How to Quit Your Job and Travel the World Overland

If you’re wondering how to quit your job and travel the world, here’s something to think about first.

Do you love what you do?

Do you live for the stuff you spend the majority of your time on?

Do you wake up each day excited, feeling creative energy cursing through your veins, ready for adventure?

If the answer is yes, you’re clearly a happy, curious, and well-balanced individual who takes no shit and seeks no one’s approval.

If it’s a “no”, it might be high time to figure out how to quit your job and travel the world.

Here’s the thing: it’s 2022, and there is no good reason to be doing things you can’t stand. There’s also no good reason to be trading your most valuable asset – your time – for a wage decided by someone else; sure, everyone needs to make a living, but how you do it is up to you.

And, look, being a freelancer or a digital nomad isn’t for everyone. But then, neither is the 9 to 5.

As a society, we still cling to the notion that a “secure” job and a steady career are the way to go.

It can be – if it truly makes you happy.

But if you’re miserable at your job, if you dream of adventures and faraway places, if you’ve got this strange yearning for mountains and sunsets and open roads deep down in your soul, and if you feel like life’s just passing you by, drowning in everyday mundanities, bureaucracy, and Netflix binges, there’s another way to rekindle that spirit of adventure. And it’s much more accessible than you think.

So here’s how to quit your job and travel the world. For a while, for a few years, or indefinitely – you decide:

The Promise of Jobs

After finishing high school, I quit three universities and at least seventeen jobs to date. Some of those jobs were interesting – a hunting yard groom, an events manager, a newsroom reporter – but most of them turned out to be either barely tolerable or straight up soul-destroying.

I vividly remember getting a job at a motorcycle dealership somewhere in the English Midlands hoping to learn more about bikes and save up enough cash to go traveling again. I’d just completed an eighteen-month ride across South America and was back in Europe, broke, alone, and itching to hit the road again.

Getting a job felt like the normal thing to do – the safe thing, the correct thing, the decent thing.

The bike shop job sounded fantastic: I’d be helping people choose motorcycles, thus contributing to human happiness. I’d be hanging out with the mechanics learning all sorts of mechanicky things; I’d meet interesting motorcycle people, and I’d earn and save money in the process. Huzzah!

Except when I showed up at work on my first day and was shown to my desk, I quickly gathered this was going to be a very different gig than I’d imagined.

My colleagues, slumped over their desks in various states of apathy and disinterest, pawed at their keyboards or shuffled around the showroom with a look of defeat on their faces, making watery tea in the staff kitchen to fight off sleep deprivation and weekend hangovers. Most of our time was spent doing pointless busywork filling out and photocopying the same finance forms, polishing racing helmets that were dusted half an hour ago, and pretending to look alive when the boss stepped into the showroom. The rest of the time, we’d help kebab shop owners pick out cheap scooters for their delivery staff; every once in a while, there’d be a middle-aged, beer-bellied, strongly opinionated customer in for an upgrade on his last year’s crotch rocket or a twenty-year-old student taking out a loan they couldn’t afford to buy a bike they couldn’t handle.

As for the mechanics, they mostly did routine maintenance and oil changes instead of building crazy custom bikes or repairing vintage classics.

After work, my colleagues would congregate at the local pub, watch a football game, or go home to microwaved dinners and TV. They all had mortgages, lots of furniture and things, and a standard all-inclusive holiday in Thailand or Cancun once a year.

They all hated their jobs.

By week two, I had learned to wear the same defeated expression on my face and make watery tea just to break the monotony, dragging out the form-filling to a ridiculously slow pace so it would last till closing time.

By week seven, something more insidious began to happen.

I stopped planning my next journey and started worrying about stuff.

Would I save enough cash for the trip?

Would my Yamaha TDM 850, a leaky, unruly beast I bought second-hand in Germany, be suitable for the journey?

What would happen when I ran out of money?

I went to the pub.

I bought frozen dinners.

Yet each day, getting up for work was harder and harder. When I got home, I’d already dread the next day, knowing that tomorrow, I’d be returning to the stuffy showroom, form-filling, and mind-numbing hours willingly wasted for a meager $1,400 a month, before taxes and after overtime. I would trade in my time, again and again and again, in coerced compliance, get very little in return, and watch the walls close in.

All of a sudden, I knew I couldn’t face any of it again.

By month three, I quit my job and left. I had less than $1,000 saved, the bike in pieces, and no clear plan in place.

I was terrified. But I also knew that if I stayed, I’d end up somewhere much worse.

