The Time I Left My 9to5
The Time I Left My 9to5
Podcast Description
In an era where the internet and creator economy are reshaping careers, a traditional 9-to-5 is no longer the only way to make a living. This podcast explores the stories of people who’ve chosen unconventional career paths—be it entrepreneurship, freelancing, or content creation. Join us as we invite guests from diverse backgrounds to share their journeys, insights, and advice on building fulfilling, nontraditional careers. Hosted on Acast. See acast.com/privacy for more information.
Podcast Insights
Content Themes
The podcast centers around unconventional career paths, primarily focusing on entrepreneurship, freelancing, and content creation. Episode examples include interviews with successful freelancers discussing work-life balance and entrepreneurs sharing their journey from traditional employment to launching startups.
In an era where the internet and creator economy are reshaping careers, a traditional 9 to 5 is no longer the only way to make a living. This podcast explores the stories of people who’ve chosen unconventional career paths—be it entrepreneurship, freelancing, or content creation. Join us as we invite guests from diverse backgrounds to share their journeys, insights, and advice on building fulfilling, nontraditional careers.
Hosted on Acast. See acast.com/privacy for more information.
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
Hosted on Acast. See acast.com/privacy for more information.
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