Life on the Road: It’s Not Just For The Young

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In less than two years I’m going to turn forty.


I believe that’s the point when I officially start planning my midlife crisis, buy a sports car I can’t afford, have an affair with the intern and wonder where the hell my hopes and dreams went.

Except, well, I don’t want a sports car, I’ve got a wonderful girlfriend that I have no desire to cheat on and I’m living my hopes and dreams every damn day. Today I’m in Mexico. Next month, Belize. The month after that it’s the US,  then Australia. By the time that birthday rolls around in 2015, I’ll have been travelling continually for nearly four years, set foot on every continent in the world and run a marathon.

And then I’ll set some really ambitious goals.


It’s Not Just About Getting Drunk and Laid Around The World

There’s a belief out there that long term travel — if it happens at all — is just for those in their early twenties. Young and carefree, the theory goes, they party their way around the world for six or twelve months, staying in dirty hostels, showering once a week, hooking up regularly and spending more on booze and birth control than every other expense combined.


Sure, that’s a thing. If you’re young and single, go for it. It’s a lot more fun than stacking boxes at Walmart or living in your parent’s basement for a year after college, and other than the hangovers and pregnancy scares, you’ll get a lot more out of it as well.

But it’s not the only thing.

There’s no law that says that the fun has to stop at thirty. Governments don’t stop giving out passports just because you don’t go clubbing until six in the morning any more. Airlines will still happily take your money whether you’re checking in a backpack or a suitcase, and guesthouse owners in Thailand couldn’t care less if you’re 23 or 73.

In fact, if you’re seriously considering a life on the road for a few months or years, I’d suggest that being a little older and wiser puts you in a far better position to do it. Not being hungover every day gives you a lot more time and motivation to, y’know, actually experience the things you’re supposedly there to see. Not bar-hopping until 3am and then wandering home through the back streets every night puts you in a much safer situation than those who do.

But there’s more, even, than that.

Despite decades of trying I’ve never managed to successfully grow a money tree to pay for my travels, and I suspect you’re in the same boat. While taking shady bar jobs and cleaning toilets in hostels is one way to keep the dream alive, there are definitely better options. I’ll talk much more about working from the road in future posts, but suffice it to say that if you’ve got the skills, experience, work ethic and contacts from a decade or more in the workforce, you’re in a far better position to earn real money than the nineteen year old on the bus to Bangkok beside you.

The fact is that if you’re considering long-term travel (and by this I mean anything from three months to thirty years on the road), your age is largely unrelated to your ability to do so.

So is nearly everything else.


Your Excuses Are Usually (Still) Invalid

A few months back I bought a bunch of new t-shirts from some friends of mine who run a kick-ass printing company (you should totally check them out, by the way). The shirts have a bunch of different sayings on them, but my favourite one is the simplest.

Dave - Excuse is Invalid

I get a lot of emails from people who would like to live a life similar to mine, but there’s apparently always a reason why they can’t. I’ve talked about this stuff a lot over the years, how the excuses are often invalid and the biggest barrier is the one between your ears. I’ve even given specific advice on why these reasons are typically bullshit and what to do about overcoming them.

What I realised, though, is that I’ve often focused on the under-thirty crowd when writing these posts. It’s not that people that age don’t need a kick in the ass to get themselves out the door and onto a plane — god knows they do — but as I’ve got older myself, I’ve realised that the things holding people back from a life of travel don’t remain the same across the decades.

Not having anybody to travel with gives way to having too many little people to travel with. The fear of not being able to get a career started when you get home becomes a fear of ruining the career you’ve already got. Questions start being asked about what to do about health care and schooling, mortgage repayments and car leases. People get more scared as they get older — I blame the media for that — and then that becomes a problem too.


Of course, some of those barriers stay the same as well. You’ll never think you’ve got enough money, or that you can make enough of it in the future. It’s always hard to swap a life you know for one that you don’t, especially if everyone around you is telling you you’re an idiot for considering it.

