101 Ways Out – Details, episodes & analysis

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101 Ways Out

Business

Frequency: 1 episode/7d. Total Eps: 23

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.

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Apple Podcasts

🇨🇦 Canada - careers
21/06/2026
#62

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https://www.linkedin.com/company/101waysout/
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https://linkedin.com/company/101waysout/
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https://www.linkedin.com/in/annepao/
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https://www.instagram.com/101waysout
12 shares
https://www.instagram.com/tay_dointhings
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https://www.instagram.com/haleyirenesings
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RSS feed quality

Good

Score global : 73%

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Way Out 23: From Corporate Gaslighting to Total Freedom with Karol Figueroa

Season 1 · Episode 23

Thursday, June 18, 2026 • Duration 01:32:14

"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 company, she watched them coldly dismiss her need for flexibility during a grueling, $100,000 custody battle.

But the real wake-up call came from her 4-year-old daughter. While Karol was working late one night to pay for a lavish lifestyle, her daughter looked at her and said the five words that changed Karol's life forever: "Mom, but I already love you."

Today, Karol is the Founder and CEO of HIK Trainings. She traded her BMW for an electric Mini Cooper, fired her toxic corporate bosses, and built a life where she has the ultimate freedom to be fully present with her family.
In this episode, you will learn:

→Why corporate loyalty is an illusion (and how to protect yourself).
→How to handle toxic managers and narcissistic gaslighting in the workplace.
→The exact financial strategy Karol used (including leveraging company stock) to fund her escape.
→Why you must uncouple your identity from your job title.
→How to stop buying your way to happiness and redefine what "success" actually looks like.

🔗 Links & Resources:
Connect with Karol & HIK Trainings: www.hiktrainings.com

Want to chat about your own Way Out? Grab some time on Vanessa's calendar: https://calendly.com/leva-app/leva-vanessa-c200?month=2026-06

101 Ways Out explores how thoughtful, capable people step away from inherited definitions of success and begin designing lives rooted in freedom, meaning, and joy.

Through intimate conversations with founders, creatives, coaches, executives, and explorers, host Vanessa Jupe uncovers the moments that changed everything: burnout, clarity, fear, courage, and the decision to choose a different path.

These are not overnight success stories. They are real conversations about identity, autonomy, money, fear, creativity, and what it actually takes to build a life that lights you up.

🎧 New episodes weekly
🌱 Part of the 101 Ways Out transformation platform

🔗 Learn more: (https://101WaysOut.com)
📷 Instagram: (https://instagram.com/101waysout)
💼 LinkedIn: (https://linkedin.com/company/101waysout/)

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Way Out #22: Putting Payroll on Credit Cards: Then His Son Was Born Nine Weeks Early with Brian Best

Season 1 · Episode 22

Thursday, June 11, 2026 • Duration 59:12

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 "safe" government pension at 24 years old after drowning in toxic bureaucracy and entitled "boss-holes". Armed with a book on starting a business that he bought in 1996, he launched Best Macs, a Kansas City-based IT company.

But building an empire wasn't a straight line. Brian shares the raw reality of his entrepreneurial journey: from cold-calling creative agencies with hand-drawn business cards, to getting crushed by the 80/20 rule in retail, to the terrifying family emergency that forced him to drop from working 80 hours a week down to just 10.

That crisis sparked his ultimate "Way Out." Brian completely transformed his business model from an exhausting, hourly "feast or famine" cycle into unstoppable, flat-fee recurring revenue. Today, at 50, he successfully runs his business from the passenger seat of an RV while taking multi-week cross-country road trips with his family.

In this episode, you will learn:

Why trading your time for money is a trap (and exactly how to escape it).
How to pivot your business model so your income becomes predictable and reliable.
The danger of the 80/20 rule: Why too much of the wrong business will kill you.
Why your talent alone isn't enough to sustain a business (and the first hire you actually need to make).
How to build a team and systems that allow you to step away without the ship sinking.

Stop researching your escape plan and start planning. Hit play to hear Brian’s masterclass in pivoting!

