Why to the Way

Love Your Mondays: Martha Malloy on Reinvention

Wed, 10 Jun 2026 06:00:00 -0400

Martha Malloy built a successful career in advertising, got promoted fast, worked on marquee accounts — and then quietly fell out of love with it. What came next wasn't a straight pivot; it was a side quest into UX research, a freelance experiment during the pandemic, a training session in New York that made her realize an entirely new profession existed, and eventually a coaching practice she built from scratch with a self-imposed one-year deadline.

The throughline across all of it is a question she keeps coming back to: do you love your Mondays?

In This Episode

How Martha went from studying car design in England to automotive advertising at BMW Canada — moving from coordinator to account director in four years — before realizing advertising wasn't personally sustainable long term and pivoting entirely into tech and UX research
The pandemic moment that pushed her to leave a full-time director of design role
The two books — Designing Your Life and Designing Your Work Life — that helped her plan her off-ramp without burning bridges, and the specific exercises she did to decide whether to redesign her role or leave
How she discovered product discovery coaching at a "Coaching the Coaches" training in New York with Marty Cagan — 50 coaches from around the world — and realized for the first time that it was a legitimate full-time profession
The business coach advice that shaped her first year as a solopreneur: time-box your commitment, give it your heart and soul, and avoid diluting your energy by interviewing for full-time roles at the same time
How she structures her embedded coaching engagements — from light-touch workshops to joining teams two to four days a week — and why the moment companies choose the "large" option was her clearest signal the business was working

Episode Highlights:

00:00 - Finding Monday Joy

00:12 - Podcast Premise Intro

00:38 - Meet Martha Malloy

01:27 - Early Career Chapters

05:37 - Bosses Vs Mentors

07:14 - Leading With EQ

10:45 - Reinvention At Work

11:38 - Morning Routine Mastery

16:46 - Pandemic Pivot Consulting

18:59 - Product Discovery Coaching

21:54 - Solopreneur Doubts Wins

27:29 - Embedded Coaching Approach

31:32 - Root Causes, Problems, and Outcomes

32:30 - Industry Agnostic Work

36:04 - Fighting Shiny Objects

37:39 - Parenting Tech Passion

39:08 - Reinvention Mantra

40:14 - AI Meeting Pressure

43:56 - Too Many AI Options

48:42 - Kids Career Reframe

51:56 - Productivity Without Tools

55:25 - Efficiency As A Love Language

56:36 - Future Jobs Unknown

57:32 - Wrap Up And Thanks

Resources Mentioned:

Designing Your Life — book by Bill Burnett and Dave Evans
Designing Your Work Life — book by Bill Burnett and Dave Evans
Willful — Canadian estate planning company; Martha's first freelance client
Marty Cagan — product management thought leader; Martha attended his "Coaching the Coaches" training in New York
Product Bets & Jams — Martha's coaching practice; https://www.betsandjams.com/
BMW Canada — Martha spent nearly five years on this account on the agency side

Martha Malloy is a product coach, startup advisor, and angel investor with 20+ years of experience helping technology teams — from early-stage startups to Fortune 500s — build products people actually want. As founder of Product Bets & Jams, she helps founders and product leaders replace gut-feel decisions with evidence-based practices that stick. She's worked across product, design, research, and marketing, and is an active mentor and investor in women-led companies.

Connect with Martha Malloy: https://www.linkedin.com/in/martha-claire-malloy/

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Email: whytotheway@gmail.com

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Disclaimer: The views, information, or opinions expressed by guests during Why To The Way Podcast are solely those of the individuals involved and do not necessarily represent those of Sarah Jeanneault, Twisted Spur Media Ltd. and/or her affiliates. Sarah Jeanneault, Why To The Way Podcast, and Twisted Spur Media Ltd. are not responsible for and do not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.

Life Reimagined: Tammy Janes on Transformation & Letting Go

Wed, 27 May 2026 06:00:00 -0400

Tammy Janes spent nearly 15 years at Unilever, built a global transformation practice from a team of two to roughly 30 people, and then was told her role was being eliminated — not because she failed, but because she succeeded so completely that the organization no longer needed her. What do you do when doing your job well is the thing that ends it? And what does it take to rebuild, network from scratch, and lead a team through a redundancy you didn't choose — all at the same time? This is that story.

