Betting on Yourself and Redefining Balance w/ Christine Song

What happens when you reach new heights in your career… before you feel fully ready for it?

In our very first episode of Let’s Table That, we sit down with Christine Song, Founder of 5 to 9 Society and former Chief People Officer at multiple venture-backed tech companies, to talk about the parts of leadership nobody posts about.

Christine’s path wasn’t linear. She moved from a corporate world that felt slow and restrictive to high-growth startups where she thrived in speed, ambiguity, and ownership. Along the way, she kept following one thing: curiosity.

Curiosity about better ways to build teams, how leaders actually grow, and what “ambition” actually means when you’re not trying to prove something.

After years of scaling companies, reporting to boards, and building at full velocity, she faced burnout and had to answer: 

“Am I building the life I want… or just chasing the next milestone?”

In this episode, we talk about:

• Why “seamless” career transitions are rarely seamless
• Startup vs. corporate culture: what’s real and what’s romanticized
• The identity trap behind chasing titles and exits
• Why being the fastest person in the room isn’t always the goal
• The hiring mistakes founders make (and why big logos don’t equal builders)
• The power of intuition, especially in HR
• Why HR must sit beside the CEO, not under finance
• What people challenges actually do to founders behind closed doors
• Redefining ambition without losing yourself

If you’ve ever:
• Worked so hard you forgot why
• Chased the next milestone hoping it would fix the feeling
• Wondered if there’s another way to build

Pull up a chair.