March 12, 2026

Why Having a Backup Plan Is Making You Fail - Burn the boats with Matt Higgins

Why Having a Backup Plan Is Making You Fail - Burn the boats with Matt Higgins

The Backup Plan Paradox: Why safety nets destroy performance and how to do better than plan B

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In 1519, Hernán Cortés landed in Mexico and promptly set fire to his own fleet. By any conventional measure of military logistics, this seems profoundly counterproductive. It wasn't.

Matt Higgins — Shark Tank investor, Harvard Business School lecturer, and accidental dropout — has spent his career studying what happens when humans remove their own escape routes. Spoiler: it tends to go rather well, and there's solid science to explain why.

A landmark Wharton study found that merely having a backup plan measurably reduces both your motivation and your likelihood of success. The safety net, it turns out, is cutting the tightrope.

  • Why the brain mistakes "prudence" for "self-protection" and how to catch it

  • The four-step process for synthesising your risk tolerance before you commit

  • How to extract more value from failure than was taken from you


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CHAPTERS

00:00 Cortés Burning the Boats
01:31 Introducing Matt Higgins
04:08 The Problem with Plan B
06:11 Managing Risks
10:53 When You Should Be Able to Retreat
15:18 Why We Should Not Romanticise Failure
17:38 Life After Shark Tank
24:30 Optimising Strengths vs Improving Weaknesses
31:48 Importance of Commitment and Setting Intentions
33:47 Inspiring Women
37:00 The Investor Anxiety Exchange
39:45 Rapid Fire Questions

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