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 High-Tech Success to Micro-School Magic: How Lauren Tarpley Found Her "Ikigai"
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 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: From Professor to Tech Entrepreneur 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.
Way Out #3: From a 6,000 Sq Ft House to Worldschooling in Spain with Jane Hermstedt
After climbing the corporate ladder and buying the dream home, Jane realized she was spending her weekends managing a house instead of living a life. Tired of the guilt she felt sneaking out of the office at 5 PM just to see her son, Jane shares in this adventurous yet deeply practical conversation how she combined a concrete vision with math to trade the American Dream for a life of travel.
Way Out #2: From Praying to Get Fired to Quadrupling Her Income with Christine Bridger
After years of climbing the agency ladder, Christine Bridger found herself praying to get fired. In this grounded, deeply human conversation, she shares how small, intentional steps, mindset work, and trust helped her leave corporate life and build a more joyful, abundant one.