I automated something and gave myself a new job

My favorite part of an automation idea is the future I promise myself: I'll never have to think about this task again.

Data will arrive from somewhere, something will process it, and the result will go where it belongs. Meanwhile, I'll be doing something else. A small arrangement in which the computer acts like a computer and I finally get to step away from it.

Then I picture myself refreshing a dashboard. Did it arrive? Did it run? Why is it taking a little longer today?

I no longer do the task by hand. I just check whether it got done. There's an important difference, of course, but this wasn't the holiday I promised myself.

The job is now called maintenance

A manual task has clear boundaries. I start, work on it, and finish. It might be annoying, but I know when it needs my time.

Automation blurs that boundary. A service the system relies on can change. The expected data might never arrive. A permission that was enough yesterday might no longer be enough today. Even if the part I wrote stays the same, the world around it keeps moving.

And maintenance doesn't always arrive at a convenient time. There's no calendar entry saying “Tuesday afternoon: tend to automation.” A notification lands while I'm focused on something else. Sometimes there's no notification at all; noticing the gap is my responsibility.

When calculating the time saved, setup time is easy to count. The “I wonder if it's working” tab left open in the back of my mind is harder to measure.

Silence isn't always good news

I don't like an error message, but at least it speaks. The system that says nothing is more unsettling.

A task can appear to have run without producing the result I expected. Perhaps it successfully processed an empty list. Sent yesterday's data again. Finished half the work and skipped the rest.

In that arrangement, the green mark on the dashboard and what I consider “done” don't agree. I'm waiting for the outcome of the work, not just for a command to run.

If the task is to produce a file, for example, the file needs to actually exist, open properly, and belong to the right day. A success message that doesn't check those things still leaves work for me.

If I answer every notification

The first solution seems to be more notifications. Started, finished, tried, retried. My phone becomes a small operations center.

But when everything sends news, it's harder to tell which message needs attention. Eventually, reading the messages becomes a regular task too. I start thinking about automating the new work created by the automation. A lovely loop; slightly funny from the outside.

What I want is simpler: if something needs my intervention, I should understand what happened. I should be able to find the last successful result. It should be clear how many times the system will retry on its own and when it will stop.

Being able to resume after an error without investigating the entire history is part of that peace of mind. Restarting the task shouldn't become a separate job of worrying about duplicate results.

Sometimes doing it by hand costs less

The fact that a task can be automated isn't a sufficient reason to automate it. For a small job I do once a month that changes shape every time, the system I build might demand more attention than the task itself.

That's a little annoying to admit. Building automation is fun. Doing the repetitive task is boring. Sometimes what I defend as efficiency also contains the urge to build something new. There's nothing wrong with that urge; I just need to put it in the right column of the ledger.

So I'd like to adjust the question. Alongside “Can I automate this?” I want to ask: “What will it take from me to trust that it's working?”

For me, the best moment of good automation isn't the first time it runs. It's the moment, some time later, when I can forget it exists. I see that the work is done and get on with my life.

There will still be maintenance. But if I'm taking attendance every morning, I haven't yet earned the free time I promised myself.