Traveling to Japan for three months because life's too short

I've been fascinated by Japan since I was a teenager. Thanks to Hayao Miyazaki (among others) the food, landscape, and architecture all exist in some dreamy, liminal space in my mind alongside wood sprites and lost civilizations.

Maybe it sounds daft, but the idea of actually visiting the country always seemed like it would break the spell somehow? Like anywhere, Japan has crime, social problems, bad weather, and if I go, me.

That said, I've had a plan (concepts of a plan 👐) to visit for years. I've recently dug out an old copy of Rough Guide to Tokyo that dates from 2011, which was the first time I started vaguely planning to go.

However, that was also the year I started working for Engine Yard, which changed the entire trajectory of my career. This was a huge deal for me, but Engine Yard landing in Dublin was also a big deal for the local startup community – Silicon Republic had an article in 2013 that gives a bit of a retrospective.

Plans to visit Japan went on the back burner.

#Fast forward a few years

Speaking of back burners, in 2019, I was burning out at my job. This was well past Engine Yard, which I had left in 2014. Our startup had been acquired, and corporate bureaucracy was slowly draining away my will over the subsequent three year earn-out. There were plenty of smart and thoughtful people around, but somehow I felt like I was getting stupider.

The work was the most mind numbing drudgery. I had begun to hate writing software, and was terrified that if I didn't leave, I might never recover my enthusiasm.

Then sometime in early 2020 I read a series of blog posts by someone who had cycled the length of Japan, and it rekindled those old plans, but now on a grander scale. This was something I could aim for – I was going to cycle the entire length of Japan.

Clearly this was a huge "my life is derailing, I must escape" signal, but my girlfriend was having a similar crisis and so we agreed on the broad strokes of a New Zealand / Japan cycling tour, taking six months or so to do the whole thing. We both had enough savings to take an extended break from work. I started cycling training in earnest.

On March 1st 2020, I handed in my notice – this was going to be the year I did Japan.

As COVID-19 wore on, it became increasingly clear that there would be no Japan trip. I finished out my notice period, and it would be almost a year before I felt like I could write code again professionally. I spent the intervening time doing not very much – I exercised, lost weight, went for long rambles in the Phoenix Park. Visited South Africa while there were still travel restrictions – that was memorable – had to get "war zone" travel insurance as it was the only option that would provide cover during the pandemic.

While I was in South Africa in 2021, David Coallier called and asked me to join as CTO of his new company, Clearword. I was ready to let go of Japan – I didn't want to spend another year on the sidelines, and so I joined David on what ended up being the most interesting and, hilariously, least personally remunerative startup we've done together. We had customers. We talked to them. We zeroed in on a niche. It felt really close to being something – but it never quite got there.

So it goes.

#2025, the year we make contact

And so here we are, in 2025. I am unemployed but am not immediately looking for work.

Emotionally though, things could not be more different.

I was disappointed about Clearword, but the writing had been on the wall for a while, and I came to terms with it months ago. I'll write that all down another time, but the gist is that I am feeling ready to start something new.

I am also turning 40 this year. Life moves pretty fast, and while I feel fitter and healthier today than I did ten years ago, I have to acknowledge that time is passing, and if I put this off now I may not have the opportunity again for a long time. And it's not just my own calendar that has to line up, but that of my girlfriend.

I also no longer feel the need to find myself by cycling the length of a country I've never even been to. I don't need a grand goal. I am going instead to soak in it. To be in the place and take it as it is. I want to do it peacefully and respectfully.

There are places I want to visit, of course – Yakushima island, the inspiration for the ethereal scenery of Princess Mononoke being top of my list.

Climbing Mount Fuji seems like it would be neat, if it works out, but mostly we both want to go off the beaten path, and avoid bustling around in crowds gawping at geishas, etc.

So – flights are booked. We are going for three months, start of May to start of August. We've booked our flights to arrive in Seoul rather than flying directly to Japan, as it gives us some options on whether we want to go north or south to start (regional flights from Seoul are relatively cheap). North, to Hokkaido, is sort of appealing with the chance of catching the sakura blossoms, but Yakushima is in the south, and it will be better to do that before summer gets into full swing.

In the mean time, I am attending evening classes in the city to learn hopefully enough Japanese to get by. Thanks to years watching anime, I have a surprising amount of vocab floating around in my head, if not all of the practical variety. This week I managed to write out my basic hiragana table from memory, which feels impressive, yet is just the tip of the iceberg.

Three months sounds like a long time, but anyone I've spoken to tells me however long they spent, it wasn't enough. We'll be traveling light and keeping our plans loose, and we are going to have some adventures.

Can't wait. 🇯🇵