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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