30 — Sunset or sunrise: it's your call 16:30 — Designing the life: relationships and the no-asshole policy 18:15 — Mind and body: built to live to 90 18:40 — Purpose: follow the energy 19:40 — Fun: are you getting enough of it? 20:00 — Funding the life you designed 21:00 — Living it: the 80/20 way 22:00 — Design, fund, live: putting it together

That's Diana Alt, and it's the perfect line to open our first guest episode under The Time Rich Project.

Diana is an executive and career coach who came out of tech. She works with people who are still in corporate and quietly wondering if this is it. Her take lines up with where this show is headed: corporate isn't the enemy. It's a client. You get to decide if the deal still works for you.

We got into:

• The four cornerstones of an aligned career (right work, right boss, environment, culture) and how to spot which one is actually broken

• Why burnout comes more from misalignment than from long hours

• "The hardest boss to fire is you," and why building a business you hate is easier than you'd think

• Mission vs. money: don't burn down the thing paying the bills to chase the thing that lights you up

• Why anyone with 10+ years of experience should have an LLC in their back pocket

• The only two things you need to make your first dollar on your own: an offer and a way to get paid

If corporate has stopped feeling good, this one gives you a way to figure out why, and what to do next.

GUEST: DIANA ALT

Executive and career coach helping people build work that aligns with who they are, in corporate or on their own. Host of the Work Should Feel Good podcast.

* Podcast & site: https://workshouldfeelgood.com

* Newsletter: https://dianaalt.com (click the "Let's Connect" button)

* LinkedIn: Diana Alt, the No BS Coach: https://www.linkedin.com/in/dianakalt/ 

LINKS & RESOURCES

Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes

The Time Rich Collective (connect with Gen Xers on the same path) → https://trp-collective.circle.so/checkout/the-time-rich-project-collective 

Website → https://timerichproject.life

Mentioned in this episode:

* Working Genius (Patrick Lencioni) — the six genius types

* Time Rich by Steve Glaveski

* Grace McCarrick — soft skills coach

CHAPTERS / TIMESTAMPS

00:00 — First guest under the new name (and how we found each other) 01:15 — Fountains and drains: choosing who you spend your time on 02:10 — Who Diana is: work should feel good 04:05 — Your company isn't your boss, it's your only client 05:00 — The biggest flex in business: firing what isn't aligned 07:00 — The hardest boss to fire is you 07:30 — The four cornerstones of an aligned career 10:40 — Why burnout is about alignment, not just hours 16:00 — The 50-hour week and how little of it is real work 16:50 — Someone says "I'm done." Now what? Find what's actually broken 20:30 — Agency, victim mode, and the clients Diana won't take 23:00 — Good people who lost confidence in what they're great at 28:30 — Diana flips it: what to build for time freedom 29:00 — Owning your calendar, and the time-blocking experiment that failed 31:40 — The scorecard: relationships, health, purpose, fun 34:00 — Low-friction income and becoming a high-functioning lazy person 35:50 — The car-buying guy doing $300K a month 36:40 — Mission vs. money: don't burn down the day job 39:50 — Everyone should have an LLC in their back pocket 42:40 — You only need two things to start: an offer and a way to get paid 44:10 — Where to find Diana

Welcome to The Time Rich Project. Same host, evolved mission, new name. This is the first episode under it, and I get into why the change and why it matters if corporate has stopped working for you.

Here's the shift: I wasn't escaping corporate. The real unlock was taking back control of my time. Once I had that, everything else opened up.

In this episode:

• Why Gen X is at a crossroads (and why it's a bigger opportunity than getting out)

• Sunrise, not sunset: you could have 30+ good years ahead, so what do you actually want to do with them?

• The four things that decide your happiness: relationships, health, purpose, and fun

• Return on hours: how to fund the life you want in the fewest hours possible

• Why your first dollar outside corporate is easier to make than they told you

• The time-blocking experiment that failed twice before it worked

You don't have to quit corporate to start living better. You do have to get intentional about your time. Corporate isn't the enemy. It's a deal. This show is about going in eyes wide open and deciding for yourself if it's still worth it.

Do what you want, when you want, where you want, with who you want. That's the whole thing. Let's go get it.

TRP Collective: https://trp-collective.circle.so/checkout/the-time-rich-project-collective 

https://stan.store/thecorporateescapee

CHAPTERS / TIMESTAMPS

00:00 — Why the name changed (again), and why this one sticks 02:24 — The real unlock: I stopped chasing paychecks and took back my time 04:39 — The Gen X crossroads: career, family, and the retirement myth 06:53 — Sunrise, not sunset: 30+ years to do what you actually want 08:20 — The four things that make you happy: relationships, health, purpose, fun 11:43 — How to check in on the four without turning it into a spreadsheet 13:10 — Return on hours: making the money you need in the fewest hours 16:30 — Make your first dollar outside corporate (easier than they told you) 18:53 — My time-blocking disaster, and what finally worked 21:15 — What you want, when you want, where you want, who with

In this conversation, Janice walks Brett through her REAL Connection System, a four-part framework for solo escapees who'd rather build a business through referrals than spend their week shouting into the LinkedIn algorithm. It's a refreshingly old-school playbook for a world that's getting more synthetic by the month.

They dig into why direct mail to strangers gets a 1% open rate while cards in envelopes hit 99.5%, the story of the CMO who sent $5,000 in chocolates and closed $12 million in deals, and why the rental company owner who shifted from "send to get" to "send to give" went from zero replies to a full pipeline.

If you've been treating networking like a phase to get through instead of the actual work, this episode is the reset. For most solo escapees, 95% of their business will come from referrals. This is the playbook for earning them.

What you'll learn

🎯 The REAL Connection System (Refresh, Engage, Appreciate, Leverage) explained step by step

🎯 Why Googling yourself in an incognito window is the first thing every escapee should do this week

🎯 The 5-comments-a-day move that beats posting (and where to actually leave them)

🎯 The "send to give, not to get" mindset shift that turns cold outreach into real relationships

🎯 How to leverage your first-degree connections for warm intros without being weird about it

🎯 Why "human-to-human" is the move in an AI-augmented world

Quotable moments

"Don't send to get. Send to give."

"95% of solo business comes from referrals."

"Direct mail to strangers: 1% open rate. A card in an envelope: 99.5%."

"How you do anything is how you do everything."

"Don't be attached to the outcome. Just keep moving."

Resources mentioned

📋 Janice's REAL Connection System (free ebook): janiceporter.com

🎙️ Relationships Rule Podcast: [LINK]

💼 Connect with Janice on LinkedIn: Janice Porter (mention you heard her on TCE)

📬 Send Out Cards: sendoutcards.com

Connect with Brett

📰 The newsletter (10K+ GenXers building life-first futures): [NEWSLETTER LINK]

🐬 The Escapee Collective. First month $1: theescapeecollective.com

Megan Collier (@megan_ugc, 300K+ on TikTok) is back on The Corporate Escapee for a Round 2 conversation, and the market has shifted under our feet. UGC, user-generated content, is now a real path to $2K to $15K a month for people who've never been in front of a camera. And the demographic brands are scrambling to find isn't 25-year-old influencers. It's GenX.

Megan walks through what she's calling the "trust recession." Polished ads are losing. Real faces, messy houses, lived experience are winning. New state laws are fining companies for undisclosed AI-generated content. The result: human creators just got more valuable, not less.

Brett and Megan dig into the cat litter brand story (where Megan got rejected, then called back asking for her 65-year-old mom instead), why GenX experience is the unfair advantage brands need right now, and the four-step play to land your first UGC deal this month using products you already own.

If you've been waiting for the "what would I actually do" piece of escaping corporate, this is one of the cleanest entry plays going.

What you'll learn

🎯 Why "we're in a trust recession" and what it means for anyone making content

🎯 The four-step outreach play (notes app, Instagram ad audit, Loom video, brands you already use)

🎯 Why your age is the asset brands are paying double for right now

🎯 How to land your first deal even if you've never been on camera before

🎯 The Loom pitch script that converts way better than cold email

Quotable moments

"We are in a trust recession."

"The ageism you felt in corporate is the exact thing brands are paying for in marketing."

"Just figure out how to make that first dollar outside of corporate. I don't care if it's 25 bucks."

"You don't need followers to do this. You need to be a real human in a world full of AI."

"The skill that got you fired is the skill that's about to get you paid."

Resources mentioned

📋 Megan's free UGC checklist: [STAN STORE LINK]

🎓 Megan's UGC course ($87, lifetime access): [COURSE LINK]

📱 Follow Megan on TikTok and Instagram: @megan_ugc

GenX is elite at overcomplicating making money. A Millennial gets a side hustle idea and is live by Sunday. A Gen Z is already filming the TikTok. A GenXer opens a Google Doc, then a spreadsheet, then researches LLC structure, then goes to bed.

Brett admits he's been part of the problem. For years he's preached solo consulting and fractional work as THE path out of corporate. It's a real path. He still believes in it. But it's not the only one, and it's not the fastest one.

In this episode, Brett walks through 8 service businesses a GenXer could start running this weekend. None of them require corporate experience. All of them work on the same model: find a known, friction-heavy problem, solve it for $500-$1,000, and stack the deals.

He breaks down the proof points (Tommy at Delivrd doing 300 car negotiations per month at $1K each, plus a friend billing $15K/month on credit card points optimization), walks through the filter for what makes a good escapee service, and runs through the full list from subscription audits to federal subcontracting to the Escapee Starter Pack.

If you're still trying to figure out your "big idea," this episode is the reframe.

🎯 What you'll learn:

🎯 Why solo consulting isn't the only path out of corporate 

🎯 The $500-$1,000 "stack the deals" model and why it works 

🎯 The 6-point filter for a good escapee service business 

🎯 8 specific service businesses you could start this weekend 

🎯 Tommy's $300K/month service business and what it reveals about every other category 

🎯 The federal subcontracting sleeper play (full episode coming)

Resources mentioned:

🐬 Join the Escapee Collective for $1 your first month: theescapeecollective.com 

🎧 Subscribe to The Corporate Escapee Podcast wherever you listen 

Quotable moments:

"GenX is elite at overcomplicating making money."

"You don't have to be light years ahead of somebody to teach them or offer a service. You just have to be slightly ahead of where they are."

"Find a known, friction-heavy problem. Solve it for $500 to $1,000. Stack the deals. That's the whole game."

"Tommy didn't invent anything. He just found a friction-heavy problem and charged people to make it go away."

"When I was in corporate, I paid somebody to do my expense reports for me every month. Was I capable? Yes. Did I want to? No. That's the whole secret."

That's not doom and gloom. That's actually the good news. Because once you accept it, you stop waiting. You stop hoping. And you start doing something about it.

