Dr. Katy Milkman on Why We Get Stuck and the Science of Lasting Change

High-Level Overview

Lewis Howes talks with Dr. Katy Milkman, a Wharton professor, host of the Choiceology podcast, co-director of the Behavior Change for Good Initiative with Angela Duckworth, and author of How to Change: The Science of Getting from Where You Are to Where You Want to Be. Starting from a survey Howes cites claiming that 80% of people feel stuck, they unpack the internal barriers that keep us in ruts (status quo bias, sunk costs, impulsivity, procrastination, forgetting, low confidence) and the research-backed tools for getting past each one.

The tone is upbeat, curious and practical. Howes asks direct, personal questions and shares his own marathon training and a device-free vacation, while Milkman, a self-described "messy" researcher who studies the problems she struggles with, grounds each idea in specific experiments. The conversation moves steadily from why we stay stuck, to how to get started, to structuring change, to recovering from failure.

The Discussion Explores:

• Status quo bias, escalation of commitment and the sunk-cost trap
• The fresh start effect and why new chapters spark change
• Belief, identity and the power of the people around you
• Breaking big goals into small pieces, and making the path fun
• If-then plans, tracking, accountability and commitment devices
• Temptation bundling and using environmental change to break habits
• Why flexible routines beat rigid ones, and how emergency reserves help us recover from failure

Deep Dive into Main Ideas

Why We Stay Stuck: Status Quo Bias and Sunk Costs

Milkman separates two kinds of barriers: structural and social ones outside our control, like inequality, and the internal ones she studies. The biggest internal barrier to even deciding to change is status quo bias, the tendency to stick with our current path because any deviation feels like a loss. Its close sibling is escalation of commitment, which is powered by our failure to ignore sunk costs.

Howes offers the example of people who complain for years about an unfulfilling relationship but stay. Milkman agrees that both biases apply. The years, gifts and trips already invested cannot be recovered whether you stay or go, so the only rational question is which path has better costs and benefits going forward. She calls the sunk-cost bias pernicious and a big reason people remain in relationships or jobs that are not working.

Once someone decides to change, a new set of barriers appears: the problem of getting started, impulsivity (overweighting instant gratification), procrastination, forgetting or flaking out on important but non-urgent tasks like retirement savings or a colonoscopy, laziness in the sense of taking the path of least resistance, and not believing you can change.

The Fresh Start Effect

To tackle getting started, Milkman describes her research with Hengchen Dai and Jason Riis on the fresh start effect. Motivation ebbs and flows, and certain moments feel like new beginnings: New Year's, birthdays, a new job, a move, a graduation, and even the start of a week or month. We organize memories like chapters in a book, so at these chapter breaks we step back and think big-picture, and we feel a shift in identity that lets us separate ourselves from past failures (the old me couldn't do it, but this is the new me).

Howes suggests that big breakdowns, like a loss or a near-death experience, often drive change. Milkman says survey research suggests such shocks create identity shifts through the same mechanism, but positive milestones can too. She describes a friend who had just earned tenure, reached the top of his mountain, and was now asking what comes next.

Belief, Identity and the People Around You

Milkman says research has not yet wrapped its arms around identity as well as she would like, but mindset work is the closest rigorous evidence. She cites Carol Dweck's growth mindset research and a study by Alia Crum and Ellen Langer in which hotel housekeepers told that their daily work met recommended exercise guidelines showed health improvements, such as weight loss and better blood pressure, compared with a group that was not told. She suspects the belief changed their behavior, like taking the stairs or putting more into vacuuming; she now happily volunteers to run up the stairs in her Philadelphia townhouse for the ketchup.

Asked how to build belief in oneself, she answers: "I think the most powerful thing is who you surround yourself with." She adds a caution that overconfidence can backfire because you stop practicing. Her model is her dissertation advisor, Harvard's Max Bazerman, whose students became tenured professors at elite schools. His secret was unshakable belief in his students, plenty of positive feedback, treating them like family, and building a team culture among competitive academics: "We weren't playing for a team, but we were a team." He also had senior students mentor junior ones.

That connects to research by Lauren Eskreis-Winkler showing that people struggling with goals benefit from giving advice rather than receiving it. Being asked to coach someone makes you feel trusted, forces you to introspect, and makes you feel like a hypocrite if you do not follow your own advice. Milkman now belongs to an advice club of former Bazerman students who solicit each other's counsel. Howes shares a similar story from Simon Sinek, who restored a friend's confidence by asking her to coach him.

Structure: Break It Down and Make It Fun

Howes describes the coach, support team and schedule he set up for his first marathon, and Milkman says that instinct for structure is exactly what research supports, instead of a just-do-it approach. Big goals should be broken into bite-sized parts, an idea rooted in the work of the late Albert Bandura. In one field experiment, volunteers committed to 200 hours a year did much better when reminded to volunteer four hours a week. In a study led by Hal Hershfield with the savings app Acorns, inviting people to save $5 a day instead of $150 a month produced something like five times more sign-ups, even though the money moved monthly either way.

