Way Out #21: From Corporate Hostility to a Sicilian Dream 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 #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 #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 #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 #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.