In this solo episode, Brett walks through the single mindset shift that changes everything for corporate professionals, whether you're planning your escape or staying right where you are. You're not an employee. You never were. You're the owner of a one-person business, and your employer is just your first and only client.

Same job. Same paycheck. Completely different relationship to it.

Then Brett walks you through the One Client Audit, the exact framework he uses with escapees inside the Collective. Six questions. Thirty points. By the end you'll know whether the client you're working for is worth keeping, worth renegotiating, or worth firing.

This episode is for the still-in-corporate crowd, the recently laid off, and anyone who's tired of living a completely reactionary work life.

👉 Run the audit yourself. Grab 3 free frameworks to take control of your work and your life: the One Client Audit, the What Do You Really Want Worksheet, and the 5Fs Scorecard. → https://stan.store/thecorporateescapee

What you'll learn:

🎯 Why "nobody is coming to save you" is the best news you'll get this year 🎯 The mindset shift that takes you from reactionary to in charge (whether you stay in corporate or leave) 🎯 The six-question One Client Audit you can run on your employer tonight 🎯 The three owner's moves: renew, renegotiate, or fire 🎯 How the hidden cost of your job is bigger than your paycheck 🎯 Why running your corporate career like a business is the prep work for running an actual one 🎯 Plus: grab the One Client Audit, the 5Fs Scorecard, and the What Do You Really Want Worksheet free in the show notes

Quotable moments:

"No one is coming to save you. Not your company, not HR, not your manager, not the economy, not the next reorg."

"You are not an employee. You never were. You're the owner of a one-person business. Your employer is your first and only client."

"Same job. Same paycheck. Completely different relationship to it."

"Trying to keep a corporate career is going to be harder than starting your own business, especially if you start running your career in corporate like it is a business."

"You've already done everything you'd have to do if you went solo. Landing a corporate job is harder than landing a client."

Resources mentioned:

📋 Download 3 free frameworks (One Client Audit, What Do You Really Want Worksheet, 5Fs Scorecard): https://stan.store/thecorporateescapee 📬 Join 10,000+ readers of The Escapee Insider newsletter: escapeeinsider.beehiiv.com 🐬 The Escapee Collective (first month $1): theescapeecollective.com

Connect with Brett:

🎙️ Subscribe to The Corporate Escapee Podcast wherever you listen 📬 Newsletter: escapeeinsider.beehiiv.com 🔗

Six-plus years ago, when corporate quit on Brett, the goal was simple: make more money than corporate was paying him. That was it. Money, money, money.

It took two years to realize money was never the real prize. What he was actually chasing was control. Freedom. The ability to design a life where work fit into it, instead of 25 years of life fitting around the job.

Most of us spend a lot of time thinking about the escape — the transition, the layoff, the leap. Not enough time thinking about what life actually looks like on the other side. And here's the thing: you can't build a future you can't picture. Most of us have never been given permission to picture one.

That's what this episode is for.

What You'll Get In This Episode

A definition of a Life First Future, the contrast with the corporate-first life most of us have been living, and a four-step exercise to help you actually see your own. Grab a notebook before you press play — you're going to use it.

Key Concepts

The shift Brett didn't expect. It wasn't more money that changed everything after corporate. It was realizing he was getting more done by noon working for himself than he used to get done in full days inside the system. Strip out the unnecessary meetings, the fire drills, the commute, the reorgs — and the time you've been giving away comes back.

Corporate-time vs. Life-time. Corporate trained us to think in fiscal years and 2-to-4-year promotion cycles. The Life First Future requires thinking in 5-, 15-, and 30-year horizons. That's not a small reframe. It's the entire game.

Why "energy" beats "purpose" or "passion." Most people get stuck looking for the One Thing that lights them up. Brett spent six years monetizing his corporate experience eight different ways before landing on The Corporate Escapee. The signal that kept him moving wasn't passion — it was energy. Each move gave him more energy than the last. That's the real compass.

You're not designing a fantasy. You're using 25 years of evidence. This isn't a 25-year-old's exercise. We have something better than time — we have data. We've lived enough to know what energizes us, what drains us, and what corporate actually delivers (and doesn't).

The 4-Step Ideal Life Framework

Step 1 — Map Four Milestones Today. 5 years. 15 years. 30 years. For each, answer four questions: Where am I living? Who am I with? What am I working on (if anything)? How do I feel each morning? This is a living document — Brett's been doing it for years and it still evolves.

Step 2 — Find Your North Star Look across the four milestones for what stays the same. The patterns are your non-negotiables. Don't get hung up on finding your "passion" — chase the things that give you energy, and follow them as they evolve.

Step 3 — Connect Today to Tomorrow Every decision becomes a filter: does this move me toward my North Star or away from it? (Brett goes deeper on this in Episode 2.)

Step 4 — Write Your Vision Statement One guiding sentence. Revisit quarterly. Brett does this with his wife as a quarterly business review — a session that fundamentally changed how he runs the post-corporate life.

Brett's Real-World Life First Schedule (mentioned in the episode):

• 6–8 AM: Deep work, client work, strategy

• 8 AM: Gym (six days a week, non-negotiable, no meetings before 10)

• Friday afternoons: Golf

• Granddaughter time, family dinners, vacations on his schedule

• Result: more done by noon than he used to do in full corporate days

The Bottom Line

A Life First Future is one where your time, energy, and decisions are organized around the life you actually want — and your work fits into that, not the other way around. Define it first. Build toward it second. Episode 2 covers the how.

If this episode hit, the best way to help is to subscribe wherever you listen — Apple, Spotify, Overcast, Pocket Casts — and share it with one who needs to hear it.

Get Busy Living

You already have permission.

Permission to want something different. Permission to design a life where work fits into it instead of the other way around. Permission to stop waiting for corporate to decide your future and start building one on your own terms.

Nobody is coming to give it to you. So Brett does.

What You'll Learn

1️⃣ Why corporate conditions you to ask for permission for everything — and how that conditioning follows you home long after you leave

2️⃣ The hidden cost of corporate that goes way beyond the paycheck — time, energy, identity, and control

3️⃣ What living life on your own terms actually looks like in practice — the real daily routine not the highlight reel

4️⃣ Why the chaos of going solo is temporary and what comes after it

5️⃣ How Brett went from scheduling every 30 minutes — which was worse than corporate — to finding his actual rhythm

6️⃣ Why the gym at 8am every morning is possible when you own your calendar and impossible when corporate owns it

7️⃣ Why you don't have to wait for corporate to kick you out to start designing something different

8️⃣ The only thing actually standing between you and the life you want

Key Quotes

"Life is too damn short to follow somebody else's plan." — Brett Trainor

"I'd rather be homeless than go back to corporate." — Laine, Escapee Collective Member

"The only thing stopping you is you. And it doesn't have to be a perfect plan. Done is better than perfect." — Brett Trainor

"Give yourself permission to want something more. Because nobody else is going to give it to you." — Brett Trainor

Your Permission Slip

You have permission to want more than what you have right now.

You have permission to design a life where work supports you instead of consuming you.

You have permission to find out what's actually possible when you stop waiting for corporate to decide your future.

Connect With Brett

Ready to stop waiting and start building? The Escapee Collective is the community for ex-corporates taking control of their future and getting busy living.

The backdrop is an AI world that most people are reading completely wrong. AI didn't shrink the opportunity for skilled humans — it exploded it. Because now there's an entire population of people who are aware of their problems, have access to the information, and will still pay someone else to just handle it.

WHAT YOU'LL LEARN

✅ Why AI makes YOUR corporate skills more valuable, not less

✅ The "skill flip" model — how to charge for what you already know

✅ What UGC is, why GenX is uniquely positioned for it, and how to start

✅ How to turn what you know into paying clients without building a course empire

✅ Why your first dollar outside corporate changes everything

THE 3 PATHS

01 — The skill flip

Tomi Mikula spent 10 years on the dealer side of car sales. He now runs Delivrd — charging consumers $1,000 flat to negotiate car deals on their behalf. 300 customers a month. $300K in monthly revenue. His customers could use AI to do what he does. They pay him anyway. Because the problem was never information — it was execution, accountability, and not wanting to deal with it. That's the model. Find a high-stress transaction, one side has information the other side doesn't, and charge to be the expert in the room. HR disputes, salary negotiation, medical billing, contractor bids — it's everywhere.

02 — UGC (User Generated Content)

Brands are paying real people — not influencers — to record short videos about products they actually use. No following required. Platforms like Billo and JoinBrands connect brands with creators, paying $150–$500 per video. GenX is ideal for this: authentic, credible, and speaks to a demographic most brands can't reach. Brett just signed two deals in one week for just under $1,000 combined. You don't need an audience. You need a phone, a face, and something real to say.

03 — Teaching what you know

Not a course empire — just solving one specific problem for one specific person who's standing exactly where you were. The AI translation angle is huge right now: small business owners know they're falling behind and will pay someone who speaks both business AND AI to help them catch up. And you don't need to be far ahead — you just need to be far enough ahead. The people in Brett's community who are winning fastest are teaching hyper-specific things to people one or two steps behind them on the journey.

MEMORABLE QUOTE

"The problem was never information. It's about execution, accountability, and people just not wanting to deal with it. Your 20 to 30 years of corporate experience puts you right in the middle of that opportunity."

This one is for anyone still in corporate feeling the slow fade of work that used to light them up.

What You'll Learn

🎯 How Kristen recognized the burnout before it broke her — and what finally pushed her to act

🎯 Why she pursued a coaching certification during the pandemic and what it unlocked

🎯 How every single client she has landed came through referrals — no ads, no cold outreach

🎯 The identity shift that happens when you leave a career that defined you for 25 years

🎯 Why creativity isn't just art — and how corporate professionals are more creative than they think

🎯 What it actually feels like in the first six weeks — the excitement, the fear, and the glass case of emotions

🎯 Why you don't have to do this alone — and why the right community changes everything

🎯 How Kristen is already thinking big with her first virtual retreat just months into her solo journey

Key Quotes

"If your gut is telling you something is off — it is off. Don't sit in it alone." — Kristen Hamborg

"We all have this fear of not enoughness. But you have to get there and trust that you can do it." — Kristen Hamborg

"Comfortable isn't always good. Getting outside your comfort zone is where the growth happens." — Kristen Hamborg

About Kristen Hamborg

Kristen Hamborg is a coach and feng shui practitioner helping women navigate major life and career transitions. After 25 years in corporate interior design she made the leap to build something of her own — six weeks in and already building toward her first virtual retreat.

LinkedIn: https://www.linkedin.com/in/kristenhamborg/

📧 kristen@studioofyou.com

Connect With Brett

If Kristen's story resonated and you're ready to stop watching from the sidelines — The Escapee Collective is the community built for corporate professionals who are done waiting and ready to build something of their own.

👉 Join us at theescapeecollective.com

Get Busy Living.

