working remotelyMany, many people just like you suffer from a disease called the ‘travel bug’.

There is no known antidote, but for many of us we are happy to be infected for the rest of our lives.

With our head in the clouds we daydream about exotic beaches, quaint cafes, ancient ruins, and mystical temples.

We peruse through travel magazines and websites, and add stunning images to our Pinterest ‘bucket list’ board.

But then ‘reality’ smacks us upside the head and we realize, “Hey, how are we going to pay for it?”

As we’ve proven in our interview series, there are dozens of travelers funding travel in a myriad of ways. Financially creating a travel lifestyle is not only possible, but more and more probable in today’s global, information and connection driven market. And for some travelers, they’ve been able to transition to traveling or living abroad without having to give up their day job.

My hubby Greg recently interviewed an expat in this exact situation. Michael Crowther got bit with the travel bug three years ago while reading a book on travel. He thought it would be incredible to give his family an international experience. Mentioning it to his wife, she agreed it would be rewarding. But how to pay for it?

Neither of them wanted to make a permanent move, so they planned on keeping their home and vehicles. How would they be able to afford expenses abroad and expenses at home, especially if Michael had to give up his job so they could go?

For two years they continued exploring options and narrowing down destinations. They eventually chose Costa Rica, and decided to approach Michael’s boss to see if he couldn’t keep his job and work remotely while they lived abroad for a year.

Travel bugAfter doing a particularly good job on a project at work, Michael was on the phone with his boss and brought it up. He was surprised at how open he was to the idea. His boss practically agreed on the spot, he just wanted to make sure they clarified a few stipulations.

A year later he and his family were making the move to a small mountain town in the Central Valley. Michael continued to work a normal schedule at their rented home in Costa Rica, and by using today’s technology, such as video conferencing and remote desktop, the office hardly noticed he was gone.

But every weekend is an incredible experience for the Crowther family, exploring beaches and rain forests; zip-lining and swimming in water holes; sitting in hot springs beneath the shadow of a volcano and making visa runs and snorkeling in Bocas del Toro, Panama. It’s an experience their family will never forget -- and one that has changed them for the better, giving them a different perspective on the world and their place in it.

So how do you get your boss to say ‘yes’ to letting your work remotely? Here’s a few tips from Michael’s interview:

1. Make yourself indispensable to your company

Obviously your boss is going to be a lot more likely to let you work from home or abroad if you provide a lot of value to the company. If they ‘can’t do without you’, then they’ll be open to accommodating your desires. Seth Godin calls this being a ‘linchpin’. Make yourself so valuable that they wouldn’t dare say no, for fear of losing you and the value you provide.

Action step: How can you become a more indispensable employee? Where can you go the extra mile and become a real asset to the company. Begin today (perhaps by reading ‘Linchpin’ by Seth Godin.) If you don’t want to invest that much effort into your current job, then look for another one. But remember that ultimately you are your own ‘corporation’ and becoming a ‘linchpin’ will benefit you no matter the employer.

2. Wait for the right opportunity

Just as you wouldn’t ask someone to marry you the first time you considered it, you don’t want to ask to your boss to let you work from somewhere else until he’s been warmed up to the concept.

Depending on your company and those ‘in charge’, the idea of working remotely may be a very foreign one. You’ll want to introduce the notion gently and indirectly, sharing articles on how it saves company’s money and improves employee moral.

Then when the time is right, perhaps after a job well done or when you’re due for a promotion, confidently make your proposal.

Action step: Do some research. How does working remotely benefit the boss and the company? How can you indirectly share this information with the powers that be? What project are you working on that you can excel at in order to ‘set the stage’ for ‘popping the question’?

3. Forgo perks or promotions

If making this lifestyle transition is something you’re truly dedicated to doing then you may want to consider ‘bartering’ for it with the boss. Because you’re an indispensable employee, you’ll likely be rewarded for it. Instead of accepting that next promotion or pay raise, appeal instead for the chance to telecommute... from a tropical location.

Action step: Start planning ahead. When is the next promotion or pay raise due? How can you create value before then, and prepare to make your appeal when the time arrives?

4. Show them that they’ll hardly miss you

With today’s technology it’s so easy to connect and work with people, even on opposite sides of the globe. Through email, Voip (voice over i.p. phones), video conferencing, and remote desktops, you can practically work ‘in’ the office, even from another country. Show your boss how easily accessible you’ll be -- so much so that she’ll hardly notice you’re not on the same continent.

Action step: Do your homework. What objections will your boss present, and what technology tools can you use to overcome them? Are there files or servers you need to access that are only in the office? You can use a remote desktop. Do you need to share files? Google Docs or Dropbox. Need to chat on a regular basis? Skype or Google Hangouts. Present solutions to their opposition and a ‘yes’ is more likely.

5. You’ll never know if you don’t ask

Michael’s not the only traveler we’ve interviewed who’s managed to convince his boss to let him work remotely. The most important thing to remember is that you’ll never know if you don’t ask. If it’s something you really want then you need to at least breach the subject with your boss and let him know it’s something you really want. Even if his says no initially, it just might open the door for future possibilities. Don’t assume it can never happen.

Action step: Are you afraid of asking? Why? And what can you do to overcome that fear? Write about it. Imagine what your life will look like when your boss says ‘yes’. What will it look like if you always wonder what the answer would have been?

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