The Truth about 3.5 Years as a Struggling Digital Nomad

(This is a pretty depressing post to be honest, but if you’re where I was a few years ago, weighing up whether or not to go for it as a digital nomad full time travel blogger, you need to read this because it doesn’t always work out – for every successful blogger telling you to go for it, there are fuck knows how many more who either gave up or (like me) doggedly continued plugging away and dug themselves into a bit of a hole. If you’re just looking for interesting travel stories, you might want to skip this post – try here instead)

All work and no play makes Jack a dull boy
Mental state after a 10-hour blogging day

I thought I was making a play for a life of freedom.

The freedom to move where I wanted, when I wanted, and not have to worry about having enough money; maybe a few months snowboarding somewhere, a few months studying Mandarin in Taipei, perhaps a month by the beach learning to kitesurf in southern Thailand, all while working a few hours a day on the laptop.

Sounds awesome. But 3.5 years later, I’m still working basically every free moment of every day on the laptop, other than the odd day I take off to try & preserve my sanity by getting out for a hike, or the few days a month I allow myself to go out to socialize & drink and take a chilled hangover day the next day (and still end up making myself do a couple hours of work even on such days ‘off’). And this still isn’t bringing in enough income to stop me needing to borrow more every month and falling further & further into debt, having long ago whittled away all savings.

And to be honest it isn’t really complete freedom to go wherever you want whenever you want if your decisions about where to go end up being taken (by necessity) according to which place you think you may be able to make some money writing about. When I wanted to be in Taiwan to give potential love a chance, I couldn’t afford to stay (by becoming a long-term language student) and went and bounced between Korea & Japan because I could actually make some income by blogging about those places (the snowboarding in particular), whereas blogging about Taiwan had no obvious monetisation and I needed to increase my meagre income as fast as possible. Fact is that most of this blog makes no money (the only bits of it that really do are the content about Japan & Korea), and the blog overall is nowhere near making a full income; the only way I’ve made any decent money other than that is by doing my other site Snow Guide Korea timed for the Pyeongchang Olympics… but Japan & Korea weren’t where I wanted to be over the last 2 years. I wanted to be in Taiwan, but financially felt I had to go off to try and make a successful snowboarding website in Korea… I hoped to get my shit together and get back to Taipei in 6 months, a year tops; but shit happened and I somehow let 2 years slip away and I lost her. Now I’m finally back in Taipei, but too late, too late. Arriving back in Taipei recently and learning she was getting married felt like the final blow at the end of 3 years of failure and has prompted a hard bout of soul searching and taking stock, one result of which is this blog post. There’s only so much failing you can throw yourself at before it becomes a self-perpetuating cycle.

Note that I’m not looking for any sort of sympathy here – I fucked up, and that’s all on me. Rather, I’m writing this to serve as a cautionary tale to those considering taking a wild leap into digital nomad blogging.

Back when my cousin was dying a few years ago, a few years older than me, I had to ask myself – were that to also be my fate, would I be happy with how I’d spent my time? If I only had 3 years left, how would I feel to have spent them slinging ESL lessons in Tokyo while trying to pay debts off in the UK? It’s a no-brainer when you really ask yourself; I hated that job and I was over living in Tokyo (incredible city, but stressful to live in); I would be seriously pissed if I ended up spending my final 3 years that way. So I quit my job and bailed. A short time later while I was visiting Korea & catching up with friends, the news came through from San Diego; he was gone, and far sooner than expected. I climbed to the highest peak in Seoul, arriving at the top just before sunset on the clearest of days with all that vast city spread out below and not another soul around save for a pair of feral cats, and I found myself bellowing at the sky. Shouting up to my dead cousin (not that I believe there’s actually a heaven up there – up just seemed like the right direction), shouting up to him and telling him I’m still here and I’d really live my life from now on, however long that may be. He was robbed of his; who was to say I wouldn’t also be? You never know. It’s a stereotypical thing to write; don’t waste time, live your best life, make every day count, seize the day. But standing on top of Bukhansan, screaming at the sky, I felt it and meant it. Now, almost 4 years on, have I kept that promise? I don’t think so. Not really – though not through lack of trying. I have tried. I’ve just failed to pull it off.

