Shipping Features ≠ Playing. Or Does It?
A Facebook flashback reminded me that silliness matters just as much as shipping.
I love being a bootstrapper. Building my own apps brings me a ton of joy — I genuinely find it fun. But recently I realized: I’ve kind of forgotten how to play.
And I don’t mean building apps or shipping features. I don’t mean “fun” in the productive sense — like hiking a new route, tracking PRs at the gym, or trying a new recipe. I mean actual, pointless play. The silly kind. The kind kids do without hesitation: running in circles, laughing at nothing, dancing in the kitchen for no reason.
Then Facebook hit me with one of those “13 years ago today” videos.
It was 14-year-old me, karaoke-ing and dancing around my house for 17 minutes straight. Pure cringe. Even teenage me had the sense to mark it private and share it with just one friend.
But watching it now? I couldn’t stop smiling. My younger self’s face was lit up with pure, unfiltered joy. I wasn’t trying to be good. I wasn’t trying to impress anyone. I wasn’t working toward anything.
I was just… playing.
And I realized: I used to be great at that. Somewhere along the way, I forgot.
That’s the thing about adulthood (and especially entrepreneurship): everything becomes goal-oriented.
You don’t just walk — you hike to optimize health.
You don’t just hang out — you network.
You don’t just daydream — you "visualize".
Every moment has to earn its keep.
And I think that’s especially true for bootstrappers. We live in a culture (and a community) that worships productivity — ship fast, measure, optimize. And somewhere in the middle of all that, play gets cut from the equation.
As a kid, I measured myself by grades and trophies. Later, it was resumes, promotions, and now… MRR dashboards and growth charts. And somewhere in that training, I stopped giving myself permission to do things with no outcome, no metric, no point.
And it’s not just productivity stealing play. It’s judgment too. Silliness became stupidity. We roll our eyes at the woman jumping in puddles after the rain, or the forty-year-old chasing bubbles in the park. But honestly, I probably judged myself harder than anyone else — for being immature, for wasting time. Doing something “pointless” suddenly meant I was pointless.
Watching that old video, I realized silly ≠ stupid. Running in circles, blowing spit bubbles, building pillow forts — that’s not childish. That’s playful. And adults (yes, even founders) need it just as much as kids.
It reminded me of my joy in karaoke, in dancing like an idiot. (And yes, I caught myself writing “idiot” — that’s how ingrained it is. I know play isn’t stupid, but my brain still labels it that way.)
So the other night, I gave myself permission to play again. Stayed up past my bedtime. Not because it was “productive,” but because I wanted to. For the first time in a decade, I let myself be the irresponsible kid — up ’til 3 a.m., rotting my brain on Facebook reels.
That night, Facebook decided I was a die-hard Kelly Clarkson fan — which was hilarious, because I probably hadn’t listened to her since I made that original cringe video. My feed was flooded with her. So there I was, in bed, belting out “Since U Been Gone.” Laughing. Playing.
It felt amazing — but let’s be real, I can’t exactly turn “midnight Kelly Clarkson concerts” into a lifestyle. I’d be sleep-deprived and hate her by next week (sorry, Kelly).
So I started investigating alternative ways to play.
I noticed how other adults approach it. Some lean on alcohol — booze lets you shrug off the judgment. Raves pull you into collective silliness. I’m not a big drinker, so that shortcut doesn’t work for me (though sometimes I wish I could silence the health lecture in my head and party like 18-year-old me).
Others find it through their kids — chasing them around the yard, making up games, seeing the world through their eyes. But I can’t even keep a plant alive, much less a child, so that option’s off the table too.
But here’s what I believe: we all have it in us. Without alcohol. Without kids. Without anything external. We just… forget.
So here I am, in my late 20s, relearning how to play.
Relearning that it’s okay to dance badly in my kitchen.
To sing Kelly Clarkson in bed.
To laugh at myself.
To quiet the voice in my head that says everything has to have a point.
Because the point is there is no point. That’s what makes it play.
And that brings me back to bootstrapping.
For me, building apps is fun, fulfilling, and meaningful — but is it really play? Or is it still too tied to outcomes, metrics, and productivity?
What do you think? Is bootstrapping a form of play for you? Or is it something different entirely?
How do you make sure you still get those short, careless dopamine hits, the laughter, the silliness? Especially if you have a day job and are building on the side with barely any time?
👉 Curious how you play.
P.S. Follow my blog - https://medium.com/@kcolban
This really hit home — it’s such a real reminder that somewhere along the road to being “productive adults,” we forget how to just play. I love how you described that difference between doing something for joy vs. doing it for a goal. It’s so true — we treat fun like it needs a KPI.
exactly glad you connected with this :)
Totally feel this. I built a site called rankiwiki and sometimes the polls there feel more like play than work. Do you think side projects can really be play, or does the pressure always sneak in?
I think there is a difference between having fun and playing. I find building to be super fun, but not a form of playing. I think side projects can be super fulfilling and fun but not that laughter silly type fo play.
What's your biggest roadblock to achieve success at the moment?
Maybe play just changes shape — now the game is building, failing, and trying again.
yes but are you still getting the silly laughter from that?
