cd ..

The Pit

|4 min read

There's a scene in The Dark Knight Rises where Bruce Wayne is trapped in an underground prison. The only way out is to climb a vertical shaft in the rock. Everyone who attempts the climb uses a safety rope. Everyone fails.

An old man tells Bruce the rope is the problem. The fear of falling is what gives you the strength to make the jump. You have to climb without it.

Bruce removes the rope. He makes the jump. He escapes.

Great scene. Terrible career advice.


I've been building side projects for a while now. Evenings, weekends, the hour before my brain turns to mush. I have a day job at a large tech company. I ship things on the side. Some of them go nowhere. Some of them are starting to look like they could become something real.

And every few weeks, the same thought shows up.

Just quit. Go all in. Stop splitting yourself. The reason you're not making faster progress is because you're clinging to the rope.

It hits hardest on the bad days. The days where I planned to do three hours of outreach and did forty minutes instead. The days where I open my laptop after work and just... don't have it. On those days, the leap feels like the only honest option. Everything else feels like I'm pretending.

But here's the thing I keep noticing: the fantasy of quitting never shows up on the good days. On the days where I actually ship something, or have a great discovery call, or solve a tricky bug at 11pm — I don't think about quitting my job at all. I'm too busy doing the work.

The leap fantasy is not my deepest wisdom talking. It's frustration looking for a dramatic exit.


There are three paths I keep cycling through.

Path one is the grind. Keep the job. Build on the side. Be disciplined. Accept that progress will be slow and uneven. Some weeks you'll crush it, some weeks you'll barely touch the thing. Keep going anyway.

Path two is the leap. Quit. Burn the boats. Give yourself no choice but to figure it out. The Bruce Wayne path. Climb without the rope.

Path three is do nothing. Complain about wanting to build something. Never actually do it. Crib about it at dinner parties for the next thirty years.

Path three is off the table. I know that much.

But I keep oscillating between one and two. Every week. Sometimes every day. And I used to think the oscillation was the problem — that I needed to pick one and commit.

Now I'm starting to think the oscillation is the experience. That most people who eventually go full-time on their thing spent years in this exact loop. They just don't talk about it because by the time they're writing the blog post, they've already made the jump, and the narrative gets cleaned up into something that sounds decisive.

Nobody writes the "I'm still at my job and I'm still not sure" post. It's always the retrospective. Always the victory lap.

This is not a victory lap.


The other thing I've been wrong about is what "discipline" means.

I used to think it meant: wake up, execute the plan perfectly, don't deviate, don't miss a day. And when I inevitably missed a day, I'd feel like the whole system was broken. Like I wasn't cut out for this.

But that framing is the trap. It turns every 60% day into a failure. Two hours of real work after your day job is not a failure because it wasn't six. It's the thing. It's literally the thing.

The people who make this work aren't the ones who are disciplined every single day. They're the ones who are consistent enough, for long enough, that the compound effect starts to show.


I think the real question isn't "should I quit."

It's: what would my thing need to look like for quitting to be an obvious, boring, practical decision? Not a heroic one. Not a leap of faith. Just... the next logical step.

Some number of paying customers. Some amount of monthly revenue. Some proof that this specific idea has legs and isn't just a hypothesis I'm emotionally attached to.

That's a target I can work toward without needing to resolve the existential tension first. The tension might never resolve. It might just be the background noise of building something on the side.

And maybe that's fine. Maybe the rope isn't the problem.

Maybe the people who climb without the rope just make for better movies.