I’m not here to sell a dream. In some cases, of course, your excuses really are valid. If you or a loved one has a terminal disease, or you’re a few million bucks in debt with no way of getting out of it, building a life on the road probably isn’t your biggest priority. If it all seems far too hard and you just don’t want to deal with it, that’s fine too. I’ll be the first to tell you that it’s not easy to overcome all of those barriers — in fact, it’s bloody difficult.

Doing this will be a big challenge, both physically and emotionally. There’ll be days before you leave where you’ll wonder if it’s all worth it — and there’ll be days on the road where you’ll be sure it isn’t. The bank account will be empty, the workload will get out of control, the bus will break down, the hotel will have cockroaches.

And then you’ll wake up to a beautiful sunrise over the mountains. That invoice you’ve been chasing for weeks will finally get paid. You’ll dip your toes in the warm ocean as your Facebook feed fills up with snowdrifts from back home, and decide to go to Cambodia tomorrow just because you can.

How do I know all this? Because this is my life… and despite the hardships, I can’t even imagine changing it.

So, over the next few weeks and months, I’m going to be covering — in detail — what it takes to shift your life to the road long-term. Not as a teenager on their gap year, or a group of twenty-somethings backpacking around Central America for a while, but as a guy in his late thirties who once had a house, a car, a cat, a well-paying job, a pension plan… and chose to do this anyway.

If I can do it at nearly forty, there’s a good chance you can too.

This isn’t something I’ve really talked about before — certainly not with this kind of focus — but, as I mentioned last week, it’s time for a change and I’m looking forward to it.

I hope you are as well.


If you’ve got any questions or concerns that you’d like addressed in these future posts, drop me a line and I’ll try to answer them!


Suburbs image via rxb

24 Responses to “Life on the Road: It’s Not Just For The Young

  • Gordon White (@gordon_white)
    9 years ago

    Very much looking forward to where you’re going with this.

  • I’m just a few weeks away from turning 50 (ugh!) and 6 months ago, I put my furniture and stuff into storage (after a to sell $5000 worth of stuff that I no longer needed), rented out the house and hit the road. I didn’t have a set itinerary – I just knew that i was heading for SE Asia, and would then see where the wind took me.

    I didn’t travel much in my younger years aside from shorter 3-4 week holidays every few years. I focused on work and paying off the mortgage which I achieved a year ago. Good sense dictates that I continue working to continue saving for the retirement nest egg, but itchy feet and despondency with dealing with city traffic drove me to toss it all in. For awhile anyhow. So that’s what I’ve done. (I should also mention that I did a 6-month stint of travel in SE Asia a few years ago when in between jobs. Rather than satiating the desire to travel, it fueled it.!)

    So I have just spent the last 5 months in SE Asia, and am currently house-sitting for friends in Australia for a month. Now I have to work out where to go to next!

    With respect to finances, I made the decision to rent my house out to sustain my travels since I don’t have an ongoing income otherwise. That’s a hard decision to some home owners; you have to do your research, hire a GOOD property manager and accept that tenants won’t care for your house as well as you do. The rent I receive pays for my travels, storage fees, property manager fees and all house related expenses. I’m not increasing my savings while doing this (which does offend my conservative, sensible side!) but my rule is that as soon as I start going backwards financially (ie have to dig into savings) then it’s time to think about heading home and back to work.

    My motivation to avoid having to go back to work ensures that I keep to my budget. But I am not travelling as a cheap, on-the-bones-of-my-ass backpacker. I stay in decent budget or flashpacker accom and will happily pay for a flight to avoid a horrid 9 hour bus ride. I don’t drink a lot of alcohol and don’t feel compelled to visit all the ‘must see’ tourist-trap attractions which saves a small fortune.

    I am worried about my budget as I move out of SE Asia and into other parts of the world: Australia is a budget killer but by house-sitting and not paying for accom, I can manage it. I’m now considering other house-sitting gigs as I look to move to other parts of the world.