🔗 Links & Resources:

Way Out #13: From 25 Years in Corporate PR to Building an Agency on His Terms with John McCartney

Season 1 · Episode 13

Monday, March 30, 2026 • Duration 47:50

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 the road: dust off his resume to work for another agency, or take the terrifying leap to chart his own path.

He chose the latter, founding JMAC PR. But John didn't just want to build another PR firm; he wanted to completely overhaul toxic agency culture. Driven by the philosophy that "we work to live, we don't live to work," John built his boutique agency with workplace wellness embedded directly into its DNA. Today, he joins us to talk about his incredible journey from a small-town reporter to a successful agency founder who puts the mental health and well-being of his team above the traditional corporate grind.

In this episode, we cover:

The Bronx Foundation: How growing up in a single-parent household with a mother who worked seven days a week as a bank teller and at a bakery instilled a relentless work ethic and grounded perspective.
The Leap of Faith: The fear of leaving behind the security of a consistent corporate paycheck to start a business from scratch, and why John decided it was worth the risk to live a life without regrets.
Redefining Agency Culture: Why John refuses to be a boss who demands 20-hour workdays. Instead, he hired a fractional HR director and a transformational consultant to meet one-on-one with his team, ensuring every employee feels seen, heard, and supported both personally and professionally.
The Reality of Founder Income: The "rude awakening" of shifting from guaranteed, predictable corporate pay to structuring an S-Corp, balancing an owner's draw with a "reasonable salary," and navigating the tight financial realities of business ownership.
Choosing Happiness Over Success: Why John actively prioritizes his mental and physical health through 10 minutes of daily meditation, two-mile walks, and therapy, proving that true success is actually found in peace and balance.

Way Out #12: She Left Corporate Innovation to Build a Human-Centered Business with Ari DeGrote

Season 1 · Episode 12

Tuesday, March 24, 2026 • Duration 01:13:02

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 management and innovation leader who realized she had hit her corporate "expiration date."

For nearly a decade, Ari led leadership growth cohorts for venture-backed tech founders at the Sprint/T-Mobile Accelerator. She was deeply proud of her work, but after navigating a chaotic "triple whammy"—returning from maternity leave, the onset of the COVID-19 lockdowns, and a massive corporate merger all within a two-and-a-half-month window—she realized she was facing a split in the road.

Ultimately, Ari realized she was running towards something rather than just running away. She took a highly strategic leap to build Upward & Inward, a solo coaching and consulting practice where she helps impact-driven leaders merge people, profit, and purpose. Today, she joins us to share her journey of redesigning her life for ultimate autonomy, getting out of the corporate box, and learning to tune back into her intuition.

In this episode, we cover:
- The Corporate "Expiration Date": How to recognize when you've outgrown your environment, and why Ari decided the risk of ignoring her passion was greater than the terrifying leap into entrepreneurship.
- Prototyping Your Exit: How Ari strategically used virtual "coffee connects" during the pandemic to validate her business and sign her first major clients before ever handing in her notice.
- Designing a "Life System": How Ari radically restructured her week, including reserving her Fridays entirely for creative writing, big ideas, and true autonomy.
- Embracing the "Woo": Why Ari practices "emotional alchemy" and somatics to tune into her body's wisdom, pushing back against the corporate conditioning that tells us to only live "from the ears up."
- Unconventional Life Hacks: Ari shares how she uses ChatGPT to organize her brain during anxiety spirals, why she joins virtual "cocoon" co-working spaces for one-minute dance parties, and how she intentionally used adult intramural kickball leagues to build her community from scratch in new cities.Ari's ultimate advice for anyone looking to make a change? Don't take yourself so seriously, treat every failure as useful data, and learn to love the "never-ending" process of iteration.Where to find Ari DeGrote:LinkedIn: Website: ----101 Ways Out explores how thoughtful, capable people step away from inherited definitions of success and begin designing lives rooted in freedom, meaning, and joy.🎧 New episodes weekly🌱 Part of the 101 Ways Out transformation platform🔗 Learn more: 📷 Instagram: 💼 LinkedIn:

Way out #11: She Left Corporate and Her Marriage to Build the Impossible With Sarah Hartenberger

Season 1 · Episode 11

Sunday, March 15, 2026 • Duration 01:23:14

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 postpartum care she couldn't unsee. Struggling to breastfeed and feeling failed by the resources available to her, she made a decision: she was going to become the support she wished she'd had.

