I’ve been writing about my AI journey for a few posts now, and I’ve talked a lot about which tools I use and how much I trust them. But I haven’t really gotten into what I’m actually doing with them day to day. That’s what this one is about.
Trip planning was one of the first things that clicked. When you’re searching for flights and hotels, every website limits what details you can give it. With AI I could be hyper specific. If I’m flying with just the kids it’s this configuration. If my wife is with us it’s that one. These are the types of hotels we like, these are the amenities we need. It could actually hold all of that and work with it.
It didn’t book anything, but it helped me build out exactly what we were looking for and where to go look for it.
Then it evolved. I used to use Trello boards to track trips day by day, reservations, what we were doing when. Now I do all of that inside the AI itself. It exports as a YAML file I can save and reload if I need to start a fresh chat. Since privacy matters to me I’ll delete a chat when I’m done with it, but the file means I don’t lose anything. I have a general preferences file I keep updating, and then a separate file for each trip. It works really well.
I did something similar for days out with the kids. I took a week off last August and it was just me and the girls. I built out a history file of things we’d done and liked, threw in our preferences, and used it to plan the week. On Tuesday we have this, I need to figure out Wednesday, here’s a restaurant nearby that fits. I’d already been doing some of that in a neglected Trello board, but this way it was all queryable and easy to update.
Date nights with my wife got the same treatment. I’d go through our preferences, confirm them with her, and then present her with suggestions. I’ll be honest, I wasn’t exactly hiding where the ideas came from. More like, hey, I told the magic box what we like and this is what it came up with. Sometimes it was completely off. Sometimes it was genuinely spot on.
More recently it’s been helping with meal planning for the kids. Mine are picky eaters, so it was a lot of back and forth on what might actually work. It helped me land on a couple of new meals and then built a schedule to track them. Basic stuff on the surface, but genuinely useful in practice.
One that I found unexpectedly cool was using it to wrangle my Trello data. I have boards for things to watch and books to read. When I tried to pull that data into an AI the file was massive. So I had the AI help me write some scripts to strip out everything I didn’t need, took a two meg file down to about 50K, and then I could actually work with it.
Which brings me to audiobook recommendations. I was a little cautious about feeding it my reading history since it builds up a fairly personal picture of you. But I write about what I read anyway, so it felt like a reasonable trade. I’d give it what I read, when I read it, what I thought of it, and ask for recommendations.
Hit or miss, honestly. Some suggestions were weird and when I pushed back on them it would just fold immediately. That should always give you pause. But when it got it right it was actually pretty useful, and interrogating the reasoning often got me somewhere interesting even when the initial answer was off.
Which is a good lead in to something I want to dig into a bit more. It does some genuinely impressive things, but it’s far from perfect, and that part matters too.