The Normal Way of Doing Things

For Lennart, trying out the normal way of things didn’t last long, either. After school, having worked his way up from a dishwasher to a kitchen manager in two years, Lennart got a house, a steady girlfriend, a decent salary, and weekends off. He’d go to work, put in the hours, come home drained of energy or the will to do anything but watch some Netflix, and go to a party on a Friday night to forget the weekdays. There was a nice comfy house, several bikes, a car, and pets. Life was comfortable; there were little pleasures here and there – taking the bike out to ride, hanging out with friends – and yet, little by little, it filled with longing for something more. Was this it? Was the comfort worth it?

Suspecting there’s more to life than a stable salary and a nice place to live, Lennart quit his job, gave up the house, and went off on a solo motorcycle trip to Norway and back. And somewhere along the way, he realized he’d never go back to “normal”. Instead, Lennart took up biology studies, lived in a tent, a campervan, then a squat building for a while, worked in wildlife research, built a tiny house and traveled as much as he could in between – until he decided he’d much rather live on the road indefinitely, even if he didn’t know how just yet.

Facing the Odds

That’s something we both have in common: after I quit my Midlands job, I’ve been broke, barely scraping by, supported for a while by an ex-boyfriend, living in a tent or the cheapest hostels possible, stuck in Peru with barely $100 to my name, terrified out of my mind, struggling, failing, and dealing with countless rejections. It took me good five years to make freelance writing a viable business, with countless trials and errors, underpaid work, fear and anxiety about where my next paycheck would come from, and total exhaustion at times. I’ve questioned my choices, banged my head against walls, and worked myself to the bone.

Lennart dived right into the deep end, too, trying to figure out a way to live and work on the road, taking up different projects, landing odd gigs, and dealing with uncertainty. Now, as his videography is taking off, we’re both able to support ourselves by doing freelance work. And it’s not always pretty – we go down dark rabbit holes sometimes, work too much, ride too little, obsess over perfection, make mistakes, underestimate our energy levels, and deal with difficult scenarios.

But neither of us would ever think of getting a “normal” job again.

This whole digital nomad thing isn’t exactly easy, nor is it effortless – but we’re now in charge of our own time. We decide how we spend it, where, and with whom. We focus on creativity instead of busywork, we’re constantly honing our skills and taking on new challenges, and while we’re sometimes too tired to even think, we’re never bored.

We’ve ridden dirt bikes across Belize, we’ve battled landslides in the Andes Mountains, we’ve swum with sharks, hiked primeval forests, raced rallies, built bikes, rode horses in the Swiss Alps, led motorcycle tours in Colombia, followed the cenote trail in Yucatan, sat around bonfires and connected with hundreds of incredible people with amazing stories to tell.

More and more, we look for meaningful work, work that comes from creative flow, work that sparks joy and inspires to go further. More and more, our confidence grows – and pays off.

Dangers of the Comfort Zone

None of this came to us quickly, effortlessly, or by sheer luck. To get where we are now, we both had to take a leap of faith, a mad decision to go for it without having a safety net or a plan B – in other words,  a risk. And while you’ll find plenty of digital nomad bloggers telling you to be sensible about it, to figure out online income while you’re still working at your day job, to save up for at least six or twelve months before you tell your boss to shove it, I’m not sure that’s the best way to go about it.

The danger is in the comfort: if you don’t hate your job but sort of tolerate it, and you’d like to go on an adventure but you’re sort of OK with the pub or the football game, too, or if you’d like to ride a motorcycle around the world but the two-week holiday isn’t too bad, either, then chances are, you’ll never leave. Comfort kills dreams – slowly, insidiously, and pleasantly. You don’t even notice it at first, and once you do, it’s usually too late. You trade adventures for safety. You become risk-averse. You settle.

And if the comfort is comfortable enough and discomfort, tolerable enough, you get stuck.

So get uncomfortable. If you’ve always dreamed of quitting your job to travel the world, hand in your notice now. If you’ve always dreamed of having more time for yourself, your own projects, and things that make you feel alive, the time to do them is now. You’re a free human, not a trained house pet. You can step off the wheel and check out of the rat race. It’s right there, at your fingertips, and you can go for it.

The Cost of Freedom

When most people with regular jobs hear of our freelance situation, they inevitably ask about safety. What if you lose your gigs? What if you can’t find new clients? What if you become sick? What about your pension plan?

True, neither of us have a safety net in the traditional sense. But we have a much more reliable one instead: skills and resilience. Even the fattest bank accounts can evaporate under extreme circumstances, and even the best jobs aren’t guaranteed for life.

If something happens to either of us, we’ll bounce back. One way or another, we’ll figure it out: we’ve been through so many scary, uncomfortable, impossible, precarious, and uncertain situations that by now, we know we can find solutions to just about anything. Lost gigs can be replaced with new ones, unexpected expenses covered by taking on more work, health issues dealt with along the way. We’re flexible, malleable, adaptable, we’re like water – and water always finds a way. That, to both of us, is our most valuable asset. And that’s the essence of being a nomad: our nomadic ancestors didn’t build storage warehouses and walls Just In Case. They kept moving, knowing that they’ll be able to provide for themselves and their kin as they go along. The same is true today.

