PODCAST · business
101 Ways Out
by 101 Ways Out
Have you ever felt stuck, trapped, and unhappy, wishing for a way out? Did you check all the boxes, climb the ladder, and realize you weren't happy? 101 Ways Out exists for that moment. In this series, I interview people from all walks of life who got to that exact point and realized they could take action to build the life of their dreams. My goal is to share their stories to inspire you to do the same.
Episodes
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The Corporate Moment That Made Her Quit for Good | Way Out #34
What happens when you climb every rung of the corporate ladder, only to realize the culture at the top was never built for you? Courtney Cook grew up in a small town with entrepreneur parents and built her career in operations, rising through corporate roles in retail. But behind the promotions…
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Way Out #33: From False Accusations to Creative Freedom with Marion Gibbon
What happens when decades of dedicated public service meet systemic dysfunction and institutional betrayal? After leading critical community health and maternal nutrition programs across Kenya, Sri Lanka, and Nepal, Dr. Marion Gibbon found herself managing high-pressure public health operations…
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Way Out #32: From Hospital Psychiatrist to Life on the Road: Continuous Reinvention | Dr. Lani Jones
What if finding your way out isn't a one-time move, but a habit of continuous reinvention? In this episode, Dr. Lani Jones, Clinical Psychologist, Executive Coach, and Speaker, joins Vanessa to share how third time’s the charm when learning to step off conventional tracks. Lani spent a decade...
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Way Out #31: From Award-Winning Educator to Modern Supportive Husband with Brian Page
What happens when couples ditch outdated gender expectations and treat both household labor and financial strategy as a true team sport? Today, 45% of women out-earn their male partners, yet the domestic care economy hasn’t caught up. In this episode of 101 Ways Out, Vanessa sits down with Brian...
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Way Out #30: From Corporate Conditioning to Living on Purpose with Integrative Coach Tammy Rising
What becomes possible when you stop asking what’s expected of you and start listening to your inner compass? In this special milestone episode of 101 Ways Out, Vanessa sits down with a very personal guest: her own coach, Tammy Rising. Tammy is an integrative success coach who blends soul and...
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Way Out #29: From Silicon Valley Hyper-Growth to Redesigning Maternity Leave with Kelly Ling
What happens when the high-speed treadmill of Silicon Valley hyper-growth collides head-on with the messy, unpredictable reality of human life? In this episode of 101 Ways Out, host Vanessa Jupe sits down with Kelly Ling, founder of Stork and Spark. On paper, Kelly had the ultimate corporate...
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Way Out #28: From a Toxic Marriage to Freedom with Mary Sinclair Kowalski
How do you walk away from marital wealth to save your sanity? In this episode of 101 Ways Out, Mary Sinclair Kowalski joins me to share her raw, unfiltered story of escaping a toxic, emotionally abusive marriage and surviving a high-conflict divorce. To the outside world, Mary had it all: she was...
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Way Out #27: 50 Years of Business, Boundary-Breaking, and the Art of the Pivot with Rick Loesel
How do you build a sustainable, high-impact career spanning five decades without losing your soul to the corporate machine? In this episode of 101 Ways Out, host Vanessa Jupe profiles Rick Loesel, a retired senior supply chain executive and consultant. From his "white bread idyllic" childhood on...
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Way Out #26: From Clinical Burnout to Health Coach with Katie Cooper
Are you a high-achieving professional struggling with severe burnout but terrified to walk away from a stable career? In this episode of 101 Ways Out, I speak with Katie Cooper, founder of Katie Cooper Wellness. Katie spent nearly two decades climbing the clinical leadership ladder in…
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Way Out #25: From Corporate Climb to Making Wine with Sarah Lyons
What happens when you achieve the high-powered media executive titles and financial success you’ve spent your life chasing, but realize your deepest need is simply to create? Former HBO Max and DIRECTV senior executive Sarah Lyons shares her journey of building Lyons Vineyard, navigating the...
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Way Out #24: From Selling to Sailing with Talica Davies
"My brain and my intellect will tell me how to do something. And my heart is going to tell me what to do." In this episode of 101 Ways Out, we sit down with Talica Davies, a sales consultant for founders who radically transformed her life by choosing happiness over success. Raised in rural Nova...
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Way Out 23: From Corporate Gaslighting to Total Freedom with Karol Figueroa
"Corporate for many people tends to be our longest emotionally abusive relationship." In this episode of 101 Ways Out, we sit down with Karol Figueroa, who achieved the ultimate corporate dream as a Director at Microsoft, only to realize the "matrix" was a trap. After dedicating 12 years to a...
