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Quit Your Job to Travel- Working Remote, Sabbatical, Job Search Abroad

In Travel Planning by TIM

If you need to quit your job to travel you’ll actually have to pull that trigger some day. We humbly present our advice on quitting your job to travel in the best way possible.

Quit Your Job to Travel: Unpaid Sabbatical for Set Amount of Time

If you love your job, don’t underestimate how much your job loves you back. It’s incredibly expensive, time consuming, and exhausting process for employers to find good employees. Even when they do find a good potential candidate that person could very likely turn out to be a degenerate once hired. If you’re a good employee, you can use this to your advantage.

If you want to stay with the company and in the role you’re in now, it wouldn’t hurt to ask for an unpaid sabbatical. It’s best to start a conversation around the idea 2-3 months before you want to leave on your trip. Depending on your role and tenure it might even warrant a six month notice.  Before you bring the subject up you should have two numbers in mind: the ideal amount of time that you’ll want for sabbatical and the minimum amount of time you’ll accept. You’ll be able to negotiate successfully if you have these numbers in mind before that conversation.

The advantage of unpaid sabbatical is knowing that you’ll have a paying job that you love waiting for you when you get home.  The disadvantage of this method is that you’ll typically top out at 3-6 months even if your employer is very liberal in their policies. At six months of travel after years of preparation you might find yourself feeling shortchanged.

Quit Your Job to Travel: Working Remote while Traveling

It may just turn out that your job loves you so much that even though they’ll let you travel they want you to keep working!  Working remote is a great option if you have it.  First, you skip the stress of being unemployed. It also keeps the money flowing into your pocket while you travel.

The disadvantage here is that you’re…well…still working.  It’s hard to completely get immersed in where you are, what you’re doing, and enjoying the experience and freedom of travel when you’re still tethered to the office.  Additionally, you’ll likely be restricted to being close to reliable (and fast) internet.  Depending on where you plan to go this can become a major challenge to overcome. Video conferencing can be extremely challenging even in the best of situations.  But hey, a CoWorking space on the beach is a hellofa lot better than your current work conditions likely are. Another difficulty is if you have to work remote during the same hours as back at home.  This means you’d be essentially working second or third shift depending on where you want to travel- not a great way to see the world.

Quit Your Job to Travel: Job Search While Abroad

If you have a nagging feeling your employer doesn’t like you, in reality, they are probably dreaming of a day when you’ll quit.  If you plan on just quitting your job and finding a new one if/when you return, two weeks notice is customary. Giving your employer ample time to find a replacement will also help you get better references should you need them. While this means you won’t be earning income while traveling there is something to be said about the experience of being completely free from the burden of time.

After we leave our school years, we truly never get to take off the yoke of responsibility for more than a day or two at a time.  Who are you to deny getting lost in that big old world out there anyway?  (And the second you’re abroad you’ll realize HOW MANY people are doing this too.)

Job searching while abroad is more difficult than you might expect. It’s certainly something that varies depending on what kind of career you’re in.  Finney and I gave ourselves three months of searching. We used the first month to put our feelers out and reaching out to old connections. Additionally, we got back in contact with friends who might be able to help network.  During month two we actively searched for jobs online, interviewed, and followed up.  By month three we were working very specific opportunities or negotiating on a start date.

Quit Your Job to Travel: Start Your Own Business (and never go back!)

This isn’t as unreasonable as it seems. We met many people abroad who left on one way tickets with a dream in their hearts. They have no intent of going back to their home and “normal” life anytime soon.

Let’s stop here and differentiate what this looks like though.  If you are pursuing this option, the primary goal is not travel; it’s to become independent of the typical career lifestyle.  If you really want to leave the country indefinitely your focus will first be on creating financial independence.  It’s actually not as scary as it sounds- many people do this.  We just hadn’t met them yet because they aren’t typically hanging out in Southern Wisconsin.  They’re hanging out in Chiang Mai, Canggu, or wherever the hell they want.

How have they accomplished becoming location independent?  Many people are working as freelancers, participating in gig jobs. Others learn new skills abroad or are just simply working in their normal job role for companies abroad.  The common thread is that most of them are able to complete all their work with a computer and the good ole internets.

There are also many ways to work abroad. Some people work temporary jobs in hospitality i.e. bar tending, working at a hostel. Others participate in woofing or under 30yr/old work visas for countries like Australia and New Zealand.

Quit Your Job to Travel: Change Careers Upon Return

Hey!  This is what I did! Extended travel offers a unique opportunity if you’ve been on a single career path for a few years . It may be one of the few moments where you have the time and clarity to focus on changing careers. You’ll have the free time to plan exactly what your new career path will look like, the time to network (even remotely) with contacts back home put things in motion, and the time to interview to line up the best possible positioning for yourself when you come home.

Potential employers that I interviewed with were intensely interested in my year abroad in my experience.  I was able to speak on goal setting, drive to succeed, and my newfound passion for my changing career path.  Despite what you might think a gap of employment for travel is not going to make you undesirable.  Instead, you will listen to countless stories in interviews of people wishing they had done the same thing.

Allison took the last few months on our trip and built her own HR Consulting business. She now has clients around the country and is able not only to work for herself but also from anywhere.  Building your own business is something that’s hard to do when you’re working for someone else.  Maybe your trip is also about building something yourself.

Looking for more information on how to make the transition back to the so called real world?  How to Come Home After Long Term Travel

Some say Diemer was raised by wolves. Others claim the spirits of the forest played a part. Most however, would agree that he was raised by his parents in a house.

A living oddity, he is one of the few living men who can legally drive a Class A dump truck but also knows why you’d pay more for a full canvas suit.

While blessed with many useless gifts, he is not a man without weakness. To this day he is unable to throw a baseball or “pigskin” in front of others without fear of ridicule.

FAVORITE PLACES: Anywhere best explored on a motorbike: Vietnam, the Philippines, Santorini and Bali.

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