What happens when a life that looked right suddenly disappears?

Alexandra Simon had already quit what had once been a dream job and was preparing to move to Mexico when her relationship ended the day before the move. Suddenly she had no fixed home, no clear next step and, in her words, felt like “a balloon without a string.”

She took the sabbatical anyway.

That decision became the beginning of a much bigger experiment. Alex spent the next year exploring emotional education, group work, mindfulness and community, eventually turning what she had learned into a course at Yale. When people kept asking where they could learn the same skills outside the university, she tried something deliberately scrappy: a one-month public experiment in New York. It sold out, people kept asking for more, and that experiment became Lifeshop.

In this episode of Escape 9 to 5, we talk about Alex’s path from Yale and Bain to public-service work, emotional education and entrepreneurship; the swimming-pool-to-ocean metaphor that changed how she understood career choice; the letter she wrote to her future self so she wouldn’t get swept up by someone else’s definition of success; and why she now treats energy as data.

We also get practical about what it means to prototype a life instead of trying to think your way into certainty: talking to people, shadowing, testing, noticing patterns and course-correcting. And Alex is equally candid about the less romantic side of meaningful work — the period when she was working all day, teaching every night and felt she was losing some of the soul while doing “work of the soul.”

Her longer-term vision is bigger than workshops: a physical place for learning and human connection where people don’t have to “work on themselves by themselves.”

Find Alexandra + Lifeshop

Website: https://www.lifeshopny.com/

Instagram: @lifeshopny

LinkedIn: https://www.linkedin.com/company/lifeshopny

🎙️ *Escape 9 to 5* is a long-form conversation series about people leaving, reshaping and questioning conventional career paths, and building lives that fit them better.