She also breaks down human design — what it is, why it works, and how she uses it to help entrepreneurs build businesses that are aligned with how they naturally operate. If you've ever felt like you're forcing something that should feel easier, this episode is for you.

What You'll Learn

🎯 Why Danielle tried to escape corporate for six years before it finally clicked

🎯 The exact moment she realized she was sitting on a business nobody told her to build

🎯 How she landed her first clients using a local networking group — no social media, no ads, no cold outreach

🎯 Why overthinking your offer is the #1 thing keeping corporate escapees stuck

🎯 What human design actually is and why it's not as woo as it sounds

🎯 How she built her business during Tuesday nights at Panera while her husband handled bedtime

🎯 Why confidence comes from doing — not from waiting until you feel ready

🎯 The push that finally got her to put in her notice — and why timing matters less than decision

Key Quotes

"I trusted so deeply that I was going to be caught. And I was." — Danielle Burken

"Business gets to be easy and fun. We just weren't taught that in corporate." — Danielle Burken

"Anybody exiting corporate has the skills to do it. They're overqualified. They just need to go have the conversation." — Brett Trainor

About Danielle Burken

Danielle Burken is a human design-based business coach and marketing strategist who helps solopreneurs build sustainable businesses in alignment with how they're naturally wired to operate. She escaped corporate in September 2023 and built a six-figure business in her first year.

🌐 Website: https://www.danielleburken.com/ 

📱 Instagram: https://www.instagram.com/danielleburken_/ 

Connect With Brett

Ready to stop watching from the sidelines and make your move? The Escapee Collective is the community built for corporate professionals who are done with corporate and ready to build something of their own.

👉 Join the conversation at theescapeecollective.com

He also covers the single biggest opportunity most escapees are missing right now — helping small and midsize businesses actually leverage AI. Not programming. Not building agents. Bringing the business judgment that 20+ years of corporate experience gives you and marrying it with the right tools. That’s the superpower. And right now, the market is wide open.

What You’ll Learn

• How Brett uses AI daily — content editing, research, strategy, operations and more

• Why AI is a content editor not a content creator — and why that distinction matters

• The SMB opportunity — 88% of small business owners know they need AI, only 14% are doing something about it

• Why the real value is pairing business judgment with AI — not programming

• The EAD framework — Eliminate, Automate, Delegate

• Brett’s current AI stack and exactly what each tool is used for

• Why he switched from ChatGPT to Claude — and what that decision taught him about auditing your tools

Key Timestamps

• 00:00 — Intro: Corporate is using AI against you. Here’s how to flip it.

• 01:00 — How Brett uses AI in his own business every day

• 02:00 — AI as content editor not content creator — keeping your voice

• 03:30 — Podcast production: from a full day to under an hour

• 05:00 — AI as strategy and thought partner

• 07:00 — The SMB opportunity — the 74% gap nobody is filling

• 09:00 — Flex staffing + AI — why small businesses don’t need full-time hires

• 11:00 — The EAD framework: Eliminate, Automate, Delegate

• 14:00 — Brett’s AI stack: Claude, Perplexity, Gemini, Canva, Riverside

• 16:30 — Close: The one-person army is here. Are you using it?

Brett’s AI Stack

• Claude — Primary thinking partner, content editor, strategy, writing, business frameworks

• Perplexity — Deep research, stats validation, sourced intel

• Gemini — Currently testing; Google ecosystem integration

• Riverside.fm — Podcast recording, editing, transcription, show notes

• Canva — AI-assisted graphics and visuals

• Durable — AI website builder (used for Small Business Hotline landing page)

Enjoyed This Episode?

If you’re using AI in an interesting way as a solopreneur or escapee Brett would love to hear from you — and potentially have you on the podcast. Drop him a note at BT@BrettTrainor.com.

Please share this episode with someone who needs to hear it — and subscribe on your favorite podcast platform. The old school way still works.

Most corporate escapees think they only have two options: find another job or figure out how to start a business from scratch. But there are actually four legitimate paths to replacing your corporate income — and one of them is seriously underrated.

In this solo episode, Brett breaks down all four paths and then goes deep on the one he doesn't talk about nearly enough: franchising.

If you've been thinking about leaving corporate but the blank page feels too risky, this episode is for you.

The 4 Paths:

🔹 Path 1 — Go Solo: Consulting, fractional, advisory, coaching, content. Monetize what you already know. Lowest barrier to entry, no investment required, and you can start while still in corporate. Brett's lane — and the focus of most of this podcast.

🔹 Path 2 — Start a Business: Build something from scratch. A passion, an idea, an agency. Full ownership but requires capital, time, and infrastructure. Often the natural evolution of going solo.

🔹 Path 3 — Buy a Business: Acquire an existing operation with revenue already in place. Faster path to cash flow but requires serious due diligence, capital, and comfort with complexity.

🔹 Path 4 — Buy a Franchise: Get into a proven system with a built-in playbook, training, support, and brand. A business in a box — and the focus of today's episode.

Why Franchising Makes Sense for Corporate Escapees:

Most people picture Subway or McDonald's. That's not the conversation. There are thousands of franchise concepts across senior care, home services, B2B services, fitness, wellness, and more — and many of them map directly to the skills you built in corporate.

What you're actually buying is a proven playbook: operating systems, customer acquisition, marketing support, training, and a network of franchisees who've already solved the problems you'll face.

Brett covers:

1. Why franchising is a business model, not an industry

2. The real pros: faster path to revenue, built-in support, proven model, equity building, franchisee community

3. The real cons: upfront investment, royalty fees, operating within someone else's system

4. Why your corporate skills — P&L, leadership, process thinking, client relationships — transfer directly

5. The ownership reframe: a job pays you, it doesn't build an asset

6. How platforms like Franzy and coaches like Entrepreneurial Source can help you research and find the right fit

7. Key questions to ask yourself before going down this path

Connect with Brett & The Corporate Escapee:

🌐 TheEscapeeCollective.com

If this episode opened your eyes to a path you hadn't seriously considered — share it with someone still sitting in a corporate job wondering what their options are. That's exactly who this is for.

And if you've made it this far — please subscribe. It helps more escapees find the show.

Live Life First. 🐬✌️

Brett sits down with Steve Jaffe, marketing veteran and author of The Layoff Journey: From Dismissal to Discovery, to talk about what most career books completely skip: the emotional and psychological toll of losing a job — and why processing that first is the key to what comes next.

Steve was laid off four times over a 30-year career. His first layoff took him years to recover from. His last one in 2023? Water off a duck's back. The difference? He finally understood what he was actually experiencing: grief.

This one is for anyone who's been laid off, is worried about being laid off, or is watching colleagues get cut and wondering when it's their turn.

In this episode:

1. Why January 2026 had the highest single-month layoffs since 2009 — and why the job market isn't bouncing back

2. How layoffs became a business strategy instead of a last resort (and what that means for your career security)

3. The stages of grief that apply to job loss — and why skipping them is costing people months of their job search

4. Why the "myth of meritocracy" is one of the most dangerous things to believe in corporate

5. The identity crisis that hits when your job title is your identity — and how to separate the two

6. What Gen Z is getting right about corporate that older generations sacrificed

7. Steve's pivot from laid-off marketing exec to published author — without a Plan B in place first

8. Why having a side hustle isn't just a trend — it's now a survival strategy

About Steve Jaffe

Steve spent 30 years in marketing and advertising — from West Coast ad agencies to in-house brand roles, including work on the iconic What Happens in Vegas Stays in Vegas campaign. After being laid off four times, he channeled those 10,000 hours of experience into his book, The Layoff Journey: From Dismissal to Discovery — a practical, grief-informed guide to navigating job loss without losing yourself in the process.

Resources mentioned:

1. 📖 The Layoff Journey: From Dismissal to Discovery — available on Amazon and wherever books are sold

2. 🌐 Website & free chapter download: https://thestevejaffe.com/

3. 💼 Connect on LinkedIn: Steve Jaffe: https://www.linkedin.com/in/jaffesteve/ 

Connect with Brett & The Corporate Escapee:

1. 🌐 TheEscapeeCollective.com

If this episode resonated, share it with someone who's currently in the middle of a layoff — or someone who should probably start building their Plan B now.

I've blocked myself at every stage—consulting, fractional leadership, and now with The Escapee Collective. Not intentionally, but by doing what corporate trained me to do: overanalyze, overstructure, and wait for perfection before taking action.

In this episode, I walk you through the three times I made the same mistake—and what I'm doing differently now.

If you're overthinking, over-structuring, or waiting for the "perfect" website, pitch deck, or system before you start—this one's for you.

In This Episode:

1. The consulting mistake: Building the perfect website, pitch deck, and pricing before having a single conversation with a client (and why it led to zero wins)

2. The fractional repeat: Doing the EXACT same thing again—new methodology, new deck, same lack of results

3. The Escapee Collective lesson: How TikTok took off with zero plan, then how I complicated it again with masterminds, classes, and modules—and why I had to simplify

4. Why corporate trains us backwards: Plan first, act second works in corporate—but solo requires the opposite

5. What actually works: Conversations, experimentation, messy wins FIRST—then structure

6. The 79% reality: Why most burned-out corporate workers won't take action (and how to be in the 35% who do)

7. How to catch yourself: Recognizing when you're building systems before you have proof

Key Takeaway:

Action beats planning. Momentum beats perfection. Get early wins first—THEN build the structure around what's working.

If you’re still in corporate, recently laid off, or already freelancing and want more stability, this is the clearest “how it works” primer you’ll hear.

What you’ll learn

• The “W2 → 1099 bridge” and why more people are getting pushed across it

• Why fractional is mostly a referral-based business (and what to do with that)

• The mindset shift: conversations, not campaigns

• John’s simple relationship model: the “10-person circle” (fractionals, independents, super-connectors)

• What companies actually care about (hint: pain, not the definition of fractional)

• Typical pricing and why fractional often lands in the $8K–$10K/month retainer range

• Why fractional is proactive leadership, not “wait to be told what to do”

• The “project first” entry strategy — and why it usually turns into ongoing leadership

• How to reconnect with old contacts without being weird or salesy

• The core principle: get involved with other people’s success

Notable moments / lines you’ll remember

• “You’ll work for the people you get referred to.”

• “Referrals come from conversations, not campaigns.”

• “Fractional is leadership — solve it and keep it solved.”

• “Most barriers are fear and assumptions… it’s hard work, but it’s not complicated.”

Resources mentioned

• The Go-Giver (Bob Burg)

• The NCG Factor (Larry Kaufman — Network, Connect, Give)

What keeps 79% of corporate professionals stuck isn't lack of skills or opportunity—it's something deeper. In this solo episode, Brett shares the story of landing his first client, making good money, and then doing something that still makes him cringe: convincing that company to hire him full-time. Nobody forced him back. He walked himself in.