So far, anyway. I suppose if I can add another 0 to my monthly visitor stats and therefore another 0 to my monthly income, I’ll have set myself up with a pretty damn sweet income stream, whether or not I want to keep being nomadic or try to be more stable somewhere. But even then it’ll have come at the cost of several years of lost (or at least questionably spent) time, sometimes living in windowless Airbnb boxes, eating like shit while trying to exist on a shoestring, with a disastrous love life to boot. I mean, self care is important whatever you’re doing… but self care as a broke digital nomad? Haha… my parents were a bit shocked when they saw me for the first time in a couple of years and had to slap me (not literally) to my senses about just how badly I was taking care of myself. Guess it had happened gradually over a period of time without me seeing it, but I’d lost loads of weight (and I’ve never had much spare in the first place) and generally looked like shit, and had retreated into some sort of shell, some sort of antisocial minimal budget autopilot mode to get me through until whenever the cash started flowing in and I could spark my real self back up again.

Sure, I could’ve eaten better by living in hostel dorms, but that would’ve been horrendous for work productivity, especially trying to build & run an online ESL business (which I was trying to do alongside the blogging). And yes, I could have based myself in SE Asia instead of NE Asia – it would’ve been cheaper, for sure. But all my business & blogging ideas related to Korea & Japan (especially due to the 2018 Winter Olympics and upcoming 2019 Rugby World Cup and Tokyo Olympics), and I was in love with a girl in Taiwan. Living in Chiang Mai because it’s cheap enough to live there on a super tight budget doesn’t strike me as freedom at all.

Would all that scrimping and hustling have been worth it if I do manage to get that extra 0 on my traffic & income? Even then, probably not, and I’m not even close to being there yet anyway so I can say thus far definitely not.

To be fair, despite working almost all the time, almost every day, I have at least managed to do a fair bit of snowboarding by spending most of the last 3 winters in Korea; but then, the only genuinely successful bit of online business I’ve done so far is Snow Guide Korea so work-wise it made total sense to be there doing that, especially with the 2018 Winter Olympics being there – but even so, it’s only been a minor success and nowhere enough to make up for the shortfall with my other efforts.

The big initial idea was the online English teaching site I set up with a few friends, but that was ultimately a painful failure. Painful in terms of a lot of time & effort expended for very little income, painful when I realised I’d totally fucked up by thinking I could get a full time income from it but after a year, then 2 years, we weren’t even close. I was still doing freelance ESL lessons too, but even with that I was failing to meet living costs. And so I went all in on my travel blog, which was initially the side project to online ESL but then seemed like my best route to an online income.

I kept thinking I’d almost cracked it, that if I just worked my ass off for a bit longer the traffic & resulting income would start flowing. And the potential still definitely is there, but it’s still mostly potential and now I’ve pretty much run out of steam and find myself unsure how to push it on to the next level. I hate social media and marketing, and despite my best efforts I haven’t been able to get good at that side of the game.

So if you’re thinking about making a play at establishing a serious, profit-making travel blog, ask yourself – are you prepared for how long that will take? Realistically you need to be thinking in terms of 2 to 3 years to be getting useful income from it (and even then you may well fail to do so). Are you ready for that massive time investment up front?

Do you have experience in digital marketing, SEO, photography, or writing? If no to all of those, you’re going to have to learn all of those, on the go, by teaching yourself (luckily there are many who’ve done it before you and created some helpful content to that end, see here, but it’s still a steep curve).

And consider that as of 2019, most of the really successful travel blogs were started between 2006-2010, maybe 2012, by bloggers who’ve mostly since opted to stop being nomads and settle down somewhere anyway.

