I Used to Think Fun Was a Waste of Time

When my business was in its early growth, I ran every activity through the same filter. Does this help me network? Does this grow the business? What’s the utility?

There was no room left for anything I did just because I liked it. Rest felt like wasted time. If you’re deep in hustle culture, that sentence probably sounds responsible. It felt responsible to me too.

I’ve flipped that. Activities I do purely for enjoyment, pickleball included, are essential for my happiness. And that happiness is what fuels my productivity.

Brooks Duncan currently has no hobbies. He called it a fatal flaw, something he realized while talking about retirement with a couple. As people age, the lack of a passion or activity to fill the void after work becomes a significant problem. He’s using this as a catalyst to find one.

What’s your retirement identity? If work went away, what would you actually do with the hours?

Your calendar and your credit card already know

You can say hobbies matter to you. Fine. Then look at two things: your calendar and your credit card statement.

If a hobby is important to you, it should appear in both your time allocation and your spending. If your calendar is full of work and social obligations but your credit card shows no spending on hobbies, your actions do not match your stated values. That external audit is the reality check. It shows where your true priorities lie.

Take five minutes. Last month’s spending. Last month’s calendar. Is a hobby visible in both?

Tetris, and a board with no gaps

You try to schedule the hobby and you cannot find a gap. That is a signal you have zero margin.

I use a Tetris analogy for calendar planning. When the pieces have nowhere to land, the board is full. The “no gap” state is an alarm that you are overscheduled.

You fix that by creating buffer time in the next week, so that when the current week rolls around, the hobby is already protected.

Look at next week’s calendar. Intentionally leave one 1-hour block empty for a hobby. Protect it before the pieces fill in.

Is it a hobby, or is it a chore?

Before you fill that block, run a practical test. Do you do this for obligation or health, or for pleasure and fulfillment?

If you exercise solely to be healthy, it is a routine. An obligation. If you play a sport because you enjoy the process and could do it for hours without strain, it is a hobby.

That distinction matters because hobbies require different scheduling strategies than obligations. Audit your “free time” activities and label each one Obligation or Hobby. If the list is all obligation, that is why those hours feel draining.

Give the hobby a next skill

Once you have a real hobby, treat it as a skill acquisition ladder.

Take paddle or coding. View the hobby as a series of progressive skills. Learning volleys, then reading walls, then strategy. You get continuous improvement, which keeps the activity from going boring or stagnant. There is always a next boss. A new technique to master. That is what keeps it mentally stimulating.

What is the next skill you want to learn in your current hobby?

Use AI for play, not just work

Experimenting with AI tools feels like a hobby for me. There is no direct financial pressure. No client deadline attached to the experimentation. I teach AI courses, and the act of playing with the technology is still driven by curiosity and learning, not obligation. That is what keeps it fresh and enjoyable.

Do you use AI for play, or only for work?

If you don’t have a hobby yet, the hardest step is deciding what to do. Brooks and I talked about that Zero to One difficulty. Use ChatGPT or Perplexity to brainstorm hobby ideas based on your existing interests and personality. Ask the AI to ask you questions about what you might enjoy. You can uncover hobbies you didn’t know existed, which lowers the barrier to entry.

Try this prompt:

Ask me questions about what I might enjoy as a hobby. Interview me about my interests, personality, and the activities that feel like play. Don’t give me a list until you’ve asked enough to make a real guess. Then suggest hobbies I probably haven’t considered, including ones I could start with limited free time.

One season, or stack it onto dead time

Brooks has two ways to make this fit a packed calendar.

The first is a Seasonal Leisure Plan, inspired by Cal Newport’s Digital Minimalism. Instead of fitting random hobbies into a busy week, pick one focus for the season. Learning to change car oil. Drawing. Hiking. Break it into weekly micro-tasks. You get a specific, low-stakes goal for your downtime, which is how you avoid the scrolling trap.

Define your Seasonal Leisure Goal for the next 3 months. One focus.

The second is Hobby Stacking, for people with limited free time. Combine a passive leisure activity with an active hobby. Watching Netflix while you cross-stitch or knit. Commuting while you listen to educational podcasts. You make progress on a skill or creative project without a dedicated block of free time. Dead time becomes hobby time.

What dead time do you already have? Commute, lunch, a show you watch anyway. What hobby could you stack onto it?

Open next week’s calendar and protect one 1-hour block for something you do purely for fun. Not for career gain. If you cannot find the gap, that is the alarm. Create the buffer in the following week so the hobby is already there when the week arrives.