I'm leaving my home and travelling for the next 2 years

Hellooooo! Welcome to my pre-travel post, looking at the whats, wheres, whys, and everything else. Let's go!

James Daly
Feb 6, 2023
5 min read

Hellooooo! Welcome to my pre-travel post, looking at the whats, wheres, whys, and everything else. Let's-a go!

I've found long-term, solo travel to have such an interesting effect: it’s an accelerant of absolute violent proportions – whatever you're working on, whatever your current goals, whoever you're growing into, gets cranked to 11. I guess the trick then becomes harnessing this.

In exactly 23 days I'll be flying to Tokyo, leaving most of my belongings in a storage unit back in Sydney, my apartment's lease ended, and no stable home for the foreseeable future. Welp.

I did this before, in 2018, but not to this extent. Back then I only went for 9 months, and I was living with my parents at the time, so my bedroom and belongings were waiting for me when I returned. This time is for longer, to more parts of the world, with the next few years wide open when it comes to concrete plans. For example, I have no idea where I'll be in July. Or October. Or where I'll be living this Christmas aaaAAAHHHH


I'm doing this as I had started feeling a bit stuck in Sydney. I don't mean to sound like I didn't appreciate where I lived – I love my little apartment home on Manly Beach; being able to enjoy the water every day, the cockatoos and lorikeets visiting my balcony, the stunning sunsets, the ferry rides to work in the city, the incredible beauty of Manly Harbour, Cabbage Tree Bay, and the beach itself, and having my family and friends so close by.

Seriously, check out this vid. This place is heaven:

A short video I made last year of everyday life living here

But I felt like I was missing something that I'd regret not grabbing, with the means and opportunity right in front of me. I don't think it was routine that bothered me, as I loved the beach-life routine, and thanks to working remotely on designstripe I felt I had the freedom to work from anywhere in Sydney.

I think it was more knowing how much was out there, seeing videos and images of so many exciting parts of the world, and creative people exploring amazing cities and cultures.

I've had this overpowering belief since I was very young that the world should be explored and uncovered in the same way an RPG map should be, or the mysteries of a book store should be, and knowing I wasn't tied down to anything here in Sydney made me feel like I'd be missing an opportunity that only comes a few times in a life.

I won't be able to buy a home for a few years, I'm single, my family are all healthy and doing well, and my team at designstripe is spread all around the world. The timing is perfect, and if I let this pass by me I'd always be wondering.

Add to this that I'm now in my thirties, now have an auto-immune disease, can feel so strongly how little time we actually have, and the desire to somehow live multiple lifetimes in my mere one, to see as much as I can and make beautiful art from the experience of doing so – it all makes sense.

This all sounds very inspiring etc etc etc, but it hasn't been easy preparing. I've really struggled with leaving my home. During covid and the lockdowns I created such a cosy apartment here, with everything I need for creative projects, work, fitness, nature, comfort, friends – I love it here. It's wonderful. So giving this up for uncertainty and unknown has been something I've needed to work through, enjoying anxiety and panic attacks along the way, as well as a whole lot of sadness at leaving something that makes me so happy.

However, I've always found that change brings opportunities that you can never imagine, and you can't grow unless you're uncomfortable and doing things beyond what you're used to, so I'm focusing on the possibilities that are on the way. What's also helped has been zooming out; trying to picture the life I want to have had when viewed in its entirety, from start to end. 1990 - ?

I also want to feel like I'm living, overcoming challenges, and exploring in the literal, romantic sense of the word. I've felt lately that when you work in front of a computer it's so easy to feel like you're seperate from nature, from the world, that you go outside into the world, and then retreat back into a virtual bubble of familiarity, that the world is "out there", a different place to the online world in which you spend so much time, and I want to feel like there's no line between these two places. This is also why I want to eventually buy and live on a sailboat, but that's another story.

Life is the most incredible open-world game, with effectively infinite fascinating characters to meet, maps to uncover, experiences to have, missions and quests to go on, skills to master, and then ultimately to inspire others to do the same. I don't want to miss out on that.

Where and when

So here's the rough timeline for the next few months.

I'm starting in Tokyo, spending all of March and April there. This should, with luck, mean exploring during cherry blossoms season, and enjoying spring in Japan. I'll be living in a short-term rental apartment and working from various WeWorks around the city.

I'll then be back in Sydney for May, for multiple family members' birthdays, and Mother's Day, and it'll be nice to ease into this new life by seeing family again relatively soon – I'm sure I'll be missing them after the first two months away!

June and July will mean escaping Sydney's winter and heading over to Europe. I don't have solid plans for where just yet, but have loved the UK and Scandinavia in the past, and still haven't made it to Italy despite having family there, so most likely something along those lines.

I'll be spending August and September in Montreal. A large part of the team at designstripe are based in Montreal, so spending a good, solid chunk of time with them will mean getting heaps of work done, and looking at our roadmap, we should be at an exciting time then to be in-person working together. We'll also be having our annual team retreat in Montreal during this time, so it lines up nicely.

I then have October still to fill, not sure yet, but thinking perhaps New York City due to it being so close to Montreal, but damn, that city is expensive, and I'm not sure if I want to put myself and my wallet through that just yet. It'd be so cool tho. We'll see.

And then it's late spring and early summer in Sydney, and a summer spent on Sydney's beaches is one of my favourite things, so I'll fly home for November (with a quick stopover in Chiang Mai for a friend's wedding) and spend the summer back here, until March/April 2024!

I'll then be heading off once more, but I haven't planned that far ahead yet. Gotta get through this year first.

If you'll be in any of these places this year I'd love to meet up and hang out – one of the biggest challenges of this nomad thing is loneliness, so I'll need friends! And if you have any recommendations for things to do/see/eat in these places please do let me know too. I apologise in advance for my many, many food allergies.

And that's about it! I'm going to try and have this blog be a mixture of travel posts and startup/business posts going forward, so I'll have some updates from Japan on here very soon.

Let's go!

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