Tag: travel planning

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.

Going on holiday

I booked my tickets two weeks in advance and my accommodation just a handful of days before the big day. 

No one in Australia does that. For instance, my friend booked a week’s stay in a cabin far, far away—five months in advance. That’s normal.

And here I was booking flight tickets to Tasmania, about to spend ten days in a city I knew nothing about. In hindsight, I’m proud of myself for choosing Launceston—it’s a delightful place to visit. But even until the last moment, the day of my journey, as I sat in the back seat of the cab, looking out at Canberra’s iconic welcome to Autumn, I wasn’t excited. Even as I went through security check, I was more alarmed that we no longer have to take out our electronics for screening than I was excited about my upcoming trip.

photo of the ocean as seen throug the flight windor

Sitting in the plane, watching the ground become bigger and bigger as we soared into the sky, I felt nothing. My glasses fogged from me breathing through my face mask, but I had the best seat in the house—the window. Still, my insides felt like a balloon that failed to balloon.

It didn’t feel like I was going away on holiday.

I landed and walked into the biosecurity area of the Launceston arrivals zone. And I texted my trusty friend and brother: Launceston Airport is a massive tent.

We queued up in what looked like a huge white canopy with three podiums with officers checking everyone’s border permit and asking each person individually if they’ve travelled to any hotspots or have any symptoms. It’s incredible how much we humans function on trust systems. Once I’d shaken my head no to all his standard questions, my officer—a stubby man wearing a polo t-shirt and pants—gadded me a card that had some contact information in case I developed any symptoms. I thanked him and walked out—and into the actual airport. It was smaller than the Canberra airport—just two conveyor belts for baggage. Brilliant and easy to find. A good five minutes later, my yellow backpack waded its way to me, and I hoisted it up on my shoulder and turned to face the exit.

Those glass doors didn’t open automatically.

No worries. I’m used to motion sensors not sensing me. I went closer only to realise that the double door had a big circular sticker on either side of the partition with text that read, “Touch to open door”. Amused and highly sceptical, I touched and viola! I was out in the chilly breeze and the sunny outskirts of Launceston.

Following the sign, I turned left, looking for a bus. The airport shuttle was supposed to be waiting for passengers who wanted to go into the city. Instead, there was a van—an approximately 15-seater vehicle with a chubby bald and smiling man waiting outside. On the van, clearly visible, was a sticker that read, The Airport Shuttle. I had to ask. “Is this the airport shuttle?”

He didn’t sneer. He wasn’t sarcastic when he replied, “It is! Where do you need to go?”

“The city, please.” As if that was a destination by itself.

“Do you have a specific place in the city?”

“Ah, yes. The Backpackers Hostel.”

“Sure thing. I can drop you off right at the door. How long are you in town for?”

I told him, and he suggested I go to the visitors’ centre and get myself a walking map. He helpfully added that it’s inside the post office, which I knew was built in the early 19th century and was still functioning handsomely.

photo of the old clock tower, Launceston
Post office, Launceston

I thanked him, paid him, and took my seat. And at long last, I removed my mask and did a full mouth rotation to make sure my facial muscles were still operating. 20 minutes later, I stood outside the hundred-year-old building—just another old building, I realised as I later wandered around town—that was the hostel I’d be staying at.

And then it hit me. 

I had ten glorious days to do anything but the things that defined my life.

photo of the suburbs of Launceston as seen from across the Tamar river
Welcome to Launceston

To be continued…

Climbing volcanoes

When I first heard that I’d be travelling to Auckland for a conference, I did the usual happy dance. I was going away for a few days, and to an exotic place I’ve never been to. For months I’d fantasied about the Te Aurora hiking trail that runs through the north and south islands of New Zealand, covering all historic and culturally-significant sites. It’s a 3000 kilometre trek, one that’d take 3 months for an experienced hiker and about 8 months for me. 

But that’s all I knew about New Zealand. Pathetic, I know. Which is why excitement ballooned in me as I clambered on to my flight, scarf and jacket on, ready to face the unknown weather conditions the kiwis were conditioned to.

Welcome to Auckland - airport entrance

When I landed at 12:30 am, it was chilly and breezy. But hey, I’m from Canberra—chilly and breezy is my jam now. I’d researched and planned to take the public bus system all the way to my hotel, a mere 500 metres from the bus stop. What I didn’t anticipate, though, is the lack of meals in my flight. Argh, vegan problems.

