Way Out #25: From Corporate Climb to Making Wine with Sarah Lyons
When a corporate merger eliminated Sarah Lyons’ twenty-one-year executive career at WarnerMedia and HBO Max, she didn't just look for her next corporate ladder; she accelerated a long-held family dream. In this episode, Sarah shares how she turned the profound grief of losing her father-in-law into a living tribute by launching Lyons Vineyard, a boutique brand built entirely on her own terms. From navigating an identity crisis after losing her W-2 EVP title to discovering how childhood self-reliance fueled her entrepreneurial grit, Sarah offers a masterclass in decoupling your self-worth from a corporate identity, building financial optionality, and stepping back into the professional world with absolute leverage.
Way Out #24: From Selling to Sailing with Talica Davies
A successful climb up the corporate ladder landed Talica in a lucrative role as an investment advisor at a major bank. But her true wake-up call didn't happen during a high-stakes sales pitch—it came in the midst of profound personal grief. Following the passing of her father, Talica faced a reckoning. Her counselor explicitly warned her not to make any major decisions while she was grieving, but Talica’s intuition was screaming at her. Looking at the "perfect" life she had built to make her highly academic family proud, she had a sudden, undeniable realization: "I don't like this guy that I'm dating. I don't like my job." In that single moment, she decided she was finally done living someone else's blueprint. She ignored her counselor's advice, left her relationship, quit the bank, and chose herself.
Way Out #23: From Corporate Gaslighting to Total Freedom with Karol Figueroa
A successful climb up the corporate ladder landed Karol in a Director role at Microsoft. But her 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."
Way Out #22: He Was Putting Payroll on Credit Cards: Then His Son Was Born Nine Weeks Early with Brian Best
The scariest moment of Brian's life forced the ultimate realization: If your business completely relies on your physical time, it is a trap. Today, his business runs on recurring revenue so he can travel the country in an RV with his family. Learn how he built a business that can run without him on this week's episode of 101 Ways Out!
Way Out #21: From Corporate Hostility to Sicily: Two Suitcases and a One-Way Ticket with Jennifer Sontag
After surviving decades of toxic corporate environments and sexual harassment, Jennifer Sontag hit a breaking point. Going through a divorce as an empty nester in her mid-40s, she sold everything she owned down to two suitcases and booked a one-way ticket to China. Despite arriving to an absolute nightmare—including an illegal visa and terrible housing—she refused to turn back. Today, she has transformed her own messy European relocation into ViaMonde.eu, a thriving citizenship concierge. She now runs her business from a stunning beachside apartment in Sicily, located in the exact town her great-grandparents emigrated from.
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 — and her body eventually made sure she knew the cost. In this episode of 101 Ways Out, the founder of A Lighter Way Consulting opens up about the extreme corporate burnout that pushed her to her breaking point, how being laid off from her executive "dream job" became the ultimate blessing in disguise, and why you do not have to sacrifice your health and happiness to be successful.
Way Out #19: From Being Told What to Make to Building a $1M Agency with Marianne Kaiser
Marianne Kaiser counted the bad mornings that she dreaded her job, and at the three month mark, she decided to leave and build her own business. She quit in June, filed her LLC on July 8th, launched Contrary Collective publicly in September, and is on track to hit $1M in revenue one year later. She also has two small kids. What got her there wasn't perfect timing or a flawless plan; it was the willingness to accept, as she puts it, that both options were going to be hard anyway, so she might as well do the thing she actually wanted to do.
Way Out #18: Rising from the Ashes: From Fired to Founder with Anne Pao
Two days after her VP role was suspiciously eliminated in an act of corporate retaliation, Anne Pao sat down at her desk, dried her tears, and created a spreadsheet titled: "Rising from the Redundancy Ashes like a Phoenix." She committed to taking one step every single day toward her new future. Today, she is the highly successful CEO of Ignite Consulting, working Monday through Thursday and making up to 45% more than her former corporate salary. Discover how Anne escaped a toxic corporate culture, broke generational cycles, and built an incredibly successful life entirely on her own terms.
Way Out #17: From Pastor to Serial Entrepreneur with Keith Davenport
In this episode, we sit down with Keith Davenport, a man whose life is a masterclass in radical transformation. Keith went from growing up in a conservative evangelical household with a childhood calling to be a pastor, to ultimately leaving his faith to identify as a progressive atheist and political candidate. After experiencing severe burnout and untreated ADHD while managing crisis communications during the COVID-19 pandemic, Keith took a massive leap into serial entrepreneurship. We discuss how he acquired a beloved local coffee shop, launched a multi-six-figure consulting firm, and founded an HR tech startup. Ultimately, Keith shares how he redefined success entirely, choosing his mental health and his role as a husband and father over traditional corporate power.
