Why It’s Worth It | Ever notice how we hoard all our fun experiences for vacation? Cramming museums, fancy restaurants, and adventures into two weeks, then return to the same old routine? Here’s what’s fascinating: we’re doing happiness completely wrong. Research shows we’d be far happier spreading those special experiences throughout the year rather than bundling them into holiday bursts. Katy Milkman explores this counterintuitive insight through the story of Sally Millington, a woman from York who transformed her life by trying something new every single week for a year.

Sally’s journey started at a climbing gym, gripping tiny footholds while her legs shook and her heart pounded. She’d never climbed before and described herself as lacking self-belief in most areas of her life. But dangling from that wall, feeling the adrenaline and accomplishment, something clicked. She realized how rarely she tried new things outside of vacations. So she set herself a SMART goal (specific, measurable, achievable, realistic, time-bound): try something new every week for 52 weeks.

The experiences ranged from mundane to magnificent. She sat in a hammock for the first time, gingerly edging into the fabric roll without falling out. She attended a gong sound bath that went sideways when someone started snoring. But the real breakthrough came at a community hall advertising “release your inner raver and your inner Buddha.” In the dark room with flashing lights, Sally started by shuffling awkwardly, feeling utterly bizarre doing staccato movements to broken beats. Then she noticed others crawling and rolling across the floor, throwing wild shapes. “Nobody is looking at me,” she realized, and became “an absolute whirlwind” on the dance floor.

Katy connects Sally’s story to a concept called hedonic editing: the strategy of deliberately arranging good and bad experiences to maximize happiness. The research, building on prospect theory, shows we get diminishing returns from each additional unit of pleasure or pain. The first M&M tastes amazing; the 17th in a row, not so much. This means we’re happier getting five M&Ms across five days than 35 at once. Conversely, we’re better off getting ten electric shocks in one session than one per day for ten days.

Ellen Evers from UC Berkeley explains the nuance: this works best when experiences feel similar enough to combine. Getting two bad grades can feel like “one terrible week at school.” But getting a bad grade AND dropping your burrito? Those feel too different to mentally bundle as one bad event. We’re actually pretty sophisticated at this mental categorization, though researchers can trick us by manipulating how similar things appear.

The implications go beyond personal happiness. Machiavelli understood this 500 years ago, advising rulers to “do all the harm you must at one and the same time” but “do good little by little, so people can fully appreciate it.” Modern CEOs package bad news into single announcements; politicians use similar strategies. Understanding hedonic editing helps us both maximize our own happiness and recognize when others might be manipulating our perceptions.

Sally’s project, which she called Challenge 52, didn’t stop after one year. She found that spreading new experiences across time made her feel like she’d “slowed down time in a weird way.” Instead of years blurring together in repetitive routine, she now has memorable markers throughout each year. From performing stand-up comedy to making pottery, from acupuncture to cricket, she’s created a life where joy comes in regular doses rather than vacation-sized gulps.

Background | In this episode, Katy Milkman hosts Ellen Evers, whose research on hedonic editing reveals how we can strategically arrange our experiences for maximum happiness.

Key Takeaways:

• Segregate gains, aggregate losses: Spread good experiences across time but bundle bad ones together. One rose per month brings more joy than a dozen at once, but it’s better to hear two pieces of bad news in one call.
• Similarity matters for bundling: We can mentally combine similar negative events (two bad grades become “a bad week”) but struggle with different ones (bad grade plus dropped burrito). Work with our natural categorization tendencies.
• Program novelty regularly: Don’t save all new experiences for vacations. Sally’s weekly challenges created memorable markers throughout the year, making time feel richer and more meaningful.
• We’re naturally sophisticated: People generally understand these principles intuitively. We know to “rip the Band-Aid off” for bad news but dole out treats over time. Trust these instincts.
• Retrospective categorization helps: When bad things happen, ask: Can I see these as one event to process and move past? This mental reframing can reduce rumination and suffering.
• Watch for manipulation: CEOs and politicians use hedonic editing to minimize negative reactions. Recognize when others bundle bad news strategically to reduce its psychological impact.
• Small changes compound: Sally started with one climbing session but built to years of weekly adventures. Even tiny shifts in how we distribute experiences can significantly boost overall life satisfaction.

Source | Choiceology: Little Bits of Happiness – Season 15, Episode 6 (June 2, 2025)

About | Katy Milkman is a behavioral scientist, Wharton professor, national bestselling author, and host of Choiceology, a Charles Schwab original podcast that melds conversations about science, research, and human quirks to help us make better decisions and avoid costly mistakes. She also produces an insightful free newsletter, Milkman Delivers (sign up on her website!). Katy believes the key to changing ourselves for good lies in better understanding the internal obstacles that hold us back.