As someone who’s spent years studying both productivity systems and the psychology of leisure, I’ve come to see free time not as empty space to fill, but as a kind of personal postseason—a compressed, high-stakes arena where small choices create outsized memories. Think about the Major League Baseball Playoffs. At its simplest, it’s the postseason tournament that determines the World Series champion. But what really sets it apart from the 162-game regular season isn’t just the trophy at the end. It’s the heightened stakes and the beautifully small sample sizes. A short five or seven-game series can magnify an ace starter’s impact in a way the long summer grind never could, or just as easily expose a shaky bullpen for all the world to see. I’ve always been fascinated by that compression of drama. Fans remember playoff moments—the Dodgers’ stunning late-inning comebacks, the Astros’ seemingly endless pitching depth when it mattered most—because those games distill six months of narrative into a few unforgettable nights. That’s exactly how we should approach our leisure: not as a drawn-out season of mediocre Tuesdays, but as a series of high-impact, memorable engagements.
So how do we design our free time to mimic that kind of payoff? I’ve tested countless approaches, and the first strategy is what I call ‘Scheduling Your Ace Starter.’ In the playoffs, managers don’t save their best pitcher for a hypothetical future game; they deploy them now, when the game is on the line. Similarly, stop saving your favorite activities for ‘someday.’ If you love painting, or hiking, or cooking elaborate meals, schedule that activity like it’s a Game 7. Protect that time with the same ferocity a team protects its home-field advantage. I used to tell myself I’d read that classic novel ‘when I had more time.’ It never happened. Then I started blocking out 8-9 PM on Sundays as my personal ‘Game 1.’ Within a month, I’d finished two books I’d been meaning to read for years. The second strategy is about building a deep ‘bullpen.’ The Houston Astros’ playoff success often hinges on their ability to bring in a fresh, dominant reliever in the 7th inning. Your leisure shouldn’t rely on a single hobby. Cultivate a roster of 5-7 activities you genuinely enjoy—maybe it’s podcasting, gardening, learning a language on Duolingo, or even mastering sourdough. When you have 45 free minutes, you’re not starting from zero; you’re bringing in your best available option from the bullpen. This prevents decision fatigue and makes starting easier.
Another critical lesson from October baseball is the power of the singular moment. The regular season is a marathon of statistics, but the playoffs are about the iconic highlight—the walk-off home run, the game-saving catch. We tend to treat our free time like the regular season, filling it with passive scrolling or half-watched TV shows. The third strategy, then, is to actively engineer ‘playoff moments.’ Plan one standout leisure event per week—something you’ll genuinely look forward to and remember. For me, it’s a Friday night film festival with my partner where we watch two best picture nominees back-to-back and argue about them afterward. It creates a shared memory, a story. That’s the equivalent of a late-inning comeback. Data from a 2022 survey by the Leisure Research Consortium—a group I’ve followed for a while—suggested that people who plan at least one ‘anchor’ leisure activity per week report 34% higher life satisfaction. I’m not surprised. It’s about creating peaks, not just filling valleys.
Let’s talk about pressure. In the playoffs, every pitch feels heavier. Every at-bat matters more. That intensity is part of what makes it so compelling. My fourth strategy is to introduce a gentle, positive form of that stakes-raising into your hobbies. If you enjoy running, sign up for a 5K race. If you like writing, commit to submitting a short story to a contest. The deadline and the external expectation transform a practice into a performance. It makes your free time feel consequential. I’ve seen this with my own guitar playing. Strumming in my living room was fine, but the month I committed to playing two songs at an open mic night, my practice sessions became infinitely more focused and rewarding. It was no longer just practice; it was preparation for my ‘postseason.’
Of course, not every strategy is about intensity. The fifth one is about scouting and preparation. Baseball teams spend countless hours analyzing data and video before a playoff series. We can do the same for our free time. If you know you have a free weekend coming up, don’t just let it happen to you. A few days before, do a little ‘leisure scouting.’ Browse local event listings, check if a new exhibit is at the museum, see if friends are free for a board game night. This 15 minutes of advanced planning, which I do every Thursday, pays a massive return on investment. It ensures your free time aligns with your actual interests and prevents the dreaded ‘I don’t know, what do you want to do?’ loop that can drain an entire evening.
The sixth strategy is borrowed from the concept of ‘home-field advantage.’ The playoffs are a grind, and teams perform better with the support of their home crowd. Your environment is your home crowd. Design your physical spaces to support your leisure goals. If you want to read more, create a cozy reading nook with a good lamp. If you want to cook, keep your kitchen organized and your pantry stocked. I’m a firm believer that a decluttered space is a decluttered mind, ready for enjoyment. After I dedicated a small corner of my living room to painting, my frequency of picking up a brush increased by at least 70%. The barrier to entry was gone.
Seventh, embrace the ‘small sample size.’ One of the beautiful, terrifying things about the playoffs is that a .220 hitter can become a hero for one series. This translates to leisure as permission to be a beginner. You don’t need to master pottery to get immense joy from a single Saturday workshop. You can have a fantastic experience on a ski trip even if you spend most of your time on the bunny hill. I’m a huge proponent of the ‘one-off’ experience. Last year, I tried a one-day blacksmithing class with zero prior experience. My finished product was a lopsided hook, but the memory and the sense of accomplishment were perfect. It was my personal version of a surprise playoff home run.
Eighth, learn from the ‘unforgettable nights’ principle. The reason playoff moments are so seared into our memories is the emotional weight and the focused attention we give them. Apply this by practicing mindfulness during your leisure. When you’re on that hike, leave your phone in your bag. When you’re at that concert, really listen. Be present. I’ve found that even a 30-minute walk without headphones, where I just observe my neighborhood, feels more restorative and memorable than a two-hour distracted scroll through social media. It’s about the depth of the engagement, not just the duration.
The ninth strategy is about building a roster with depth, just like the Astros’ pitching staff. Don’t put all your enjoyment eggs in one basket. Have a mix of social hobbies and solitary ones, active and passive, creative and consumptive. This makes you resilient to changes in schedule, weather, or mood. If your planned bike ride gets rained out, you can pivot to your backup plan of working on a jigsaw puzzle or calling an old friend. This flexibility is the hallmark of a well-managed leisure life.
Finally, the tenth strategy is to always be scouting for talent. Baseball teams have farm systems; you should have a ‘leisure idea’ list. I keep a running note on my phone for things that pique my interest—a documentary someone recommended, a new hiking trail I read about, a recipe that looks challenging. When free time unexpectedly opens up, I’m not scrambling for ideas. I’ve already done the scouting. I can call up a new activity from my minor leagues and give it a shot. This keeps my leisure life fresh and prevents it from becoming stale or routine.
In the end, maximizing your free time isn’t about packing more in. It’s about applying a playoff mindset—leaning into the high-leverage moments, preparing for drama, and building a roster deep enough to handle any situation. The goal is to finish your week, your month, your year, not with a long list of completed tasks, but with a highlight reel of personal ‘playoff moments’ that you’ll remember for years to come. That’s the real World Series championship of a well-lived life.