This mistake cost him 18 months and taught him the hard truth: leaving corporate is tactical, but breaking your dependency on it is psychological. Brett breaks down what corporate dependency actually is (hint: it's not just the paycheck), why going solo alone reinforces that dependency, and the two critical milestones that finally sever the tie.

If you're still in corporate and thinking about making a move—or you've already left but still feel the pull—this episode will help you understand what you're really up against and how to break free for good.

What You'll Learn:

1. Why corporate dependency is psychological, not financial

2. The three things you're actually dependent on (and it's not what you think)

3. Why isolation amplifies doubt and keeps you stuck

4. The two milestones that break corporate reliance

5. How to avoid the mistake that sent Brett back 18 months

6. Why community matters more than tactics when going solo

Key Quotes:

1. "I hadn't really thought about why I did it, but it was really my dependence and my reliance on corporate."

2. "What I really broke it down into three areas: I wanted control of my future, control of my money, and control of my time."

3. "When you go alone, you have nothing else except yourself to talk you in or out of what you're doing."

4. "Once you get to the point where you're confident that you can bring in that next deal, you know you're never going back."

5. "I wasn't escaping corporate per se. I didn't have to stay there. I had options."

Resources Mentioned:

The Escapee Collective: Join Brett's community

Subscribe & Connect: If this episode resonated with you, please subscribe to The Corporate Escapee Podcast on your favorite platform. New episodes drop multiple times per week featuring guest interviews and solo deep-dives like this one.

Looking to break your corporate dependency? Visit TheEscapeeCollective.com to connect with others on the same journey.

In this solo episode, Brett breaks down three trends shaping the Escapee economy in 2026:

1. a corporate metric that’s quietly driving layoffs,

2. the rapid expansion of revenue streams outside corporate,

3. and why small businesses are moving away from full-time hires in favor of fractional and specialist talent.

If you’re still in corporate, this episode helps you see what’s coming.

If you’ve already escaped, it explains why demand for your experience is only growing.

This episode is for you if:

1. You’re questioning whether corporate is still a safe long-term bet

2. You want practical ways to monetize your experience outside a job

3. You’re curious how small businesses are really hiring and growing now

The 3 trends covered in this episode

Trend #1: The metric driving modern layoffs — Revenue Per Employee (RPE)

Why boards and executives are fixated on RPE, how it incentivizes headcount reduction, and why even “healthy” companies continue cutting roles.

Trend #2: The explosion of revenue streams for escapees

Fractional leadership, consulting, advisory, UGC, content creation, mentoring, and more—why monetizing what you already know is the fastest, lowest-friction path to income.

Trend #3: The small business go-to-market model is changing

Why businesses are ditching traditional silos, hiring specialists instead of full-time staff, and how this shift creates long-term opportunity for experienced operators.

Key takeaways

• Corporate risk is structural, not cyclical

• Escapees have more income options than they think

• Small businesses want outcomes, not headcount

• Your experience is often more valuable outside corporate than inside it

If this episode helped you rethink corporate risk or life after it, connect with Brett on LinkedIn or email him at bt@bretttrainor.com. And if there’s a topic you want covered in a future solo episode, let him know.

This is a practical conversation about network-first business development, creating momentum without feeling “salesy,” and why the long game matters more than the perfect plan.

What you’ll learn

• How Ashley landed her first fractional roles through her existing network

• Why “pick your brain” beats cold outreach for most escapees

• The content → connection flywheel: using LinkedIn engagement to reopen relationships

• What fractional work can feel like behind the scenes (and why it can get lonely)

• How Ashley uses frameworks + a single grounding slide to lead discovery conversations

• Why you must keep “breadcrumbing” even when client work gets busy

• The reality of income volatility — and how to reduce the “oh crap” moments

• Portfolio career thinking: experimenting with speaking, books, and new revenue streams

• A fun (and honest) AI/TikTok viral experiment — and what it taught her about unit economics

• The mindset truth: escaping requires hustle — but it’s a better “hard” than corporate

Key quotes

• “You’re in here for the long game.”

• “People are sick of being sold to on LinkedIn.”

• “Always be top of mind… keep breadcrumbing.”

• “Both paths are hard. Choose which hard you want.”

Resources & mentions

• Connect with Ashley on LinkedIn: https://www.linkedin.com/in/ashleyevenson/ 

• Ashley’s site: AE Marketing Collective: aemarketingcollective.com

• AI slide tool mentioned: Gamma (export to Google Slides / PowerPoint)

If this episode hit home…

If you’re still in corporate and thinking about an exit strategy:

• Start with one conversation this week.

• Don’t pitch. Ask for perspective.

• Keep one weekly “breadcrumb” habit so you don’t disappear when you get busy.

About the guest

Ashley is a fractional marketing leader with experience across agency, brand, and consul

In this episode, Brett sits down with Catherine Jelinek, founder of The Skinny Platform, to talk about the shift from being “defined by your role” to being known for your thinking, your story, and the outcomes you create.

Catherine shares why so many high-performing corporate pros struggle in the “formless” world outside corporate, how to create structure without recreating corporate, and why the fastest way to clarify your thought leadership is often talking it out—not trying to write it alone. They also get into “skinny books” (short, high-impact nonfiction) and how to use AI and conversation-based drafts to accelerate publishing and content creation.

What You’ll Learn

• Why corporate identity feels safe—even when corporate is miserable

• How to replace “job title identity” with outcome-based positioning

• Catherine’s framework for navigating change: Forming → Storming → Norming → Performing

• How Brett created structure outside corporate (without turning life into a calendar prison)

• Why most people can’t “see” their own differentiators—and how a mirror helps

• Why conversation + transcripts can be the fastest path to content (and even a book)

• The “skinny book” approach: short, readable, practical nonfiction that people actually finish

• How to use AI to generate multiple story arcs and content angles—without losing your voice

Key Takeaways

• You don’t need to reinvent yourself. You need to reframe yourself.

• Progress outside corporate isn’t linear—so you need your own way to measure wins.

• If you want thought leadership, stop trying to “perfect-write” it. Talk it out first.

• Your story isn’t just for a book. It can power your LinkedIn, website, offers, and messaging.

About Catherine Jelinek

Catherine is the founder of The Skinny Platform, an alternative to ghostwriting for entrepreneurs and thought leaders. The Skinny Platform helps people clarify their story, shape it into a compelling narrative, and turn it into a short, high-impact book—faster than the traditional publishing process.

Connect with Catherine

• https://www.linkedin.com/in/cjelinek/

• Email: catherine@theskinnyplatform.com

• Websites: theskinnyplatform.com

I recently had the chance to join John Arms on his podcast: Fractional Unfiltered Link: https://open.spotify.com/episode/0z9pQOOMZEVI4T2NvoOiqP?si=uJoycF4LRGyZQNB4MofrtQ

John was kind enough to allow me to share this with my audience.

Corporate has done a number on people. A bad one. For 30 minutes we bitch about what is and was, and then we spend 30 minutes on how to thrive in the post corporate world.

This episode also includes real-time audience coaching around “job hugging,” starting from zero, and how to simplify your entry point so you can land your first client.

What you’ll hear in this episode

1. Why corporate feels colder now (profits over people, layoffs as strategy)

2. The “solo employee” mindset: treat your employer like your first customer

3. Why job searches after 45 can feel like PTSD — and how to reframe it

4. How Brett monetized his corporate experience in 10 different ways

5. Why chasing “big deals” first can slow you down (and what to do instead)

6. The good / better / best ladder to get in the door with business owners

7. Why community and relationships beat lone-wolf execution

8. The difference between being capable and being confident (and how corporate crushes confidence)

9. The simplest success ingredients: take action, build relationships, stay curious

10. Live coaching: why “starting from zero” is hard — and how to find your “entry problem” so you can get traction

Key frameworks + concepts mentioned

1. Corporate is a transaction (not a family): loyalty is gone, act accordingly

2. Start before you hit the breaking point: build an exit strategy while you still have income

3. Small wins stack: don’t wait for the home run

4. The 3 revenue levers every business cares about:

5. Problem-solving > selling: discovery conversations look a lot like job interviews

6. “Done is better than perfect”: unlearn corporate perfectionism

7. Community as leverage: don’t do this alone

8. Job hugging: holding on until you’re forced out — and why you still need a plan

Memorable lines / moments

1. “Layoffs are a business strategy now.”

2. “You are your own company — even if you’re still employed.”

3. “It’s not a tightrope between skyscrapers. If you misstep, you’re six inches off the ground.”

Call to action

If corporate feels unstable — don’t wait for it to get personal. Start building momentum now:

1. Have one conversation this week

2. Identify one “must-solve” problem you can help with

3. Get your first small win and stack it into the next one

They’re not.

In this solo episode, Brett breaks down a pattern he’s seen across hundreds—if not thousands—of conversations with corporate escapees: success outside corporate has far less to do with talent and far more to do with action.

This episode is for anyone still in corporate, recently laid off, or quietly wondering if there’s another path—but feeling stuck, underqualified, or unsure where to start.

What You’ll Learn in This Episode

• Why the most talented corporate professionals often struggle after leaving

• The real traits shared by people who successfully escape—and stay out

• Why overthinking your offer is one of the biggest mistakes escapees make

• How job interviews and client conversations are essentially the same thing

• Why “sales” after corporate is really just problem-solving

• How small wins (not big plans) create momentum

• Why redefining success becomes inevitable once you regain control of your time

• How to safely test a solo path while still in corporate—or during a job search

Key Takeaways

• You don’t need more experience to get started—you need movement

• Confidence comes after action, not before

• Business owners care about outcomes, not job titles

• Your network is your greatest advantage if you’re willing to use it

• The biggest risk isn’t trying—it’s never testing what’s possible

If You’re Still in Corporate (or Recently Laid Off)

You’re not behind.

You’re not underqualified.

And you already have skills people will pay for.

The fastest way forward isn’t a perfect plan—it’s one conversation.

Join the Escapee Collective

If you’re tired of figuring this out alone, the Escapee Collective is a community for corporate castaways and escapees at every stage—still in corporate, newly out, or building momentum.

Peer groups. Live sessions. Real conversations. Real progress.

You can find the link in the show notes or visit TheEscapeeCollective.com to learn more.

This is a tactical episode about what actually works when you’re leaving corporate: why you should “throw spaghetti at the wall” early, how to stop doing random coffee chats, and how to use relationship marketing and audience borrowing to land clients faster — without turning into a sales robot.

