Kill your darlings, they keep saying

For a few months now, I’ve been working with Claude Code on an experimental project. It’s a system to help me document my days and emotions while I attempt to walk the entire length of New Zealand.

Most people who walk this trail document their journey on social media. Instagram is naturally the best fit, because it’s audiovisual and doesn’t penalise you too much if you don’t post chronically. TikTok is another popular choice. For those who use these two platforms to post shorter videos throughout their journey, YouTube is the endgame. Open it up and you’ll see day by day logs, hour-long documentaries, and detailed series that capture the essence of what it’s like to be on this epic adventure.

I wanted to post on Instagram as well. But I also wanted to document daily notes just for myself. As notes. That I can look back on. Like a journal, in written form.

So I planned it. I knew I might be too tired after walking 8-9 hours to sit down and type into a phone. Even though I’ve written several long-form pieces on my phone before, part of me doubted that I’d do that on trail.

It was easy enough to build the shell. The interface was decent with an option to record voice notes, that would be transcribed and cleaned up before saving. And because I like to double check my work and double bag my electronics, I also decided to have a text-only log. That way, I could write or talk into my phone, depending on my mood.

I tested it. Neither the record button nor the save text button worked. I sat down to diagnose. After a lot of back and forth and enabling and disabling the developer menu on Safari, I learnt how to verify the error. A bit more back and forth with Claude Chat and we finally fixed the save text button. By then, it was 2am and we still needed to figure out what was wrong with the audio record button.

So I fell asleep and forgot about the project for two weeks. That was my reality throughout this process—I didn’t magically build a fabulous thing over a weekend. It took me months. Work and life happened. No matter how much I wanted to ignore the world and play with Claude, I had other commitments to honour, a father recovering from surgery, and a family that loves to be dramatic.

When I eventually returned to Claude, we went through several attempts to fix the issue before realising I needed to sign up to a voice transcription service, connect its API to Claude, and only then would my record button work.

Obviously, that’s common sense. However, I was under the impression that Claude Chat, with all its mightiness, could transcribe audio. In the planning stage, I didn’t ask the question specifically so Claude didn’t tell me.

Now I know Claude can’t transcribe audio. Neither can ChatGPT. But Perplexity does a pretty good job—it even transcribed Tamil, my first language.

Then I had to contend with two options: Sign up to a transcription tool and connect that to my Claude app. Or ditch the voice recording feature entirely.

The purpose of this project was to be able to talk into my phone. I didn’t want to get rid of it.

I took several days to think it over and kept coming back to the same idea: What if the transcription connection failed mid-way?

I’ve worked in tech long enough to know that every piece of tech you plug into another piece of tech—like adding more weight to your bicycle rack—is a potential point of failure. This is how software works. When something’s off, you check the plumbing, where things connect with each other, because that’s almost always the cause for a leak.

I went down that thought process rabbit hole. If transcription does fail for whatever reason, I would know fairly quickly. But there’d be no way to fix it while I’m on a 3000-km tramp. I mean, strictly speaking I could, but it’d be tedious and not what I’d want to do on trail anyway.

Then there’s the issue of backup. I wanted all my entries (text and voice) to be backed up to my Zoho WorkDrive account. In case I dropped my phone in the Whanganui river, everything I’d done until that point would still be safe. If transcription fails and I fix it, then I’d also have to re-check the backup status. All of this is super simple when I have a laptop connected to a stable internet connection, sat in my home with a hot coffee by my side. It’s torture to work all of that out on my iPhone, with spotty internet, in the backcountry, sitting on an uncomfortable rock, hungry and sore from walking all day.

If transcription fails and I don’t fix it, I won’t have an alternative voice recording system that’s as efficient and battery-conscious as the one I was trying to build. My phone’s voice notes would be fine, but they’d become messy. They won’t be automatically location-tagged or categorised by emotions and regions—a feature I definitely wanted.

Eventually, I decided to remove the voice option altogether. Going the extra mile to build it didn’t guarantee reliability. The extra work and admin didn’t justify the risk.

This was my biggest disappointment in the whole process: Having to kill the thing that got me started.

Even without the voice recording feature, I still have other potential points of failure in my app. I’ve done what I can to minimise niggly issues, but the real test would be on trail. One way to find out.

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This is post 3 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 Araroa—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 gesture—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 technology—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 notebook—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 Conservation—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 welcome—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 me—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 about—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 almost—but they show the true depth of native land rights.

The land always owns us—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 people—both native title holders and those who bought property under the modern ways of life—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.

Could I be happy?

I was chatting with a friend recently and said I could be happy stacking shelves at the supermarket.

Walking home after that meeting, I kept replaying that moment. Because I’d said the quiet part aloud, and I wondered what that’d sound like to someone who values their career growth and ambition.

But the bigger internal question was whether I’d truly be happy stacking shelves, or if I just said that because my best friend recently started a job stacking shelves, and I’ve been hearing all about it.

For the record, my friend thinks it’s a boring job. It’s a lot of heavy lifting and staring at hundreds and hundreds of chip packets and cola bottles and stifling the urge to comment on why we have a health crisis—for about 10 hours a day.

I’d be bored, too. It’s like hand weeding your garden in winter. There’s so much to do with so few creative challenges, and it feels never ending.

Could I be happy, though?

In hindsight, weeding my garden every other Saturday with my friend brought me so much joy. It was a comfortable routine—it didn’t require me to talk or perform all the time, I could find a comfortable position to sit at, and when we stopped for coffee, we saw the meaningful change our work had made.

Now, obviously, the stress is different when it’s your livelihood and not just a hobby.

But I also think we tend to mix up happiness with a certain job description. Happiness can come from being content with where we are and what we do. For some people, that sounds like having a low bar, but I’ve found that that doesn’t prevent me from chasing big goals, doing hard things, and giving my 100%. It just means that joy doesn’t have to depend too much on those things.

In a time…

When artificial intelligence scrapes everything we’ve created,
every poem, every song, every essay, and news article,
that story of you crying in the bathroom over a girl—spilt milk, of looking at supermarket deli meat and remembering your dead mum’s curry, of celebrating with your dad after a football win.
Everything remembered, synthesised, now artificially recreated.

In a time when artificial intelligence scrapes everything we’ve created,
showing us what life used to be like
reminding us of that time we asked ourselves…
what would we do if money weren’t an object?
We’re not quite sure, we argue over it
mourn the loss of a private memory, like a child whose pencil’s been snatched away from her…

In a time when artificial intelligence scrapes everything we’ve created,
uniting us by our miseries
and fears—
we return to those spaces we used to inhabit
the back of coffee shops
window seats at double decker buses
nooks and crannies of the city library
and the depths of spoken word communities
to seek solace
hoping for others who seek it, too

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