Sure, there are some big ‘bloggers’ that started more recently, but they tend to be social media driven affairs, all about the bullshit Instagram ‘influencer’ account rather than a solid foundation of good travel writing on a website; so again ask yourself, am I a social media whizz? Can I kick ass at digital self promotion, or am I willing to cheat & fake it? If, like me, you pretty much hate social media and refuse to fake it, you’re going to struggle with that.

And even if you do smash it out of the park, you may not find it’s what you expected anyway. Consider for example Nomadic Matt, Expert Vagabond, Adventurous Kate, Never Ending Footsteps; these guys all smashed it out of the park – took off travelling, launched a blog at the start, and within a few years had successful online businesses earning them a 5-figure monthly income as they travelled – and yet still they all stopped full time nomadism.

That wasn’t the case for me. Most of those leading travel bloggers had pre-blogging backgrounds in digital marketing, photography or graphic design, or other such relevant skills. I had none. My travels were initially funded by bartending gigs and ski resort work (instructor, liftie, scrubbing toilets, whatever to get my snow fix) supplemented by credit card debt (bad idea), and later on by ESL teaching as I fought to get to grips with said credit card debt.

My blog came later yet, as I tried to escape the ESL classroom. I’d read all the above-mentioned blogs and thought I could do it too. Having already done a lot of travel, I wasn’t even looking to live as a full time digital nomad traveller – I had a wealth of travels already under my belt, scores of travel tales to write up and thousands of photos to use, so I figured I’d build out my blog on the side while staying in Taipei and focusing on the online ESL company we were building.

As already explained though, that ESL site totally failed, a slow-motion failure and reality slap-in-the-face, and so I went all in on my blogging, aiming to emulate those successful full time bloggers who’d already ‘made it’.

They were living the dream, having arrived in the place most aspiring travel bloggers are aiming at. And yet, even after making it as leading travel bloggers, after a few more years of nomadism each of them still eventually wrote a piece about why they couldn’t do the digital nomad lifestyle any more, why it was time to stick in one place long term:

Why I Quit Being a Digital Nomad (Expert Vagabond)

The Beginning of the End of My Travels (Nomadic Matt)

Why I Moved to Portugal (Never Ending Footsteps)

The exact reasons vary from case to case, but the common issues are burnout & exhaustion, lack of stable social life, loneliness, and the fact your love life will be a disaster if you don’t hit the jackpot of falling for a fellow digital nomad. Fall for a local somewhere and you’re into the realm of sliding doors, decisions & consequences, what ifs & if onlys; either your nomadic life will be over, or you’ll forever be wondering what might have happened with that person (and perhaps with lasting regrets that it did not), perhaps with only weeks to make the call.

And all that’s even for bloggers getting 100k+ hits a month and therefore thousands (in some cases over 10k) of dollars a month.

Imagine dealing with all those same issues without such impressive website traffic or very much income. Like me for the last few years. Or like this guy who only did it for a few months but wrote this refreshingly honest post about the digital nomad lie (in which he notes that it’s profitable to sell dreams i.e. when travel bloggers tell you how amazing their life is, making 10k dollars a month while sitting on the beach AND YOU CAN DO IT TOO, remember that they’re getting a big commission if you start a website using their links. It’s in their financial interest to make you want to do it even more).

So imagine it and ask yourself if you’re prepared to take the risk you could end up in that situation. If not, you might be better off never attempting a serious travel blog in the first place. If you reckon you can handle it, good luck – but it’s important you’re prepared for these possibilities.

Even if you do succeed, how long can you keep on being a chameleon, adapting to each new set of surroundings as you go, starting over time after time? As stimulating as that is, it grows old. So do you. I’m already well over it – I’ve actually spent the majority of the last 3 years of my attempt to be a successful travel blogger in Seoul, Tokyo, or Taipei. Three cities I know well, feel at home in, and have well-established social networks in; but not places where I can easily stay longer than a few months, rent a nice apartment long-term, get a piano & guitar, a nice snowboard setup, and all the other stuff I’d like. The constant need to make visa runs, or move there for 3 months then here for 3 months and on & on, is really draining after a while and not at all conducive to my passions and hobbies.

