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The School of Greatness · September 4, 2026 · 01:38:47

Why You Feel Stuck and How to Actually Change | Dr. Katy Milkman

Dr. Katy Milkman
Show Notes

Dr. Katy Milkman joins Lewis Howes to reveal why 80% of people feel stuck—it's not about willpower but underlying biases and sunk cost thinking. She unpacks the fresh start effect, temptation bundling, and the power of flexible backup plans to make habits stick. Drawing on her own research and her book "How to Change", she shares the exact if-then plans and commitment devices that help override impulsive choices. Milkman also offers a candid look at her own work-life balance struggles and what she’s doing to be more present with her young child. The conversation equips listeners with science-backed tools to forgive themselves for past failures and start again smarter.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Canon

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Harness the Fresh Start Effect
Katy Milkman explains that temporal landmarks (Mondays, birthtdays, new zip codes) reset our motivation, making us more likely to pursue change.
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Temptation Bundling: Pair What You Dread with What You Crave
Milkman shares how she made herself crave going to the gym by only allowing herself to listen to Harry Potter audiobooks while exercising.
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Commitment Devices and If-Then Plans
Milkman advocates using commitment devices and specific if-then planning to lock in future behavior when motivation is high.
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Highlights

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80% of People Feel Stuck — It’s Not About Willpower
Dr. Milkman points out that the majority of people feel trapped, and the real culprits are psychological biases, not a lack of self-control.
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Flexible Backup Plans Beat Rigid Discipline
Research from Marissa Sharif shows that having an emergency reserve of "skip days" or a flexible plan makes goal adherence more successful than demanding perfection.
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Reframe Big Numbers into Small Daily Wins
The Acorns savings study demonstrated that breaking down a large annual savings goal into a small daily amount (like $5) makes the goal feel trivial and easy to maintain.
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Rigid Perfectionism Breaks Habits, Not Willpower
Milkman explains that the biggest reason people fail at habits is not weakness, but an all-or-nothing mindset that causes them to quit after one slip-up.
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References

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How to Change — Katy Milkman (2021)

Misc

✧Katy Milkman gets honest about choosing late-night work over time with her five-year-old and shares her plan to change that pattern.
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