Hooked on Streaks: With Guests Chloë Hamilton & Jackie Silverman

May 5, 2025
How can streaks be both motivating and demotivating?

After you listen

A good way to maintain a beneficial streak in your financial life is to put the streak on autopilot—for instance, by setting up regular automatic contributions into a retirement fund. 

  • To hear more tips on how to mitigate the biases that could derail your financial plan, listen to the Financial Decoder podcast

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. 

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