That Sounds Risky with Sara Emmerson

Comfort Zone Kills Growth | Alec Takahashi on Lighting the Biggest Stages & Betting on Himself

Tue, 22 Sep 2026 05:00:00 -0500

Alec Takahashi and I go back a long way. We first met at a Christmas concert I was producing, back when he was on the road with Lincoln Brewster. I loved that name so much I later gave it to my son. So it's a full-circle joy to have him on the show now, because in the years since, Alec has become one of the most respected lighting and production designers working today. He's the co-founder of BKD Creative, he's toured with Thomas Rhett for nine years, and in 2023 he won the Parnelli Award for Lighting Designer of the Year, one of the highest honors in live events, and he believes he's the youngest person ever to take it home.

The line that named this episode is his, not mine. Comfort zone kills growth. Alec has lived that sentence since fifth grade, when a teacher handed him the light board for the cafeteria talent show and told him he might do this for a living. He started cold-emailing production managers at fourteen. He chose the road over college and graduated high school six months early to work full time at his church. And at the end of 2016, with nothing lined up, he walked away from that steady job to see what the road held. That meant couch-hopping, living out of a suitcase, and sitting in a Nashville Starbucks at six in the morning with his luggage, not knowing where the day would take him. A few years later he started a company in the middle of COVID.

We talk about the risk that scared him most recently. A month before rehearsals for a Thomas Rhett tour, management pulled a truck of gear and the whole design fell apart. Instead of fighting over the truck he couldn't control, Alec flew to Chicago, walked the storage floor of his lighting vendor, and redesigned the entire show in four days. It became one of his favorite years. It's the clearest picture I know of the three levels of control, full, partial, and none, and of pouring your energy into the part you can actually change. We also get into why he refuses to be the smartest person in the room, why human connection can't be handed to a chatbot, and the risk he's taking right now that he honestly dreads.

In this episode:

Why comfort zone kills growth, and how to keep choosing the uncomfortable thing on purpose
The fifth-grade talent show that started a career, and the teacher who spoke it into existence
Cold-emailing tour managers at fourteen, and the connection that came back around a decade later
Choosing the road over college, and graduating early to go all in
Walking away from a steady job at Christmas with nothing lined up
The Nashville Starbucks at 6 a.m. with a suitcase and no plan
Starting a company in the middle of COVID
The truck that got cut a month before rehearsals, and the four-day redesign that saved the tour
The three levels of control, and why he only spends energy on what he can actually change
Treating stress as your body equipping you, not breaking you
Never being the smartest person in the room, and why he still seeks mentors and becomes one
Protecting human connection in a world of AI chatbots
The risk he is taking now that he genuinely dreads

Do It For The Story | Olivia Curry on Turning Pro, Title Fights, and Saying How You Feel

Tue, 15 Sep 2026 05:00:00 -0500

Olivia Curry walked into a Muay Thai class above a 7-Eleven in Evanston because the student rate was forty dollars a month and she had just watched a martial arts movie. She was not an athlete. She describes herself as a dork who happens to be stubborn. Fifteen years later she has fought twice for a middleweight world title and is ranked fifth in the world.

In this episode she tells Sara what that actually costs. The eight-week camps and the weight cuts. The pro and con list she made before turning professional, where the whole pro column came down to one half-joking line. The fight she took against a woman who was 12 and 0 with 11 knockouts, a weight class above her, on a card with twenty thousand people watching, where Vegas had her knocked out inside four rounds and she went the distance instead. The world title fight in Atlanta that was cancelled at the weigh-in after six weeks of camp, with her mother and sister already in the arena.

She also talks about her father, who had ALS and died this past spring, and what he taught her about being scared and going anyway. And when Sara asks for the one risk everyone should take, her answer has nothing to do with boxing.

Chapters

00:00 Welcome, and who Olivia Curry is01:53 A $40-a-month gym above the 7-Eleven in Evanston04:23 "I just kept moving the goalposts"10:14 Her dad, ALS, and where the mental toughness came from12:53 The pro-and-con list that said "Eternal glory"16:08 The man in the arena, and the 20,000-person card22:04 Inside an eight-week camp29:12 Walk-out music, and "If I die, I die"33:45 Ranked fifth in the world, and making peace with it49:49 Atlanta: a world title fight cancelled at the weigh-in57:14 The sweetest win, and four ringside tickets01:03:18 Rapid fire, and the one risk everyone should take

Find Olivia

Instagram: @oliviarosecurryWeb: oliviarosecurry.comDirecting and editing: picturenorth.com