Getting there wasn't simple. Sarah didn't have a healthcare background — just degrees in communications and Spanish and a drive that, as she puts it, makes people want to get out of her way. She took anatomy, physiology, biology, and nutrition courses from scratch. She negotiated a part-time role at her old marketing job to fund the transition. She clocked over 1,000 clinical hours. And when the governing body changed the certification pathway mid-journey and threatened to set her back seven years, she found another way.

Then her marriage ended — and rather than retreat to the safety of corporate, she went all-in on her business. Today, Nurture Lactation KC is a team of 7 IBCLCs serving families across Kansas City, operating in-network with major insurance providers, and fighting publicly for lactation care to be recognized — and covered — as the essential healthcare it is.

In This Episode

The "nap time warrior" years: how Sarah built her certification while working part-time and raising a toddler
Why she negotiated a flexible role at her old company, and what her mom's advice had to do with it
Sink or swim: going full-time in her business after her divorce
The moment she realized she "likes to go against the grain" in her 30s
Fighting insurance companies to enforce what the ACA already requires
Why she caps her own income, and why that's actually a power move
"Who made these rules? I'm making new ones."

Way Out #10: From High Control Religion to Freedom Abroad With Andie Eggimann

Season 1 · Episode 10

Monday, March 9, 2026 • Duration 01:27:35

"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 to her master's program because the church told her she was "a wife now." She got married young, started having kids, and learned to question her own instincts.

But as Andie slowly deprogrammed and found her way back to herself, she began noticing those same high-control patterns — the demand for hierarchy, the narrowing of identity, the use of ideology to justify control — spreading across the broader American landscape. She recognized it immediately: she wasn't just escaping a church. She was escaping a country moving in the same direction.

So she and her husband packed up their family of seven — including children with significant developmental delays — and moved to Portugal.

In this episode of 101 Ways Out, Andie shares:

The slow, invisible mechanics of high-control environments
How she and her husband deprogrammed and rebuilt a true partnership of equals
What actually made them take the leap — and how they went from "accidentally nomadic" to planted in Portugal
The logistics of moving a family of seven abroad, including kids who needed extra support
Why aging parents and kids at home don't have to be dealbreakers for living abroad
How she went from drowning in America to breathing freely

This conversation is a masterclass in reclaiming identity.

Time stamps:

00:00 – "I feel more alive than I've ever felt before"

Way Out #9: From $400 in the Bank to Retired at 40 with Aaron McHone

Season 1 · Episode 9

Monday, March 2, 2026 • Duration 01:13:31

"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 (Financial Independence, Retire Early).

But the story didn't end with a permanent vacation. After six years of "pure bliss" as a stay-at-home dad in Costa Rica and Puerto Rico, Aaron did something even more unexpected:
He went back to work.

In this episode of 101 Ways Out, Aaron shares:
- How he paid off his house and all debt by his early 30s
- The "debt snowball" method that changed his financial trajectory
- What it’s really like to be retired for six years with four young kids
- The "plot twist" that led him back to the corporate world as a consultant
- Why your identity shouldn't be tied to a title—even the title of "retired"

His 10-year template for designing a life you actually want to live

We talk about:
- The "boring" middle of financial independence
- Trading conference calls for school drop-offs
- The "boys who brunch": finding community as a stay-at-home dad
- Why he wasn't scared when he finally got laid off
- Lifestyle inflation vs. retirement reality
- Redefining success so you get "happiness for free"
- And why he still chooses to snuggle his kids a little longer

If you’ve ever felt like 65 is too long to wait…
If you’re curious about the reality of the FIRE movement…
If you want to know how to reclaim your time before it’s gone…

This conversation is a masterclass in intentionality.