In This Episode:

How Tammy went from wanting to be a lawyer to spending six years in management consulting across three verticals — CPG, financial services, and pharma — before finding a home at Unilever for nearly 15 years, holding 10 or 11 different roles in that time
What it actually felt like to tell her team their roles were being eliminated — and how she coached half of them into other positions inside the organization while processing her own exit at the same time
The six-month sabbatical she took after Unilever: why she chose to stop, what she did with the time (a personal trainer, five books, and time with her then-toddler daughter), and why she says she would tell anyone going through the same thing to do the same
Why networking is the one career investment Tammy says she neglected when she felt safe — and the specific coffee chat tip her career coach gave her that made every meeting less about asking and more about giving
Her personal purpose statement developed through a full-day Unilever workshop: "To be perfect enough to raise the bar" — and what the "perfect enough" qualifier means for how she avoids analysis paralysis
Why organizational transformation fails when it's either rushed (60 days) or too slow (endless meetings), and the phased, win-by-win approach she believes actually sticks

Episode Highlights:

00:00 - Redundancy and Pivoting

00:19 - Podcast Premise

01:00 - Meet Tammy

01:41 - Law to Business Pivot

03:35 - Consulting Beginnings

05:28 - Choosing Unilever And Purpose

09:21 - Proudest Wins At Unilever

10:27 - Agile Ways Of Working

13:24 - Team Made Redundant

16:06 - Sabbatical and Networking

21:10 - Empathy Led Leadership

23:36 - Purpose and Motivation

26:28 - Transformation Advice

27:30 - Timelines That Stick

29:59 - Career Vision Flexibility

31:20 - Life Reimagined Mindset

33:06 - Impact Beyond The Job

34:21 - Gut Check Corporate Return

36:08 - Networking Anxiety Trust

45:12 - Energy Regeneration And Balance

50:56 - Learning Through Podcasting

52:30 - Questions After Layoffs

53:37 - Closing and Call to Action

Resources Mentioned:

Unilever — multinational consumer packaged goods company and Tammy's employer for nearly 15 years
Sofina Foods — one of Canada's leading manufacturers of primary and further processed protein products and Tammy's current employer
Leaders Eat Last, book by Simon Sinek
Next Up — Toronto-based women's professional organization
Schulich School of Business at York University — where Tammy completed her undergraduate business degree
Knorr What's for Dinner campaign — in-store marketing campaign Tammy worked on during her Canadian trade marketing role at Unilever
Dove Self-Esteem Program — Unilever's self-esteem workshops for young girls; Tammy delivered workshops in schools
Paul Polman — referenced as Unilever CEO during Tammy's early years; credited with embedding purpose into the business

Quotes:

“ If you do your job well, you should make yourself redundant in the hope that you go onto the next thing. “ - Tammy Janes

“ So I took about six months off, sabbatical, just took a break. You know, I figured I'm not gonna get this time back with my daughter. I got a personal trainer, I read five books. Like, it was just a good break that I needed.” - Tammy Janes

“ Why is, why are we all so scared to talk about this when it happens to people all the time?” - Sarah Jeanneault

“ A really good tip of just do some quick homework before you meet with the person. Find out what they're working on, what's going on with them, and, you know, offer up, "Hey, I might know someone that does this, and would you be interested?" Or even asking the question of, "Is there any way I can help you? Thank you for your time.'" - Tammy Janes

“ Come out with a purpose statement. And mine was, "To be perfect enough to raise the bar."” - Tammy Janes

"People don't fear fear, they fear the unknown that fear brings." - Tammy Janes

Tammy Janes is a transformation and strategy leader whose career spans management consulting, nearly 15 years at Unilever in 10-plus roles, and her current position as Director, Business Performance at Sofina Foods. At Unilever she built and led the global agile ways-of-working practice, growing a capability team from two people to approximately 30 before the function was successfully embedded into the organization. She is known for leading with empathy, driving continuous improvement, and building teams that outlast her.

Connect with Tammy Janes: https://www.linkedin.com/in/tammy-janes/

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This show is produced by Twisted Spur Media Ltd.

Brand Builder, Risk Taker: Jennifer Blackburn on Knowing When to Leap

Wed, 13 May 2026 06:00:00 -0400

Jennifer Blackburn has held roles at Unilever, Nando's, Canadian Tire, Skip, and is now CMO of Clearly Canadian — and not one of those moves was a straight line. The pivot that surprised her most wasn't a bold leap toward opportunity; it was a quiet moment doing virtual homework with her three-year-old daughter at 3am from a different time zone, realizing the right role at the wrong time in your life is still the wrong role.

This episode is for anyone who's ever wondered whether ambition and a good life can actually coexist.