The second key idea comes from Ayelet Fishbach and Kaitlin Woolley. Most people pursue goals by choosing the most efficient route, but those who choose the most enjoyable route persist longer. When people were encouraged to pick fun ways to exercise or study math (music, markers, snacks), they achieved more. As Milkman puts it, "People achieve more because they persist longer when they find ways to make it fun to do what's good for them." We underestimate this because of impulsivity: we overvalue how the present moment feels.

If-Then Plans, Tracking and Accountability

Milkman explains Peter Gollwitzer's research on implementation intentions: people who make concrete if-then plans (if it is Thursday at 4 p.m., then I go train at this location) follow through far more than those who plan to do it sometime. Her own work shows that simply writing down the date and time you will get a flu shot makes vaccination more likely, and asking voters when, where and how they will vote increases turnout. These tactics are now widely used in health care and elections.

Tracking also helps, because visibility lets you reward yourself. In one study, people who could see their water use in real time in the shower cut back. Milkman loves when her Fitbit buzzes at 10,000 steps. Accountability works because it changes the cost-benefit calculation, and it belongs to a category economists find strange: commitment devices, where you penalize yourself for failing. The most effective put money on the line. In one study, smokers who could deposit money for six months that they would forfeit if they failed a nicotine test had a 30% higher quit rate. Howes adds that "you pay attention to what you pay for," and Milkman agrees this taps into our failure to ignore sunk costs: "It's sort of a mistake that we do it, but it works." Websites like stickK and Beeminder let people create these contracts.

On breaking promises to ourselves, Milkman notes that repeated failure does erode confidence, but we have what Dan Gilbert calls a psychological immune system, and fresh starts may be part of it. Keeping promises and seeing streaks, like those in language apps, builds momentum. Her top-level advice is to diagnose your specific barrier and match the tool to it rather than grabbing tactics off the shelf.

Temptation Bundling and Changing Your Environment

Milkman's first personal experiment came in graduate school, when she was too exhausted after computer science and business classes to study or exercise. She began allowing herself to listen to gripping audiobooks, like Harry Potter or James Patterson's Alex Cross novels, only at the gym. Soon she craved workouts, sometimes stayed too long to hear what happened next, and came home refreshed and ready to study. Her grades improved. She calls this temptation bundling, and large randomized trials have since shown it increases exercise. Examples include saving a favorite podcast for cooking or chores, or only gossiping with a friend on morning walks.

The best time to start a new habit is at a fresh start, especially one that includes a physical change. If you grab donuts on your commute, a new job or route breaks the cue. Wendy Wood's research found college transfer students whose environments changed most were best able to form new exercise and social routines. Milkman compares staying in the same environment to breaking up but continuing to live in separate rooms of the same home.

Flexibility Beats Rigidity

Milkman's most surprising experiment, run at Google with John Beshears and others, involved about 2,500 employees trying to build a gym habit during a month-long Fresh Start Challenge. One group was rewarded for going at the same time every day; 85% of their workouts happened at that time. Another was encouraged to mix it up, and only half of their workouts were at their usual time. The researchers expected the consistent group to build the stronger habit. The opposite happened. The rigid group went slightly more at their preferred time but tended not to go at all if they missed it, while the flexible group had backup plans and went more overall. "They've built a no matter what habit," she says.

She relates this to tennis, where you never train only under perfect conditions because real matches bring sun in your eyes and awkward shots. Her advice is to have a first-best, second-best and third-best plan.

Recovering From Failure: Emergency Reserves

Milkman calls recovery from failure the most important understudied topic in her field. She describes the what-the-hell effect: after a small slip, like one donut on a diet, people abandon the goal entirely. Her Wharton colleague Marissa Sharif studied emergency reserves (Milkman calls them mulligans): set an ambitious goal, like exercising seven days a week, but allow two emergency passes a week. That structure beat both a plain seven-day goal and a five-day goal, because people strive for the tough target without giving up after a miss. Calling them emergencies keeps people from using them casually. "Understand how to forgive yourself," she says, and social support helps too.

Milkman is candid about her own struggle with work-life balance, having worked late into the night on vaccine research during the pandemic and on her book while her five-year-old was in Zoom pre-K. She now keeps her phone away at family dinners and outings. Howes describes a vacation where he left all his electronics at home, which Milkman calls a commitment device. They note that society already builds in pledges, like engagements and the Hippocratic Oath, and she cites research in which doctors who posted a pledge in their offices prescribed unnecessary antibiotics far less often.

Conclusion

Milkman's three truths sum up the episode: find a way to make the path to achievement fun, use fresh starts as chances to begin again, and remember that "rigidity is the enemy of habit and success" because life keeps throwing curveballs. Around those truths sits a practical toolkit: ignore sunk costs, surround yourself with people who believe in you, coach others, break goals into small steps, make if-then plans, track progress, put something at stake, change your environment, and give yourself limited room to fail. Her definition of greatness fits the same idea: having a North Star and building your life's structures around it.

This is a summary of "Why You Feel Stuck and How to Actually Change | Dr. Katy Milkman" from The School of Greatness, giving you the GIST so you can decide if you want the REST. Listen to the full episode.