Sure, I could go somewhere else entirely, take off for Chiang Mai or Bali or Oaxaca, make a new bunch of friends and be okay, maybe even get stoked again on exploring somewhere new… but if I’m honest, the thought of actually doing that right now makes me feel really quite depressed. For one, I just can’t be fucking bothered. I really can’t. But it’s not just that; it’s that it isn’t enough. As I said above I have at least managed to do a fair amount of snowboarding in Korea recently, in the course of making & running Snow Guide Korea, but it’s a serious pain in the ass trying to live nomadically when you’ve got a snowboard & bag of ski gear; several Seoul friends have done me huge favours by letting me stash my shit with them while I was elsewhere (as I type this in Taipei, my board & kit bag are in my mate’s closet in Seoul).

As for playing music, I’ve barely touched a piano in years – they’re a little large to be carrying around. But in ‘normal’ i.e. non-nomadic circumstances, music is a key part of my daily life and mental well-being. I always have a harmonica or two with me while travelling, but I’m not so good at harmonica and don’t get the same fulfilment from it – plus I’m reluctant to subject anyone in earshot to my attempts!

And then there’s the relationship aspect. As I type this I’m nursing broken ribs from a recent snowboard crash in Korea, and a broken heart from returning to Taipei to find the girl I was still in love with has well & truly moved on. The heart hurts a lot more than the ribs, that’s for sure, and I find myself agonising over all the what-ifs, second-guessing over whether I should have come back here sooner or whether I should even have not left Taipei at all. I mean, I wouldn’t have left if I’d had sufficient money to pay for full time Mandarin lessons and thus a long-term student visa… and I’d have been back here a year ago if I hadn’t snapped my arm in another snowboard crash, or 18 months ago if this blog had actually taken off. Or perhaps I should’ve taken a job at an ESL cram school or kindergarden, a job I’d have hated but would’ve got a visa from. Who knows, maybe then I’d have got the girl. And, I must acknowledge, maybe it wouldn’t have worked out anyway – but I’ll never know because I wasn’t here to try, and I’m struggling to be ok with that decision.

But here’s the thing – you may be thinking, there’s plenty more fish in the sea, stop overthinking things, roll with the punches, move on… but when you’re always moving on from place to place, you are very likely, eventually, to go through some similar heartache, to have to make a decision that feels like an absolute wrench. And with this lifestyle, that heartache will often come wrapped up in regrets about decisions you made, the sometimes crucial timing of things, the sliding doors moments. I’m writing this while still very much feeling all this raw & fresh – in a few weeks or months I’d probably write something less melancholy, but for those considering attempting this lifestyle it’s more instructive to write down how gutted I am right now, while it’s still so intense. Broken hearts always suck, that is true; but when you’re living nomadically, without your usual support network, without real stability, and your nomadic lifestyle is largely to blame, it’s even harder to take.

If you’re lucky, you meet your significant other who’s also a digital nomad. Jackpot. Otherwise, it’s gonna be hard. If you’re in your early 20s and happy to just shag around while you travel around then I guess you can fairly safely ignore this – for now – and best of luck.

So where does all this leave me right now? Well, I went all in and I went bust; the risk you take. Which leaves me licking my wounds and considering my options. Risks are called risks for a reason – if you play, you may lose. I may yet still ‘win’ with this blog, all is not yet lost, but even if I eventually do it’ll feel like a pyrrhic victory and very hard won indeed.

