Are you having any fun?
The journey is the whole thing. Great things do take a long time, but fun is what keeps you motivated for the long haul.
There’s a myth that building something big—like a company, an open-source project, or any ambitious goal—must feel soul-sucking. That if you’re enjoying yourself, then maybe you’re not grinding hard enough. That perhaps you’re being naïve or soft.
I think that’s backward. Great things do take a long time, but fun is what keeps you motivated for the long haul. Fun is like fuel. It powers you through the late nights, the rough patches, the big pivots—without leaving you burned out, resentful, or at risk of just giving up.
The Biggest Risk: Quitting
Most startups (or big creative undertakings) don’t fail because of lack of money, or a competitor coming out of nowhere. They fail because the people running them give up. And why do founders give up? They’re miserable. They spent years living in a grinding, joyless environment, waiting for some distant milestone to validate all the pain. When the milestone doesn’t arrive on schedule—or arrives and feels anticlimactic—disillusionment sets in. The founder flame goes out.
But what if you never hated the journey? What if you actually had fun building your company or your project? You’d be way less likely to quit, more likely to maintain your energy, and ironically, more likely to reach those ambitious milestones. Because a happy team sticks it out.
Fun in Action: From Apple to Atlassian
If you think fun is a distraction, look at some of the most storied tech teams in history:
Apple’s Macintosh Team: They worked insane hours, yet they raised a pirate flag above their building and pulled pranks on each other. Even in a pressure-cooker environment, that playful energy helped them produce one of the most revolutionary products in computing.
Pixar: Scooters in the halls, Nerf battles in the office—they’ve created an entire campus designed to encourage collisions of creativity. Their teams work ridiculously hard under tight movie-production deadlines, but they keep each other’s spirits up and create hits over and over.
Atlassian’s “ShipIt Days”: Periodically, Atlassian lets employees spend 24 hours building anything they’re passionate about. People form spontaneous teams, eat pizza all night, and ship prototype features. It’s intense, but it’s also fun. Some of their best product innovations originated here.
My Friend Davide
I grabbed coffee with my friend Davide today, a hardware startup founder. He’s about to turn 30, has a long-term girlfriend, and is racing to build something the world needs (he’s even applying learnings from the Mom Test). He’s hustling on every front—building, marketing, selling, hiring. The road ahead looks brutal: the next four years are make-or-break for the company, but they’re also make-or-break for his personal life.
Anyone in his shoes is at risk of doing that “black out and wake up” in a four-year scenario, with 50 employees, a company worth hundreds of millions, but no real lived memories. Conventional success… minus any joy. (Luckily, I think Davide is self-aware enough to avoid this fate - but even then, it’s a risk).
This is the trap. I’ve reached a few “milestones” in my own journey, only to realize how fleeting the celebration feels—sometimes you’re only elated for an hour or two. If you’ve deprived yourself of happiness along the way, the payoff can feel strangely hollow.
My Own Journey Having Fun
I co-founded my current company, Graphite, at the start of the pandemic. It was a weird time: everyone was stuck indoors, often feeling isolated. We could have forced ourselves into a drab, 24/7 grind. But we made it a point to keep it fun.
We’d go on socially distanced runs together.
We’d break up workdays with StarCraft II matches—laughing and trash-talking each other, even if it meant staying up late to code afterward.
We pranked each other by adding hidden memes to the website.
One time, two of us snuck a cartoon weasel into the code so it would flash across the site only for our unsuspecting CEO. Whenever he complained about the bug, we acted like we had no idea what he was talking about. This went on for a month, until a customer demo was interrupted by the little blue weasel. We had to come clean, but it was worth it—everyone had a blast, and we still got our work done, sometimes staying even later because we were enjoying ourselves.
Strength in Positive Rituals
It doesn’t have to be elaborate or expensive. Just do small things that break up the monotony:
Work a week from Mexico: New sights, sounds, food, and cheap flights can recharge everyone’s creative batteries.
Team Meals: Order good takeout or open a bar tab after hitting a milestone.
Healthy Social Activities: My cofounders and I used to do a weekly $100 shared restaurant meal to talk openly about our biggest challenges. Now, we’ve upgraded it to a regular bathhouse hang—three hours of sauna, cold plunges, and conversation. We usually keep talking and working until 10 pm because we want to.
Random Hackathons: Let your engineering or design team drop what they’re doing for a day and build something fun, weird, or purely experimental. One engineer on our team built a Resy bot that we all abused for a year to get the best Soho reservations.
Pranks & Inside Jokes: They’re silly, but they build trust and lighten the mood.
Think of these moments as insurance against burnout. Fun is not fluff—it’s an asset that keeps morale high, fosters tighter bonds, and extends your team’s runway.
The Goal: Don’t Die (and Don’t Quit)
Plenty of legendary companies faced extended slowdowns or near-death experiences. HP started in a garage, Google took a while before AdWords became a big moneymaker, and countless open-source projects simmer for years before they blossom. The founders who stuck around weren’t necessarily the ones who loved stress; they were the ones who made life sustainable.
If you stall out for a year or two, do you really want to keep pushing if every day is joyless? Probably not.
But if you and your cofounders are still having the occasional laugh, still doing weekly runs or monthly pranks, the idea of continuing feels a lot less painful.
The “fun factor” is a hedge against the single greatest threat to any big venture: giving up.
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Hard Work Doesn’t Have to Be Joyless
None of this is to say that real grind and intensity aren’t part of the journey. You might be pulling all-nighters, shipping code at 2 am, or traveling nonstop to meet investors. That’s part of the deal. But it’s orthogonal to having fun. You can do both simultaneously. If Pixar can animate blockbuster films under insane deadlines and still ride scooters in the halls, if the original Mac team could brand themselves as “pirates” while cramming for product demos, there’s proof it’s possible.
In fact, the positivity might even enhance the grind: if you genuinely enjoy being around your team, you’re more likely to work those extra hours without resentment.
Life is Short: The journey is everything. If you hate the journey, you might hate your life.
Fun Powers Momentum: Tiny doses of fun—an hour at the gym, a bar tab, a hackathon, a silly meme in the code—can keep you going through tough times.
Less Likely to Quit: A culture that embraces fun is infinitely more sustainable and less prone to founder or team burnout.
So I’ll say it again: Make your work fun. Try a new environment, plan a team-building prank, or schedule a “ShipIt Day.” If you’re working on something great, you want every advantage to keep you going for years. And if you end up missing the milestone? At least you won’t regret the time you spent—and you might even surprise yourself by persevering until the big win finally hits.
If you have your own tips or hilarious team stories, I’d love to know. We can all use a little more fun in our lives.