Find Sara

saraemmersoncoaching.com

Divine Therapy | Anna Powell on Being Stalked, Wrestling with God & Writing the Book Anyway

Tue, 08 Sep 2026 05:00:00 -0500

Anna Powell spent about ten years as a publicist, which is a job about telling other people's stories well. The one she could not tell was her own. The night before her very last final exam in college, she opened an email from one of her professors confessing an obsession with her. She took the exam. She graduated. She moved to Chicago, started her career, and put it behind her. Almost two years later, to the day, she started seeing him. On her commute. In a store window she walked past. And then at 5:30 in the morning in the gym of her own building, because he had moved into it.

What we spend most of this hour on is not the six years. It is what those years did to her faith and what she did with them a decade later. Anna stopped being able to ask God why and went and studied the book of Job instead. She calls that season divine therapy, and she means it kindly. The book started in 2014 as non-fiction about suffering, got shelved when she found out she was pregnant, and sat untouched for eight years. What restarted it was a Christmas card. She had nothing to put for herself, so she wrote that she was back to pursuing her dream of writing a book, mailed it to everyone she knew, and could not take it back. Then her husband Dan asked her one question about her intention that turned the whole thing into a novel.

In His Sight came out in March, told from two points of view, Piper's and the man following her. Anna finished it before she turned forty because she decided it was now or never. Here is the part I keep thinking about. She survived the thing. Surviving it was not the risk. The risk was handing it to strangers and letting them read it. If you are sitting on something you have been carrying for years, this one is for you.

In this episode:

The email the night before her last final exam
Two years later, and he was living in her building
What being followed does to how you see yourself
Losing her faith and going looking for it in the book of Job
Divine therapy, and what suffering built that nothing else could
Leaving a ten-year PR career, and the identity crisis on the other side
A son born with a rare heart defect, and letting the work go
The Christmas card that made the book real
The one question from her husband that turned non-fiction into a novel
Two agents, one shelved manuscript, and ten years to a finished book
Who actually shows up when you put something into the world
Now or never: finishing it before forty
The question every reader asks her about the love interest
Rapid fire, and the one risk she thinks everybody should take

Not Healed, But Healing | Tim Timmons on Living in the Between, Surrender & the Gift of Cancer

Tue, 01 Sep 2026 05:00:00 -0500

Tim Timmons and I go back about thirty years. He played at my wedding. He worked alongside my dad, Stan, for years, and somewhere in all of that he became one of those friends who changes how you look at your own life. Twenty-five years ago he was told he had five years to live. Stage four, incurable, tumors that are still on his liver today. He is still here, he is still writing, and he will tell you plainly that he is not celebrating cancer. He is celebrating the perspective it handed him.

What we ended up talking about is the space in between. Tim has a rule for it. He is trying to use more words that end in I-N-G than words that end in E-D. Not "I learned this," but "I am learning." Not "I figured it out," but "I am figuring." Not healed, but healing. That one small change is the whole posture of his life, and you can see it in the biggest calls he has made. Walking away from a church job he held for fifteen years. Funding a record on Kickstarter with no safety net. And then deciding he would never open a door for himself again. No schmoozing. No pushing his way into rooms. He has kept that for fifteen years, and in that time he has signed record deals, co-written a Grammy nominated song, and watched Milo Ventimiglia play him in a movie.

He also talks about the failure, and he does not soften it. A church called The Following that he and a friend built and then talked themselves right out of, until forty people were meeting in an Orange County motel alongside the people who lived there. It fell apart. He calls it the greatest failure of his life and the three years he grew the most. His new song Between is out now, and he says it is the most personal one he has written. If you are sitting in your own in between right now, waiting on an outcome you cannot control, this hour is for you.

In this episode:

The grammar rule he lives by: more words ending in I-N-G than E-D
Quitting a fifteen-year church job, and why he says working for God sucked the life out of him
The Kickstarter that no label wanted, until every label wanted it
Five years to live, twenty-five years ago, and what that does to how you spend a Tuesday
The experiment he has run for fifteen years: never open a door for yourself again
Surrendering the outcome, and why he had to stop being the CEO of everything
The Following: the church that failed, and the three years he grew the most
Why the biblical word for hope has almost nothing to do with outcomes
Watching Milo Ventimiglia play his hardest moments, and finding compassion for himself
Why we are so good at moving past grief and so bad at actually grieving
The X he writes on the underside of his wrist every single morning
Cancer is the dumbest. The perspective is the gift.

