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Exactly How Do You Fund Your Adventure Travel Lifestyle?

A reader writes:

I would be very interested in how you fund your adventures / lifestyle. I know this is always a bit of an awkward one, but I think there are many people in the community that would be interested in ways to make extra income, source sponsorship and budget for adventures.

Thanks so much for what is by far the most interesting question I’ve received for a while.

It’s interesting partly because it’s about pulling back the curtain, and partly because I’m not sure I’ve got a simple answer to it!

Nevertheless, seeing as it’s the season of setting goals and directions for the year ahead, I’m going to make an attempt in the hope that my story will be useful to others.

Let’s make the attempt less awkward by avoiding concrete figures, though. I’m not being cagey; I just genuinely don’t think it’ll help answer the question. For the last few years I’ve made Armenia my base, and translating my finances from Armenian drams into pounds/Euros/dollars would strip it of context. My lifestyle is also highly unorthodox, and full analysis would be complicated, the results irrelevant.

Instead, let’s drill down to the core principles that led to the life of adventure I (appear to) live today. That, I think, is where we’ll find a useful answer to the underlying question: what’s your secret?


In 2012 I was riding down the U.S. West Coast when I got wind of an upcoming book launch in Pasadena. The book in question was called The $100 Startup, and its author, Chris Guillebeau, wrote a blog called The Art Of Non-Conformity, which I’d been following for a while.

His blog ranged wide, but the common theme was escaping “the system” and living on your own terms. Among ways to achieve this, one oft-mentioned concept was to quit exchanging time for cash – otherwise you’d always lack one or the other, and both are needed for adventure.

(I think this one concept neatly encapsulates both your question and my answer, but let’s continue down this road anyway.)

I made it to L.A., met Chris at the book launch, and bought a copy (get it here if you’re interested). I read it on the plane home and made the snap decision that I, too, would quit exchanging my time for cash. I wanted to spend more time on adventures; this was the way. Yet I was aware that – should I succeed – the paradigm shift could also serve goals beyond travel and adventure. (This proved startlingly true.)

Once on that path, however, I soon found myself at a crossroads. Suddenly there were endless ways to make a living differently – and, with them, endless ways to spend all my newly reclaimed time… yep, working.

If you’ll kindly entertain a tangent: the society that bred you and me considers work the main source of identity. ‘So what do you do?’, ask new acquaintances – meaning, of course, ‘so what kind of work do you do?’. And if you don’t have any work, you might reply, ‘I’m between jobs’ – because to say, ‘oh, I don’t really do work’ would be to voice an unutterable shame. Not working is practically unthinkable.

I could become a professional blogger, podcaster, or YouTuber (the word “influencer” wasn’t yet in vogue). I could become a corporate motivational speaker on the back of obscure past expeditions (a popular choice). I could become a walking, talking billboard for a billion brand partnerships (less glamorous than it sounds).

But I realised that what I really needed for my adventures wasn’t money. It was time.

And it seemed the most sustainable way to create time would be to build a passive income.

There are lots of ways to do this. Property ownership is perhaps the most time-honoured: become a landlord; live on the proceeds. Other types of investment can be similarly leveraged. The only assets I had, however, were intellectual property. Would a similar strategy work?

I went on a huge creative binge. In the latter half of 2012, I published most of what is now the cornerstone content of TomsBikeTrip.com. My platform was sovereign; my writing honest; readers trusted me. (I was lucky to do this when I did, before the web was awash with AI-written spam blogs saturating every conceivable niche. It wouldn’t work today.)

Then I made a few partnerships with makers and retailers I felt good about endorsing, on a referrals-for-commission basis. To my great surprise, this simple little machine whirred into life, and in 2013 I was able to scale down my freelancing, spend more time blogging, and – perhaps a better measure – go on my first trip funded by the proceeds. (I never wrote about this one: I spent a few weeks hitch-hiking and Couchsurfing around Iran in order to learn Farsi.)

Another broadly useful principle came in here: when in doubt, be helpful. This highlights what you can offer that people value. For my part, I analysed every reader email and blog comment I’d ever received, then categorised and ranked them by topic. Advice on buying gear, apparently, was what most people wanted my help with. I wrote an ebook called Essential Gear For Adventure Cycle Touring and published it. It was an instant hit, adding another trickle to my passive income stream and bringing my goal of more time a step closer.

