A little while ago, I decided to create something with Claude Code to help me document my upcoming hike along Te Araroa—or TA. It’s a 3000 kilometre walk from one end of New Zealand to the other. I’m going southbound—so from Cape Reinga at the top to Bluff at the bottom of the South Island.

I’ve never done a multi-day hike before. I’ve done lots of day hikes of varying complexities but I’ve never had to worry about not having phone signal for long stretches or being out in the wild having to fend for myself. So I don’t know what that would do to me physically and psychologically. Which is fine, and is kind of the whole point of doing the hike—to challenge myself in ways I never have before and to hopefully find the courage and resilience within me to keep going.

I don’t know the person I’d become on trail, so building any piece of technology for this person is a bit tricky. I mean, would I want to sit down and write long drawn essays at camp after walking 25 kilometres a day? What would my tolerance be like after 20 river crossings and a big gash on my foot, surrounded by sandflies? Would I even care about writing the story then as I care about it now? Maybe, but also maybe not.

And that’s a problem. Because good technology understands the user’s mindset and behaviours. For instance, if you’re sat in an office with access to unwavering internet, you take it for granted that Safari will load your website without glitches. But when you’re going in and out of network areas all day, would you prioritise sending a message to your now-single and post-heart-surgery dad or would you try and open a website?

So many questions and so few answers. That’s what I was dealing with when I first went back and forth with Claude to see what we could build together.

As nerve wracking as that was, it was also one of the best lessons from this process: I had to do my best without assuming anything about my future self.

So I started making a list of things I need to factor in, while still allowing room for failure.

My solution needed to be as light weight as possible. It needed a daily journal log, and tags and categories to filter entries by. It needed to work offline, sync online. Mobile first, basic interface, less scrolling, big font, dark text, automatic location tagging that matches the TA route map, periodic data back-up, built-in language checker… all the things I needed to figure out how to do.

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This is post 2 of 5.