    So..that’s my story of how you CAN travel in your mid-age years. It’s frustrating to hear people say how ‘lucky’ I am to do this. It’s not luck. I just worked out a way to make it work.

    • great to read! very motivating! sounds like you have a good solid plan! enjoy it!

    • Great advice and information here from Lisa — if you’re in a similar situation to her, you could do a lot worse than take this stuff on board!

  • Oh yeah… and the cat gets a little holiday of her own at my parent’s place.

    I’ll look forward to seeing what other good info you have to share. Good stuff!

  • TL:DR — It’s not for everyone, I’m always wary of “YOU CAN DO THIS” stuff. So I’m glad you’re taking a someone measured point of view.


    A few random things (some of them repeating what you’ve said above)
    — If you have job skills that require nothing more than a stable internet connection.
    — If you have a safety net in place — you own a home you can rent, you have big savings, you have an escape route in place.
    — If you are okay with absorbing a certain amount of risk (some folks simply aren’t, and that’s not a character flaw, they’re just different).
    — If you don’t have financial obligations like education loans or credit card debt.
    — If you don’t have family obligations like aging parents or kids.
    — If you’re relatively healthy and/or dealing with supremely manageable conditions.
    — If your home country has affordable life long health care/socialized medicine.

    Bugging out ‘older’ (shut up) can be awesome, and I love the way many not-20 long term travelers get out of backpacker bubbles for interesting things.

    But I also think it’s easy for some in a way that it’s simply not for others. It favors the wired, for starters. The “pick up money around the world” myth remains a tenacious one, and one limited to those with a certain baseline privilege and skill.

    Weird peripheral analogy — I was walking to the bus yesterday and I watched a guy unloading a furniture truck give the folks from the gym the total stink eye. The gym rats were running around the block in gym clothes carrying those weighted ball things, what are they called? They paid money to a trainer to tell them to do that. I’m thinking the furniture truck guy is maybe less likely to bug out than the gym rats. I could be wrong — maybe he’s got skills that translate to him continuing to earn, or maybe at 40+ he’s got savings that let him absorb risk. But maybe not.

    On a personal level, in spite of the fact that my job is technically restricted only by the need for that elusive solid internet connection, I have found that out of sight is out of mind for many of my clients. My career — something I’m not willing to throw over at this point, especially since I spent my 20s and 30s avoiding employment and have terrifyingly little retirement savings — continues to advance through face time. I keep hoping that will change, but evidence continues to be against it, ironic, given that I’m in tech. ((sigh))

    Anyway. Do continue. Sorry to interrupt. Sort of. Not really.

    • Yup, this. All of it, really. Probably the only thing I’d add is that just because your current career doesn’t lend itself particularly well to being mobile long term, that doesn’t mean that you can’t reinvent.

      That applies to me, in some ways — although I had the benefit of an IT background (and therefore understood my way around web servers, HTML and the rest), my direct skills and experience weren’t particularly transferable to working remotely. I’d always had a passion for writing (if not a job doing it), though, and eventually figured out a way to combine all sorts of things in ways that people would pay me a little bit of money for.

      Of course it’s still easier for some than others, but I don’t think the door is closed on those who can’t see a direct path from where they are right now to where they’d like to be. Everyone’s different, and sometimes a little lateral thinking (and probably, talking to people who are already living some version of the life you’d like to be) can yield a way forward where none was obvious before.

  • A-hem. That grumpy cat “NO” is meant to be “Now….” A Freudian typo if ever there was one.

  • A really interesting read. Thanks mate

  • Great stuff Dave! Really looking forward to the next few posts about this.

