Is now the best time to quit your job and go travelling? (2021)

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Why quit your job and go travelling now
Why now might be the best time to quit your job and go travelling, instead of putting it off for years

Do you keep hearing of people taking time off to travel and think “I’m so jealous, I wish I could do that, but —” and think of a reason why not?

Ever wonder how they justify it and make it work? So did we.

We’ve spoken to a LOT of people who have done this or thought about it. Here’s what we’ve learned.

1. There’s never a perfect time

It always seems like there’s a better time just down the road… but is there really?

The career cycle is endless. Promotions, raises, new projects, headhunter calls… there’s always a carrot dangling in front of you. As life goes on, pressure on relationship and family fronts rear their heads.  But here are a few dangerous questions:

  • Are those carrots things you’ve lusted after your whole life?
  • Is the pressure on your relationship insurmountable — have you talked to your loved ones about your dreams?
  • If you wrote down a list of your wildest dreams, would that promotion be on them? Or just a stepping stone to what you “really” want?
  • Are you doing things to live up to an image of yourself that you think others (colleagues, classmates, parents) have of you?

These are just a few of the questions many have to face as they choose between their own dreams and the ones others impose upon us. Choose your own destiny.

2. You can make adventure travel part of your career story

Sometimes, we can combine our dreams and our current career (or a different one) in a beautiful synergistic dance.

Take languages. Many employers see having learned a language (fluently! Basics get you no points) as an attractive bonus, a sign you can commit to learning a skill, as well as a potential asset in certain roles. Maybe you think you can learn one while working and you slog away at Duolingo every day on your morning commute, but that usually goes nowhere. It’s not your fault — it’s hard to fit it in. On the other hand, it’s amazing how fast you can learn a language if you dive in head first and make it your sole, dominant focus for a month or more.

Or take volunteering. Many of us look forward to giving back in our later years. Why not embark on an ambitious project now, or help someone else with one of theirs? There’s so much we can do in the world and so many people and organisations in need. Once you’re out there you’ll be amazed how much you can contribute (if you’re staying long-term and contributing to the community). And if you ever come back to your current life, people will value your contributions highly.

Finally, travelling is becoming the new MBA. Many choose an MBA as an excuse to travel. In the same vein, many are beginning to travel as a way of developing their cultural awareness and skills.

3. Travelling can be a lot cheaper than you think

Yeah, Paris, London, Japan, New York and Australia are expensive. But have you thought about

  • Nicaragua, a tropical country with beautiful beaches and no mosquitos?
  • The Yunnan province of China, known for its rolling tea fields and eternal springtime?
  • Or Talinn, Estonia, a city that looks like a fairytale but equipped with high-speed internet and a buzzing startup economy?
A view over Tallinn at Dawn. Living in Estonia can be amazing
Tallinn, Estonia

Want to know how much this could cost? We have been building travel itineraries that come to just $2,000 per month in living costs… for two. That’s including flights and staying in multiple countries, plus taking care of our health along the way and continuing to enjoy local life. In some places (like Kaohsiung, Taiwan) we spent even less! It’s amazing how much you can save once you commit to living like a (wealthy) local, staying off the beaten tourist path and ignoring $100/day activities.

4. This might be the last year you can do it, because… life happens

Warning: this might be a little dark. But it’s worth thinking about.

Think of all the things you’re planning in your life: family plans, education, moving to be closer to family, and others.

Now think about the things that you’re not planning for and which could happen to you.

  • A family member (or you!) might develop a serious health problem that needs attention.
  • You might have children a little earlier than you expect (surprise!).
  • A war might break out, just like the papers keep claiming.
  • The economy might collapse… again.
  • Your team, division or company might fold.

These things are not only terrible and disrupting to your life — they’re extremely common. I’m sure at least one of the above has ALREADY happened to you. You can’t prevent them, nor plan around them, so take control of your own destiny and act now.

Epilogue — We wrote this in 2018, before 2020 happened.

5. Finally… You might never have to get a job again

This is my favourite one: You might just find you never have to work again.

Many people, once they embark upon a life of travel, find themselves rethinking what they actually want out of life. Some people even make full time lives out of it.

For example:

  1. Will Hatton, who started The Broke Backpacker now makes five figures a month online through online marketing.
  2. There’s also Benny Lewis, aka The Irish Polyglot, who decided to start learning languages in his twenties, and now sells language coaching services.
  3. David Nihill decided he wanted to become a better speaker, so he decided to take the ultimate plunge and become a stand-up comedian for a year. He wrote a book about it (Funny Business) and now offers courses on comedy.

In short, a little creativity and hustle and you might never go back to your desk job again.

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