Way Out #16: She Walked Out of Manhattan Publishing With $25,000 and No Plan with Alisa Messeroff
Alisa Messeroff was a Manhattan publishing associate who said “fuck you” to her director, walked out after a broken promotion promise, and moved to the Caribbean with $25,000 and no plan. What followed was a head-to-toe hives diagnosis that nearly killed her, a decade-long journey with plant medicine, a spirit guide named Iribella, and a multi-modality practice that now spans breathwork, Reiki, mindset coaching, and empowerment photography across Breckenridge and Tamarindo. This is her way out.
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 didn’t have a plan. Just a conversation where she heard herself say: “I think I just have to build my own thing.” This is what happened in the year that followed.
Way Out #14: Leaving a $200K Salary to Build an Indoor Dog Park with Devon Brown
“It didn’t start as ‘I want to be an entrepreneur.’ It started as ‘I don’t want to be here anymore.’”
Devon Brown spent 10 years in corporate America, made $200K, and still sat in a bathroom doing the math on how many more years she had until retirement.
The answer? 40 something. Her answer? Nope.
Meet the woman who’s building Chicago’s premier indoor dog park — and living proof that the way out sometimes starts with a medication shortage and a morning walk with your husband. 🐾
Way Out #13: From 25 Years in Corporate PR to Building an Agency on His Terms with John McCartney
John McCartney is the founder of JMAC PR, a boutique PR and marketing agency that helps technology companies grow and scale. After a 25-year career in public relations across New York, San Francisco, and Los Angeles, he decided to bet on himself and chart his own path as an entrepreneur.
Way Out #12: She Left Corporate Innovation to Build a Human-Centered Business with Ari DeGrote
We are often told that if you follow the rules and land a great corporate job, you will ultimately feel fulfilled. But what happens when you reach that milestone and realize your personal growth has completely flatlined? For corporate innovation leader Ari DeGrote, the realization was stark: she hadn't just hit a wall—she had hit her 'expiration date.' Read how Ari prototyped her exit and proved that leaving a stable career doesn't have to mean running away from something toxic; it can simply mean running towards a life of total autonomy.
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 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.
Way Out #10: From High Control Religion to Freedom Abroad With Andie Eggiman
Andie Eggimann 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.” Fortunately, she found her way out of high control religion, and eventually, the United States.
Way Out #8: From Tech to a Micro-School in Nature: What Cancer Made Clear with Lauren Tarpley
After a 20-year career in tech strategy and customer success, a breast cancer diagnosis at 34, and 11 surgeries, Lauren Tarpley reached a moment of clarity. When corporate culture revealed itself in the wake of her medical leave, she chose not to double down — she chose to redesign. Today, she’s building a micro-nature school on six acres of raw land, running The Farmacy CHS, and living what she calls 97% her dream. Lauren’s Way Out isn’t about escape. It’s about reclamation.
Way Out #7: From Emmy-Winning Oprah Producer to Entrepreneur and Puppeteer with Lisa Weiss
She spent years at the pinnacle of television as an Emmy-winning producer for Oprah’s Super Soul Sunday. But when a layoff coincided with a high-risk pregnancy, Lisa Weiss was forced to reimagine her identity without the safety net of a "dream job." In this episode, Lisa reveals how she escaped the trap of the "unlived life," why she turned down venture capital advice to follow her gut, and how a 7-minute puppet show about mansplaining unlocked more business confidence than any boardroom meeting.
Way Out #5: From Corporate Art Director to Watercolor Artist with Ken Stanek
Ken Stanek doesn’t have a "career path" in the traditional sense. He has a series of experiments, pivots, and intuitive leaps that eventually landed him exactly where he belongs.
From shivering as a bike messenger in NYC winters to designing PowerPoints for pharmaceutical giants, Ken spent two decades trying to fit his creative square peg into a corporate round hole. Today, he is a full-time artist, muralist, and illustrator who has finally stopped pretending.
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 to be strong. Push through. Don’t complain. Be grateful for the tenure, the house, the title.
Dr. Risa Stein did all of that. By her mid-30s, she had checked every box: PhD, marriage, child, tenure-track career. From the outside, it looked like success.
On the inside, it was slowly killing her.