What you’ll learn

• Why “sequence over strategy” matters more than the perfect plan

• The hidden risk of being too strict and narrow early on (and why it creates regret later)

• How Michelle built her business through relationship marketing, not content churn

• “Audience borrowing” as the fastest way to build trust and pipeline

• How to approach connector conversations vs. client conversations

• Why your early goal is simple: learn how to make money and stack wins

• A practical way to think about packaging: repeatable frameworks, flexible middle

Key moments / highlights

• Graduating into chaos: the day Lehman fell and what it changed

• Founder-for-hire: getting a salary while living the startup founder life

• Affordable internet in inner cities — and what customers actually did with it

• “Fractional CEO” before fractional was trendy

• The rule: don’t build with blinders on for too long

• The shift from “networking for jobs” to networking as a long-term business asset

• The line that matters: say something that people can’t “unsee” after the call

Michelle’s core concepts (worth stealing)

• Sequence over strategy: the order of moves beats the elegance of the plan

• Throw spaghetti first: test offers, clients, and problems before you commit

• Connection avatar: define who’s worth meeting so networking doesn’t waste your life

• Trust transfer: get introduced through people/places your audience already trusts

• Audience borrowing: build relationships with people who “own the room” your clients are in

Best quote energy

• “Learn all the rules so you can go break them.”

• “It’s more important the order you do things than how good you are at it.”

• “I’m totally unemployable.” (Escapee anthem)

Connect with Michelle

• Website: themichellewarner.com

• Podcast: Sequence Over Strategy (short, practical episodes; curated playlists on her site)

Connect with Brett / The Escapee ecosystem

• If corporate is broken and you’re looking at an exit strategy, this is your sign.

• Join the community: TheEscapeeCollective.com

Brett sits down with Alex Smereczniak, a former EY consultant who left corporate early, built a high-growth business in the laundry space, and later launched Franzy—a platform designed to make franchising easier to research and navigate.

This conversation covers the mindset shift that helps people stop overestimating the risk of leaving, plus why franchising can be an underrated “business with guardrails” path for escapees who want ownership without building from scratch.

What we cover

• Alex’s escape story: college entrepreneurship → EY → leaving after a year and change

• The moment that validated his decision: an EY partner’s biggest career regret

• Why fear is often self-created—and how to get past it

• A practical worst-case scenario exercise to reset your risk tolerance

• Why franchising is a business model, not an industry

• Franzy’s concept: “Zillow for buying and selling franchise businesses”

• How AI + coaching can narrow thousands of franchise options into a realistic short list

• Underrated franchise categories and trends (senior care, home services, turf, and more)

• The “corporate is one customer” reframe—and why ownership builds equity

Key timestamps (approx.)

• 00:00–03:30 – Alex’s corporate stint + why he left fast

• 03:30–08:30 – The EY exit interview story: “It wasn’t my ladder”

• 08:30–12:30 – Why making money outside corporate is more possible than people think

• 12:30–20:30 – The worst-case scenario exercise (the fear-killer)

• 20:30–28:30 – Alex’s journey building a scaled laundry business + why franchising clicked

• 28:30–33:30 – What franchising actually is (and what most people misunderstand)

• 33:30–40:30 – Franchise categories you probably haven’t considered

• 40:30–46:30 – Equity, control, and why “owning” beats “leasing” your career

Big takeaways

• Most people overestimate the risk of leaving corporate. The real risk is staying dependent on one employer.

• You don’t need a perfect plan. You need small wins and momentum—then you adjust.

• Franchising can be a fast path to ownership because you start with a proven playbook, support, and guardrails.

• Ownership builds equity. A job pays you, but it doesn’t typically create an asset you can sell.

Who this episode is for

• Corporate pros who want out but feel stuck because of risk, family, or finances

• Escapees who want a “business with guardrails” instead of starting from scratch

• Anyone curious about franchising beyond the usual fast-food stereotypes

Resources + links

• Franzy https://franzy.com/

• Alex on LinkedIn: https://www.linkedin.com/in/alex-smereczniak-40310329/

In this conversation, Tom breaks down his escape story, why “local + in-person” is making a comeback, and how Wingman’s franchise model flips the typical franchise script — where the franchisee focuses on relationships and sales while the central team handles fulfillment and delivery.

If you’re stuck in corporate and can’t see a path out, this episode gives you a practical look at what “building your own lane” can really look like — without pretending it’s easy.

Join the Escapee Collective: TheEscapeeCollective.com

What You’ll Learn

• Why Tom left corporate early (and what corporate policies taught him about ceilings)

• The side-hustle-to-business path: how one small project turned into real clients

• How to think about risk when leaving: your monthly “number” vs. replacing a salary

• Why entrepreneurship can swing from best day to worst day in 30 minutes — and how to handle it

• The “digital mayor” concept: becoming the trusted local hub in your town

• Why Tom believes physical locations + community presence still win in a digital world

• A modern franchise approach: franchisee sells + builds relationships, HQ team delivers

• Why customer service and trust are the real differentiators in crowded markets

Key Quotes

• “The problem’s now. Two weeks from now, it’s worse.”

• “As an entrepreneur, you can have the best and worst day within a half hour.”

• “I want you to be the digital mayor of your town.”

• “If you do what you love, the money follows.”

Mentioned in This Episode

• COBRA and how Tom thought about early-stage risk

• Networking groups, chambers, community events, and “planting seeds”

• Using a podcast as a lead generator (and why it worked)

Connect with Tom

• Email: Tom at wingmanplanning.com

• Website: WingmanPlanning.com

• Social: Instagram / Facebook / TikTok / LinkedIn (search “Wingman Planning”)

In this episode, Brett sits down with Pia Silva (No BS Mastery) to break down a simple model for building a highly profitable solo (or two-person) business — built around intensives, clear boundaries, and pricing for outcomes (not hours).

Pia shares how she and her husband went from $40K in debt to $500K in revenue by shifting from long, drawn-out projects to a focused, high-value intensive model. Then she explains her signature framework — the 50-25-25 Rule — and how to reverse-engineer your pricing based on the life you actually want.

If you’re a corporate escapee (or future one) trying to make real money without recreating the corporate grind… this is the blueprint.

What you’ll learn

• Why most “big ticket” projects are often the least profitable

• Pia’s 50-25-25 Rule for profit + freedom (and how to use it to price your offers)

• How to design offers so you make your monthly revenue in 50% of your client hours

• The two levers to grow profit without working more:

• Increase value (real + perceived)

• Decrease time (intensify delivery)

• A smarter version of “good / better / best” packaging (without selling deliverables)

• How to use a Lead Product (paid) instead of free proposals to build trust fast

• Why warm networks beat websites and content in the early stages

• How to build boundaries that prevent scope creep (without sounding rigid)

• The mindset shift escapees must make: sell outcomes, not time

Key frameworks + concepts mentioned

• The Intensives Model: Focused delivery in a compressed timeframe vs. dragging projects out for months

• 50-25-25 Rule: Make your total revenue in 50% (or less) of your client-working hours so you have time for life

• Lead Product Method: A paid diagnostic/strategy step that replaces proposals and tees up an easy upsell

• Boundaries via Process: Clear steps + expectations reduce pushback and scope creep

Resources from Pia

• Scale Solo Playbook: NoBSMastery.com/playbook

• Price to Freedom Calculator

Connect with Pia

• Instagram: @pialovesyourbiz

• LinkedIn: Pia Silva

In this solo episode, Brett breaks down the two core reasons most corporate escapees fail—and more importantly, how to avoid them.

Failure here doesn’t mean experimenting and choosing corporate again. It means wanting out, trying to go solo, and giving up before momentum ever takes hold.

If you’re thinking about leaving corporate—or you’ve already made the leap—this episode will help you understand what really trips people up and how to build a path that actually sticks.

Resources Mentioned

 The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective

What You’ll Learn in This Episode

• Why not getting an early win is the fastest way to lose confidence

• How long gaps without income create doubt, panic, and backtracking

• Why most escapees don’t lack skills—they lack momentum

• The hidden cost of isolation and loneliness when you go solo

• Why “doing it alone” dramatically increases emotional swings

• How peer support and feedback shorten the learning curve

• Why community works better when people are at similar stages

• The difference between education, theory, and applied learning

• What successful long-term escapees all have in common

Key Takeaway

Going solo doesn’t fail because you’re not smart enough or experienced enough.

It fails when:

• You don’t get a win early

• You try to figure everything out alone

Momentum and connection matter more than perfection.

Resources Mentioned

 The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective

You can also reach out directly to Brett on LinkedIn with questions about the community or your escape path.

In this episode, Brett sits down with Mark Hayward, former PwC and KPMG consultant turned podcast host and podcast guesting entrepreneur, to break down his escape from corporate—and how podcasting quietly became one of his most powerful tools.

Mark shares how he started a podcast while still in corporate, not to make money, but to build confidence, find his voice, and explore what life outside the corporate box could look like. That passion project eventually opened doors to consulting, coaching, real estate experimentation—and ultimately a business built around helping others grow through podcast guesting.

This is a real, honest conversation about experimentation, false starts, energy, and why podcasting works differently than most people expect.

What We Cover

• Leaving PwC and KPMG after a 14-year corporate career

• Why Mark started a podcast before leaving corporate

• The role experimentation plays in finding your escape path

• Why not every revenue stream is worth keeping

• Coaching vs. consulting vs. creative work (and the energy test)

• Podcast hosting vs. podcast guesting — and how each actually works

• Why guests often get more business than hosts

• How podcasting builds confidence, clarity, and opportunity

• Practical advice for corporate professionals who know they want out—but don’t know what’s next

Key Takeaway

You don’t need a perfect plan to escape corporate. You need momentum, experimentation, and a way to get into conversations that open doors. Podcasting can be one of those doors.

Connect with Mark

• Website: podcastintroduction.com

• Podcast: Business Growth Talks

• LinkedIn: https://www.linkedin.com/in/mark-hayward-163721a0/ 

Listen, subscribe, and share

If corporate feels off—but you can’t see the exit yet—this episode will help you think differently about your options.

In this episode, you’ll learn:

• Why the “side hustle first” approach builds confidence and reduces risk

• The simple sales story that unlocks referrals: Client → Problem → Outcome

• How to activate your network without sounding awkward or salesy

• Why “fractional” isn’t always the fastest path to revenue — and what is

• The real goal: stop trading time for money and start selling outcomes

• Sam’s 3-part productization path:

1. Niche down to best-fit clients

2. Solve painkiller problems (not vitamins)

3. Build a portfolio of offers, including productized work

• The two killers of the independent path: no early wins + isolation

• Why productizing your expertise helps both client work and job searches

Key quotes / soundbites:

• “The most pernicious trade independent builders make is trading time for money.”

• “Your sales story is three things: who you serve, their problem, and the outcome.”

• “Nobody is hiring a generalist right now. They want been-there-done-that experts.”

• “Trial and error at this stage of your career is expensive.”

Resources mentioned:

• Indie Collective: IndieCollective.co

If you know corporate is broken—but you’re not ready to quit—this episode is for you.

