"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/)

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:

• Read Brian's full story on the blog: https://www.101waysout.com/interviews/way-out-22-he-was-putting-payroll-on-credit-cards-then-his-son-was-born-nine-weeks-early-with-brian-best
• Connect with Brian Best & explore his managed services: ⁠BestMacs.com⁠

Don’t forget to subscribe so you never miss an inspiring story of everyday people doing extraordinary things to find their freedom!

#101WaysOut #Entrepreneurship #RecurringRevenue #RVLife #LeaveCorporate #SmallBusinessTips #ITManagedServices #WorkFromAnywhere #TimeFreedom

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.

John's ultimate advice for taking the leap? Figure out what brings you joy and what you are good at, then just jump in. The worst-case scenario is that it doesn't work out and you go back to working for someone else—but you owe it to yourself to try.

Where to find John McCartney:

• Website: jmacpr.com
• LinkedIn: John McCartney
• Email: john@jmacpr.com

------------------------------------------ 

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: ⁠https://101WaysOut.com⁠

📷 ⁠Instagram⁠

💼 ⁠LinkedIn⁠

🎥 ⁠YouTube⁠

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: https://www.linkedin.com/in/aridegrote/
Website: upwardandinward.com

----

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: https://101WaysOut.com
📷 Instagram: https://instagram.com/101waysout
💼 LinkedIn: https://www.linkedin.com/company/101waysout/

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."
• What lights her up: seeing moms recognize their own power

Connect with Sarah

Instagram: @NurtureLactationKC

Website: nurturelactationkc.com

Email: hello@nurturelactationkc.com

Find 101 Ways Out

Website: 101waysout.com

"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"
• 01:08 – Introducing Andie: trip designer and move-abroad expert
• 03:02 – The #1 limiting belief: moving abroad with kids
• 19:46 – Getting pulled into high-control religion in college
• 20:15 – "Religion isn't a problem. High control religion is."
• 23:24 – Getting married young and quitting her master's degree
• 32:45 – The long road of deprogramming
• 42:05 – Christian nationalism and recognizing the pattern
• 48:08 – "Every time I left America, I felt like coming up for air"
• 51:39 – Becoming "accidentally nomadic"
• 57:30 – Portugal: first stop, now home for three years
• 1:00:22 – "I'm able to be present to my life a lot better here"
• 1:09:04 – Was it scary to leave? (Two very different answers)
• 1:15:45 – Happiness or success — which would you choose?
• 1:19:26 – Most liberating decision: "Learning to listen to myself"
• 1:26:23 – Where to find Andie

Follow Andie's Work

• 📷 ⁠Instagram⁠, ⁠YouTube⁠, & ⁠Threads⁠: ⁠@OneDaringAdventure⁠
• 🌎⁠ ⁠Get Me Out of Here Workshop⁠⁠ — a first step for anyone wondering if life abroad could work for them

Listen to more stories of reinvention: 🎧 ⁠Subscribe to 101 Ways Out

⁠

#MoveAbroad #HighControlReligion #ExpatsAbroad #LifeInPortugal #FamilyAbroad #101WaysOut

"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 - https://www.101waysout.com

#FIREMovement #FinancialIndependence #EarlyRetirement #IntentionalLiving #101WaysOut #DebtFree #StayAtHomeDad #CareerPivot #redefiningsuccess

"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 ⁠https://thefarmacychs.com/⁠

🏫 The Southeastern Academy ⁠https://thesoutheasternacademy.com/⁠

📘 Type A Guide to Cancer ⁠https://amzn.to/40omWxt⁠

📘 Type A Guide to Survivorship ⁠https://amzn.to/4kOMcq4⁠

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:

• Website: ⁠StoryBeatStudio.com⁠
• Project: ⁠ObjectDiaries.com⁠
• LinkedIn: ⁠Lisa Weiss⁠

------------------------------------------ 

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.

🔗 Learn more: ⁠https://101WaysOut.com⁠

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/

------------------------------------------ 

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

💼 ⁠LinkedIn⁠

🎥 ⁠YouTube⁠

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 stop pretending. He quietly built his portfolio, "manifested a layoff," and used his severance to jump into a full-time art career.

In this episode, Ken shares his refreshingly honest business strategy: "F*ck around and find out" in the best of ways.

We discuss why you don’t need a master plan; you just need the willingness to throw pasta at the wall and see what sticks. From painting pet portraits in a Slack channel to landing massive mural commissions, Ken reveals the messy, terrifying, and exhilarating reality of working for yourself. In this episode, you will learn:

• The "Body Check": How Ken knew watercolor was his medium (and corporate wasn't) based on physical reaction.

• The Exit Strategy: How to use a corporate job as a runway to build your safety net.

• The Financial Reality: The truth about self-employment taxes, fluctuating income, and the "exhilaration vs. terror" ratio.

• The "Maus" Story: How a stint as a NYC bike messenger led to his most prized possession.

Resources:

• Follow Ken: ⁠@StudioNumberNine⁠

• Check out his work: ⁠www.studionumbernine.net⁠

------------------------------------------

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

🔗 Learn more: ⁠https://101WaysOut.com⁠

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 academia checking every box—PhD, tenure, marriage, house—until a near-death health crisis forced her to stop.

We discuss how she went from “suffocating” in a tenure-track career to launching a digital health startup, SeeInMe, in her 50s. If you feel successful on paper but stuck in real life, this conversation is the permission slip you’ve been waiting for.

👇 IN THIS EPISODE WE COVER:
➡️ The danger of the "high-achiever" coping strategy
➡️ The medical emergency that changed her life instantly
➡️ How to pivot when you are terrified of losing your identity
➡️ The exact email subject line she used to ask for help (“Help. I’m suffocating.”)
➡️ Why she traded the safety of academia for the chaos of startup life
➡️ How to build a life that feels as good as it looks

🔗 MENTIONED IN THIS EPISODE:
SeeInMe: https://seeinme.com/
The Best Damn Life Workbook: https://www.amazon.com/Best-Damn-Life-Workbook-Personally/dp/0985677937
Connect with Dr. Risa Stein: https://www.linkedin.com/in/risa-stein123/


TIMESTAMPS:
00:00 - Introduction
09:53 - The making of a high achiever
16:36 - The near-death wake-up call
29:38 - Overcoming the fear of leaving academia
35:14 - Redefining success & happiness
40:05 - The "Help, I'm suffocating" email

#CareerChange #Burnout #Psychology #Entrepreneurship #101WaysOut #RisaStein #MentalHealth #MidlifePivot
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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
🌱 Part of the 101 Ways Out transformation platform

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

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, Jennifer shares her zigzagging journey from being a teen mom who launched a successful boutique, to a corporate retail buyer, to eventually booking a one-way ticket to Shanghai. She opens up about the raw reality of arriving in a foreign country to an absolute disaster, how she pivoted to save her own dream, and how she eventually found her way to Europe. Today, Jennifer is the founder of Viamond, a European relocation and citizenship concierge, running her business from her dream apartment in Sicily.

In this episode, we cover:

• Why achieving the ultimate "dream job" on paper is often a nightmare in reality.
• The raw truth about navigating sexual harassment in the corporate world.
• How to handle the terror of a massive pivot when everything goes completely wrong.
• Why Jennifer traded her goal of making the "40 under 40" list for a life of simple happiness and autonomy.

3 Tips for Wayfinders:

1. Stop researching and start planning. You can spend 20 years researching your dream, but it will never happen until you set a hard date. Give yourself a deadline, put it on the calendar, and work backward.
2. Trust that you can survive the worst-case scenario. When Jennifer arrived in China, she was there illegally and her housing was a disaster. Instead of panicking, she trusted her grit, booked a room at the Ritz, and figured it out.
3. Your trauma can become your trade. Jennifer's frustrating, messy experience navigating the Italian citizenship process organically led her to help others, ultimately birthing a massive relocation company.

Follow Jennifer's Journey: If you want to explore moving abroad, securing dual citizenship, or just want to follow her beautiful Sicilian life, visit her at ⁠Viamond.eu⁠ or reach out to her on Reddit where she is known as the legendary "China cat lady"!

Find your own way out

The 101 Ways Out 30-Day Program takes you on a journey from where you are to where you're meant to be. ⁠Learn more here⁠.

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 adding up. She was trading her son’s childhood for a title and a massive mortgage.

In this deeply practical conversation, Jane pulls back the curtain on the logistics of leaving. She explains how her family used data, modeling inflation, investments, and cost-of-living projections, to know exactly when they could pull the ripcord.

