I once forgot to follow up with a customer so badly that by the time I remembered, they were already evaluating a competitor. That was fun.
Anyway, I have ADHD. You might have guessed.
The Catalog of Failures
My brain will not check Slack unprompted. It will not remember your email from Thursday. It definitely, definitely will not remember that a $50K renewal is due next week, not unless something makes it impossible to forget.
It will, however, spend four hours at 11 PM researching moon phases for a fishing trip. Thanks, brain.
I’m also on the spectrum. Which means I have what I generously call “task-switching friction” and what my calendar used to call “missed meetings.” My brain locks onto one thing and the rest of the world goes quiet. This is occasionally a superpower. It is frequently a catastrophe.
For a while I tried to fix it. None of it worked. Not sustainably. Not for me.
The Realization
At some point I stopped trying to fix myself and started trying to work with myself.
This sounds obvious. It was not obvious. It took years and one spectacular failure and the quiet decision that I was going to engineer around my own brain rather than trying to rewire it.
So I did the only thing that made sense. I made the computer do all of it.
What 1,300 Automations Actually Means
Not what they do. What they mean.
Every automation I’ve built is something that used to live in my head. A follow-up due tomorrow. An account going quiet. A renewal sneaking up. An alert I should probably check. All of it (the whole overhead of not forgetting things) used to take up active mental space, requiring maintenance, burning attention just to keep from dropping.
My brain doesn’t have that kind of reliable storage. I’ve known this for years. What I didn’t know, until I started building systems, was how much energy I was spending just keeping things from falling over.
The automations didn’t just offload tasks. They offloaded the anxiety of potentially forgetting. “Remember to follow up with this customer” is one kind of weight. “Worry that you’ve forgotten to follow up with this customer” is a different, heavier one. 1,300 scripts removed the second kind.
The fishing script too. Yes, it tells me whether to go kayaking based on barometric pressure and moon phase. More importantly, it tells me not to worry about whether I’m making the right call. One less thing to hold. One less decision occupying space that could go somewhere better.
My head is clear. Not because I got better at holding things in it, but because I stopped needing to.
1,300 tiny decisions offloaded. Turns out that adds up to something that looks a lot like mental clarity.
The Punchline
1,300 automations later, I’m running customer success for a $5 million company across five continents.
Not because I got better at checking Slack. Not because I finally found the right planner app. Not because I learned discipline.
Because I built 1,300 tiny crutches and put them in a trench coat and it looks like a functional adult.
The trench coat metaphor is load-bearing here. None of the individual automations are impressive. A Slack alert when a customer goes quiet. A weekly email summary that would take me 20 minutes to write manually. A script that checks whether renewal dates are approaching and surfaces the ones I haven’t touched. Small, boring, obvious.
Together they make up the operating system that lets my brain be what it actually is (pattern-recognition machine, relationship engine, strategic thinker) without also having to be a calendar, a task manager, a follow-up tracker, and a Slack notification that fires itself.
What This Is Not
This is not a “ADHD productivity hacks” post. I’m not going to tell you to try the Pomodoro technique.
This is not a “AI will save you from yourself” post. Most of these automations are embarrassingly simple Python scripts. The sophistication isn’t in the code.
This is not advice, exactly. What works for my brain might not work for yours. The specific implementations don’t matter.
What I’m actually saying is this: if your brain won’t do the boring stuff consistently, that’s not a moral failing. That’s information. Information about what needs to be engineered around.
The robodaddy apocalypse people are worried about? The AI taking over? It’s just a bunch of ADHD kids who got tired of missing things. We’re not taking over. We just automated the parts we couldn’t do and moved on.
The Thing Nobody Says
Here’s what no one told me when I was reading the “ADHD productivity” blogs and buying the notebooks: the goal isn’t to become someone who doesn’t need systems. The goal is to build systems good enough that you stop needing to be someone who doesn’t need them.
My ADHD brain is not broken. It’s just running a different operating system than most people’s. The automations aren’t patches on a broken system. They’re an interface layer between my OS and the rest of the world.
The automations aren’t a productivity strategy. They’re the natural output of a brain that treats repetition as an emergency. Not ambition. Not discipline. Just an extremely low tolerance for doing the same thing twice, combined with enough time at a keyboard to do something about it.
I didn’t build them in spite of ADHD. I built them because of it.
Blake Bailey runs Bailey Business Ventures, an AI transformation consulting practice. He has 1,300+ production automations, an embarrassing amount of fishing data, and exactly zero working planners.