In this year-end solo episode, Brett walks through 7 practical steps to help you rethink your relationship with work, assess how happy you actually are, and explore whether there’s a path outside corporate—without making a risky leap.

This isn’t about quitting your job.

It’s about getting prepared, taking back control, and testing what’s possible using the experience you already have.

Whether you’re 25 or 65, this episode helps you stop being reactionary and start designing what comes next.

What You’ll Learn

1. Why most people stay stuck—even when they’re miserable

2. How to reframe yourself from “employee” to “business owner”

3. The 5-factor scorecard to measure your real happiness

4. Why you’re already a solopreneur with one bad client

5. How to inventory your skills without thinking in job titles

6. A simple way to calculate your real market value

7. How to design a future that integrates work into your life—not the other way around

The 7 Steps Covered in This Episode

1. Reframe Your Reality – You don’t need new skills or a new degree

2. Establish Your Happiness Baseline – Money isn’t the whole story

3. See Yourself as a Solopreneur – You already have one client (corporate)

4. Define What You Really Want and Need – Financially, personally, realistically

5. Take Inventory of Your Skills and Energy – Focus on problems you like solving

6. Calculate Your Value – A simple formula to find your hourly baseline

7. Design Your Ideal Future – Work backward from the life you want

Key Takeaways

1. It’s easier to find your first customer than your next job

2. Small wins build confidence faster than big, risky bets

3. You don’t need permission to start testing a new path

4. Done is better than perfect

5. Control comes from action, not planning

Final Thought

You don’t have to leave corporate to take back control.

But if you don’t start preparing, another year will pass—and you’ll be having the same conversation again.

If you’re still in corporate… good luck.

And if you’re ready to take the first step—this is it.

My guest Diane Kennedy (CPA) breaks down what most new escapees get wrong about taxes and business structure — and why the real first question isn’t “LLC or S-Corp?”

It’s: Are you building a business… or replacing a paycheck?

From there, we get into the most common setup for solopreneurs (LLC + S-Corp election), how to think about deductions without getting cute, and why “keeping it small and keeping it all” is the solopreneur cheat code.

We also bring in Lisa Dini from Lettuce, who explains how they help solos run the S-Corp model without turning you into an accountant.

Heads up: This is educational, not legal/tax advice. Talk to your pro for your situation.

What you’ll learn

1. The real first question for escapees: build a business vs replace a paycheck

2. Why “LLC vs S-Corp” is usually the wrong framing (and what Diane recommends instead)

3. Why Diane believes you should set up an LLC early (asset protection + flexibility)

4. The 3 “buckets” of income for solopreneurs: Earned, Leveraged, & Passive (the holy grail)

5. A simple way to think about deductions: ordinary + necessary (and how to find write-offs you already have)

6. How S-Corps can help you keep more of what you earn (salary vs distributions, plus other benefits discussed)

7. Real-world Q&A on: partners, joint ventures, and multi-state setups, California “special rules” , Schedule C vs S-Corp timing, Solo 401(k) and related retirement ideas

Resources Mentioned:

Lettuce.co: https://hubs.ly/Q03Yz8KX0

Tax Calc: https://hubs.ly/Q03Yz8Rf0

Tax Prep: https://hubs.ly/Q03Yz8JY0

Guests

Diane Kennedy

CPA and long-time solopreneur. Diane helps business owners structure their business and income in smarter ways so they can keep more of what they earn and operate like a real business.

Lisa Dini (Lettuce)

Lettuce helps solopreneurs run an S-Corp model efficiently, without drowning in admin and accounting work.

Brett breaks down how to treat your “escape plan” like an insurance policy—not a dramatic leap off a cliff. You don’t have to quit your job tomorrow. But you do owe it to yourself to be prepared for the moment corporate quits on you… or you finally hit your breaking point.

Instead of trying to convince you to go all-in on a solo business, this episode walks you through how to build a plan you can keep in your back pocket—so you’re not starting from zero if things go sideways.

Download the FREE Starter Kit

Join the Collective

In this episode, you’ll learn:

• Why the gap is so big between people who know corporate is broken and those who actually take action

• How to think like a “prepper” (without going full doomsday): planning so you don’t have to plan in the middle of chaos

Step 1 – Define what you actually want

Step 2 – Get clear on your financial reality

Step 3 – Take inventory of your skills and energy

Step 4 – Shift from job title to problem-solving

Step 5 – Reframe your current employer as just one client

Also:

• A simple formula to value your time

• Annual salary × 1.25, then drop three zeros → a shockingly accurate baseline hourly rate

•. Why many escapees replace their corporate income in ~20–25 hours per week

• Why you don’t need 100 customers

• How 2–5 good clients can replace (or exceed) your corporate pay

• Why most of those opportunities will come from networking and referrals, not job boards

Who this episode is for

• You’re still in corporate, you know the system isn’t built for you, but you don’t see a clear path out

• You feel stuck between “I hate this” and “I don’t know what else I’d do”

• You’re curious about going solo, but the idea of just quitting and “figuring it out” feels reckless

• You want a practical, low-risk way to prepare now, so you’re not scrambling later

Or if you’ve ever felt invisible in corporate…

Or if you’re building a life outside of corporate and wondering why some conversations connect and others fall flat…

This episode will hit you hard.

Today, Brett welcomes back Jake Stahl — author of the brand-new book Own the Room and creator of the STRATA framework, a system for reading people, decoding signals, and communicating with true presence instead of performance.

Twelve years ago, Jake lost everything to opioid addiction — his marriage, his home, his reputation, and the identity he’d spent decades building. But his path back didn’t begin with a new job or a second chance.

It began with learning how to read people.

Jake realized that most communication has nothing to do with the words being spoken. It’s the signals beneath them — the micro-expressions, the posture shifts, the emotional triggers — that determine whether someone trusts you, connects with you, or shuts down entirely.

Today, Jake breaks down STRATA, the six-part framework you can use to own every room you enter:

• Signal: What you broadcast before you say a word

• Trigger: The moment resistance appears

• Reframe: How you shift someone’s lens without force

• Anchor: Making the insight stick

• Transfer: Turning your idea into their idea

• Action: Where the next step becomes inevitable

We talk about how STRATA applies to sales, relationships, leadership, marriage, friendships — and most importantly, the escapee journey. Because leaving corporate and building your own path requires one core skill:

👉 You must connect with people in a way that feels real.

This episode gives you the playbook.

Connect with Jake Stahl

• LinkedIn: https://www.linkedin.com/in/jakestahl/

• TikTok: @JakeTheMindMechanic

• Podcast: https://thejakestahl.com/podcast/ 

• Book: Own the Room: https://thejakestahl.com/books/

That’s where Claire Sullivan found herself.

On December 1st, 2023, corporate quit on her — and she took what most people would call the riskiest step possible:

She built a business… the same day.

• Filed an LLC

• Registered everything needed to operate

• Posted on LinkedIn that she was going out on her own

• Listened to what the market actually wanted

• And replaced her former salary by the end of the week

Is that typical? No.

Is it possible? Absolutely.

And more importantly — the steps she took are repeatable for anyone stuck in a corporate job that no longer works for them.

This is one of the most real and honest conversations we’ve had on what it actually looks like to escape corporate — emotionally, financially, mentally, and practically.

Who This Episode Is For

This one is for you if:

• Corporate has stopped making sense

• Every job application feels like it goes into a black hole

• You’re burned out but can’t “just quit”

• You want control over your time, income, and health

• You don’t think you have “enough” experience to go out on your own

• You just need one real example of someone who actually did it

Connect with Claire

Maven Course: How to Layoff-Proof Your Career by Becoming a Solopreneur: https://maven.com/clair-sullivan-associates/launch-your-solopreneur-business?promoCode=ESCAPE

LinkedIn: https://www.linkedin.com/in/dr-clair-sullivan/

Most solo businesses are focused on getting clients—but ignore the compliance risks that can quietly wreck everything.

Former tax attorney and CFO Michael Williams joins Brett to break down the ADA, privacy, and regulatory issues small businesses face—and how a $100K GDPR mistake pushed him to finally build Clym.io, an all-in-one website compliance platform.

Michael also shares the remarkable story of raising a seven-figure VC round… then paying it back to regain control and stay true to his vision.

In This Episode:

• The hidden ADA & privacy risks solopreneurs overlook

• Why most accessibility lawsuits hit small businesses

• How AI-powered scans fuel compliance lawsuits

• How Clym.io uses one snippet to manage 150+ regulations

• Why Michael left a cushy CFO role at 38

• The identity shift from employee → builder

• What it’s really like to take VC money—then give it back

• Why taking action beats waiting for the “right” time

Connect with Michael & Clym

Website: https://clym.io

More From Brett

Escapee Starter Kit, resources & links → https://linktr.ee/bretttrainor

We talk about leaving corporate, taking action, finding traction on TikTok, and the honest story behind building the Corporate Escapee movement. If you’re stuck, burned out, or thinking about going solo, this one will hit home.

In this episode, we cover:

• Why taking action is the #1 skill corporate trains out of you

• My path from 25 years in corporate → consulting → fractional → building 10+ income streams

• How TikTok unexpectedly became the platform that changed everything

• Why 80% of my 76K TikTok followers are over 40

• The moment one video brought in 300+ strategy call requests in 48 hours

• The three stages of an escapee: Curious, Motivated, and Liberated

• Why your path out of corporate isn’t a leap — it’s a shift

• The reality of layoffs, RTO mandates, and the “profits over people” era

• Why authenticity beats production quality every time

• The mindset shift corporate doesn’t prepare you for

Why this conversation matters

A lot of people want out of corporate, but they overthink the first step. This episode breaks down what actually works — and why you already have more than enough experience to start.

Connect With Catherine

Check out Catherine Jelinek’s podcast:

👉 Breaking Through the Noise

Available on Apple, Spotify, and YouTube. Follow and support her work — she’s having the conversations corporate workers need to hear.

Neil shares how a simple testimonial project for a startup turned into something much bigger—a repeatable, productized service that helps founders uncover the stories and insights hidden inside their customer relationships.

If you’re stuck in corporate and wondering what you would even sell, this episode will help you see the path: start with what you already know, listen for the real problem, and bet on yourself.

What You’ll Learn

• Neil’s escape path: agency burnout → COVID pivots → higher-ed → solo

• The “Root Thread” deep testimonial approach and why it delivers strategic customer insight

• How to productize what you already do without boxing yourself in

• Why referrals and local networks are enough for a one-person business

• How Neil priced his offer and why undercharging early is part of the process

• The 4 levers every offer should hit: save time, save money, make money, reduce risk

• Why betting on yourself beats betting on corporate stability

Key Takeaways

• Your corporate title doesn’t matter—your ability to solve problems does

• Productized services make selling and delivery easier

• Customer conversations reveal the real value you offer

• Solopreneurs don’t need 100 clients—you need a few right-fit ones

• You can always go back to corporate… but very few people want to once they leave

About Neil K. Carroll

Neil is the founder of vidwheel, helping startups and small businesses capture deep customer stories through Root Thread testimonial interviews and his hardware-enabled Mini Studio (VidKit 3).