Jane traded the American Dream for an ex-military RV in South America, and eventually, a quiet village in Spain.

Tune in to hear:

• Why you need a "core assumption" of possibility before you start planning.
• The financial reality of trading a 6,000 sq ft house for an 80 sq ft truck.
• How to build resilience in your kids through "worldschooling" (and navigating foreign bureaucracies).
• Why "success without happiness" is no success at all.

Follow Jane

• 🌐 Niveus Travel
• 📲 Instagram @niveustravel

Jane Hermstedt is proof that you don't have to choose between being a responsible parent, a successful professional, and a wild adventurer. You just have to be willing to sell the house, trust the spreadsheet, and occasionally, get stuck in Patagonia.

About 101 Ways Out

🛤️ 101 Ways Out shares real stories of thoughtful, capable people who reimagined their lives. These aren’t overnight success stories—they’re deep, honest conversations about intuition, healing, fear, freedom, money, and the courage to choose a new path.

Connect with 101 Ways Out

🌍 https://www.101waysout.com
📸 Instagram: @101waysout

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 industry, she found herself as the "last person standing"—and realized the terrifying truth: the corporate machine wasn't going to save her. She was going to have to save herself.

In this episode, Christine takes us through both the strategic and the internal pivot of her exit. She shares how she moved from a "puddle of tears" in her driveway to becoming the happiest, most confident version of herself.

She didn't just trade a job for a new career. She traded anxiety for agency—and happened to quadruple her corporate income along the way.

In this conversation, we explore:

• The Breaking Point: Why "praying to get fired" is a warning sign you can't ignore.

• The Inward Shift: Navigating the identity crisis of "Who am I without the big job?"
• The "Dabble Map" Strategy: The practical tool she used to replace her salary with 65 diverse projects.
• The Myth of Focus: Why being a "scattered" generalist is actually safer than being a loyal specialist.
• The Real ROI: How she stopped bargaining with the universe and started building her own safety net.

If you are successful on paper but suffocating on the inside, this episode is your permission slip to build a life you actually own.

Connect with Christine

Christine has intentionally kept a low public profile. If you’re curious to see the end result of some of what she’s built, you can explore her home and lifestyle brand:⁠

🌿 Company & Cottage⁠

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

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 the dream—until a lunch break epiphany changed everything. He and his wife sold everything, moved to the Virgin Islands, and began chasing what really matters.

🌴 But it wasn’t the scenery that changed his life—it was what he learned along the way.

This episode dives into:

• Why changing your zip code doesn’t fix internal misalignment
• The hidden depression that surfaced while skiing 100 days/year
• How therapy, meditation, and breathwork helped Mike rebuild from the inside out
• His journey from bartending to coaching burned-out professionals
• The myth of retirement—and why deferring joy is a dangerous practice
• The intergenerational trauma around money, work, and self-worth
• And why embodying joy may be the most radical thing you can do

“If I didn’t stop and enjoy my life, I’d be slapping every generation in the face who came before me. They suffered so I could be free.”

🎧 This is not just a story about quitting a job—it’s about healing, redefining success, and creating a life aligned with your values.

More stories: ⁠https://www.101waysout.com⁠

Connect with Mike:

🌿 ⁠The Self-Hospitality Collective⁠

📬 ⁠The Circle of Free Thinkers⁠

📲 Instagram + TikTok: ⁠@mikemesseroff⁠

Connect with 101 Ways Out:

📸 Instagram: ⁠@101waysout⁠

🌍 Website: ⁠https://www.101waysout.com⁠

🛤️ 101 Ways Out shares real stories of thoughtful, capable people who reimagined their lives. These aren’t overnight success stories—they’re deep, honest conversations about purpose, healing, fear, freedom, and the courage to choose a new path.

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 being a "workhorse."

But muscling through eventually takes a devastating toll.

In this episode, Haley opens up about the extreme corporate burnout that pushed her body to its absolute breaking point — and how being laid off from her executive "dream job" ended up being the ultimate blessing in disguise.

Today, Haley is the founder of A Lighter Way Consulting, where she uses her decade of HR experience to help driven women in tech navigate burnout and partners with startups to humanely handle layoffs.

She shares her strategies for dealing with the terror of entrepreneurship, how to honor your body's natural energy cycles, and why she is manifesting abundance one penny at a time.

