When Did You Stop Taking Risks? The Hidden Cost of Playing It Safe

Brandon Thielk and co-host/producer Holly Deschenes introduce Permission to Evolve with a focus on “permission to take risks,” emphasizing that the danger isn’t only failure but also staying stuck in dry, unfulfilling stability. They connect risk-taking to building self-trust by turning attention inward, detaching from shame-based stories, taking small manageable steps, and confronting discomfort to gather data and strengthen decision-making. Brandon explains how people often stop taking risks after struggle leads to security, which can become a prison, and argues for balancing certainty with needed uncertainty, variety, and renewal. Using triathlon and career examples, they discuss how once-exciting challenges can become routine, requiring new variables, neglected skills, fresh mindsets, or even new chapters. They close by encouraging reflection on future regret, choosing the right “dose” of uncertainty, and sharing ways to connect with Brandon’s coaching and content.

00:00 Welcome and Topic

00:15 Why Take Risks

01:46 Question of Week

02:08 Building Self Trust

08:48 When We Stop Risking

10:34 Stability Versus Variety

15:15 Regret and Perspective

16:34 When Risks Get Boring

18:23 Refreshing Motivation

24:32 Specific Ways to Mix It Up

25:21 Reinventing Training and Work

28:00 Identity Shifts and Chapters

33:34 Building a Runway

36:15 Avoiding the Hard Thing

39:41 Final Takeaways

43:41 Where to Find Brandon

44:32 Wrap Up and Goodbye

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