Follow Aaron’s Work
🔗 Aaron McHone on LinkedIn - https://www.linkedin.com/in/aaronmchone/
🌎 Live Your Wage - https://liveyourwage.com/Listen to more stories of reinvention:🎧 Subscribe to 101 Ways Out - #FIREMovement #FinancialIndependence #EarlyRetirement #IntentionalLiving #101WaysOut #DebtFree #StayAtHomeDad #CareerPivot #redefiningsuccess

Way Out #8: From Tech to a Micro-School in Nature: What Cancer Made Clear with Lauren Tarpley

Season 1 · Episode 8

Monday, February 23, 2026 • Duration 01:13:35

"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 breaking point.

When she returned to work and heard someone refer to her life-saving medical leave as a “vacation,” the corporate mask fell.

Instead of doubling down, she redesigned her life.

Today, Lauren lives on six acres of land where she is building the Academy of Agriculture & Technology — a micro-nature school rooted in survival skills, intentional technology, and raising sovereign kids. She runs The Farmacy CHS (because food is medicine), manages over 80 birds producing rainbow eggs, and is creating a life she calls 97% her dream.

In this episode, we talk about:

Surviving cancer while working in tech
The moment corporate culture revealed itself
Why “power is only perceived”
Getting laid off during the Silicon Valley Bank collapse
Measuring soil, not metric
Health as wealth
Protecting your bandwidth
And what it means to “do it scared”

This conversation isn’t about quitting. It’s about reclaiming.

🌱 Follow Lauren’s Work

Lauren is building a life rooted in soil, sovereignty, and survival skills.

Learn more about:

🌾 The Farmacy CHS

Way Out #7: From Emmy-Winning Oprah Producer to Entrepreneur and Puppeteer with Lisa Weiss

Season 1 · Episode 7

Monday, February 16, 2026 • Duration 01:24:19

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 of Oprah’s Super Soul Sunday. But when a sudden layoff coincided with a high-risk pregnancy, Lisa was forced to reimagine her life without the safety net of a corporate identity.

In this episode of 101 Ways Out, Lisa joins Vanessa to discuss the messy, non-linear path from "dream job" employee to reluctant entrepreneur. She opens up about the trap of listening to the wrong advice (and building a tech company she hated), the liberation of performing a puppet show about mansplaining, and how she and her husband use a "10-Year Family Vision" to design a life of intention.

In this episode, we cover:

The Reality of "Trash TV": What she learned working on The Jenny Jones Show versus Oprah.
The Crisis: Navigating a layoff while pregnant and the fear of being "unhireable."
The False Start: Why she spent months building a "scalable" MVP she didn't care about—and how she corrected course.
Creative Courage: How a 7-minute puppet show unlocked her business confidence.

Connect with Lisa:

Way Out #6: She Left Her Marriage and Corporate For a Camper Van and the Smokies with Taylor Surdyke

Season 1 · Episode 6

Monday, February 9, 2026 • Duration 01:01:54

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, and then in her career.

We discuss her spiritual awakening, how she negotiated an 8-month exit strategy from her corporate job, and why she is selling it all to live in a camper van in Appalachia. Taylor proves that if you can walk away from a marriage that is "fine" but not "right," you can certainly walk away from a job that is just a paycheck.

Taylor breaks down how she recognized the "karmic patterns" that were keeping her stuck and the specific moment she decided to trade her 9-to-5 for life on the road. We talk about the terrifying freedom of the unknown, how to spot the signals that your life is out of alignment, and her number one piece of advice for anyone waiting for the perfect time to pivot: "Do it scared."

Follow Taylor:

https://www.instagram.com/tay_dointhings/

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101 Ways Out explores how thoughtful, capable people step away from inherited definitions of success and begin designing lives rooted in freedom, meaning, and joy. Through intimate conversations with founders, creatives, coaches, executives, and explorers, host Vanessa Jupe uncovers the moments that changed everything: burnout, clarity, fear, courage, and the decision to choose a different path. These are not overnight success stories. They are real conversations about identity, autonomy, money, fear, creativity, and what it actually takes to build a life that lights you up.

🎧 New episodes weekly

101 Ways Out – Details, episodes & analysis

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101 Ways Out – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other35

LinkedIn10

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Latest published episodes

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