How To Work Remotely While Traveling The World

Step 1: Don't Believe Beyoncé...You're Irreplaceable (Sort of)

Anyone can be replaced. Before popping the question to your employer, make sure they value you enough to even entertain the idea of you working remotely. Are you an asset to the company? If you took a leave of absence for a week or month, could they manage without you?

Do they depend on you to get things done? This may sound arrogant but these are questions you'll need to ask yourself. Also, employers are often open to being more flexible for their star employees. So, ask yourself, are you a star?

Most people are surprised by the leverage they can have at work if they are great employees that can't be easily replaced. If you're not a star employee, there's always time to improve but you may want to hold off on packing your bags until you can show your boss that you can't easily be replaced.

Step 2: Do Your Research

Before you begin keying 'best beaches' into your search engine, start researching the country you are most interested in working remotely from. You want to select a country that won't make your remote work life difficult.

How will you work reliably while there? Do they offer work cafes or will you need to rent a workspace? Does the country have website/app restrictions that can only be accessed using a VPN? Is there a difference in time zones? What equipment and software will you need to ensure your daily work schedule goes as planned? How will shifting your work schedule impact your workflow?

These are some of the questions you will need to have answers to prior to submitting your proposal. There are many helpful blogs and articles online to help make the decision on location a tad bit easier.

Step 3: Creating the Proposal

Before pitching your idea to your boss, create a proposal that includes everything they'll need to know about the opportunity. