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Relentless drive isn’t the problem for most high performers. The real breakdown happens when self-belief collapses after early success and hustle turns into motion without direction.

This episode is part of The Best of Habits & Hustle, a series where we revisit some of the most impactful conversations we’ve shared. In this one, I’m joined by Rob Dyrdek to challenge the idea that working harder fixes everything and explore why success stalls when it isn’t intentionally designed. 

We also talk about rebuilding belief after hitting bottom, mastering time as a strategic advantage, and designing systems that create real wealth without burning your life down.

Rob Dyrdek is a serial entrepreneur, producer, and former professional skateboarder. He is the creator of Ridiculousness and the founder of Dyrdek Machine, a venture studio that has built 18 brands with six exits totaling over $550M. Rob is also the CEO of Existence and the mind behind Time Creationism, a framework focused on engineering time at scale.

What We Discuss:

(00:02) Losing self-belief after early success and why hustle stops working

(11:38) How subconscious belief shapes trajectory more than effort

(13:27) Hitting rock bottom and the decision to reprogram belief

(19:18) Why self-belief isn’t motivation, it’s data and mastery

(46:41) Designing time as a strategic asset instead of reacting to life

(52:03) Why balance must come before scale, not after

(56:47) Building systems that create wealth without burning your life down

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Find more from Jen:

Website: https://jennifercohen.com

Instagram: @therealjencohen 

Books: https://jennifercohen.com/books

Speaking: https://jennifercohen.com/speaking-engagement

Find more from Rob Dyrdek:

Instagram: @robdyrdek

Facebook: @robdyrdek

Youtube: @robdyrdek