If you are exhausted from trying to prove your worth to toxic corporate environments, Haley's story is a beautiful reminder: you do not have to sacrifice your health and happiness to be successful.

───────────────────────────── IN THIS EPISODE: ───────────────────────────── ▸ The trap of the "workhorse" mentality and how to recognize when your body is sounding the alarm ▸ Why achieving the ultimate corporate title and salary might not actually bring you peace ▸ How to handle the fear of the "messy middle" of entrepreneurship ▸ Redefining success: from seeking external validation to building a grounded certainty in yourself

───────────────────────────── 3 TIPS FOR WAYFINDERS: ─────────────────────────────

1. Treat fear like a passenger, not the driver. Haley recommends personifying fear as a scared three-year-old version of yourself. Put them in the backseat and remind them: "You don't get to drive this car. I'm driving."
2. Follow the energetic breadcrumbs. If you have a yearning or a pull toward something more, that is your truth — and it deserves to be followed. Start leaning into the things that bring you joy. Those small breadcrumbs will point you toward your next step.
3. Communify your life. You do not have to figure out your next steps alone. Find people already doing the things that make you say "I could never" and start having conversations with them. Community is how you take the tiny steps forward you need to launch your own dream.

───────────────────────────── CONNECT WITH HALEY: ───────────────────────────── Instagram: https://www.instagram.com/haleyirenesings/ Email: hello@HaleyScruggs.com

FIND YOUR OWN WAY OUT:

https://www.101waysout.com/101-ways-out-thirty-day-program

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 Creative Director who escaped the toxic burnout of the traditional agency world to build her own fractional empire, Contrary Collective.

While Marianne took the leap into entrepreneurship with two toddlers at home, this isn't just a story about balancing motherhood and business. It is a masterclass in radical boundary-setting, unapologetic outsourcing, and industry disruption. Marianne breaks down exactly how she built her agency to run like a "hair salon for creatives." This unique structure enables her to partner top-tier talent directly with clients on passion-led projects without the unpaid weekends and corporate red tape.

We dive deep into the messy middle of entrepreneurship, including how she survived a terrifying dry spell, the exact words she used to turn down a client who tried to slash her budget to a third, and how she completely redefined what "success" looks like.

And the payoff for betting entirely on her own authority? Marianne is now projecting a $1M revenue close rate for this year.

If you are struggling with imposter syndrome or waiting for the "perfect time" to leave a job you hate, Marianne will inspire you to borrow some self-confidence and make the leap. As she brilliantly puts it: "If someone else trusts you to do the job, you're probably underselling yourself."

In this episode, we cover:

- The "30-Day Post-It Note Countdown" that led to her resignation.

- Why she intentionally built a fractional, 1099 agency model.

- How to set firm boundaries when clients try to underpay you.

- Why letting go of "mom guilt" (and unapologetically outsourcing the laundry) made her a better CEO and mother.

- The power of being of service to others when your business hits a slow period.

Follow Marianne

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

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 tight leash around the neck" of his employees. After it went too far, she formally reported her manager to HR for bullying and harassment. She was met with a retaliatory rating on her performance review. In the text, he explicitly complained about her HR escalations. 

Anne went away on vacation, but when she returned, everything changed. She was called into a meeting and told her position was suspiciously eliminated due to "redundancy".

Instead of letting a toxic corporate culture defeat her, Anne created a spreadsheet titled "Rising from the Redundancy Ashes like a Phoenix" and made a commitment to take one step every single day toward her new future.

Today, Anne has completely reclaimed her autonomy. She is the founder and CEO of Ignite Consulting, a fractional go-to-market and RevOps firm. She also founded RevOps Village, a thriving community of over 700 revenue professionals, and co-leads Women of Pavilion. By betting on herself, she not only gained the freedom to choose who she works with and when she works, but she now earns 25% to 45% more than her corporate salary while working fewer hours.

In this episode of 101 Ways Out, Anne opens up about her incredibly difficult exit from corporate tech, her nomadic and challenging childhood, and how to successfully pivot into fractional leadership.

In this episode, we cover:

➜ The Reality of Retaliation: Anne's harrowing experience with a hostile work environment, navigating HR, and ultimately being pushed out of her VP role.