When you quit your job to travel the world, you’re taking responsibility into your own hands. You’re no longer dependent on the whims of your boss or supervisor. You’re no longer tied to one paycheck, you no longer need to ask permission to leave early, you answer to no one, and you make your own decisions. Some of them will be the wrong ones, some of them will be naïve or stupid, some of them will get you nowhere – but along the way, you’ll learn what works and what doesn’t. You’ll find your own way to be in this world, on your own terms, and by your own standards.

Freedom is equally exhilarating and terrifying for precisely these reasons: you, and you alone, are in charge of your life.

The Illusion of Safety

Ever since the industrial revolution, wage labor has become the norm. You finish school, maybe university; you get a job, you get promoted, you get paid.

That’s how it works – that’s how it’s always worked – and anything else is either fanciful, impossible, or just plain sketchy. Right?

Not really. As humans, we have existed on this planet for hundreds of thousands of years. And, sure, we always worked, one way or another; but for most of the time, we worked for ourselves and our community. We hunted and gathered, farmed and built things, produced goods and works of art; but we only recently began selling our time. A medieval nobleman or merchant may have wanted to buy a blacksmith’s sword; or several swords, perhaps, or even the entire smithy, if they so wished. But it would never enter their minds to buy the blacksmith’s time and claim everything he produced during that time for their own.

Paid work isn’t something “we’ve always done”. It’s something we invented barely a century and a half ago, starting with peasants working the baron’s land for rent, then moving to factory work and finally, offices.

And it’s not necessarily the worst idea. Some jobs can be rewarding and fulfilling, others generously compensated, and a rare few may be both.

The trouble is, we somehow came to accept that jobs are the only idea. Notice how it’s always “get” (get a job, get a promotion, get a salary) rather than “create” (create your own job, create income)? Notice how little choice there is, and how little encouragement to think for yourself and find your own way to be in the world?

Jobs may be a good idea for some people, sometimes. Hell, they may even be great. But it’s not the only narrative out there, and it’s not the only way to make a living.

How to Quit Your Job and Travel the World

So if “traditional” jobs are only one option among many, if you’re a free human being capable of making your own choices and living life on your own terms, and if you’re itching to get started, where do you actually begin?

Take stock.

Are you happy? Are you fulfilled? Are you doing things you love as much as you want to?

If not, what’s your dream? What’s the one thing you can do for hours, losing track of time, the world falling away?

What’s your it?

For us, it’s the combination of creativity, overland travel, and adventure. For you, it might be something completely different – but whatever it is, don’t let go of it. Hold on to it. Nourish it. Wonder at it. Follow it.

Next, see where you are financially. Houses, mortgages, loans, savings, stuff – take a good long look, then get rid of excess. No, a new coffee maker or a flatscreen TV won’t fill the hole in your soul. A solo ride across Mongolia, on the other hand, just might.

Now, make a plan. What will you do when you quit your job? Start an online business? Freelance? Find odd jobs as you travel? Persuade your current boss to let you work remotely?

Whatever it is, zero in on it, and set a date to hand in your notice. With a deadline looming, you’ll have no other choice but to kick yourself into gear and make it happen. A plan gives a vague vision clear contours, and even if you don’t know how you’re going to make it now, solutions will start appearing as soon as you begin working towards your goal.

Getting Started

We know: it’s scary as hell, but doesn’t it make you feel more alive just thinking about it? Once you’ve made the decision, it’s time to get started. We’ve got some resources to help you out, or at the very least, offer some starter ideas:

Read next: How Much Does It Cost to Travel the World?

Read next: How to Fund a Motorcycle Trip from Zero

Read next: Digital Nomad Jobs: How to Start Working Online

Read next: Motorcycle Traveling: What’s The Worst That Can Happen?

Along with these suggestions, there are a myriad plus one ways to jumpstart this whole living on the road business. Instead of working online, you may choose to work intermittently – we’ve met travelers who work for four or five months, save up, then carry on traveling. Others get jobs along the way – from guiding tours to building websites for hotels, there are countless ways to make a living as you travel. Others still simply sell everything they’ve got, travel for a few years, then figure stuff out; there’s no right or wrong way to do this. The point, though, is to get going, even if the road ahead isn’t entirely clear yet.

Don’t wait for the perfect circumstances: there’s no such thing. Don’t wait until you’re ready – you’ll never be ready. It’s not about having everything perfectly aligned, the next five years clearly mapped out, all the what-ifs safely solved. It’s about stepping out of your comfort zone in search of something bigger, following your dream, and making it happen.

So stop worrying and overthinking.

Pack up your stuff, get on your bike, and hit the road.

What happens next is up to you.