The Time I Left My 9 to 5

Christine Song spent ten years moving from corporate HR into high-growth startups, serving as Head of People and CPO across multiple companies, hiring executives, supporting founders, and navigating the speed and pressure of early-stage environments. Eventually, she walked away from the C-suite to build something of her own. Today, she’s the founder of Five to Nine Society, an invite-only network...

In this episode of The Time I Left My 9 to 5 , Maggie sits down with Jia Chen, a 21-year-old founder, indie musician, and content creator who turned down software engineering offers from Disney and Intuit to build her own company. Jia shares her journey from studying finance to switching into computer engineering, winning 23 hackathons , and raising six figures in funding after a viral pitch video...

This isn’t just a story about quitting a job — it’s about rediscovering meaning after you’ve already “made it.”
 Zach Wilson, data engineer turned creator and founder, walked away from a high-paying career in big tech to build something of his own. What started as a leap toward freedom became a deeper journey into burnout, identity, and what success really means once you already have it.
 In this...

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In this episode of The Time I Left My 9 to 5, Maggie sits down in San Francisco with Maddy Zhang, a senior software engineer and content creator with over 100,000 followers online. Maddy opens up about her journey from studying computer science at MIT to landing roles at Amazon, Microsoft, Google, and Airbnb. She shares how she navigated rejections, defined impact in her work, and built a creative...

Robb Gilbear’s journey has been anything but linear, from dropping out of high school, building record labels, and DJing internationally to climbing the corporate HR ladder before founding Growth Habit, a coaching business built on boldness and authenticity. In this conversation, Robb shares why leaving the 9–5 was a “20 out of 10” decision, the hidden costs of job security, and why entrepreneursh...

Selina Li grew up in Hong Kong playing competitive golf for 16 years, even representing the national team, before heading to Penn to study economics. That path led her into a quant role at JP Morgan — but the 9-to-5 left her searching for more. Selina left finance to pursue computer science at Cornell Tech, where she started building Gymii, an AI-powered nutrition tracking app inspired by her athl...

In this episode of The Time I Left My 9 to 5, we dive into the inspiring journey of Robert Ciborowski, CEO and co-founder of Chatforce. Skipping the traditional route, Robert transitioned directly from graduating from the University of Toronto to building his own startup. He shares his background, the challenges of founding a company, and the dynamic of working with three co-founders. Robert discu...

Welcome to the very first solo episode in the history of The Time I Left My 9 to 5 podcast! I asked on my Instagram what questions you had when it comes to considering leaving your 9 to 5, and I am answering all of them in this episode. I intentionally designed this episode to be research and statistics driven so that you can walk away with actionable frameworks that you can use to apply to your s...

In this episode, Jenn, a former global head of business operations, discusses her challenging transition to becoming a yoga teacher and later a professional coach. She opens up about the identity shift, financial concerns, and personal growth she experienced during this transformative period. Jen shares insights into how she balanced multiple ambitions, navigated significant life changes, and ulti...

Ever felt stuck in a job that doesn’t excite you? Or maybe you’ve spent months—even years—chasing a side hustle with no results? Janis Ozolins knows exactly how that feels. For four years, he tried everything—YouTube, blogging, podcasting—with  zero  measurable success. No audience. No money. Just relentless trial and error. But he never gave up. In this episode The Time I Left My 9 to 5...

In this episode of The Time I Left My 9 to 5, Kiki Couchman is a Stanford grad who left her job in private equity to build a yogurt company with her best friend. Kiki is the cofounder of Beny Yogurt, and I have to say, she's probably one of the coolest founders I've ever interviewed in the history of this podcast. Kiki's story is one of calculated risk-taking and determination, as she left behind...

In this podcast episode, Ashna Mankotia, a former product manager and current content creator, delves into her transition from working in tech to establishing her apparel brand, Bazaar Customs. Laid off just before her 30th birthday, Ashana took it as an opportunity to pursue her entrepreneurial dreams. During the conversation, she talks about her community-building endeavor, Saffron, which she op...

Megan Lieu is a former data scientist who transitioned to a full-time content creator with over a quarter-million followers on LinkedIn and Instagram. In this episode of The Time I Left My 9 to 5 Podcast, Megan shares her journey from relying on traditional job roles for identity and stability to betting on herself and building a successful side business that surpassed her tech salary. She discuss...

If you have been thinking about starting a side project for a while but unsure how to take that first step, Nick offers some invaluable advice in this episode! Nick Singh is a LinkedIn top voice, best selling author, and founder of DataLemur, a platform that has helped over 200,000 people prepare for SQL and data science coding interviews. Nick’s story isn’t just about leaving a 9-5. It’s about re...

Rahul SonWalkar, an ex-software engineer at Meta and Uber, has scaled his tech startup, Julius AI, from 0 to 1 million users within the first year. His work has been so impactful that Harvard Business School now teaches analysis to their MBA students using Julius—an incredible achievement for a company that started from scratch. It’s impressive to see what he’s built in such a short time, especial...

In the debut episode of The Time I Left My 9 to 5, host Maggie Ma introduces the podcast, aiming to explore the stories and lessons from those who have moved away from traditional career paths. This podcast isn't about quitting for quitting's sake but rather about discussing career choices and redefining success on personal terms. Maggie shares her own journey from a data scientist in tech to an e...