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

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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.


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