Who will I be on trail?

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

Map of Aotearoa New Zealand with the Te Araroa trail running through it
Source: https://www.teararoa.org.nz/map/

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 hikeโ€”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 youโ€™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. Thatโ€™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 checkerโ€ฆ all the things I needed to figure out how to do.


This is post 2 of 5.

The notebook guy started it

For a few months now, I’ve been actively thinking about and planning for the biggest trip of my life so far: Te Araroaโ€”or TA. Basically, a long walk from the top of the North Island of New Zealand to the bottom of the South Island.

An essential part of the research is watching YouTube videos of other hikers that have gone before me, to learn from their experiences, to observe their gear, and methodologies and incorporate the lessons in my own planning and preparation. In one such video, I saw a brief scene where a hiker walks into a hut and greets the rest of the hikers who return the gestureโ€”clearly they all know each other. And one of the hikers in the hut looked up from his notebook in which he’d been scribbling something.

It was the first time I saw a video of someone writing in a notebook on TA. Most people use technologyโ€”cameras, voice recorders, phones, drones. It’s not a big deal, if you think about it. Journaling is such a common habit and a lot of hikers do it. I just hadn’t seen anyone do it on a five-month endurance hike like TA.

That got me thinking about my own trip and how I’d document my journey. I hadn’t thought about that particular thing before. I loved the idea of writing on a notebookโ€”in fact, I think I’ll still have a notebook. I’d appreciate the sheer analogue-ness of it after a hard day of walking.

But I also knew, within five seconds of watching that video, that I couldn’t rely only on handwritten notebooks to document my trip. One accident on the Whanganui river canoe section and all my notes would be dripping, dead weight.

I could use the Notes app on my phone, I considered. But they’d be so scattered. I didn’t know if I could trust myself to have the discipline to date and location-tag every entry, especially when I might be going through rainy, windy, sleety, scree slopey environments every day.

So I decided to find an alternative option that’d work a bit more… the way I want it to.

As a marketing copywriter who once obsessed with being found online, I’m ashamed to admit this: I didn’t even research what other options might be out there. Instead, like so many people of my generation and industry, I figured I’d just ask Claude.

For months I’d watched people on LinkedIn rave about Claude Code and brag about how they kept hitting their limits. There were proud posts about being on the highest paid plan of Claude Code because they were just building so much cool shit that the peasant version wasn’t enough anymore.

I hadn’t tried Claude Code yet because I didn’t know what I’d build. It seemed rather frivolous to pay for it for the sake of poking it and seeing if it’d poke back.

That clip of a guy writing on his notebook was the impetus I needed. I sat down with Claude Chat to talk it through. What could I build with Claude that could be useful for me on trail, and help me learn the basics of Claude Code and building a solution on it?

So I started experimenting with Claude Code. I’m building something to help me document my trip, and structure it in a way I can look back on and appreciate in the future. But as with any experiment, although the excitement and novelty of it buoys me, I also wonder if what I’m building will truly withstand the trail. I guess there’s only one way to find out.


This is post 1 of 5.

The land owns us

I’m walking Te Araroa (TA) later this year. There, I’ve said it. For the first time since I fell in love with the idea seven years ago and seriously started planning for it last December.

Loosely transliterated to “The Long Pathway,” Te Araroa is a 3000 kilometre (1800 miles, if you’re that way inclined) tramping/running trail that goes through the entire length of New Zealand. From the top of the North Island, Cape Reinga, to the bottom of the South Island, Bluff, the trail snakes through iconic forests, mountains, lakes, rivers, and volcanic craters. It’s one hell of a way to travel through the country.

What I love most about the trail is not its length or its majesty. It’s the fact that this trail only exists because of the kindness and generosity of humans that owe nothing to the people who walk the trail every year.

1800 kilometres of the 3000-km trail is on public land monitored, managed, and cared for by the Department of Conservationโ€”colloquially known as DOC, a little nod to the inimitable healing power the Department and its humans seem to have on the land.

The remaining 1200 kilometres are on private land. The Te Araroa Trust and DOC work closely with these private landowners to make sure the trail continues to live on for people who come from thousands of miles away to experience it. It’s a lot of work, negotiating with and reassuring these owners that hikers aren’t always a scourge on their land, and that the world deserves to see and appreciate Aotearoa in its entirety.