He combines interviewing skill, remote production, and AI-assisted analysis to help companies extract messaging, proof, and product insight directly from their customers.

Connect with Neil:

LinkedIn: Neil K. Carroll

Website: vidwheel.com

Episode Summary

After nearly 30 years in corporate communications, Ed Patterson didn’t just leave corporate—he left the country. He and his partner planned their move to Portugal, secured residency, and designed a new life where work no longer sits at the center. We cover what it really takes to prepare (financial, legal, lifestyle), what he’d do sooner, how he reframed success to “quality of my day,” and practical advice for anyone considering a similar shift—whether you move abroad or simply want more control at home.

Chapter markers

• 00:00 Intro: Why Ed left corporate and the U.S.

• 00:45 Ed’s background: PR/Comms, crisis, agency + in-house

• 03:00 The Portugal plan: residency, D7 visa, timelines, consultants

• 05:35 How they prepared: roles, finances, finish lines, advisor sign-off

• 10:50 Healthcare and costs: private insurance, day-to-day expenses

• 14:40 Redefining happiness: “quality of my day,” health, sleep, energy

• 20:13 Advice to 30- and 40-somethings: plan for when you want to—and when you have to

• 26:14 Do an inventory: skills, network, gaps, use corporate to upskill

• 30:11 Action over waiting: fractional, contracts, bridge income

• 33:06 The “adventure years” mindset and inviting questions

• 35:23 Close

Key takeaways

• Plan with intent: set a finish line, pressure-test with a financial advisor, and define roles at home.

• Consider geo-arbitrage: lower costs can pull your finish line forward by years.

• Optimize your day: sleep, movement, and mental space beat title-chasing.

• Treat corporate like your one client: extract skills, network, and education while you’re there.

• Build optionality: fractional work and short contracts can bridge income during transitions.

• Do the inventory: skills, network, marketable experiences, and gaps to close before you jump.

• Prepare for both scenarios: when you choose to leave—and if corporate chooses for you.

• Health matters: design a life you can actually enjoy.

Guest

Ed Patterson:

• LinkedIn: https://www.linkedin.com/in/edpatterson1/

• Instagram: https://www.instagram.com/twoguysinportugal

Callout quotes

• “We hit our finish line sooner because our costs dropped by a third to a half.”

• “I sleep better, eat better, and feel more creative. That was impossible when work ran my day.”

• “Plan for your choice—and for the day you may not have one.”

Note from Brett:

This Greatest Hits episode is one of the most shared conversations we’ve ever had — and for good reason. If you’re trying to land your first clients or grow your solo business, Bob’s Go-Giver principles are a masterclass in creating value, building trust, and turning relationships into revenue.

I wanted to bring this one back for our thousands of new listeners. There is so much value to be learned from Bob and a core to solopreneur success.

Listen for three big takeaways:

👉 How to define value vs. price and articulate your worth.

👉 How to make referrals your #1 growth engine.

👉 Why receiving is just as important as giving.

What You’ll Learn:

• The difference between price and value — and why focusing on value creates loyal clients.

• The Law of Compensation: your income equals how many people you serve × how well you serve them.

• Why authenticity and consistency inspire trust.

• How to stay open to receiving so opportunities can flow back your way.

• Simple frameworks for building a referral flywheel that compounds over time.

Links:

• Solo Health Collective: https://hbgsolo.com/

• Tom Morrissey LinkedIn: https://www.linkedin.com/in/tommorrisseyhbg/

What You’ll Learn

• Who qualifies & how it works: EIN required, brief medical history, plan in your business’s name (self-insured structure for solos).

• How it’s different: Not ACA and not a sharing ministry; three high-deductible options ($2.5K / $5K / $10K) with 100% coverage after the deductible and no annual/lifetime max.

• Network & Rx: Open network with MultiPlan/PHCS PPO; pharmacy via Pharos Rx; prior auth for big procedures.

• Costs & fit: Age-rated pricing—often competitive vs. ACA when you compare total cost + design—but not for everyone (medical questionnaire matters).

• Service that doesn’t stink: Human, concierge-style support (aka you can talk to a person).

• The road ahead: Optional “Solo-Plus” wellness track (full lab panels 2x/year) to drive better health and better underwriting; watch items like portable benefits and association health plans that could expand options for independents.

Timestamps

00:00 Welcome & why healthcare keeps people stuck

02:00 What Solo Health Collective is (and isn’t)

04:00 Tom’s background (Cigna → self-insured solutions for small employers → solos)

07:30 Why underwrite the business of one (EIN)

10:30 The cost problem (everywhere) & what drives premiums

15:00 Getting a quote in minutes; three plan designs; preventive care at 100%

18:45 Networks (MultiPlan/PHCS), open access, prior auth for big bills

21:00 White-glove support & Trustpilot traction

22:45 Who it’s not for (questionnaire fails; ACA may be better)

24:30 Simplicity: deductible = out-of-pocket; families cap at 2x deductible

25:40 Future: biomarkers program, better health → better rates

30:30 Policy watch: portable benefits & association health plans

34:30 Final advice: know all your options; compare total cost & design

About Our Guest

Tom Morrissey is a benefits industry veteran (40+ years) and co-builder of Solo Health Collective, a national health plan purpose-built for self-employed business owners with no W-2 employees. Previously with Cigna serving mid-market and national accounts, Tom now focuses on accessible, concierge-level benefits for one-person companies.

Disclaimer

This episode is for educational purposes only and is not insurance, legal, or financial advice. Compare options (ACA, off-exchange, group, and Solo Health Collective) and choose what fits your situation.

In this episode, Brett sits down with Jenni Gritters, author of The Sustainable Solopreneur and coach to creatives, consultants, and coaches who want to build profitable, flexible, and fulfilling solo businesses.

Jenni shares her journey from The New York Times to building a six-figure business working just 25 hours a week. Together, Brett and Jenni unpack what sustainability really means—financially, mentally, and emotionally—for Gen Xers who’ve left corporate (or are ready to).

They dive into:

✅ The “three-to-four-year wall” most solopreneurs hit—and how to move past it

✅ Building multiple revenue streams without chaos

✅ Shifting from survival mode to intentional growth

✅ Why sharing your numbers builds trust (and confidence)

✅ How to measure success beyond money—using purpose, time, and happiness

If you’ve escaped corporate or are thinking about it, this conversation is your roadmap for building a business—and a life—you actually want to sustain.

Connect with Jenni Gritters

📘 The Sustainable Solopreneur 

🌐 jennigritters.com

💌 Newsletter: The Sustainable Solopreneur

Connect with Brett Trainor

🎧 Subscribe to The Corporate Escapee Podcast

📩 Download the FREE Escapee Starter Kit

In this episode, I’m joined by Michael Himmelfarb, one of the original corporate escapees, to talk about why the real opportunity with AI isn’t automation…it’s augmentation.

Michael shares how he rebuilt his consulting business by combining AI efficiency with human judgment, creativity, and experience — proving that the GenX advantage lies in knowing how to apply wisdom to new tools.

You’ll learn:

• How to blend AI with your experience to create faster, smarter offers

• Why augmentation beats automation for consultants, advisors, and fractionals

• How to sell outcomes, not titles — and why buyers care more about value than ever

• Why your corporate scars, empathy, and critical thinking are your new superpowers

If you’re a GenX pro still in corporate (or newly escaped), this conversation will show you how to use AI to amplify your expertise — not replace it.

Guest

Michael Himmelfarb — Pricing & product marketing strategist helping companies modernize pricing/packaging with AI-augmented consulting. Connect on LinkedIn and mention this episode for his 48-hour sprint details.

LinkedIn: https://www.linkedin.com/in/michaelhimmelfarb/

Resources mentioned

• Anthropic’s “automation vs. augmentation” idea (discussion)

• Shout-out: Naveen Aggarwal (technical enablement/automation support)

For GenX Escapees

• Grab the Escapee Starter Kit: https://stan.store/thecorporateescapee 

• Join Escapee Collective Plus: https://escapee-collective.circle.so/checkout/escapee-plus-subscriptions 

Chapters

• 00:00 Welcome back, OG Escapee + today’s focus

• 01:29 From fractional CMO to pricing & packaging specialization

• 03:53 The buyer shift: clarity, speed, and specific problems

• 04:22 The 20/80 idea: what humans do that AI can’t

• 07:40 Automation vs. augmentation (and why it matters)

• 10:33 Hybrid delivery: standardized outputs + human judgment

• 12:25 Human superpowers: creativity, prediction, empathy

• 14:09 Beyond pricing: applying the model across functions

• 15:45 Productized sprints → recurring revenue possibilities

• 17:23 Big-firm disruption and the GenX advantage

• 19:33 Learning curves, iteration, and avoiding “prompt pack” hype

• 26:13 Focus, trade-offs, and building a simple offer

• 30:28 Shout-outs & resources + workshop idea

• 31:30 Michael’s ask + how to connect

If this episode hit home

Share it with a fellow GenX pro, leave a quick review, and DM Brett if you want the link to the free Starter Kit PDF or details on Michael’s sprint.

In this solo “CliffsNotes” episode, Brett breaks down how to actually make money from your corporate experience — not theory, not startup fantasy — just 17 real ways GenXers are doing it (plus 2 bonus options if you’ve got some capital to invest).

Whether you’re still in corporate wondering if there’s a way out, or already on the outside trying to replace your income, this episode is the playbook. From fractional and advisory work to user-generated content, workshops, and buying a small business — Brett shares what’s working, what he’s tried himself, and what might fit your life right now.

You’ll hear:

• Why your experience is more valuable outside of corporate than inside

• 17 proven ways (and 2 bonus paths) to monetize what you already know

• How GenXers are replacing their corporate income in ~25 hours a week

• The difference between consulting, fractional, advisory, and coaching

• Why “monthly service packages” might be the fastest on-ramp for freedom

• Real examples from Brett’s own journey — what worked and what didn’t

• How to future-proof your income before corporate “quits” on you

This one’s packed with ideas you can start exploring right now — no fancy website, no new degree, and definitely no corporate BS.

Mentioned paths include:

Solo Consulting • Fractional Leadership • Interim Roles • Advisory • Coaching • Business Development & Affiliate Deals • Services / Subscriptions • Paid Communities • Sponsorships • Influencer & Content Partnerships • Workshops • Speaking • User-Generated Content (UGC) • E-Commerce • Tech-Enabled Services • Plus: Buying a Business & Franchises (the two “bonus” options)

If this hit home, follow the show so you don’t miss the next “CliffsNotes” drop.