In 2014, tired of publishing dry information, I tried something different – because my true creative drive was in telling the stories that accompany every good adventure, not in tech specs and product comparisons. Together with my friend Leon, I went on two boundary-pushing expeditions: by foot, bike and packraft along Iran’s longest river, the Karun; and by horseback along the Rio Santa Cruz in Argentine Patagonia.

To tell these stories, we made two feature-length adventure films. We crowdfunded tens of thousands of pounds and spent an exhausting year working on producing, promoting and publishing them. Yet in the end, aside from some laurels handed out by niche film festivals (now I was an “award-winning filmmaker”), we had two long videos that struggled to cover the annual fee for Vimeo Pro. Neither of us received a penny for the months of work we put in, and we still never have.

I learned yet another important lesson that year: you define success.

I’d made the mistake of seeing the films as products, rather than platforms. Fixated and overconfident, I thought all ideas could be moulded into passive income generators. That this was wrong seems obvious in retrospect. I’d drained my bank accounts, and on one occasion, while editing Karun in a Soho basement, actually slept in Richmond Park as I’d run out of couches to crash on. “Starving, award-winning filmmaker”, anyone?

This seems relevant because I see an awful lot of “do what you love” rhetoric floating around the adventure-outdoor-lifestyle space. While it certainly delivers the buzz that motivational speakers need to gain glowing testimonials, and helps personality-brand owners cultivate great tribes of acolytes, it’s mostly guff. “Love what you do” seems better advice: even if writing 100,000 words about bicycle pannier attachment systems wasn’t exactly fun, the result – a tool of demonstrable value – must surely have been improved by putting my heart into it.

Licking my wounds, I wrote and published How To Hit The Road: A Beginner’s Guide To Cycle Touring & Bikepacking in 2017. Having found a working formula, it was time to scale up. This book was designed as a brain dump of everything useful I knew on the subject before I vanished for a while: I was, at that point, drifting away from cycle touring and bikepacking, and all because of a little idea called the Transcaucasian Trail…

Today, together with my modest cohort of Patreon supporters (membership is now open for 2024), the model above continues to cover life’s essentials, whether at home or on the road. It can be boiled down to an unwavering focus on serving the community of cycle tourers and bikepackers, a small catalogue of products, and a few carefully-chosen commercial partnerships.

I write this from the window seat of a high-speed TGV between Stuttgart and Paris; one leg of a two-week train journey from Armenia to England to spend the festive season with my parents. As I’d dimly anticipated early on, most of my work on the Transcaucasian Trail has been self-funded, free of the strings that come with donor funding and all the better for it. And cycle touring and bikepacking has become a nice way to get away from “important projects” and do something self-gratifying every now and then.

Ironically, I now freelance again, only as a trail planner rather than a coder (more on my most recent trail project here). It’s a specialised skill that’s currently in demand in Armenia, and because it mainly involves poring over maps and exploring wild mountains, I’m happy to do it because it doesn’t feel like work. Seems I ended up doing what I loved after all, even if there were a few turns in the road.

You mentioned budgeting, and I can’t imagine any of the above being successful had I not first got to grips with my personal finances.

I used to make spending decisions based on the contents of my wallet and bank account on a given day, never really knowing where my money came from or where it went, save for the hastily-calculated number I put on my tax return. It suited my personality: ever the non-conformist, I avoided structure and authority on a habitual level, and while young, free and single I just about made it work.

Now, the picture is more complex. To keep on top of things, I’ve become one of those annoying people who keeps every receipt, has an expense-tracking app (Toshl, since you asked; no affiliation), does annual budgets, and occasionally even audits themselves.

It may sound ridiculous, but hey, you asked how I fund and budget for adventures, and the basic answer is through very careful planning.

You also mentioned sourcing sponsorship. The short answer is that I used to, and now I don’t, even though I’m probably more sponsor-able (is that a word?) than ever. This is personal choice: I manage stakeholder relationships for the Transcaucasian Trail in Armenia on a much bigger scale, so the last thing I want is the same kind of thing impinging on the adventures I go on for the hell of it!

That’s it for now. I’m sorry the answer wasn’t simpler, but at least it all has a simple outcome: enough money and time for all the travel and adventure I care to do.

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