In This Episode

Why Jennifer left a successful six-year run at Canadian Tire to join a hyper-competitive tech company — and how walking into an interim CEO, a new CEO, and two different bosses in her first six months taught her more than any stable role could
The Nando's lesson: how a global brand with deep purpose and a dream job on paper became the clearest signal that career decisions can't be made without factoring in where you are in your personal life
Why Jennifer puts almost no weight on how long someone stayed at a company when she's hiring — and what she looks for instead (hint: it's not the polished pitch)
How Jennifer thinks about the career ladder versus the career zigzag — and why she believes knowing your north star matters more than following a prescribed path upward
What it actually takes to revive a nostalgic legacy brand like Clearly Canadian for a generation that never grew up with it — and why that challenge is the one she's most excited to unlock
The interview process at Nando's that included a five-hour psychology assessment in London with jet lag — and what Jennifer says she learned about herself from it

Episode Highlights:

00:00 - Reviving a Legacy Brand

00:25 - Podcast Premise and Intro

00:50 - Meet Jennifer Blackburn – Clearly Canadian CMO

01:42 - Nostalgia Stories and Brand Magic

04:56 - From Doctor Dreams to Marketing

06:19 - Unilever Training Ground

08:36 - Marketing Then vs Now

10:26 - Pivot to Tech at Skip

12:23 - Risk Support and Overwhelm

13:35 - Choosing Growth Together

16:02 - From Skip to Clearly Canadian

16:51 - Wrong Turns in Life

21:52 - Hiring Mindset on Short Tenures

23:26 - Interviewing for Authenticity

25:41 - Most Intense Interview Experience

27:00 - Working Parenthood and Energy

27:57 - Work Life Balance Lessons

29:18 - Career Pivots And North Star

30:47 - Transition Season At Home

32:31 - Favorite Clearly Canadian Flavor

33:09 - Gut Check On C Suite Paths

35:16 - Switching Industries And Growth

39:10 - Travel For Work Reality Check

42:25 - Remote Work And Productivity Debate

44:04 - Sleep Time Zones And Car Rules

46:58 - What We Missed And Wrap Up

48:09 - Podcast Wrap Up

Resources Mentioned:

Clearly Canadian — the brand Jennifer currently leads as CMO; https://clearlycanadian.com/
SkipTheDishes — Canadian food delivery tech company
Canadian Tire — Canadian retail company
Nando’s — global restaurant brand
Unilever — global consumer goods company
PepsiCo — multinational food and beverage corporation, referenced as a training ground for CPG marketers alongside Unilever
Kroger — US grocery retailer

Quotes:

“And I think there’s tends to be scrutiny on that versus why stay longer if it's not working for you?” - Jennifer Blackburn

“ Doing virtual homework with my daughter at three in the morning buy time. And she's like, mommy, why is it dark where you are? And it's bright where I am.” - Jennifer Blackburn

“ I think sometimes you think the trajectory must go straight up at all times or else I'm not achieving.” - Sarah Jeanneault

“ It is really kind of looking internally first to say like, what do you want, like what's your north star in what your career, and this might be a stepping stone to your end. It may not be, you know, the, the, the whole way there.” - Jennifer Blackburn

“ It's not just about the job, it's not just about the company. It's also about how does this fit into your, your lifestyle and what tradeoffs are you able or willing to make or not.” - Jennifer Blackburn

“ People being honest and genuine versus trying to be pitchy and selling of their experience. I really try and look for that humbleness, that authenticity.” - Jennifer Blackburn

Jennifer Blackburn is the CMO of Clearly Canadian, where she leads the work of evolving a beloved legacy brand for the next generation of consumers. Her career spans CPG, retail, foodservice, and tech — including brand leadership roles at Unilever, PepsiCo, Nandos, Canadian Tire, and SkipTheDishes. Known for building high-performance teams and revitalizing iconic brands, she brings an entrepreneurial mindset to every organization she joins, whether it's a multinational or a private equity-backed startup.

Connect with Jennifer Blackburn: https://www.linkedin.com/in/jennifer-blackburn-9b5958a/

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Leaping Over Obstacles: Carolyn Lawrence on Leading Change

Wed, 29 Apr 2026 06:00:00 -0400

Carolyn Lawrence walked away from her dream job — Global DEI Leader at Deloitte — not because it wasn't working, but because she could no longer see what was next. What followed was a masterclass in exactly what she'd spent her career teaching others: how to read a system, resist the urge to fight it head-on, and move through obstacles with strategy instead of force. If you've ever felt the fire to change something but watched it fizzle the moment you walked back to your desk, this episode is the one you've been waiting for.