When I lived in India and Australia, I’d often see swathes of private property fenced off with stern signs that trespassers will be frowned upon and prosecuted. I hated that. I yearned for a world where roaming is a basic right and passing through is welcomeโ€”as long as you behave responsibly.

It’s a naive thought. There’s no country in the world that will allow random humans to walk onto and through other people’s property without explicit invitation.

Which is why Te Araroa is special. Anyone is allowed to walk through 1200 kilometres of private property without the fear of retribution.

However, that doesn’t mean that you can do whatever you want on that property. There are rules, written and unwritten. There are protocols, best practices, and basic human decency principles that every walker is expected to follow.

My past self would’ve raised eyebrows at this. I would’ve vehemently argued that land should not be “owned” by private individuals because it’s for everyone to appreciate and enjoy. The land-owning few enforcing rules on the rest of us seemed like a moral wrong to meโ€”especially when the land has been around for far longer than humans.

In the last few years, however, my perspective has shifted.

I still strongly believe that we don’t own the land; the land owns us. I believe that humanity has wasted itself by conjuring rules and regulations around who owns which part of land and for how long.

But now, I also believe that people who’ve invested their life in serving and conserving the land have the right to protect it against pests, humans and otherwise.

I will never let a horse, however sweet and charismatic, into my garden patch of broad beans. It’ll destroy the integrity of the land. I have a responsibility to my broadies and that means keeping out anything that might harm the life of the land.

Everyone who cares for land in the same way has the same responsibility. As soon as I realised that, I understood that this what native land titles were all aboutโ€”not to carve up land for use and abuse but to treat the land with the respect and grace it deserves. First Nations people embody this. I’ve never heard an Indigenous person talk about land ownership as an entitlement. They talk about it as a responsibility and an honour to stand guard.

Australians have a habit of starting every event and gathering with an acknowledgement to Country. It goes something like this: “We acknowledge the [name of native tribe] people, the original custodians of the lands that we’re meeting on today.” Australia didn’t respect the Original Custodians or the Country in its long, brutal, and bloody Colonial history. Even today, native land title is a heated topic in parliaments and dinner tables across the country. Despite that irony, the script reflects something meaningful. We so often unthinkingly utter those words, like a chore almostโ€”but they show the true depth of native land rights.

The land always owns usโ€”not the other way round. But there has also always existed a group of custodians who take on the heavy burden of nurturing the land, and living on the land long after the passers by are gone. So they should have a say in whether and how rest of us can walk through the land.

So when I say Te Araroa is special, it’s because these peopleโ€”both native title holders and those who bought property under the modern ways of lifeโ€”have come to agree to share their homes and back yards with the rest of the world. With no expectation other than we leave it as we find it.


Photos of The Escarpment Track, a 10km trail in Wellington, NZ. This trail forms a part of Te Araroa.

Strange thoughts

When I saw that my favourite podcast had an episode with Jacinda Ardern as the guest, I instinctively tapped to listen.

Iโ€™m one of the millions of people who admired Jacinda Ardernโ€™s leadership from afar.ย When she was prime minister, I only knew about New Zealand as a great hiking spot. My view of her work and approach to leadership was rather narrow. But since moving here, Iโ€™ve heard lots of varying perspectives of her time as leader, and grown to appreciate the nuances that come with a job like that. Iโ€™ve also concluded that political theatre is sadly not an accurate reflection of the kind of society we ought to be building.

The podcast episode was lovely. Jacinda was honest and funny and surprisingly relatable. I enjoyed hearing about her childhood in the Mormon Church and then the sharp contrast of her adult life of sharing a flat with three gay men. Life has a wonderful way of making us confront our discomforts.

But then she and the host had an exchange that made me gasp. Iโ€™m paraphrasing:

JA: It (breast cancer scare) wasnโ€™t the primary catalyst for leaving, but it was the first moment I remember thinking, โ€œOh, maybe you could leave.โ€œ And I thought, โ€œWell, thatโ€™s a dark thought, isn’t it?โ€

Host: I think a lot of women have that thought, โ€œIf I get sick I can leave!โ€

JA: Yes! Honestly when you start thinking that way, that has to be a catalyst for sitting down and having a serious internal conversation.

That little conversation caught me off guard because I recognise it, in myself and others. I know both women and menโ€”but mostly womenโ€”who find it easier (and preferable) to have an external factor make that decision for them, whether at work or in life, rather than taking on the cognitive burden of making the call themselves.

What is it about living that makes us think that way?