Five Questions Before You Quit Your Job To Travel

published by Bren

Last updated: May 17, 2020

It sounds like the ultimate dream.

No more ironing shirts, or rush hour traffic. No more of that fucking alarm clock.

Man, I used to really hate that alarm clock.

Quitting your job to travel is pretty in these days. The drudge of life after school gets onto you pretty quick, and you’re suddenly dreaming of adventuring in faraway places. All those damn travel blogs out there only fuel the fire.

Here’s the thing though.

This might not be for you. Just because I like it, doesn’t mean you will. Just because I can handle it, doesn’t mean you can. It’s really not for everyone.

I try to give you the truth about living on the road. I told you why I do it. I tell you the good stuff. I tell you the bad stuff. In the end it’s a personal decision. Travel, yes. Leave your 9-5 and travel the world full time? Maybe.

Do you really hate the 9-5?

In my first year of travelling, I bunked with this American guy for a couple of nights. He was a third grade school teacher. We were chilling in our dorm talking about all the places we wanted to go to, and then he suddenly dropped the bomb.

“But that would mean I’d need to leave my job, and I love my job.”

I was in shock. He loves his job. What kind of weirdo loves their job?

But he did. He was the first person I’d met in my entire life who loved his job – he was out here travelling the world and was actually missing going to work.

I was an accountant. I worked in an office of accountants. None of us loved our job. In fact, all we ever talked about was how much we didn’t love our job. But I still think, possibly, there’s a 9-5 job out there I would enjoy. I just never found it.

Ask yourself, do you really want to quit your job and travel the world, or do you just want to quit your job?

If you hate your 9-5, maybe all you need to do is: Find a new 9-5.

Are you really ready to jump all in?

I started small. I suggest you do too.

I took unpaid leave and went to Spain for five weeks. Then I went back to work.

Then I quit my job and vegetated at home for a month.

Then I went to Tanzania for two months, and came home.

Then I went to South America for three months, and came home.

Then I went to China for a year, travelled Southeast Asia for two months and came home. Only then did I know for sure that life on the road was for me.

There are a lot more challenges to long term travel than people realise. It’s tough out here – physically tough, mentally tough, emotionally tough.

It can be sad to see someone sell the house and car, quit the job, start an online business, buy a one way ticket and then see it all fall to pieces. They hate the road. It’s lonely. They’re wearing dirty underwear. They run out of money. Diarrhea, again. No wifi today. Another scammer. Crying. Getting fat. These are the realities of a traveller’s life.

Quitting your job is already a big step. A multi-month trip is another. Maybe you’ll go home early. Maybe you’ll try again a few months later, and maybe you won’t. There is no shame in either.

If it burns inside of you, go for it. There is absolutely nothing wrong with taking the risk. You just need to be prepared for it to not work out.

Are you leaving on good terms?

I left on good terms with everyone. My friends, family, my old boss.

This is important.

I gave my old boss four months notice. Four months. I went into her office on the first day back in January and told her I’ll be gone by May. She appreciated that a lot.

Remember, you’re travelling. You’re not disappearing forever. Over the past few years I’ve visited my old office several times to say hello. The first few times my old boss even offered me my old job back. Had I hated life on the road, I would’ve really appreciated that. In fact, I’ve known many travellers who returned home and walked straight back into their old job after a few years on the road.

This is why it’s important to leave on good terms. Bridges are valuable and can be hard to rebuild.

Are you saving hard enough?

You can never have enough money on the road.

I’ve met people running out of money out there and it’s miserable. They’re eating one meal a day, looking for a work exchange, trying to hitch hike home across the Indian Ocean.

Don’t be that guy.

Save religiously, obsessively even. Stop buying coffee. That’s $3 a day. Don’t go out on Friday – another $50. Don’t cut your hair this month. Take lunch from home. You don’t need a new phone.

I wore the same suit to work every day for three years. My workmates laughed at me. I didn’t care. You shouldn’t either.

Trust me, every dollar counts out here. If you’ve budgeted a $10,000 trip, save $12,000. Save $15,000. And then a bit more. The hard work starts at home.

Why do you want to travel?

People often ask us, what are you running away from?

Other than the rain, and my ex-girlfriend, not much…

The thing is, we all travel to run away. People will tell you that’s not okay, but it is. Go wander. Find yourself out there.

The only caveat is, you need to know what you’re running from, and why. Sometimes (usually) it’s a tough question, but you need to answer it and own it. Travel doesn’t solve all your problems. It doesn’t make everything okay again. It can give you clarity, inspiration and strength. It may spit you out an evolved version of you, strong enough to face the old demons. But whatever you’re running from won’t go away with travel.

Travel is not an antidote. It’s a catalyst.

I didn’t like who I used to be. I put on a shirt and tie, did tax returns for fat millionaires. I didn’t want to be an accountant. I looked in the mirror and asked, who the hell is that guy? I wanted to be someone else. So I didn’t just travel. I spent long nights studying the languages of the world, learned to fight, learned to dance, learned to surf, read books, volunteered with the poor. Travel didn’t solve my problems. It helped me solve them on my own. I used travel to become the person I wanted to be. Maybe I’m still working on it, but I’m no longer running away.

You don’t need all the answers right now. It’s okay to drift for a while. If you want to buy the one way ticket and get lost, go for it. But remember, travel isn’t about doing nothing. It’s about doing absolutely everything. Know why you’re out there. Look for it, find it. But don’t get lost forever.

There’s a pretty amazing journey in front of you. It can be hard to look so far ahead, but you’ll be coming home eventually. These five questions should help you leave it the right way.

Good luck!


Sounds like a dream: Quit your job, travel the world. But sometimes it's not everything you thought it would be. And let's be honest - you're not really that sure about it, are you? These are the five questions you're missing.

Loved this? Spread the word

You might also like:

Share your thoughts!

Your email address will not be published. 

  1. This post really hit home for me. I loved it but also hated it because it made me realise some of the realities of traveling full time. I have always said I want to travel forever and work from anywhere I like but the reality is I probably couldn’t do it forever. I would miss routine and stability. I still want to travel and at the very least do a RTW trip but I need to remember.. I will be coming home. Thanks for being inspiring!

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}


My newsletter includes exclusive stories, updates, giveaways and more. 100% free. 

Zero spam. Unsubscribe anytime.