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Way Out #22: Putting Payroll on Credit Cards: Then His Son Was Born Nine Weeks Early with Brian Best
Are you stuck in a career where your income is entirely tied to how many hours you clock? What if you could decouple your time from your money, and run your life from anywhere? In this episode of 101 Ways Out, we sit down with Brian Best, a self-proclaimed "computer nerd" who walked away from a...
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Way Out #21: From Corporate Hostility to Sicily: Suitcases and a One-Way Ticket with Jennifer Sontag
What does it take to sell everything you own, pack two suitcases, and move across the world? For Jennifer Sontag, it took surviving hostile corporate environments, navigating a divorce, and hitting a breaking point where she realized: if not now, when? In this incredible episode of 101 Ways Out,...
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Way Out #20: Laid Off From Her Executive "Dream Job": The Burnout Story with Haley Scruggs
For years, Haley Scruggs believed that success required pain. From grueling 80-hour weeks selling books door-to-door in college to becoming a top-tier technical recruiter for fast-paced startups like Bumble and The Zebra, Haley built her career on the belief that her worth depended entirely on...
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Way Out #19: From Being Told What to Make to Building a $1M Agency with Marianne Kaiser
What do you do when the agency that promised you the world starts making you question your own value every single day? If you are Marianne Kaiser, you track your misery on a 30-day Post-It note countdown, and then you walk away. In this episode of 101 Ways Out, we sit down with Marianne, a former...
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Way Out #18: Rising from the Ashes: From Fired to Founder with Anne Pao
How Anne Pao Turned Corporate Retaliation into a Fractional Empire Anne Pao was a top-performing VP, hitting 85% of her OKRs and consistently earning 100 NPS scores from her teams. Her manager, however, was a nightmare. He treated his team poorly and openly expressed that he liked to "keep a…
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Way Out #17: From Pastor to Serial Entrepreneur with Keith Davenport
If you wanted to script the ultimate story of a radical life pivot, you would be hard-pressed to write something more dramatic than Keith Davenport’s journey. From a conservative evangelical pastor to a progressive political candidate, and finally to a neurodivergent serial entrepreneur, Keith…
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Way Out #16: She Walked Out of Manhattan Publishing With $25,000 and No Plan with Alisa Messeroff
When Alisa Messeroff was three years old, she had her first spirit visitation—a presence at the foot of her bed that she found magical, but which terrified her overprotective mother, who told her she was making it up. For the next two decades, Alisa silenced the thing that made her different and...
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Way Out #15: From Startup Toxicity to Building a Balanced Life with Anna Duin
Anna Duin spent 11 years doing marketing at startups — always doing the work of multiple people for the price of one. She navigated layoffs, negotiated flexible hours, and went through two terrifying years with a seriously ill child while her last company turned toxic. When she finally left, she...
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Way Out #14: Leaving a $200K Salary to Build an Indoor Dog Park with Devon Brown
“I did the math on how many years until retirement and said f*** that.” Devon Brown spent a decade climbing the corporate ladder — leading massive projects, earning six figures, and waking up every day wondering “is this it?” It took a national ADHD medication shortage to crack her eyes open to...
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Way Out #13: From 25 Years in Corporate PR to Building an Agency on His Terms with John McCartney
After dedicating 25 years to the fast-paced public relations industry across New York and San Francisco, John McCartney realized his career had plateaued and he was no longer feeling challenged. When his agency faced headwinds at the beginning of 2020, John found himself at a definitive fork in…
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Way Out #12: She Left Corporate Innovation to Build a Human-Centered Business with Ari DeGrote
We are often told that if you work hard, follow the rules, and land a great corporate job, you will ultimately feel fulfilled. But what happens when you reach that milestone and realize you feel completely stagnant? In this episode, we sit down with Ari DeGrote, a former corporate change…
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Way out #11: She Left Corporate and Her Marriage to Build the Impossible With Sarah Hartenberger
What do you do when you're frustrated by a broken system? If you're Sarah Hartenberger, you spend five years becoming the expert who fixes it. Sarah came from the world of corporate market research — working with global brands, climbing the ladder — until the birth of her son revealed a gap in...
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Way Out #10: From High Control Religion to Freedom Abroad With Andie Eggimann
"Every time I left America, I felt like I was coming up for air." Andie Eggiman spent over a decade in a high-control religious environment — one that slowly dismantled her confidence, buried her career ambitions, and told her exactly who she was allowed to be. She gave up a full-ride scholarship...
