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 for operators, founders, and investors.

In this episode of The Time I Left My 9 to 5, Christine Song shares why she outgrew the startup people-ops path, how she knew she was in the “danger zone” of boredom, and what shifted as she stepped into entrepreneurship. We talk about founder dynamics, performance, backdoor references, building a reputation you can stand behind, the realities of burnout, finding grounding outside of work, and how she grew an audience by saying what most people in HR won’t.

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00:00 Introduction

01:57 Christine’s Career Journey

03:24 Transition to Entrepreneurship: Building Five to Nine Society

04:18 Inside the Role of a Chief People Officer

06:22 Startups vs. Corporate: Challenges, Rewards, and Key Differences

08:15 Taking the Leap into Entrepreneurship

11:25 Support Systems, Runway, and Assessing Risk

15:10 What Five to Nine Society Is and Why It’s Invite-Only

25:36 Why Founders Need to Diversify

26:20 Building a Network Through Social Media: The Good and the Bad

31:06 Balancing Work and Personal Life

35:00 The Realities and Challenges of Startup Life

37:42 Making the Leap (Again) into Entrepreneurship

42:14 Christine’s Vision and Advice for Aspiring Entrepreneurs

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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. Jia opens up about navigating parental expectations, building Sprint.dev to 20,000 users and $48K profit, and balancing creativity across music, tech, and social media.

Whether you’re a student, early-career creative, or aspiring founder, Jia’s story is a masterclass in following curiosity, betting on yourself, and building in public.

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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 conversation, we unpack what it really takes to build a meaningful life after success — systems over ambition, investing and learning from a new form of education, integrity over hype, and the long game of finding purpose in your work.


If you’ve ever wondered what comes after achievement, this episode will hit close to home.

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