Desperation Breeds Creativity | Annie Aiello on Starting Over and Building the Show She Needed

Tue, 25 Aug 2026 05:00:00 -0500

Annie Aiello grew up the youngest of six in a Chicago Italian family where the currency was academics and athletics, and the artist in her got quietly shushed. So she took the safe route. Business degree. Art minor, because that was allowed. Ad agency. Then an MBA, because she wanted something with more meaning in it than a widget.

Twenty-three years into a marriage she had promised herself she would never leave, she left it. She walked out of ministry into a corporate job that doubled her salary and made her miserable, and found herself a single mother trying to get two teenagers to college.

What she built out of that is Always Olivia, a national Olivia Newton-John tribute show. She started it because she needed joy and she needed money and she had exactly one skill nobody could take from her. She funded part of it with the proceeds from the house she had to sell.

This episode is about the mechanics of that. How she found the people who already knew how to do what she needed to do. Why the wigs, of all things, were the place she almost quit. What it took to walk out on a stage in a 1970s wig with her whole family in the audience, certain she was about to be laughed at. And what it costs to become a beginner again in public, twice, once on a stage and once, at fifty-something, back in the dating world.

Annie Aiello. Mother. Creative Voice. Singer. Songwriter, Lead singer of "Always Olivia," the Ultimate Olivia Newton-John Tribute, Producer, Child of God.

In this episode:

- Why "desperation breeds creativity" is not a consolation prize, it is a method

- The rule she runs her life on: when you do not know how to do something, go learn it from the people who do

- Flying to Vegas to meet a Cher tribute artist, Bob Mackie's understudy, and the woman who costumed Olivia at the Flamingo

- Choosing to put the house money into the show instead of into retirement, and finding an investor for the rest

- The wig that nearly ended it before the first show

- Standing backstage thinking "I am going to be so interpreted as a joke," and walking out anyway

- Giving a portion of every show's proceeds to the Olivia Newton-John Cancer Wellness and Research Centre, after losing both parents to cancer

- Throwing out perfectionism when you lead a band, because every crowd is different

- Being a beginner again at fifty-something, on stage and in the dating world

Sara's frame that runs underneath the whole hour: we only do things if we want it enough or we need it enough, and the best intersection is when both are present.

Be Too Much | The WanderLust Girls on Style, Friendship & Betting on What Makes You Weird

Tue, 18 Aug 2026 05:00:00 -0500

Emily Bache and Abigail Breslin have been best friends since they were eleven, grew up sharing one closet, and never actually chose their own name. A street photographer shouted "there's those WanderLust Girls" at them on a sidewalk, and it stuck. Fifteen New York Fashion Weeks later, they've styled for Playboy, Macklemore, Bloomingdale's, Jack White, and Major League Soccer.

In this conversation they tell Sara how a college blog started because one of them owned all the tops and the other owned all the pants, how they cold-emailed their way into 65 shows at their first Fashion Week with no credentials and nobody to vouch for them, and how a client's offhand comment sent them across the street into a bank to ask a stranger how you start a company. They also talk about the lunch invitation they almost turned down that became a Playboy job, the day they showed up in thigh-high boots and boas to what turned out to be bootcamp, and the SNL emergency that proved who was actually in their corner.

The thread running through all of it: every time someone advised them to tone it down and look more normal, it cost them. They tried it once, wore blue jeans, and watched followers leave. The thing that makes you weird is usually the thing people came for.

In this episode:

• Why the weird invitation is usually the one holding the door open

• How to ask for something bigger than you think you're allowed to

• What happens when you tone yourself down to be more marketable

• Why you don't have to feel ready, you just have to ask the embarrassing question

• How being wrong alongside someone makes risk survivable

• Why a $100 job is still a relationship, and how small gigs come back years later

Follow Emily and Abigail at @wanderlustgirls and thewanderlustgirls.com.

Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Go Back to Go Big | Johanna Lyle on Reinventing Yourself into a Six-Figure Design Business

Tue, 11 Aug 2026 05:00:00 -0500

Interior designer Johanna Lyle didn't start in design. She went from theater performer to video producer before a COVID-era reinvention turned a paint-splattered DIY Instagram into a six-figure design business. In this episode she tells Sara how she took a humbling pay cut to learn the craft, launched her own firm during a cross-country move with a husband about to hit zero income, and ran a Chicago clientele from Boston because that's what actually worked. She gets honest about the client she had to walk away from, the gut feeling she ignored, and why saying no is sometimes the bravest thing a business owner can do. It's a story about being willing to go backward to go forward, and trusting yourself when the timing is never right. Named a "Next Wave Designer" by House Beautiful, Johanna proves the greatest opportunities usually start with something that sounds risky. Follow Johanna: joelyleandco.com and @jo.lyle.design. Work with Sara: https://saraemmersoncoaching.com

Bounce Forward, Not Just Back | Jessica Maren on the Biology of Resilience

Tue, 04 Aug 2026 06:00:00 -0500

What if resilience isn't just about mindset — what if it's rooted in your biology? This week Sara sits down with Jessica Maren: speaker, writer, and resilience educator who blends science-backed strategy with honest storytelling to help people stop spiraling and recover from setbacks. In this conversation: why your brain goes looking for a problem when life is finally calm, how chronic stress quietly rewires you to scan for the next fire, why failure feels so personal (and what to do about it), the difference between bouncing back and bouncing forward, and how a former elite athlete learned to regulate her nervous system on the biggest stages — including the private ones at home. Practical, refreshing, and a little bit science class. Follow Jessica @jessica.maren. Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Say Yes When Everyone Says No | Stan Endicott on Risk, Playfulness & a Life Well Lived

Tue, 28 Jul 2026 08:30:00 -0500

This week the guest chair belongs to the person who taught Sara to take risks in the first place: her dad. Stan Endicott is a musician and producer who spent decades making records in Los Angeles, the co-founder of Slingshot Group (one of the country's top coaching and staffing teams), an author, and the creator of the IMPROVLeadership model.

In this conversation: why we stop taking risks as we grow up and how to get the playfulness back, why grit can be terrible advice, the truth about the 10,000-hour rule, the one question to ask your boss instead of asking for a raise, the day he moved across the country with no job waiting, and the time he became one of the first outsiders to hear "I Wanna Dance with Somebody" before the world did.

Warm, funny, and full of the kind of wisdom you only get from a life of saying yes.

Learn more about Stan's work at slingshotgroup.org. Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Say Yes to the Whole Catastrophe | Amy Donovan on Courage, Failure, and Betting the House

Tue, 21 Jul 2026 05:00:00 -0500

Sara's own coach of six years takes the guest chair. Amy Donovan, MCC, one of the first 150 coaches in the world, co-founder of PRIME Coaching Academy, and co-author of Who's the Boss?, has spent 25+ years coaching leaders through the decisions that scare them. In this conversation: the $5.5 million collapse that cost her nearly everything and the walk in the woods that started the rebuild, why courage always comes before confidence, how to borrow belief when yours runs out, the regret people actually carry at the end of their lives, and the t-shirt Amy had made that says it all: just say yes to the whole catastrophe. If you are standing at a crossroads, a part of you has already decided. This episode is about trusting it. Learn more about Amy at primecoachingacademy.com. Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Why You Need a Ridiculous Dream | Gareth Pon

Tue, 14 Jul 2026 05:00:00 -0500

Gareth Pon said yes to climbing Mount Kilimanjaro before he Googled what it actually was. That one naive yes turned out to be the blueprint for his whole life.

In this episode of That Sounds Risky, Sara Emmerson sits down with Gareth Pon, an award-winning photographer, filmmaker, and creative director who pioneered Instagram in South Africa, moved across the world on the strength of a single social-media message, and now leads social-first creative for some of the biggest brands on the planet. His path was never a straight line. It was a string of small, slightly terrifying yeses that compounded into a remarkable career and an even more remarkable life.

Gareth and Sara talk about why risk is a muscle you build one rep at a time, why comfort is the killer of creativity, and why everyone needs one ridiculous dream. His is going to space, which is why there is a hidden rocket in every photo he posts. It is an honest, funny, faith-filled conversation about betting on yourself before you feel ready.

In this episode you'll learn:

Why saying yes before you feel ready is how brave people actually build a life
How small risks train the muscle that makes the big leaps feel possible
Why comfort kills creativity, and how to keep reinventing yourself
How relationships and generosity, not talent alone, open the biggest doors
Why you need one ridiculous dream, and what happens the moment you believe it could come true
How faith and letting go of control can free you to take bigger risks

"You need to have a ridiculous dream, because the moment you believe that dream can come true, everything else in your life becomes possible."

Follow Gareth's work (and hunt for the hidden rocket) at @garethpon.