👉 Want help figuring out your best path out of corporate?

Join the Escapee Collective for $20/month (locked for life if you join before December) and connect with other GenXers building freedom on their own terms.

🔗 Links in the notes:

• Download the free Escapee Starter Kit – https://stan.store/thecorporateescapee

• Join the Escapee Collective ($20/mo for life before Dec): https://escapee-collective.circle.so/checkout/escapee-plus-subscriptions 

• Connect with Brett on LinkedIn: https://www.linkedin.com/in/bretttrainor/

• Email: bt@bretttrainor.com

In this conversation, Brett and Paul explore how AI, automation, and virtual assistants can help GenX escapees scale their businesses without hiring full-time employees. Paul also explains how he’s helping medical professionals escape the bureaucracy of healthcare and build profitable, flexible practices in functional medicine.

They cover why every solo business owner eventually pays an “Ignorance Tax,” how to turn that into an automation advantage, and why building your digital backbone early—CRM, SMS, AI follow-ups—can save years of frustration. Paul also shares a powerful “found money” idea: adding an ADA accessibility widget to your site that qualifies you for a $5,000 federal tax credit every year.

What You’ll Learn:

• The Ignorance Tax: when to stop DIY-ing and pay for speed and expertise

• The tech stack every solo business needs to scale (CRM, SMS, email, AI)

• How to delegate effectively and build your first small remote team

• Lessons from doctors escaping into functional medicine and how that model applies to corporate escapees

• How to find “found money” opportunities like the ADA tax credit that deliver instant ROI

Key Moments:

00:00 – Welcome back and recap of Paul’s first appearance

02:00 – Why medical professionals are escaping corporate medicine

09:00 – The Ignorance Tax and when to hire help

10:30 – The best automation and CRM tools for solos

20:00 – ADA tax credit: how it works and why it matters

28:00 – How small, AI-enabled teams are outpacing big companies

35:00 – The mindset shift from worker bee to queen bee

39:00 – Continued learning, avoiding the comfort trap, and staying curious

41:00 – Where to connect with Paul and learn more

Resources Mentioned:

• Paul Durelli – Digital Kahuna: www.digitalkahuna.com

• CRM Tool – Go High Level

• Book – “Pro Voice” by JT O’Donnell

Connect with Paul:

Visit www.digitalkahuna.com for courses, automation services, and details on the ADA $5,000 tax credit offer.

We dig into choice vs. circumstance, how to reframe fear and uncertainty, and simple steps GenXers can take while still in corporate. No dogma required—just a better operating system for work and life.

You’ll learn

• What a “Life Quest” is and how to spot yours

• How to move from reaction and fear to sovereignty and action

• A 30–60 day Next-Chapter Script exercise to regain control

• Why love-over-fear is a leadership OS (not a sermon)

• First small steps for still-in-corporate escapees

Timestamps

00:00 – Why this convo is different

01:20 – Lisa’s corporate path → calling

05:40 – Awakening without the woo

10:40 – Choice vs. reaction in corporate (and life)

12:40 – Reframing uncertainty & fear

16:10 – What corporate gives you—and when it plateaus

20:25 – Purpose, practically: defining mission without dogma

26:50 – Starter steps if you’re stuck (clarity, script, small bets)

30:10 – Why Lisa’s book is free + how to use it

35:10 – Frameworks beat retreats (avoid meandering)

36:45 – Wrap + where to connect

Links & resources

• Free book: Life Quest: Your Role in Saving the World: https://lisapetrilli.com/

• Connect with Lisa: https://www.linkedin.com/in/lisapetrilli/

 About Lisa

Lisa Petrilli is the founder/CEO of Higher Conscious Leadership and a former corporate exec (Medline, Baxter). She helps leaders move from mind/body mastery to soul-level purpose and practical action.

CTA (one small step)

Download the free book, then spend 10 minutes today writing your 30-day script. Prompt: “If nothing at work changed, how would I live the next 30 days differently?”

In this episode, he and Brett dig into how GenX escapees can win clients by going local-first and relationship-heavy, not enterprise-style transactional.

You’ll Learn

💡 How to build a referral engine from scratch:

→ Daily LinkedIn connects with a simple, honest message

→ Wait 24 hours

→ Invite to a virtual coffee

→ Leave every chat with 2–3 new intros

💡 Why owner conversations are precious—and how to uncover real problems instead of pitching surface ones.

💡 How to package your offer with paid discovery + 90-day sprints instead of scary year-long scopes.

💡 Why going local first builds faster trust (and how that expands nationally).

💡 How adding exit-planning expertise creates credibility and future opportunities.

Guest

Robert Lock — Founder, Buffalo Mountain Sales Strategies | Advisor with Sales Acceleration | Based in Denver, CO

Connect on LinkedIn: https://www.linkedin.com/in/lockrobert/

Keywords

GenX • Corporate Escape • Solo Consulting • Fractional Leadership • SMB Sales • Discovery Calls • Networking • Sales Acceleration • Denver

• A ticket waitlist of more than 3 million people

• Stadiums of 70–80,000 fans packed to see Banana Ball

• 17 Major League Baseball parks sold out on their 2025 World Tour

This conversation captures Jesse’s philosophy before the explosion—and it’s more relevant than ever for GenX escapees and founders building solo businesses. His blueprint proves you don’t need to be the biggest, you need to be the only.

In this episode:

• Jesse’s “ONLY” framework for standing out (Own the problem, Noise, Love, Why)

• Why customers are transactional but fans never leave

• How small first/last impression touches create “happy tears”

• The 5 E’s of experience: Eliminate, Entertain, Experiment, Engage, Empower

• Why constraints drive creativity (and why experiments beat iterations)

• The Visionary + Integrator combo every founder needs

For Escapees:

A great example of what following your dreams can lead to. Also, great insights for building a solo business.

If you’re landing your first client or building a lifestyle business, Jesse’s insights map perfectly: different is better than better. Create fans, not customers—and let them do your marketing for you.

Resources

• Jesse Cole LinkedIn: https://www.linkedin.com/in/yellowtuxjesse/

• Books: Fans First & Find Your Yellow Tux

I like to connect the dots and showcase what's possible if we break out of our comfort zones

🔑 In This Episode:

• Why Conrad left a full football scholarship (and $250K in value) at Kansas to find his true path

• How he walked on to Iowa State’s Top 25 basketball program after not playing for 3 years

• His role as the team’s “Chief Energy Officer” and how he brought discipline and heart into everything he did

• How struggle, loneliness, and discomfort became the fuel for transformation

• The importance of self-awareness, emotional honesty, and earning your identity

• Why he’s building a speaking career focused on pouring into others—and how that fills him with purpose

• How he structures his solo life post-athletics and why discipline still anchors him

✨ Why This Episode Matters for GenXers:

• If you’ve been telling yourself it’s too late to start over… listen to this episode.

• If you’ve been waiting for the “right time” to make a move… listen to this episode.

• If you’ve been going through the motions… this is your wake-up call. 🫵

Conrad may be GenZ—but his mindset, energy, and willingness to act despite fear is a blueprint for anyone ready to take back control.

Brett’s Take:

“This episode hit me. Conrad’s honesty, discipline, and self-awareness are things most of us spend decades trying to develop. But more than that, he took action. He walked away from safety and toward purpose. GenXers—we can learn a lot from that.”

🔗 Connect with Conrad:

• LinkedIn: https://www.linkedin.com/in/conradhawley

• Just Google him—he’s easy to find and open to speaking engagements and collaborations.

Key Takeaways

• GenX Advantage: We’ve lived analog → digital → internet → mobile. We know how to train people—now we train AI. We also know when outputs are “off.”

• AI as Fractional Workforce: Treat AI like your on-demand researcher, analyst, designer, scheduler, and SDR. One subscription, many “roles.”

• Start with Singles: Stop chasing six-figure whales out of the gate. Package $1–5K/month services that solve one need deeply, repeat it across clients.

• Outcome > Hours: Price the result (clean CRM, personalized outreach engine, faster proposals), not your time. AI compresses hours into minutes—that’s the point.

• Productize the Process: Turn your workflow into a mini system: inputs → AI-assisted steps → valuable output. Reuse 80%, customize 20%.

• Risk Wins Deals: Month-to-month + clear ROI beats open-ended fractional promises for most SMBs.

Practical Use Cases We Cover

• Lead gen & personalized outreach at scale

• CRM cleanup & contact enrichment

• Proposal/slide creation (e.g., Gamma)

• Research & meeting prep “briefings”

• Contract review & red-flag summaries

• Agents & light automations (only after nailing the manual workflow)

Simple Monetization Paths (Examples)

• $2–5K/mo: “Done-for-you” outbound engine (200 targeted emails, replies routed, CRM updated).

• $1–3K flat: CRM cleanup + enrichment + basic dashboard.

• $1–2K/mo: Founder research briefs + talk tracks before key meetings.

• $3–8K setup + $1–3K/mo: Build a lightweight, repeatable micro-SaaS/workflow (pricing, content kits, hiring screens) for a niche.

Timestamps

• 00:00 Intro & why AI is a GenX superpower

• 03:30 From big-corp AI to solo/SMB impact

• 06:10 Training people vs. training AI (and knowing “good”)

• 11:20 AI as your fractional team: practical tools & roles

• 16:45 Thought partner use case (Brett’s real examples)

• 23:30 Singles over home runs: structure simple wins

• 29:45 Value pricing when AI compresses your time

• 34:20 Risk, ROI, and easy “yes” offers for SMBs

• 38:45 Partnering to productize (stack skills → stack revenue)

• 42:50 Action plan & where to find Naveen

Memorable Lines

• “AI is the great equalizer—your fractional workforce in one subscription.”

• “Don’t sell AI—sell a solved problem that AI helps deliver.”

• “GenX knows what ‘good’ looks like. That’s the edge 20-somethings can’t fake.”

Resources Mentioned

• Explained Consulting: explained.consulting

• Gamma for slide/proposal generation

If you’ve ever asked yourself, “How would I actually make money if I left corporate?” this episode is for you.

Lee Ann and I break down practical, low-risk ways GenXers can start monetizing today—without swinging for six-figure fences or waiting years to replace a corporate paycheck.

In this episode, you’ll learn:

• How User-Generated Content (UGC) works and why it’s perfect for GenXers who don’t want to be influencers.

• The new inventory-free e-commerce model that lets you launch products without warehouses or Amazon risk.

• Why the Connector Model (introductions + network leverage) is a hidden path to retainer + commission income.

• How to get paid for hiring advisory—helping SMBs make better hires using your experience.

• Why small, repeatable service retainers often add up faster than chasing one big consulting deal.

• The mindset shift from swinging for home runs to stacking singles for steady cash flow.

Enjoy and let us know what you think!