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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Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

Podcast YouTube: @thetimeileftmy9to5.podcast

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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Hosted on Acast. See acast.com/privacy for more information.

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 outlet through social media.

From the realities of Big Tech to handling online criticism and finding meaning beyond work, Maddy’s story is full of insight and inspiration for anyone pursuing a career in tech—or looking to express themselves outside of it.

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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 entrepreneurship is both the biggest challenge and greatest self-development journey. We dive into identity, ego death, money mindsets, and how to give yourself permission to create meaningful work in a changing world.

If you’ve ever wondered what it really takes to leave the corporate path and build your own, this episode is for you.

📲 Stay Up to Date with the Show:

Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

Podcast Youtube: ⁨@thetimeileftmy9to5.podcast⁩

Chapters

- 0:00 Intro

- 2:40 Returning to Entrepreneurship: The Old Market is Gone

- 6:06 The Trade of Entrepreneurship: Choosing Passion Over Stability

- 12:54 Is Entrepreneurship Really for Everyone?

- 15:46 Finding My Path Early: Dropping Out of High School

- 17:30 Entrepreneurship in the Blood: Ice Cream Bikes, Hustles & Military Discipline

- 19:21 Giving Myself Permission: Outsider Energy, DIY Flyers & Sharing a Bill with Daft Punk

- 22:29 Parenting & Struggle: Redefining Success While Raising Kids in Debt

- 25:49 The Corporate Pivot: From High School Dropout to HR

- 32:27 Realizing Music Was Avoidance & Coaching Was the Path

- 34:24 Going All-In on Growth Habit

- 38:06 From Golden Handcuffs to First Clients: Advice for Sarah & Marcus

- 47:33 Reframing Sales: Why Coaches Struggle to Sell & How to Shift

- 52:45 The Common Denominator in Every Thriving Practice

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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 athletic background.

*Use promo code "MAGGIE" to get 15% off Gymii!*

In this episode, Selina shares her journey from sports to finance to startups, the identity shift she faced leaving golf, the reactions she encountered when walking away from a prestigious job, and how she grew Gymii from an idea rooted in a personal challenge into a fully launched app.

📲 Stay Up to Date with the Show:

Host Instagram: / @maggieindata

Podcast Instagram: / thetimeileftmy9to5.podcast

Podcast YouTube: / @thetimeileftmy9to5.podcast

Chapters

00:00 – Introduction

01:51 – Selina Li’s Story in Brief

02:51 – Starting Gymii: The First Steps

05:27 – What is Gymii?

06:30 – Leaving Competitive Golf After 16 Years

08:43 – Life at JP Morgan: Lessons from the 9–5

13:30 – Quitting Finance: Reflections and Reactions

18:23 – The Cornell Tech Experience

23:40 – Finding the Right Co-Founder

26:32 – Future Plans & Advice for Aspiring Entrepreneurs

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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 discusses Charforce's innovative approach to AI automation, their unique features, and the successful strategy that garnered early investor interest. He provides valuable advice for aspiring entrepreneurs on ambition, building the right team, and the importance of lifelong learning. This episode is a deep dive into the life of a young founder making waves in the AI-driven startup landscape.

Host Instagram: https://www.instagram.com/maggieindata

Podcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcast

Podcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast

Chapters

00:00 Highlight Overview

01:20 Robert's Journey from University to Startup

04:35 Early Coding and Game Development

08:10 Building the Capstone Team

12:39 Family Influence and Support

17:13 The Six-Month Gray Area

21:13 The Birth of Chatforce

22:48 The Three Co-Founder Dynamic Revisited

25:14 Empowering Knowledge Workers with AI Agents

28:15 The Philosophy Behind Chatforce

31:33 Getting Noticed by Investors

39:50 Advice for Aspiring Entrepreneurs

41:56 The Importance of Independent Learning

43:59 Leveraging AI Tools and Resources

53:09 Balancing Building and Learning

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