Sara Emmerson is a certified life, business, and executive coach (ICF PCC) who helps capable people stop overthinking and make the brave move they've been putting off. Learn more and work with Sara at saraemmersoncoaching.com. New episodes weekly, so follow along.

You Don't Have a Strategy Problem, You Have a Belief Problem | Q&A with Sara Emmerson

Tue, 07 Jul 2026 05:00:00 -0500

Most people who feel stuck don't have a strategy problem. They have a belief problem. In this episode of That Sounds Risky, life and executive coach Sara Emmerson answers the questions she was asked as a guest on another show, and the answers turn into a masterclass on leadership, mindset, sales, and doing the scary thing anyway.

Fresh off a podcast interview with a host in London, Sara brings the best questions back to her own listeners: What does leadership actually mean? How important is mindset in success? What does sales really mean? Who does she coach, and why does this podcast exist at all? Her answers hold whether you're an executive, a business owner, an entrepreneur, or a creative who knows you're capable of more.

In this episode you'll learn:

Why leadership is creating clarity in uncertainty, and why it starts with leading yourself first
The difference between a strategy problem and a belief problem, and which one is actually keeping you stuck
Why confidence doesn't come before action, it comes from taking action
How fear, self-doubt, perfectionism, and other people's opinions keep high performers plateaued
Why sales is service: helping someone see the gap between where they are and where they want to be
The two kinds of regret, and why "I wish I'd tried" is the one you can't fix

Is It Fear or an Excuse? The Story That's Keeping You Stuck

Tue, 30 Jun 2026 05:00:00 -0500

Fear rarely shows up looking like fear. It shows up sounding reasonable. "I just need more time." "I need more clarity first." "Now's not the right season." If you've been saying the same line for months, this episode is for you.

In Episode 2 of That Sounds Risky, Sara Emmerson breaks down how to tell a real reason from a fear wearing a disguise, and what changes once you can see it. She walks through the RISK test, a simple way to check whether the thing you keep saying is information or fear: Repeated (how long have you been saying it?), Isolate (what's the fear underneath?), Sacrifice (what's it costing you to wait?), Keep moving (one small action in the next 24 hours).

She also makes the case that staying stuck is its own kind of work, that readiness was never a feeling you wait for, and that confidence shows up after you move, not before.

In this episode:

How to tell a real reason from an excuse (the RISK test)
Why "I need more clarity" is often a courage problem, not a clarity problem
The hidden cost of staying exactly where you are
Why every version of your life requires work, so choose the work that's worth it
How to take the next brave step before you feel ready

"Readiness isn't a feeling. It's a decision."

Sara Emmerson is a certified life, business, and executive coach (ICF PCC) who helps capable people stop overthinking and make the brave move they've been putting off.

Learn more and work with Sara at saraemmersoncoaching.com. New episodes weekly, so follow along.

How to Take a Risk When You Don't Feel Ready | That Sounds Risky Ep. 1

Thu, 18 Jun 2026 14:48:00 -0500

Readiness isn't a feeling. It's a decision. In the very first full episode of That Sounds Risky, life and executive coach Sara Emmerson shares why she almost didn't start this podcast, every excuse, every "what if I fail publicly", and what it really takes to begin something before you feel ready. Through honest and often funny stories (a childhood turtle named E.T., a painfully awkward high-school audition, an American Idol tryout at Soldier Field in front of 20,000 people, and a six-week leap that moved her across the country at 23), Sara unpacks why confidence comes after action, not before, and why the greatest risk is usually spending your life wondering "what if?" If you've been waiting to feel confident, prepared, or certain before you start the business, make the career change, or pursue the dream, consider this your permission to begin. Work with Sara at saraemmersoncoaching.com.

That Sounds Risky: A Podcast About Courage, Risk & Taking the Leap (Trailer)

Thu, 18 Jun 2026 14:45:00 -0500

Risk is often the price of a meaningful life. Welcome to That Sounds Risky with Sara Emmerson, a life, business, and executive coach who helps capable people move from overthinking to action. This is the show about the decisions that stretch us, the fears that hold us back, and the courage it takes to build a life you're really proud of. Each week, Sara shares honest stories from her own journey, leaving a career, starting a business from scratch, taking risks that didn't make sense on paper but changed everything, plus practical coaching tools and mindset shifts to help you take the next right step. Whether you're considering a career change, building something new, healing from disappointment, or just feeling that nudge that there's more for you, you're in the right place. Start here, then dive into Episode 1. New episodes weekly. Learn more at saraemmersoncoaching.com.