Really enjoyed reading your post! Went through the same phase few years ago and started to play some board games with my partner and friends. Such a great way to actually play and bond with your love ones. We might even try to play some D&D soon! When alone with free time, I pick a puzzle and can spend hours to finish it but what a blast. Also playing like a kid with your dog brings a lot of pure joy too!
Hope you will never forget your inner kid and get time to play more.
thanks :)
Love this. As a bootstrapper I’ve mistaken shipping-dopamine for play for years. What helped was creating a tiny “play budget” in my day: 10 minutes where outcomes are illegal—sing badly, sketch nonsense UIs, record a one-take voice note that must be deleted after. Strangely, my copy and product ideas got better because my brain stopped optimizing. It feels like resetting the “judgment filter” before I get back to work.
Question: If you could add one ritual that injects pointless joy into a weekday (no alcohol, no goals), what would it be?
omg I love the play budget idea.
Maybe like a weekly girls night or karaoke night or dance party. Something silly
"relearning how to play" That's a great sentiment!
thanks
Really loved this post — the line between shipping and playing hit hard. It’s so easy to lose that sense of joy when you’re deep in the grind. I’ve been feeling the same while building —spike trying to keep it fun instead of just chasing tasks and metrics. Thanks for the reminder to make room for play again. 🎮
thank you :)
Building should be fun. If it's not, what's the point.
I think there is a difference between having fun and playing. I find building to be super fun but not a form of playing.
This is a beautiful piece. Hope everyone can enjoy building!
Thanks!
For me, bootstrapping can feel like play, but only when I’m experimenting, when it’s messy, not polished. The moment I start tracking churn or ARR, it’s over. Feels like a job again.
I totally get what you are saying!
Bootstrapping can feel like play, but only when the stakes feel low. The moment you need MRR to survive, it stops being play and starts being performance.
this was such a refreshing read. The honesty, the self-awareness... chef’s kiss 👏
thanks!
If you’re trying to stay focused while working or studying, you should try Mixora — it’s a free focus web app where you can set timers (15, 25, or 50 mins), track streaks, and even create Spotify playlists based on your mood or favorite artists. 🎧
It also has relaxing background sounds like rain, café, or forest that you can customize.
Super simple, no signup needed → mixora . xyz
Lately, I’ve been experimenting with ways to stay focused while working, and I ended up building a small web app called Mixora.
It lets you set timers (15, 25, 50 min), track streaks, and listen to ambient sounds or Spotify playlists while you work.
No signup needed — just open it and start focusing.
If you want to try it, just search for mixora . xyz — it’s free and surprisingly effective for getting into flow.
I always feel guilty after having fun without a goal. Playing without a purpose doesn’t help with what I’m working on, though it might help me relax a little.
That really hit home — it’s so easy to forget how to just play without a goal or metric attached. I think bootstrapping can feel playful at times, but it still carries pressure and expectations. True play, the kind that’s pointless and joyful, is something I’m trying to let back into my life too — even if it’s just dancing in the kitchen for no reason.
This really resonated with me, Kaia. I also build side-projects and realized I’d lost that “pointless” play too.
Funny enough, the one thing that helped me get it back wasn’t shipping a feature — it was gaming. In my breaks I jump into (a private server version of Brawl Stars) because it’s pure low-stakes fun: unlimited characters, no grind, just quick matches and silliness.
It reminds me why I started building in the first place — experimenting, messing around, not worrying about metrics. Curious if you’ve found any little “play hacks” like that which work for you?
I havent found anything similar. I find building to be fun and then i take a break and try to go play outside typically.
As founders we often confuse building with playing — but they’re not the same. Bootstrapping is fulfilling, but it still ties joy to outcomes and metrics. Real play is what reminds us we’re more than our dashboards. Thanks for the nudge — I think we need both to stay sane and creative.
Exactly how i feel. Thanks!
How do you balance being playful and being disciplined? Because while scheduling a “play time” sounds good in theory, it often feels like yet another task to check off. Maybe there are ways to build in spontaneity or silliness more organically, so it doesn’t feel like another item on the to-do list?
What do you think is your business roadblock to achieve success at the moment?
It does feel like a checkbox sometime.. now im trying to "smile" like literally smile 15 min a day lol and it sends dopamine to my brain but its another check box lol.
Haha, I get that it’s funny how even self care can start to feel like another task on the list. But honestly, the fact that you’re intentionally doing things that boost your mood says a lot about your mindset. Little habits like that might seem small, but they really add up over time. Keep it going progress counts even when it feels like a checkbox!
What's your plan for this Q4 season?
I love this reflection — as founders, we often forget how to just play without purpose. Features are important, but creative freedom and spontaneity fuel long-term passion.
Automating for users (like forecasting dashboards) can easily become too transactional. When I was building my own project, I reminded myself to carve out time for experimentation — no KPIs, just fun.
On a side note, when I’m not working on SaaS, I dive into retro gaming (especially Tekken 3). You can see some of that nostalgia at (tekan3apk) — it’s my way of balancing productivity with play.
Thanks :)
It’s so important to play both during and outside of building lol