101 Ways Out

What happens when you climb every rung of the corporate ladder, only to realize the culture at the top was never built for you? Courtney Cook grew up in a small town with entrepreneur parents and built her career in operations, rising through corporate roles in retail. But behind the promotions, a culture that didn't align with her values, a CEO whose words made her cringe, and constant exhaustion...

What happens when decades of dedicated public service meet systemic dysfunction and institutional betrayal? After leading critical community health and maternal nutrition programs across Kenya, Sri Lanka, and Nepal, Dr. Marion Gibbon found herself managing high-pressure public health operations in the UK through the height of the COVID-19 pandemic. But behind the titles, severe budget cuts, bureau...

What if finding your way out isn't a one-time move, but a habit of continuous reinvention? In this episode, Dr. Lani Jones, Clinical Psychologist, Executive Coach, and Speaker, joins Vanessa to share how third time’s the charm when learning to step off conventional tracks. Lani spent a decade training to become a clinical psychologist at a major children's hospital, only to find the healthcare sys...

What happens when couples ditch outdated gender expectations and treat both household labor and financial strategy as a true team sport? Today, 45% of women out-earn their male partners, yet the domestic care economy hasn’t caught up. In this episode of 101 Ways Out, Vanessa sits down with Brian Page, former Milken National Educator of the Year and founder of Modern Husbands. Brian shares what led...

What becomes possible when you stop asking what’s expected of you and start listening to your inner compass? In this special milestone episode of 101 Ways Out , Vanessa sits down with a very personal guest: her own coach, Tammy Rising. Tammy is an integrative success coach who blends soul and strategy to help individuals, moms, and business owners step into alignment, calm, and genuine purpose. To...

What happens when the high-speed treadmill of Silicon Valley hyper-growth collides head-on with the messy, unpredictable reality of human life? In this episode of 101 Ways Out , host Vanessa Jupe sits down with Kelly Ling, founder of Stork and Spark. On paper, Kelly had the ultimate corporate playbook: UC Berkeley grad, Deloitte CPA, and a key leader who helped scale DoorDash’s learning and develo...

How do you walk away from marital wealth to save your sanity? In this episode of 101 Ways Out, Mary Sinclair Kowalski joins me to share her raw, unfiltered story of escaping a toxic, emotionally abusive marriage and surviving a high-conflict divorce. To the outside world, Mary had it all: she was married to a Microsoft executive and vacationing at luxury Disney resorts. But inside her home, she li...

How do you build a sustainable, high-impact career spanning five decades without losing your soul to the corporate machine? In this episode of 101 Ways Out, host Vanessa Jupe profiles Rick Loesel, a retired senior supply chain executive and consultant. From his "white bread idyllic" childhood on Long Island to the high-stakes world of international logistics in London, Rick has spent his life brea...

Are you a high-achieving professional struggling with severe burnout but terrified to walk away from a stable career? In this episode of 101 Ways Out , I speak with Katie Cooper , founder of Katie Cooper Wellness. Katie spent nearly two decades climbing the clinical leadership ladder in occupational therapy. But when the COVID-19 pandemic stripped away the resources of her healthcare system, she f...

What happens when you achieve the high-powered media executive titles and financial success you’ve spent your life chasing, but realize your deepest need is simply to create? Former HBO Max and DIRECTV senior executive Sarah Lyons shares her journey of building Lyons Vineyard, navigating the jarring identity shift after leaving corporate life, and designing a reality where you never have to wish a...

"My brain and my intellect will tell me how to do something. And my heart is going to tell me what to do." In this episode of 101 Ways Out, we sit down with Talica Davies, a sales consultant for founders who radically transformed her life by choosing happiness over success. Raised in rural Nova Scotia with intense academic pressure and facing the painful reality of racism that left her feeling lik...

"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 batt...

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"...

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...

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 ope...

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 fract...

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...

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...

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 Cit...

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...

“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 mo...

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 p...

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,...

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 availa...

"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, start...