I touched down with a rumbling stomach, and the only place open at 2 am (security checks are a pain in the ass) that isn’t a McDonalds or Hungry Jacks was another burger place: Lord of the Fries—a complete, vegan junk food chain. Oh, well.

Dumping the public transport system, I chose the capitalist corporatism of Uber to feed myself. When I slept that night, it was 3:40 am and Batman was on television.

Every time I’m in a new place, my energy levels are so high that it baffles me. I was up and charged to explore at 9 am. I soon realised how cool Auckland’s public transportation system is: their bus card, called AT HOP, comes in two variants—a standard plastic card like the rest of the world or a key tag for practicality. Of course I went for the key tag! 

With a dangling key tag full of bus cash, the streets had become my oyster. Wandering around the neighbourhood, I went past the Sky Tower, spotting it from everywhere I stood. It’s a telecommunications and observation tower in the heart of the city, and like any massive piece of architecture, a tourism magnet. I’d seen a few towers to know my money’s better off someplace else, but I did take plenty of photos for free.

Sky Tower in Auckland

After all, Canberra has its own tower—the central point of focus for many a camera folk and sun gazers.

So far Auckland seemed abundant in glorious buildings. And every shop—cafes, restaurants, bars, quoted reasonable prices. Auckland is far more affordable than what I’d become used to. Nothing to complain. 

When I looked up activities nearby, my top hits were Mount Eden and One Tree Hill. Two dormant volcanoes, havens for trekkers. Bring it on, I thought as I traced the route first to Mt. Eden.

Panoramic view from Mount Eden, Auckland

The bus got me there in about thirty minutes from the city. As I ascended, I came across a notice board declaring the Mt. Eden trek as part of the coast to coast walking trail—the same Te Aurora I’d had my eyes on for ages. Elated, I told myself this’d be a practice session for when I’m indeed ready for the actual one.

Coast to Coast Walkway sign at Mount Eden, Auckland

It was easy enough. Joy and excitement are great motivators when you’re climbing a hill far more massive than yourself. I felt a spring in my step with every forward step. I smiled at trees, chuckled at bushes bursting with blossoms, and marvelled at the study ground that pushed me back as I pressed down on it. 

All around me, nature showered in hundreds of shades. Flowers in yellow, white, purple, and red laughed at me as I scaled their home, welcoming but also doubtful—as if they weren’t sure I’d make it all the way up the mountain. Ha, I never shun from a challenge like that.

View from Mount Eden, Auckland

Breathing in some of the freshest air I’ve experienced, I powered through. The higher I went, the more I saw of a deep gash in the ground. A valley sunk downwards, a clear sheen of grassland except it looked like a mountain turned inside out.

When I got to the top I saw it for what it was: a massive hole in the hill, covered with green, green, and more green.

Mount Eden, Auckland

As I looked around at the city, spotting the Sky Tower and the thousands of miniature homes that housed Aucklanders, I knew I was in utopia.

Sitting on a pile of rocks not long after that, basking in the rather hot sun, I savoured my raw chocolate caramel slice, engulfed in the uplifting scent of wet plants. 

It only got better as I left for One Tree Hill.

This one had more plains to walk through before the actual climb up. A well-paved pathway led me through light green meadows spotted with darker bushes, water tanks, sheep, and tiny humans scurrying across the vastness that enveloped them. 

On the way to One Tree Hill, Auckland

Unlike Mount Eden, the higher I went on One Tree Hill, the more greenery I saw patched by the unmistakable signs of human. I’ve always hated people’s irresistible urge to leave marks in places, to emboss their presence, to shove their opinions and fantasies on unassuming nature. And yet, there it was—a massive heart carved on the ground, names of long lost lovers scratched into the earth, without the least regard. Love can be so cruel at times.

At the top stands a tower, a memorial for Sir John Logan Campbell. Scotsmen Cambell and Willian Brown were the first Europeans to settle in the region, and together they built the first house and set up the first shop. Campbell was also a member of parliament and a prominent social figure before that. No wonder he’s called the Father of Auckland.

Daylight lingered as I descended from the hill. Spring had reached Auckland and I set out to wander the streets—there was still so much to see. But first, coffee. And some glorious raw treats. Well, why not?