You’re running low on scratch. Flat broke in fact. You’re screwed and your kinda’ jobs just aren’t available.

People are suggesting other travel jobs and methods of making money, but they’re all terrifying – customer service, bar work, waiting staff, selling booze cruise tickets in that crazy party hostel. You can’t do any of those!!

You’ve got a choice. Dive into the deep end and force yourself to swim or else you can throw your entire efforts into the online world.

If you choose option B, you can’t half-ass it.

Teaching online, freelance writing or affiliate marketing are pursuits that take time, effort and dedication to build a profile, a reputation and a steady income. Even after investing all that time and effort, there’s no guarantee you will succeed.

If you want guaranteed cash, it’s time you pushed your boundaries. A people-facing job may not be for you, but once you face that fear head on, you’ll be a stronger person after it.

So what jobs can you do on the road that will make you grow and ultimately become a more confident person?


Woman with excited face at the entrance of a old and dilapidated home in the woods

Door-to-Door Sales

You must be fugging joking, right?! Walk up to someone’s door and disturb their day with an annoying pitch of some rip-off product. It’s surely only a matter of time before someone punches you in the face.

Hell, you’d want to punch yourself in the face by the time the day is done! Why would anybody willingly do this job, knowing they are one of the most annoying people in someone’s day?

Stuck for choice and money, I found myself getting my training wheels with an affable Canadian guy in a large housing estate in Sydney one sunny Spring day.

It was nervy and often deflating to see door after door be closed in our faces, but the product was actually a good one – we were approaching existing customers of a gas company and offering them a cheaper subscription. It really was a bargain!

However, not many people had the patience to see that. With every failure came a lesson.

By the end of the day, we had perfected the art of the pitch and bagged a few subscriptions.

Although I didn’t stick it out to become a salesman for life, the experience taught me the importance of how people will listen if you make it all about them. In turn, the experience made me a little more confident when pitching ideas of any kind.

On the road, you’ll meet all sorts and find yourself in tricky situations where you may need someone’s help. Being able to get to the point quickly and convince strangers to your way of thinking is a great asset to have.


Man behind bar in black polo shirt holding large bottle of Jim Beam whiskey.


For many introverts, this is a nightmare. To be constantly under the limelight as hordes of drunks descend on the bar, hollering and waving for your attention, baying for your service and expecting it with a smile and a joke, regardless of the cheek they throw your way.

Somehow I survived four years of it at the student’s union bar of my university. To be fair, it wasn’t that bad. In fact, it was one of the most fun jobs I’ve ever had.

I’ve even worked a couple of bars since. Of course you will encounter drunks, cheeky bastards and downright ignorant morons who deserve a good slap round the beak with a bottle of water.

But in the end you learn a little of the acerbic wit and quick banter that thrives in bars and ultimately become better able to handle high-pressure social situations.

Furthermore, if you work in backpacker bars you’ll soon have an abundance of new friends from all over the world and will never be stuck for travel companions on the road.

You’ll know all the best shots and fun drinking games. Maybe you’ll even pick up a few party tricks from the bar too! Plus, after a wild night working at the bar, your alone time never felt so good!

Two men training muay thai outside on blue mats while another man sitting down watches.

Customer Contact Center

If facing people is too terrifying, a better option is to hide in the comfort of an office.

Between coffee breaks and sneaky surfing online, the workload in a call centre or support desk is rarely overwhelming. I ended up working 10 months in New Zealand for a company that managed the home repairs in Christchurch after the 2011 earthquakes.

Having angry and grieving homeowners scream, rant and cry down the phone can be a little unsettling, but over time you get assertive with the tough ones and empathetic with the sad ones.

By the end, I found myself much more comfortable in dealing with other people’s strong emotions and felt at ease in tackling any escalating situation before it got out of control.

When you’re travelling, there will be drama. If you can deal with someone crying and screaming about their destroyed house and dying mother, then settling a dispute over a snorer in the dorm or a missing bottle of cider from the fridge should be walk in the park.

Being able to listen and analyse are skills most introverts already have. This job will put them to good use and make tackling big problems on the road easier.

Kangaroo standing alert in orange orchard with many trees bearing fruit behind.



As far as rites of passage go, there aren’t a whole lot of serious backpackers who can’t list fruit-picking among their past travel jobs. But how in the name of Jiminy Cricket is pulling a few apples out of a tree going to make you more confident?

Well, believe or not, I am not the most physically active person when it comes to having a day job. It’s not that I’m lazy or unfit or morbidly obese and unwilling to walk. I just prefer to use my mind and save my physical energy for things that are…well, fun!

Escaping your comfort zone in Australia is possible in many ways and getting a job picking fruit is just one. Test yourself by doing things you aren’t comfortable with and you will be forced to learn, and forced to grow.

For me it was driving tractors and using tools, I continued in this vein by working several construction jobs in Sydney. When you gain experience in new industries, your confidence surges as you begin to wonder about the possibilities. What else can you do?


Man in white shirt smiling for photo with two young Korean girls.


Teaching English

Ahh the ultimate travel job! The ESL industry is booming around the world.

People are making careers for themselves in many countries, earning great money in places like Korea, Japan and the UAE.

Personally, I spent my schooldays dreading class presentations and fearing the moment that the teacher would say it’s my turn.

It didn’t matter that I loved to read or that I had practiced like hell. Once that moment came my throat would seize up, my palms would sweat puddles and my chest would tighten as I struggled to focus my view on anything but my toes.

For someone like that, teaching English may sound like the worst idea ever. But the great thing about teaching abroad is that almost none of the kids will understand you!

You don’t have to be a super knowledgeable, wise sage like Gandalf with the charm and aplomb of Sean Connery every time you speak. The kids will be too fascinated by your skin, eyes and general alien appearance to care what gobbledegook you’re babbling.

After the first week, those initial nerves disappear. By the time the kids figure out you aren’t a legendary teacher, it won’t matter. You’ll have developed a new-found confidence and assurance when you speak.

Not only that, but you’ll learn to explain yourself much more clearly and articulate things in a logical flow so that you can be understood by everyone in your new country.

These traits find their way into your regular behavior, making you a more confident and assertive person as time goes on. And when you’re out on the road, that’s always a good thing!

Check out my Kick-Ass Guide to Teaching English in South Korea to learn all about it!

What travel jobs have helped you come out of your shell? Work your way down to the comments below!