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.

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Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

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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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