Spent 8 months using AI wrong while traveling

Lifestyle

Okay so I've been working remotely from like 12 different countries this year and I thought AI was going to be this massive productivity unlock. But it wasn't. At least not at first.

I'd use ChatGPT or Claude to plan my work week, and by Tuesday the whole thing would be useless because I'd be in a hostel with shit wifi, or I'd be exhausted from an overnight bus, or I'd lose an entire morning dealing with visa stuff. The plans looked great on Sunday night. They just had nothing to do with my actual life.

It took me embarrassingly long to realize the problem wasn't the AI. It was that I was prompting it like I had a normal desk job with predictable hours and a routine. Which is... the opposite of nomad life.

Here's what actually started working:

I stopped pretending my schedule was stable. This sounds obvious but I kept writing prompts like "help me be productive this week" without mentioning that my "week" involved two time zones, three different accommodations, and maybe 15 actual work hours if I was lucky. Once I started being brutally honest about the chaos, the output got way more realistic.

Like instead of "plan my work week," I'd write: "I have maybe 20 hours of decent focus time over the next 5 days, wifi is unreliable, I'm tired from travel, what are the 2-3 things I absolutely need to get done and how do I structure them so I don't need to be clever about it."

I realized vague flexibility was killing me. I used to think leaving things open-ended was smart because "you never know what'll happen when you're traveling." True. But what actually happened is I'd get a vague plan, then spend mental energy every single morning re-deciding everything. By the time I figured out what to do, half my energy was gone.

Being weirdly specific in prompts meant less decisions later. Like "I work best between 8am-12pm, I need everything done in 4-hour blocks, I can't do calls after 2pm my time", that kind of detail made the plans actually stick.

The real constraint isn't time, it's energy and logistics. Goals are fine but they don't change. What changes constantly is whether you have wifi, whether you slept, whether you spent 3 hours that morning trying to find a SIM card. I started including this stuff directly in prompts and suddenly the plans didn't immediately collapse.

There's this thing where AI will give you options, which sounds helpful until you're sitting in a cafe in Chiang Mai trying to decide between four different approaches to your work and you just want someone to tell you what to do. Now I explicitly ask: "give me one approach, make it simple, no options."

The format that finally worked for me:

"I'm working from [city], inconsistent schedule, realistically 4-5 hours of focus time daily, low energy afternoons. I need to finish [specific thing]. Give me a 3-day plan with max 2 priorities per day that won't break if one day goes completely sideways."

That's it. No fancy frameworks. Just forcing the AI to work within reality instead of some imaginary productive paradise.

The weird thing is once I stopped trying to optimize everything and just asked for sustainable minimums, I actually got more done. Not because the AI was smarter, but because the plans matched my actual life.

Anyway, i have 5 prompts examples that show how prompts should actually be structured, if you want them, just let me know.

Posted Dec 29, 2025, 7:50 PM UTC

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