Making shipping my default

I’ve struggled to get things out the door. The reality is I’m scared.

Here’s what it actually looks like. I finish something, I look at it, I find something that could be better, and I decide it needs to be done before anyone sees it. That’s the moment the project dies.

What I’m really scared of is someone using something I made and not thinking it’s great. But just knowing that is what is going on in my head has never once helped me ship.

Simple rules

I tend to intellectualize my problems and have found stupid simple rules cut through that.

Complex patterns are great. I just can’t self-administer them. A system with conditions and exceptions is a system that needs a manager. Simple rules miss the nuance but build the boundaries cleanly, and I can remember them without looking anything up.

1. Ship daily
2. Plan weekly
3. Retro monthly

Every day something goes live. I have a goal for the week, it’s never scheduled to the day. I wake up, work on my list, and ship what I complete.

What ship means

Ship means someone could find it. It doesn’t mean I broadcast it.

This is the part that de-risks the whole thing. If every iteration has to be announced, then every iteration is a verdict, and I’m going to fear all of them. If I can just ship and move on, shipping costs me nothing. Broadcasting stays for the things I’m most proud of.

Findable, not announced. That’s the bar.

Why these rules

The rules slice through my fear because they created a new measurement. One that only works for me and who I am.

My tendency is to perfect, so I measure volume. I know I naturally want to slow down and go deeper, so the rule pushes the other way. If I shipped a ton of junk I’d need rules to do the opposite.

That’s the whole trick. The rules aren’t good rules. They’re rules pointed away from where I drift. Copying mine won’t help if you drift somewhere else.

Holding the line

I retro progress and direction monthly only. No quick pivots, no tooling refactors, no dramatic life changes inside the month. I hold the line and recap after the work is done.

Everyone preaches fast iteration. But I don’t pivot because I learned something, I pivot because I got uncomfortable, and those feel identical in the moment. A month is long enough that I can tell the difference in hindsight.

The three timescales hold each other up. Daily shipping keeps the weekly plan honest. The monthly retro keeps the weekly plan from getting renegotiated every time I get bored.

I miss days. When I do, I ship the next day and don’t make it mean anything just get back up and keep going.