Escape 9 to 5

Lydia.CLinzi

Freedom, Agency and Meaning. Ever thought about ditching the regular 9 to 5 to chase what truly lights you up? I'm on this path to. This podcast is all about that leap of faith—no guides, no guarantees, just real stories from those brave enough to pursue a life beyond the ordinary. Join me as we uncover the untold journeys of dreamers and doers who are carving their own paths. Let's figure out this together.

  1. 23h ago

    Alexandra Simon - How to Prototype a Life That Feels Like Yours

    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.

  2. Aug 22

    Every No Is a Vote for Yourself | Ify Walker

    There are choices I’ve made that still scare me: saying no to the sensible thing, walking away from something that used to fit, choosing a version of myself I can’t fully see yet. Ify Walker gave me language for those moments: each one can be a vote for yourself. Somewhere along the way, without really realizing it, I think I’ve been casting those votes too. Saying no to things, people, events and choices that no longer serve me. Trusting my own judgment a little more each time. Slowly becoming someone my eight-year-old self would probably look at with amazement. That doesn’t mean the choices become easy. Life is still uncertain. Every decision still comes with doubt, and none of us gets to control what happens next. But there is something powerful about knowing: I chose this. I voted for myself. That is what stayed with me after this conversation with Ify. Ify Walker is the founder and CEO of Offor. Her path has moved through teaching, law, fundraising and entrepreneurship, including raising roughly $40 million at Teach For America before building Offor. We talk about her first career rebellion, why “a no isn’t fatal,” the danger of chasing approval until it becomes self-abandonment, what she calls the work twisties, rebuilding trust in your own judgment, and what happens when even meaningful work you chose for yourself starts asking you to change again. And we laughed. A lot. This ended up being exactly the kind of Escape 9 to 5 conversation I hoped this show could hold: relaxed, honest, occasionally ridiculous, and somehow leaving me with a little more strength to keep going. If you’re standing in front of a choice you can’t completely control, maybe the question isn’t whether you can guarantee the outcome. Maybe it’s simply: what would it look like to cast one more vote for yourself? 🎙️ 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. 💌 Stay ConnectedThe First 60 Dayshttps://lydiaclinzi.substack.com/Sunday Not Bluehttps://www.lydia-c-linzi.kit.com/Instagramhttps://www.instagram.com/lydiachenlinzi☕ If something here made you think, smile, or breathe a little deeper:https://lydia-c-linzi.kit.com/products/buy-me-a-not-so-blue-brew© 2026 Lydia C. Linzi

  3. Jul 11 ·  Bonus

    I Was Wrong About Escaping the 9–5 | 36 Conversations Later

    I used to think escaping the 9–5 happened in one brave moment. You quit. You leap. You start a completely different life. After 36 conversations with founders, authors, creators, and people who stepped away from the default path, I no longer think that is how it usually happens. Most people build a bridge long before they quit. A bridge made from private clues, tiny experiments, uncomfortable asks, money fears, and enough small proof to trust themselves with the next step. This is a special solo episode of Escape 9 to 5, looking back at what the first 36 conversations changed for me. I share five lessons: 1. The escape starts before you quit. 2. Proof matters more than confidence. 3. Money fear does not magically disappear. 4. Sometimes you have to ask anyway. 5. There is no arrival. Freedom means choosing the pressure you are willing to live with. The episode includes moments and ideas from conversations with Anne-Laure Le Cunff, Gillian Liu, Erin Wade, Paul Millerd, Andrew Wilkinson, Michia Rohrssen, and other guests who have generously shared the honest, unresolved parts of building a different life. One line from Michia stayed with me long after we stopped recording: “The whole world is waiting for you.” Not necessarily waiting for you to quit tomorrow. But perhaps waiting for you to send the message, run the experiment, follow the curiosity, or begin building the bridge. I’m deeply grateful to every guest who has given their time to this podcast. These conversations have changed how I understand work, risk, freedom, and what it means to build a life that feels more like your own. Explore Escape 9 to 5: https://www.dayzeroproduction.com/escape-9-to-5 Watch the full podcast archive: https://www.youtube.com/@LydiaCLinzi/podcasts About the show: Escape 9 to 5 is a podcast about people who leave default paths and build more deliberate, self-directed lives. Hosted by Lydia Linzi, a former investment banker turned climate-tech founder and creator. Connect with Lydia: https://www.dayzeroproduction.com https://www.instagram.com/lydiachenlinzi

  4. Jun 6

    Brian Dean: What Happens After You Get Freedom?

    Most people know Brian Dean as the founder of Backlinko and co-founder of Exploding Topics. He built his life from his dad’s basement into selling two companies. But this conversation isn’t just about how he did it. It’s about what came after: the strange, quiet, surprisingly stressful question of what freedom is actually for once you finally have it. We get into the first business that failed, the years of trial and error before anything worked, building an audience before earning a cent, geo-arbitrage, Portugal, tennis, why passive income is never really passive, and how AI is reshaping search. But underneath all of it is the question I kept coming back to: Is happiness about having more, or about learning to want less? Find Brian:Programs.com: https://programs.com/Backlinko: https://backlinko.com/Exploding Topics: https://explodingtopics.com/YouTube: https://www.youtube.com/@BrianDean/videosLinkedIn: https://www.linkedin.com/in/brianedean/ Escape 9 to 5 is a long-form podcast about people who stepped away from the conventional path to build more deliberate, self-directed lives. Listen and subscribe:https://www.dayzeroproduction.com/escape-9-to-5 Follow Lydia:Instagram: https://www.instagram.com/lydiachenlinzi/LinkedIn: https://www.linkedin.com/in/lichenlydia/Website: https://www.dayzeroproduction.com/ Newsletter:Sunday Not Blue: https://www.lydia-c-linzi.kit.com/The First 60 Days: https://lydiaclinzi.substack.com/

  5. Apr 6

    What Happens After You Make It? He Retired at 31 and Started Building Again | Michia Rhossen

    He sold his company for $110 million at 31. Retired. Traveled to Antarctica twice. Visited Richard Branson's private island. Then came back to build again.This is a conversation I've been trying to have for two years. Michia Rhossen and I first connected through the Part-Time YouTuber Academy in London, and we finally sat down on my last day in Hong Kong before flying back to London. No script, no preparation.What we ended up talking about wasn't the grinding stories or the exit mechanics. It was what happens after. What success means when money is no longer the goal. Why comfort was the scariest part of his journey. And how he's now building three companies, not because he has to, but because he realized that not building was the selfish choice.If you take one thing from this episode, let it be this: "If I'm still excited about what I'm doing, then I think I've won. And if we have 100 million users and I'm not excited, then I've lost."Find Michia: @askmichia on Instagram and YouTubeThis is Episode 34 of Escape 9 to 5. Connect with Michia Instagram / YouTube: @askmichia Explore more from Escape 9 to 5 Podcast archive: https://www.dayzeroproduction.com/escape-9-to-5 Escape 9 to 5 is a podcast by https://www.dayzeroproduction.com/ and hosted by Lydia Chen — real conversations with people who left the traditional path and built something of their own. New episodes monthly. Connect with Lydia: @lydiachenlinzi on Instagram | lydiaclinzi.substack.com

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3.5
out of 5
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About

Freedom, Agency and Meaning. Ever thought about ditching the regular 9 to 5 to chase what truly lights you up? I'm on this path to. This podcast is all about that leap of faith—no guides, no guarantees, just real stories from those brave enough to pursue a life beyond the ordinary. Join me as we uncover the untold journeys of dreamers and doers who are carving their own paths. Let's figure out this together.