➜ The "Redundancy Ashes" Blueprint: The exact step-by-step approach Anne took to build her consulting business from scratch immediately after losing her job.

➜ Building a Fractional Empire: How Anne leverages her deep expertise in operations and business intelligence to run Ignite Consulting.

➜ The Power of Community: Why Anne built RevOps Village and how making consistent "deposits" into your network is the ultimate lead-generation tool for entrepreneurs.

➜ Redefining Success: How Anne balances being a present mother and partner while working Monday through Thursday—proving you don't have to choose between success and happiness.

Connect with Anne Pao:

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

Ignite Consulting: www.igniteconsulting.co

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 has completely dismantled and rebuilt his life on his own terms.

In this episode of 101 Ways Out, Keith opens up about his profound transformation. He shares the historical discoveries that shifted his worldview and led him to step away from the church, and the grueling burnout he experienced managing crisis communications for a county of 600,000 people during the COVID-19 pandemic. Ultimately, it took a terrifying breaking point—and an urgent care visit for severe anxiety and undiagnosed ADHD—to push him to completely abandon the traditional career path.

Today, Keith is a thriving serial entrepreneur building an ecosystem of businesses in his hometown of Gardner, Kansas. We discuss how he launched his consulting firm, Blazer Strategies, acquired Ground House Coffee using seller financing, and founded the HR tech startup MythicHire to eliminate resume bias.

Update Since Recording: True to his serial entrepreneur nature, Keith has had a massive year since we sat down to record. He has stepped out of the CEO role at MythicHire to launch 030 Holding Company, a venture dedicated to acquiring small businesses using seller financing. His mission is to protect small business legacies and increase community wealth by creating jobs, increasing wages, and building profit-sharing tracks. They acquired their first business, Madison Street Threads, in October. He has also withdrawn from a planned 2026 State House run to focus entirely on his family, teaching business acquisitions at JCCC, and local advocacy—like working directly with his local police department to find humane alternatives for the unhoused.

In this episode, we cover:

• The Courage to Pivot: How to walk away from the path you thought you were "called" to when it no longer serves you.
• Mental Health as a Catalyst: Navigating extreme corporate burnout, late-diagnosed ADHD, and anxiety as an entrepreneur.
• Acquisition Entrepreneurship: How to successfully buy a business using seller financing.
• Redefining Success: Why Keith chose being a good dad and husband over traditional corporate power.

Connect with Keith Davenport:

• LinkedIn: linkedin.com/in/keithmdavenport
• 030 Holding Company: (Keep an eye out for his latest venture!)
• Blazer Strategies: blazerstrategies.com
• Ground House Coffee: groundhousecoffee.com
• MythicHire: mythichire.com

Listen now to hear Keith's incredible story of finding a Way Out!

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 performed the version of “normal” she was handed: high school, college, a corporate job in New York City.

In her corporate, she was promised a promotion two years in a row, and denied both times. The last was the straw that broke the camel's back.

Alisa looked her director dead in the eyes, said "F You", slammed his sliding glass door, and walked out.

Within weeks, she and her husband, Mike, had given up their Manhattan apartment, sold most of what they owned, and moved to St. John in the U.S. Virgin Islands.

Alisa threw herself onto a catamaran crew, worked as a guide, and taught herself photography on a camera she bought with her own money.

Then, on the last day of their time in St. John, the hives started.

She was covered from head to toe. Her tongue swelled. She took prednisone and ended up with moon face. A parade of American doctors couldn’t name what she had, and one of whom told her she would likely have to live on steroids for the rest of her life. She was terrified that she was going to die.

Out of money and out of options, Alisa and Mike decided to continue their journey around the world, from Hawaii to Australia. Alisa said, “If I’m going to die, I’m going to die doing what I love.”

A woman in a caravan park in Broome, Australia, whom Alisa now calls her angel, booked her an appointment with a naturopath. Four days after starting a protocol of Chinese herbs, the hives subsided. Alisa would not find out until years later, back in Costa Rica, that what she actually had was alpha-gal syndrome—a tick-borne illness that makes your immune system attack mammal products. Diagnosis finally came after a decade of symptoms.

That is only part of her story.