In This Episode:

Why pushing hard for change inside an organization can backfire — and what to do instead (the "what we resist persists" principle Carolyn learned the hard way at Deloitte)
The exact tactic she used to get a skeptical senior leader to voluntarily open up their hiring process — and how that single conversation unlocked 19 of 20 DEI KPIs moving in the right direction over four years
How Carolyn embedded inclusion scores into annual performance reviews tied to variable compensation — and why the COO sitting in on those reviews changed everything
The four maturity levels of organizational inclusion, from "checking a box" to "this is just how we do business" — and what it looks like when a company truly doesn't need a DEI strategy anymore
What it actually felt like to leave a dream job at Deloitte Global: the fear, the six months of community conversations, the third-of-asking-price first client, and the pivot to "impact strategist" that changed how she talks about her work
Why equity at home directly creates equity at work — and the Deloitte study that proved men carry hidden burdens too

Episode Highlights:

00:00 - Change That Backfires

00:30 - Podcast Premise Intro

00:56 - Meet Carolyn Lawrence

02:51 - Purpose And Career Path

03:58 - Early Equity Awakening

05:26 - Role Model Eureka Moment

07:53 - From Inspiration To Systems

09:25 - Curiosity Over Confrontation

12:46 - Deloitte Strategy Story

17:47 - Accountability That Works

22:10 - Coaching Passionate Teams

23:58 - Finding Your Voice

27:41 - Leaving Deloitte To Leap

31:20 - First Pitch To New Positioning

34:00 - DEI Maturity Levels

35:26 - DEI Maturity Integrated

36:36 - Equity Starts At Home

38:18 - Flexible Work Inclusion

39:41 - Hybrid Work Preference

40:31 - Sport For Wellbeing

42:19 - Meditation For Clarity

43:55 - No Regrets Lessons

45:06 - Leaping Over Obstacles

46:12 - Where To Find Carolyn

46:39 - Gut Check Debrief

48:24 - Building Teams Mentorship

53:28 - Podcasting Career Path

59:28 - Purpose And Impact

01:01:53 - Question We Missed

01:03:43 - Final Sign Off

Resources Mentioned:

Heather Reisman — CEO of Indigo Books & Music (referenced as Carolyn's early inspiration)
Deloitte — the global consulting firm where Carolyn led DEI strategy and global people leadership
Women of Influence — the social enterprise Carolyn previously led
A Clear Path — Carolyn's own company - https://clearpathtoimpact.com/

Quotes:

"If I want to inspire change, resisting or fighting it is actually going to strengthen it. Like what we resist persists." - Carolyn Lawrence

“So I tracked the numbers at Deloitte. I was in that role for four years. Our numbers on literally 19 out of 20 KPIs that we measured. In the right direction. So that method works and I can prove it.” - Carolyn Lawrence

“I was very afraid and thought multiple times that I perhaps had lost my mind because here I was global diversity, equity and inclusion leader for Deloitte. Where do you go from there?” - Carolyn Lawrence

“You can't go from a great inspiring talk and then go and stand in a boardroom and yell off the top of your lungs. Hey everybody, I am completely inspired. I'm gonna change everything. Everybody come and listen.” - Sarah Jeanneault

“This year I’ve been looking at obstacles a little differently and trying to think about them as stepping stones and that I'm leaping over them, not with effort and strength, but with this internal lightness and power within.” - Carolyn Lawrence

Carolyn Lawrence is an Impact Strategist who helps leadership teams eliminate the invisible barriers blocking results. With a decade at Deloitte — where she built Canada's inclusion consulting practice and served as its first Global DEI Leader — plus firsthand experience as a purpose-driven business owner, she's a sought-after advisor for organizations navigating growth and change.

Connect with Carolyn Lawrence: https://clearpathtoimpact.com/

https://www.linkedin.com/in/carolyn-lawrence-619bb16/

Connect with Us!

http://www.whytotheway.com

Email: whytotheway@gmail.com

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Why to the Way

Tue, 21 Apr 2026 15:25:00 -0400

Why to the Way is hosted by Sarah Jeanneault. Each episode explores a real dilemma, crossroads moment, or personal crisis that forced someone to make a defining choice. Together, they unpack what happened, what the guest ultimately chose, and the deeper reasons behind that decision. Then Sarah and Heather weigh in themselves, debating what they would have done if faced with the very same situation. This is a podcast about perspective, decision-making, and the moments that shape who we become. Every episode invites listeners into the tension with one central question: What would you have done?

Connect with Us!

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