Choiceology with Katy Milkman

Hooked on Streaks: With Guests Chloë Hamilton & Jackie Silverman

May 5, 2025

Chloë Hamilton, a journalist known for her work in The Guardian, joins Jackie Silverman, an assistant professor at the University of Delaware studying consumer behavior. They dive into the motivational power of streaks—how apps can inspire commitment but sometimes lead to unhealthy obsessions. Hamilton shares fascinating stories, including a dedicated runner's extreme streak, while Silverman reveals how breaking a streak can trigger feelings of failure. The discussion emphasizes strategies to promote ‘streak repair’ and balance in habit formation.

31:27

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Episode guests

Jackie Silverman

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Quick takeaways

Streaks, like daily writing or running, serve as powerful motivational tools that foster accountability and commitment to habits.

Breaking a streak can lead to feelings of failure and demotivation, highlighting the need for flexible strategies to maintain engagement.

Deep dives

The Power of Daily Writing

Jerry Seinfeld's success as a comedian is significantly attributed to his dedication to daily writing, exemplified by his 'don't break the chain' technique. This approach involves marking every day he completes his writing on a calendar with a red X, creating a visual streak that motivates him to maintain his habit. The psychological benefit of this method lies in its ability to reinforce routine and commitment, serving as a constant reminder of his progress and the importance of discipline in creative endeavors. Seinfeld's practice illustrates how establishing daily habits can drive long-term success and instill a sense of accountability.

Intro

5min

The Power and Pressure of Streaks

5min

The Motivating Power and Pitfalls of Streaks

3min

The Psychology of Streaks: Motivation and Setbacks

13min

The Motivational Power and Pitfalls of Streaks

4min

Streaks have long been logged in the world of sports. And for tracking habits, like daily writing. But now apps encourage us to keep streaks going for just about anything. Messaging friends, learning new languages, meditating, exercising, you name it.

In this episode of Choiceology with Katy Milkman, we explore the motivational power of streaks. And we look at ways to alleviate the demotivating effects of breaking a streak.

We speak with journalist Chloë Hamilton, who wrote a story for The Guardian about how a daily ritual can enrich your life or become an unhealthy obsession. Chloë heard from a range of people logging streaks—from daily language practice to simply kissing their partner each morning. One of the more extreme examples included runner Tom Vickery, who has run every day since August 2019. And not just in rain or shine, but after 200 mile runs, in sickness and health, even on a vacation, which included laps on a ferry boat.

Next, Katy speaks with Jackie Silverman, an assistant professor of marketing at the University of Delaware, where she studies consumer behavior and streaks. Her research shows that people often adopt a "streak-keeping" goal in addition to their original motivation for an activity. Breaking a streak can be demotivating due to the feeling of goal failure and loss aversion. Silverman suggests that apps and individuals should emphasize intact streaks, downplay broken ones, and offer opportunities for "streak repair"—or flexibility to help people recover and stay motivated.

Choiceology is an original podcast from Charles Schwab. For more on the show, visit https://schwab.com/Choiceology.

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