Everything to Know About Quitting Your Job, Travelling, and Getting Paid at the Same Time
Some top tips to make your travel dreams come true – and how you can afford to do it at the same time
Mila Supinskaya Glashchenko / Shutterstock
Who hasn’t sat at their desk or stood doing the same-old day jon and wondered; surely it can get more exciting than this? Pretty much everyone has that daydream where they quit and hit the road, washing dishes or picking fruit to scrape enough along the way to afford food and lodgings.
The good news is that, in the world of social media, digital nomads and flexible working arrangements, it’s actually never been easier to thrust a resignation letter at your boss and head out into the big wide world. Here’s a really quick intro to switching to a more fulfilling lifestyle of work and travel and some top tips to make your adventures as stress-free as possible.
Before you go
Remember that it’s not all sunshine and Instagram bliss
Sorry to start off negative, but it has to be said! Thanks to endless social media fees and travel adverts, we’re absolutely conditioned to think that travelling is some sort of utopian dream. And it absolutely can be. But it can also provide some unique challenges, and, unpopular opinion, difficult choices and moments.
Travelling is often about compromise. Unless you find the magic formula, or you have money already, staying at five star resorts every night isn’t going to be realistic. And even if you do, moving from spot to spot with no consistency and potentially a limited support network can be a drawback after a while.
You may also find that it’s difficult to focus on work all of a sudden if there’s a stunning beach within your eyeline, or if you’re hungover from that full moon party. Remember that you’ll need to set aside time to fulfil your work commitments too, so there will be instances of missing out on certain things if you have a deadline to meet or contract that you need to stick to to get paid.
Travelling itself can be taxing too. Intense planning is often required just to get to the right places, and then it’s scary when it all goes wrong. Oh, and you’ve run out of cash halfway around the world? tikes.
What we’re trying to say is that travelling and working may seem like the ideal escape, but a touch of resilience and awareness is needed, especially if you’re not a big risk taker or don’t like jumping out of your comfort zone. However, these challenges can become part of the fun once you’ve had a few of them, so embrace and move on from that missed flight, stolen belonging or close shave!
Consider backup funds before booking the flight
Landing paid work over the internet has got a lot easier, which we’ll talk about in a second, but as with any flexible work, things can go up and down. If you work to a timescale and put aside an ‘emergency fund’ to at least get you back home if something goes wrong, then that adds an extra layer of control and peace of mind.
Don’t burn your bridges
Dropping that ‘I quit’ email into an inbox and slamming the door on the way out may seem like fun on a bad day, but what happens if you find that you’re extremely homesick, or need a touch of reality after months on the road? Selling that home, removing yourself from your career or putting relationships on pause may seem exciting, but they’re all super important to have when the inevitable yearning for normality pokes up its head! Again, this is down to personality, and many people have no connections or concerns, but think about renting instead of selling or taking a career break rather than resigning fully if possible.
Do a test run
Before blowing your life savings on a year or two’s worth of flights, why not do a journey for two or three weeks at first and get a feel for hostel life and working and travelling. If you love it, great, keep going, or if you learn some things about yourself, reset, replan and try again!
Securing income
Drazen Zigic / Shutterstock
Finding an income that will pay for your travels while you’re on them can be both a balancing act and a challenge. Many of us may be used to remote or homeworking post-Covid. However, if you’re an office stalwart or have done the same job for a long time, the thought of having to prospect for work or monetise an idea or content to make enough money to live can be daunting.
This is where to pays off to have a skill, angle or offering that is almost always in demand, that you can rely on to pay the way in a tight spot.
For example, if you know how to code, or build wesbites, or shoot high quality film, then a life on the road may be second nature to you – all you need is a laptop or iPad and Wi-Fi. However, if you’re used to working bar jobs or in retail, it’s time to find your ‘niche’ that you’re going to rely on for money.
One extremely popular way to earn while travelling is to post your experiences to social media. Many travel influencers have done extremely well from posting general or informative videos about their journeys (see Drew Binsky, Nomadic Matt and even Mashtag Brady), but ask them and they’ll tell you it’s all down to hard work, consistency and a touch of luck. You’ll need to become a social media expert and learn the other marketing tricks like affiliate marketing that turn lots of video views or blog post clicks into real money.
If you already have an online following, then consider going full time as an influencer. We’re always looking for social media names to work with our partner brands!
But remember that, even if you’re down to your last dime, there’s always a way to make money. Offer to clean windows, work restaurant shifts, drive an Uber, work as a tour guide or do your real-world job for a little while to get back on your feet. Again, it’s about resilience and a bit of planning!
Just remember to have the right visas and rights to work – nobody wants to get deported for working illegally.
Great places to find work online
You could write an entire book of work sources, but here are a few tried-and-tested places to pick up work you can from a laptop or phone over even patchy Wi-Fi:
Upwork
Fiverr
LinkedIn
Working Nomads
Remote.co
People by the Hour
Freelancer.com
Ideas for things you can earn money from doing pretty much anywhere
If you prefer to control your own work, then these ideas are a starting point:
Selling your travel photos (decent camera or high-end phone required)
Starting a travel blog
Virtual assistant
Teaching your language online
Building websites / digital business
Dropshipping
Writing reviews
Surveys (big time investment vs payout, sometimes)
Budgeting
encierro / Shutterstock
An absolutely top piece of advice, even if you are making good money while travelling, is to budget well and make smart choices. Yes, it sounds deeply boring, but living a life where hotels / hostels and constantly eating out is the norm, things can get expensive very quickly if you aren’t careful. Plus, being tight with certain spending choices unlocks more opportunities and things to do further down the line, which actually enhances your experience overall.
It doesn’t have to be anything major, either. Hop a bus instead of splurging on a taxi, switch your fizzy drink to a bottle of water or even just get the right travel credit card. Those small savings will eventually turn into another plane ticket, a better hotel room or an unforgettable experience. Trust me, you won’t remember those Instagram-heavy coffee places as much as you’ll remember a flying lesson or zip line adventure.
Getting paid
Guess what? In times of uncertainty, it takes longer for people to send you money. And if you’re a freelancer, with no real backup or legal support, you’ll paid at the very last moment possible sometimes, or not paid at all!
Here’s where having solid terms of business, or ideally a contractual agreement with payment terms, can really help. Sites like Fiverr etc. guarantee payment as long as you do what you say you’ll do, but bear in mind the prospect of not getting paid on time or having to chase payments if you negotiate within organisations directly.
If you get paid in cash, be very wary of local tax and visa rules and consider asking for a small amount upfront so you aren’t left high and dry when someone says they aren’t happy with your work or disappear entirely.
Keep your home country’s bank account or set up a PayPal, CashApp, Zelle, Venmo or whatever is used locally so you don’t have to start transferring between countries and paying high conversion fees.
Think hard before borrowing
If you don’t have the desire or motivation to fully fund yourself and turn to family borrowing or a loan or credit card to pay for your adventures, then take some time to think about whether the interest and paying back your debts at a later date is actually a palatable option. If you’re fine with living now and paying later, then still budget wisely and make sure you can afford your payments. Debt stays debt and it’s becoming increasingly harder to go completely off the radar. It’s really not worth the hassle!
The wrap up
Hopefully this article has revealed a few things you may not have thought about yet, or if quitting to travel is just an irregular fantasy. But the good news is that there are LOTS of paid opportunities in the travel sphere right now, whether you’re great in front of a phone camera or just good at cold emails and convincing sales pitches. So with a bit of planning, plenty of resilience and a positive outlook, you’ll certainly be able to make working and travelling at the same time a possibility!
