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Is Playing It Safe Holding You Back?

October 26, 2026 · 30 min

Show notes

Waiting until things feel safe before making your next move? You might be waiting a while. In Worth the Risk: The Seven Myths That Keep Us from Taking the Chances We Need to Take, economist Allison Schrager challenges the idea that uncertainty is our biggest problem—and asks what we lose by avoiding it. Then, in her 2021 book Choose Possibility: Take Risks and Thrive (Even When You Fail), technology executive Sukhinder Singh Cassidy takes on the pressure to make one perfect, life-changing leap. Together, they explore how to get moving without treating every decision like a bet on your entire future.⁠⁠⁠⁠

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