Indie Techies Newsletter

Turn the work you repeat into something AI can help with.

Find something you do again and again. Show AI how you handle it, so it can help you next time. Repeat that, and the small improvements start to add up.

15+ years building softwareUpwork Expert-Vetted

Tom Ilsinszki outdoors beneath palm trees
Keep it human.

One task.
Better every time.

Each pass teaches AI a little more about the way you work.

Small problems.
Personal solutions.

Custom software is expensive to build and maintain. With AI, you can describe how you work in plain English—making tailored help practical for smaller, everyday problems.

For lawyers, accountants, food-truck owners, creators, and anyone with a task that keeps coming back.

It started with software.

I've been building software for more than 15 years, so I already knew how I wanted the work done. But AI would often start building too early, make too many decisions at once, or produce changes that were difficult to review.

Instead of correcting the same problems every time, I wrote down my process: plan before coding, discuss difficult decisions one at a time, and keep every change reviewable. The more clearly I showed AI how I worked, the more useful it became.

Then I noticed the same opportunity elsewhere: preparing monthly invoices, planning and scheduling social media content, and keeping track of other tasks that repeatedly come back.

Now I'm exploring how far this idea can go—first with my own work, then with independent professionals and small-business owners. I want to find real recurring problems, see whether AI can make one part easier, and share honestly what works and what doesn't.

Things I'm teaching my AI

I'm starting with problems I know well. Some already help me today; others are experiments I'm still building.

  1. 01

    Preparing my monthly invoices

    Every month, I convert payments from USD to EUR, enter everything into Excel, and prepare the files for my bookkeeper. I'm teaching AI to handle those repeated steps with me.

    Building now
  2. 02

    Managing my social media content

    I use AI to develop ideas, plan and schedule posts, and keep track of what I've already published—so I don't have to rebuild the process each time.

    Using now
  3. 03

    Building software my way

    I've taught AI to plan before coding, discuss difficult decisions one at a time, and keep changes small enough to review.

    Using now

These are my own recurring problems. Next, I want to meet people with completely different work, understand what they keep doing manually, and see whether AI can make one part easier.

Real problems.
Small experiments.
Honest results.

Twice a month, I'll share a recurring task I've tried to make easier with AI—from invoices and social media to software and everyday business admin.

You'll see what I tried, what worked, what didn't, and what you can apply to your own work.

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What's the annoying thing you keep doing?

Whether you run a business or work for yourself, bring me one task that keeps coming back.

We'll look at how you handle it today and see whether AI could make one part easier. Sometimes AI won't be the right answer—and that's useful to learn too.

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Follow along

Follow the experiments on TikTok, Instagram, and YouTube, or see my professional work on Upwork.

  • TikTokShort experiments
  • InstagramBehind the process
  • YouTubeLonger field notes
  • UpworkProfessional work

Pick one task you do again and again—and make the next time easier.

Show AI how you handle it. Keep the instructions that work. Improve them the next time the task comes back.

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