We’ve pretty much pulled the plug on our ESL business (my business partner wanted to have another crack but I really don’t have the heart for it anymore), and while I’m not pulling the plug on my blogs (as I’ve just put way too much work into them and they do at least make some money) I have doubts now as to whether I’ll ever fully crack having a full income just from blogging; plus I’m struggling with heartache, with debt, with the lack of music and fitness, the lack of stability, and the isolation. Yes I go out and socialise on weekends and have a blast, but the rest of the week can get pretty solitary. It might be time to accept I need to get back in the ESL classroom, though I’ve been thinking that for some time and the thought fills me with dread; I’m going to give blogging 6 more months, mostly to see how things go with my new site Rugby Guide Japan (with the Rugby World Cup happening in Japan 6 month from now). If things haven’t picked up considerably by then, it’ll be time to put blogging on the back burner.

And you? Really, if you’re looking at all the big travel bloggers and telling yourself yeah I can do that, seriously do have a good hard think about all of the above before you take the plunge. Understand that there’s a fair chance you might only end up making life tough for yourself. If you’ve got money in the bank to support yourself initially it should help (in fact it’s probably crucial), but then to be honest I did at first, used it all, and still went heavily into debt again – consider setting a strict time limit at which to pull the plug and quit before you fall behind. I should’ve done so, but kept convincing myself I just needed to push a little further and I’d crack it.

But so far I’ve published some 500,000 words on my blogs (with the lion’s share on this one), roughly the same number of words as Lord Of The Rings or War & Peace. Imagine spending 3 years writing a LOTR sized blog, but you can’t make a living from it. It’s not a good feeling, not at all, and if it leaves you trying to live on a super-tight budget it really gets to you over time. It’s robbed me of my mojo, well & truly.

Back when I started building this blog, if I’d known that nearly 3 years later I’d still only have website traffic in the low to mid 5 figures, still only be scraping scraps of income together and borrowing to make up the shortfall, still living in a string of cheap Airbnbs, and having fucked up my love life to boot, simply put I would never have done it.

If you still fancy it after considering all that, see my post here about how to actually get started with blogging.

Of course, if you’re just starting a blog for fun while you travel and not particularly targeting a long-term digital nomad lifestyle, that’s a bit different. You don’t need to worry so much about all this shit! Just get stuck in, keep your expectations realistic, and see how it goes.

Note also that what I’ve said here mostly relates to blogging (and also online ESL); there are many ways to be a digital nomad, and blogging is one of the harder options (see this post & this post on Generic Dreams for good explanation & discussion). Over a decade ago (ouch!) when I was bartending in New Zealand, one of my friends there from Canada was travelling with her boyfriend who worked for a Vancouver video game company and was still doing so remotely from NZ, still on his full salary. His salary was many times greater than a backpacking bartender’s, and I marvelled at the freedom he had, snowboarding & backpacking in NZ while still on a full corporate salary. That was my first encounter with a digital nomad – though in fact he was only doing it temporarily for her and preferred simply living in Canada. But anyway, if you can swing something like that – a software or other proper tech or corporate job which you can do remotely – that is the way to do it. Though again, note that even nomads in that bracket still also write posts about the darker side of their lifestyle, the isolation, the disjointed friendships, the disastrous love lives:

Why the Digital Nomad Lifestyle Is Not Sustainable (DigitalNomadSoul)

The Ugly Truth About Being a Digital Nomad (DigitalNomadSoul)

What No One Told Me About Becoming a Digital Nomad (Generic Dreams)

The Dark Side of the Digital Nomad (Mark Manson)

Some distinctly non-unicorns & rainbows reading material for you there – but really, if you’re considering giving it a shot, unicorns & rainbows isn’t what you need to hear.


Any questions or comments? Give me about below and I’d be happy to discuss them with you.


2 comments on “The Truth about 3.5 Years as a Struggling Digital Nomad
  1. Jane says:

    Hi Simon,

    It may not have made the income you hoped it would but there have been a great deal of people you’ve entertained (and educated) through your blogging.

    I’m a great believer in all things working out in the end. With your rich life experiences and clearly a knack for being adaptable and multilingual, all you’ve gone and done is laid yourself a humungous foundation from which you can build anything.

    Best of luck and all that for the next 6 months .. and beyond.

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