  • great read! really looking forward to reading the new stuff! motivating as always

  • im 59 –ive been traveling 28 years and the last 15 -love-n -life –going back to Thailand as im getting treated for cancer – going to start my blog
    my travels this year are new Zealand-austrailia-india-bhutan-nepal-greece-turkey-Iceland-portual-somewhere in Africa -Italy and 10 more European countrys -plus many in central n south America-life is short -live da dream baby

  • Love this post Dave. I’m 27 and even now I feel older than most here in Australia but I think that my age, even though just a few years older than most of the backpackers, gives me such a better perspective than them and I’m more determined to seek adventure rather than stories that start with ‘I got so drunk…’. Here’s to travelling for many years to come! 🙂

  • I am 42 and did my first solo backpacking trip at age 40. I finally did it BECAUSE I was 40. It made me sick to be so old and to not yet have crossed that off the list of things I want to do in life.

    I am looking so forward to reading where you go with this.

  • Hey, it must be a “fortee” in that image, right!? 😉 Jokes aside Dave, great post contemplating on “transformative travel” and such. You certainly would see a different person in the mirror today if you never would have been bold enough to leave in the first place and are most likely happy with what you see. Even though age my change the way you travel and the way you discover, it should never influence your urge to explore in general. Settling down is not a matter of age, but of a certain mindset. So there rather will be the moment to stay put, not an age to do so…
    I really like following part of your post: “… how the excuses are often invalid and the biggest barrier is the one between your ears.” Hell yeah! Mind the gap… 😉

  • The other thing which starts making it tricky to travel when you get into your forty’s is perhaps having family sickness or a grandparent on their own. Sometimes there are valid reasons for not being able to travel when you get older, no matter how much you want to, and I know it is still a choice, but still, a much harder one…

    • Yep, agreed. Much and all as I talk about how — for me — life on the road is a very good thing, it’s not for everyone and sometimes circumstances beyond your control will conspire to stop you from doing it no matter how much you want to. Those circumstances will probably change at some point, for one reason or another, but it could be a long time coming — and that’s hard to take if all you want to do is hit the road right now.

      It’s one of the reasons that I decided to make the leap myself, actually (I talk about it a bit on my About page) — I was fortunately enough two years ago, and still today, to be in a situation where I had enough money to take a chance, and didn’t have any health issues (mine or anyone else’s) that would stop me from doing so. I know that won’t always be the case.

  • Dave, nice post. We just started our long term travel journey just a month back. We are doing this by with our third world savings and will be spending first world style in lot of countries.

  • Very well said. I guess its true that you only live once so travel while you’re young. 🙂

    • That’s kinda the opposite of what I’m saying in this post. Or at least, you don’t have to travel *only* when you’re young.

  • I admire your courage to do what you do. My travel aspirations are to travel to Europe to absorb the art. I’m a 60 year old woman but young at heart, have a small sail boat that I sail in what I believe is the most amazing harbour in the world. New Zealand,Bay of Plenty,Tauranga.I’m trying to recreate my self as an artist. I work at a job that destroys me but caught up in the own your own home with my 2 cats and 1 dog feel trapped and sometimes despair that I will achieve my dream of being a self supporting artist.Surrounded by the “beige brigade” of unimaginative people it’s difficult to hold on to the dream. You are an example to me that I must never give up.

    • I’m so impressed that you’re looking to follow your passions now, at an age where many people would be too afraid to do so. And yep, while I’ll never criticize anyone for making different choices about things like home ownership than what I have, it’s true to say that paying a mortgage for 20+ years often comes at a price beyond just the numbers on the monthly statement.

      All the very best for your new direction — and hold onto that dream!

  • You and Travelfish were my go-tos for three trips to SEA. Thankfully I had read about Otres Beach and Kampot–Now we’ve been home a year and a half. Getting itchy and loved your take on Mexico. The connections with people on the road are so rich and existing quite nicely with a small amount of “stuff” is such a great lesson —more Americans should try it. My husband is 73 but he is a great travel partner and never ceases to be open to new adventures. Family is tying us up for awhile but winter is coming and . . . .

    • So glad I could help at least a little, Patti — although I know that Travelfish is a far better resource than my site for traveling around SE Asia! So great to hear from people who are about as far from the typical 20-something travel demographic as possible — it’s a reminder to us all that where there’s a will, there’s a way.

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