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Way Out #9: From $400 in the Bank to Retired at 40 with Aaron McHone
"Ultimately, I want peace." After 13 years at USAA, Aaron reached a point most people only dream of: he retired at 40. He didn't win the lottery or inherit a fortune; he and his wife spent years living intentionally, eliminating every cent of debt, and following a movement known as FIRE…
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Way Out #8: From Tech to a Micro-School in Nature: What Cancer Made Clear with Lauren Tarpley
"I am elated with 97% of my life." Lauren Tarpley says this without hesitation. After a 20-year career in tech strategy and customer success, a breast cancer diagnosis at 34, six rounds of chemo, radiation, immunotherapy, a double mastectomy, staph, MRSA, and 11 surgeries, Lauren reached a…
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Way Out #7: From Emmy-Winning Oprah Producer to Entrepreneur and Puppeteer with Lisa Weiss
She was an Emmy-winning producer at the pinnacle of her industry. Then, she lost it all and found something better. Lisa Weiss spent nearly two decades mastering the art of storytelling on some of television’s biggest stages—from the chaotic energy of The Jenny Jones Show to the spiritual depth…
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Way Out #6: She Left Her Marriage and Corporate For a Camper Van and the Smokies with Taylor Surdyke
On paper, Taylor Surdyke had it all: the husband, the suburban house, and a rising career in logistics management. But deep down, she knew something was wrong. In this episode, Taylor shares the defining moment she realized that "safety" wasn't a good enough reason to stay—first in her marriage,...
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Way Out #5: From Corporate Art Director to Watercolor Artist with Ken Stanek
Interested in learning how to manifest a layoff and start a creative career? You're in the right place. Ken Stanek spent 20 years in corporate design jobs that sucked the soul out of him. From DIRECTV to pharmaceutical ad agencies, he felt like he was wearing a mask every day. So, he decided to...
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Way Out #4: She Had Tenure, a Marriage, and a Child: It Was Slowly Killing Her with Dr. Risa Stein
Most of us are taught that strength means pushing through, never complaining, and achieving at all costs. But what happens when that definition of "success" nearly kills you? In this episode, we sit down with Dr. Risa Stein, a clinical psychologist turned tech founder, who spent 25 years in...
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Way Out #3: From a 6,000 Sq Ft House to Worldschooling in Spain with Jane Hermstedt
Do you think you need a massive passive income stream or a trust fund to quit your corporate job and move abroad? Jane Hermstedt is here to prove you wrong. Jane didn't leave her Director role at AMC because she "found herself" on a yoga retreat. She left because the math of her life stopped…
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Way Out #2: From Praying to Get Fired to Quadrupling Her Income with Christine Bridger
Have you ever sat at your desk and secretly prayed to get laid off? For 20 years, Christine Bridger did everything right. She climbed the executive ladder at massive agencies like Digitas and Razorfish. But while her title said "Success," her body said "Help." When layoffs swept through her...
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Way Out #1: Corporate Ladder to Costa Rican Freedom with Mike Messeroff
From corporate career to Caribbean clarity—why Mike Messeroff walked away from “having it all.” What happens when you follow the rules, hit every milestone, and still feel empty? In this first episode of 101 Ways Out, I talk with Mike Messeroff, a former JetBlue manager who seemed to be living…
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ABOUT THIS SHOW
Have you ever felt stuck, trapped, and unhappy, wishing for a way out? Did you check all the boxes, climb the ladder, and realize you weren't happy?
101 Ways Out exists for that moment.
In this series, I interview people from all walks of life who got to that exact point and realized they could take action to build the life of their dreams.
My goal is to share their stories to inspire you to do the same.
HOSTED BY
101 Ways Out
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Frequently Asked Questions
How many episodes does 101 Ways Out have?
101 Ways Out currently has 34 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is 101 Ways Out about?
Have you ever felt stuck, trapped, and unhappy, wishing for a way out? Did you check all the boxes, climb the ladder, and realize you weren't happy? 101 Ways Out exists for that moment. In this series, I interview people from all walks of life who got to that exact point and realized they could...
How often does 101 Ways Out release new episodes?
101 Ways Out has 34 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to 101 Ways Out?
You can listen to 101 Ways Out on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts 101 Ways Out?
101 Ways Out is created and hosted by 101 Ways Out.
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