The other half is the spiritual journey she spent most of her life running from:

• A vision on an acupuncture table of a little boy being hit by a truck came true three months later in her own neighborhood.
• A Quantum Healing Hypnosis Technique (QHHT) session where she met a spirit guide named Iribella, who told her the hives were her teacher, not her enemy.
• Two separate Reiki sessions where, by her own account, spirit stepped into her body and used her as a conduit. One of which, she would later learn, had intervened with a client who had a handful of pills in her hand the night before.

Today, Alisa is in her early 40s. She splits her year between Breckenridge, Colorado and Tamarindo, Costa Rica.

She and Mike are openly polyamorous.

She is a certified Reiki practitioner, a breathwork facilitator, a professional photographer, a mindset and manifestation coach, and a business mentor.

She is also, by her own admission, “very woo... but also very grounded,” and she is enrolling this fall to become a clinical herbalist, completing the loop Iribella told her about five years earlier.

Her mantra: “Everything is always working out for me,” has become a core belief. She sits in it. She feels it surge through her body. And she has built a life that lets her wake up, every single morning, genuinely excited about what is in store.

This is one of the most spiritually fascinating conversations we’ve had on the show. If you have ever wanted to be connected to something greater than yourself, this is the show for you.

Website: alisamesseroff.com

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 didn’t have a plan. She just knew it was time to build her own thing. This is what happened in the year that followed.

Anna Duin grew up in a family that didn’t follow conventional rules. Born in Stockholm, Sweden to missionary parents, homeschooled, moved to Kansas City at 8. Her mom’s mantra: your time and your freedom are your biggest assets. Build a life that reflects what you actually value.

It took Anna about 11 years in startup marketing to really hear it.

She went to school for psychology, pivoted to entrepreneurship on a whim senior year, and spent the next decade doing marketing for startups — some that folded, others that just wanted three jobs done for the price of one. She negotiated flexible schedules. She stalled out at the individual contributor level. And then her youngest son got sick.

NICU. A deaf diagnosis. Ten different doctors. Two years of navigating it all while her final startup grew more toxic by the month. When she left, she didn’t have a vision. She had a recruiter conversation and an almost-saying-it-for-years moment of honesty.

What happened in the year that followed is a masterclass in what building a freelance business actually looks like — the part nobody puts in the LinkedIn post.

In This Episode
• The psychology major who stumbled into entrepreneurship — and never looked back
• Why “I do marketing” is invisible — and what she says instead
• Her youngest son’s medical crisis — and how two terrifying years clarified everything
• The Starbucks barista years and the questioning skill she still uses with clients and in networking
• Getting specific to be referable: the moment the whole system started working
• The 15-minute close — from referral intro to signed contract in one afternoon
• Why she took a 25% pay cut for a retainer client — and why she’d do it again
• The burnout → imposter syndrome connection she wishes she’d known sooner
• “When you’re the contractor, you get to be the hero” — her sister’s advice that changed how she sees her work
• Happiness or success? Happiness. No question.

If you enjoyed Anna's story, please hit like and subscribe for more interviews with founders finding their way out!


Connect with Anna
LinkedIn: https://www.linkedin.com/in/duinanna/

Find 101 Ways Out
Website: 101waysout.com


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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.



🎧 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/)

“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 what she’d been missing.

What followed was an 8-month awakening that ended with a handshake pact on a morning walk with her husband: by September, she’d be done. She actually quit in August.

In this episode, Devon takes us from her idyllic St. Louis childhood to expat life in Paris, through a decade at Epic and Grainger, to the moment she sat in a corporatebathroom doing retirement math and decided she wanted none of it. She’s now building Zoomies Chicago — the city’s premier indoor dog park — with investors, an SBA loan, and a signed lease.

In This Episode:

• Growing up between St. Louis, Paris, and Colorado

• A decade in corporate America at Epic and Grainger

• The ADHD medication shortage that became an 8-monthawakening

• How she finally told her husband, “I’m not happy,” on amorning walk

• The four hardest months of her life were between making thepact and actually leaving

• Financial identity, dependence, and the money mindsetwork she’s doing

• Ayahuasca, inner child healing, quitting alcohol, andspiritual practices

• Zoomies Chicago — investors, SBA loan, and what’scoming next

Find Devon at ⁠zoomieschicago.com⁠ and ⁠@zoomieschicago on⁠ all platforms.

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🌐 Hear more stories at ⁠101WaysOut.com

⁠🧭 Find your own way out through our ⁠30-Day Program⁠.