ExperimentsMay 13, 202613 min read
I Tried to Automate My Life with AI: False Hope, Letting Go, and a Little Bit of Magic
I spent weeks setting up AI to handle the repetitive stuff. Some of it worked. Some of it spectacularly didn't. Here's what actually stuck.

A morning in Can Tho, sitting in front of the screen, waiting for a bot to send me the weather. It was supposed to be one small test in the whole chain of automation I had sketched out for my own life. Instead it was the first time I understood that the dream of AI untangling everything can wobble more than you imagine, and that the one who needed an update might be me.
I am the type who has to try things. When people started talking about AI changing the world, about automation turning a working day into a series of light taps, I could not resist the urge to make it real. I used to run a business, and there was a stretch where I chased every checklist and kept a pile of habits from the kind of successful-person posts that show up each morning. But once I moved to working solo with AI and automation, all the promises of a weightless life started showing small cracks I had never prepared for.
I started with simple things: saving appointments, sending birthday reminders (which I never remember correctly, though I can recite the memes), letting n8n pull commodity prices every morning. A few of them ran beautifully. Watching the error lines on the screen thin out, I smiled and wondered whether I had just bought back a few hours of real life.
Then one evening I wired a few small tools together, hoping everything would still be running when I woke up. Instead, at three in the morning, my phone buzzed with n8n firing error after error: one extra character in a command, or an API that changed its shape without telling anyone. A strange sinking feeling arrived as I sat up, yawning, thinking, why exactly am I doing this to myself?
Something about chasing automation made me see that the human part of me had to adjust so it would not become the lab rat of the system I had built. Back when I led a team I believed everything could eventually be reduced to a formula: get the checklist template right and you are done. Later I saw that the habit of controlling everything was exactly what exhausted me most on the days the bot refused to behave.
Automation sounds like liberation. What it actually does, day by day, is map out the dependencies you could not see. Sometimes I ask myself: do I want the machine to take the worry, or have I just gathered all my worry onto a new object called a workflow? Some days I am delighted when everything runs smoothly. Other days one broken snippet is enough for every good feeling I have towards technology to vanish inside two lines of an error message.
The funny part is that once the machine settled down, I missed the falling-apart feeling of a stopped bot. It still has a strange pull. Maybe because I do not control all of it, so every repair feels like clearing a level, even when the prize is only a few dozen minutes of lost sleep.
I started accepting that automation does not rescue any day completely. It takes a few repeated motions off my hands and brings a new kind of nuisance in return: the worry that the system will break while I am out, or twenty messages arriving mid-meeting to tell me the AI assistant has just run into a problem.
Sometimes over morning coffee I open my phone to check a process, then stop and ask myself: if I keep chasing these status lines, how is this different from running the company, except that the responsibility is now attached to a combination of AI and machines instead of people?
One afternoon, with birds outside the door and me about to fix a small automation, my wife walked past and asked: if everything gets automated, what will you do all day? I did not have an answer ready. There is something about owning the rhythm of your life that has nothing to do with the number of logical processes, and everything to do with the accidental moments. A bird's call getting into the room. A workflow snapping without warning.
Some things automate, and some things have to stay messy
Here is the paradox: the more I automated, the clearer it became which things will never fit into a workflow. Let the AI handle sending a client a quote. But typing a sudden message to check on someone you love, or sitting down to breakfast in a noisy pho shop, are things no bot can schedule a reminder for.
It turns out the machines carry the tasks I dislike, and in doing so they expose the things only a human is disorderly enough to keep alive. One day I laughed out loud at a message the bot sent to the wrong person, mixing up its forms of address, tagging the emotion completely wrong. That was when I remembered that what makes a day stay with me is never the parts that ran correctly. It is the small mess I could laugh at.
Working with AI has forced me to be more patient with the machines and with myself. On the days the bot runs well, I am grateful for the progress. On the days it falls over, I remind myself that this is fine too. At least there is something to fix, something to be annoyed by, a sign that I am a person living an actual life and not a perfect workflow running inside my own head.
I keep experimenting. I will still spend part of my morning drawing new flows to take the small chores off my plate. But I have also started to value the failures, the stretches where nothing runs, the error messages that arrive at two in the morning. Because of them, some day I will genuinely let go of the expectation of controlling everything. And on that day I will give myself half a morning of doing nothing, with a coffee that went cold a long time ago, which is one thing no AI has ever reminded me about on time.
Have you ever handed something over to AI, and how did it feel when the workflow suddenly fell apart? Is there anything you found only a real person can take care of, no matter how loudly the technology is praised?
Tinkerer in financial economics, serial entrepreneur, and professional stumbler. 99% failures, 1% still here.

