Triggering Confidence Through Discomfort

How do you stay focused and steady when your work revolves around pressure, fast decisions, and a schedule that never slows down?

In this episode of Habits & Hustle, I sit down with Robert Herjavec, entrepreneur, Emmy Award winner, and lead Shark on Shark Tank, to explore the mindset and habits that keep him clear and effective when the stakes get high.

He shares the discipline that keeps him steady under pressure, the lessons that reshaped his definition of success, and how he protects his energy in a world that rewards noise. We also talk about the routines that anchor him, how he filters opportunities, the role curiosity plays in high performance, and what staying grounded looks like when visibility comes with real cost.

Robert Herjavec is a Croatian-Canadian entrepreneur, investor, and television personality. He founded BRAK Systems, one of Canada’s leading internet security companies, and sold it to AT&T Canada for $30.2 million. He is an Emmy Award winner, the lead Shark on Shark Tank, a cybersecurity expert, keynote speaker, author, and lifelong car enthusiast known for his approach to steady, forward action.

What We Discuss:

• (18:45) Choosing discomfort as a real growth strategy

• (20:01) How confidence grows when you say yes, fail, and improve 1 percent daily

• (21:16) Why self-control is the performance skill most people ignore

• (11:22) The real difference between millionaires and billionaires and why it matters

• (25:47) The psychology of great sales and how curiosity becomes your edge

• (31:05) How to parent with privilege and still raise kids with grit

• (40:50) How he actually ended up on Shark Tank

• (52:01) Why small interactions can change someone’s life

• (59:17) The fitness fundamentals that matter after 60

• (1:02:10) How he rebuilt his body in his 60s through routine and discipline

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Find more from Jen: 

Website: https://www.jennifercohen.com/

Instagram: @therealjencohen  

Books: https://www.jennifercohen.com/books

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Find more from Robert Herjavec:

Instagram: @robertherjavec

X: @robertherjavec

TikTok: @realrobertherjavec

Youtube: @robert-herjavec