How Anyone Can Combine Work and Travel

Do you aspire to have the freedom to travel and see the world, but don’t want to – or can’t – abandon your career? Are you following the prudent path, yet remain in a persistent state of wanderlust as you day dream over travel blogs and Facebook albums? Do you dream of finding a way to combine work and travel? Is the elusive “one day” your only solace?

I envied the vagabonds who quit or forwent real jobs to backpack around the world. Yet, that wasn’t completely for me. I enjoyed my work and I wanted to build and grow organizations, disrupt industries, and be intellectually challenged along the way.

It took me some time to figure this out, but work and travel need not be an either/or proposition. You can do both in today’s world. I worked hard to marry the two and have since visited some 50 countries while earning solid income (and equity) with work that I enjoy. And here is the kicker: the travel actually benefited my career.

If work and travel is something you crave, then don’t continue with the status quo, only to regret it when you’re older. Get creative and challenge your perceived limitations. Here are a few ideas to help get you started:

1. Negotiate for small pieces of time

If you’re delivering results in the workplace, you have more options than you think. Tell your employer that you need a temporary leave of absence. Pick a defined period of time, rent your place out on AirBnB, and go for it. Organizations always want good talent; hiring costs are high, and training replacements takes time – so letting you go for a month is often a better option than seeing you leave for good. Take your time off and come back rejuvenated.

2. Find a job that allows you to work remotely – or transition your current job to do so

Companies are increasingly supporting – or at least tolerating – distributed teams. Request to work remotely in your current role for a period of time or find another job that allows it. Meetings are becoming increasingly virtual and distributed, and there are a myriad of tools available to support this system (find some of my favorite remote tools here). You may fear that your employer will resist the idea, but you never know until you ask. Companies like Buffer, WordPress, and Mozilla, have even moved to 100% distributed team environments. If you’re a freelancer, most people will never know or even care that you’re a digital nomad. Besides the opportunity to work and travel, there are productivity benefits for working remotely. Read Remote: Office Not Required if you are considering it for your organization – or simply want talking points to help sell your boss on the idea.

3. Stretch your vacation days

Turn a 3-day weekend into longer trip by the leaving afternoon before the weekend starts, taking a couple days off, and returning the morning of the day you have to be back at your desk. Take the full 4 days of the short week off and you are able to leverage both weekends. Think a short international trip is financially excessive or too time intensive? Most of us spend the same amount of money for a wedding weekend (after flight, hotel, and gifts), without hesitation, as it would cost to fly to Costa Rica and stay in a guest house on the beach for a few days. Don’t require the pressure of an invitation to treat yourself to a quick, but more exotic, getaway. This method is more rushed, but it at least allows you to continue to work and travel.

4. The adult version of a gap year

Take advantage of your natural transition periods. Switching jobs? Going back to school? Budget in an extra couple of weeks or months off in between. If your new employer requires an immediate start, keep it short, but at least take a week or two off in between. Say that you’ve already committed and don’t fall victim to their heightened sense of urgency. I’ve hired many people, and when I find the right fit for my company, I rarely let them slip away because of a marginally later start date. If you’re worried about your paycheck being deferred by a week or two, use credit card miles (you should accrue these through your normal life’s spending), stay in hostels, put your place on AirBnB, don’t eat for a month, and find other ways to get creative with your budget.

5. Take a mini-retirement

Instead of deferring retirement to the end of our career, you’ll be happier and more productive taking mini-retirements throughout your life. You’ll better enjoy the time traveling when you’re young and healthy as well. Take 1-12 months every few years to do what most interests you and visit the places you’ve always wanted to see. You can also leverage the time off to do resume-building projects – like learning a foreign language or volunteering.

6. Find a local project abroad

Find resume-building jobs or projects abroad. This will help you stand out from your peers in future interviews, as you’ll seem more interesting and diverse. Find a local charity or project to volunteer for in exchange for room and board. If you’re a consultant or freelancer, chances are that someone in the foreign country you want to visit could use your services too. You will continue to practice your trade and generate income while gaining a unique experience that distinguishes you from your competition when you return. After all, how many graphic designers can talk about their clients in faraway lands? If this doesn’t apply to you, find a company or organization with international offices and request to work abroad for a period of time. These opportunities make work and travel a requirement.

I view people as Isaac Newton views objects: they tend to stay at rest unless an external force acts upon them. This is why most adult professionals that fulfill their world travel dreams do so only after getting fired or having a midlife crisis. Without these negative forces, many simply never live out their dreams. Don’t let this happen to you. Take control of your life and find ways to incorporate work and travel into your career plans – even if you start with small steps, like spending a couple days in Cape Cod before transitioning to a couple months in Cape Town.

Do you have any good examples of how you combined your work and travel? I would love to hear about it.

I hope this helps you combine work and travel!

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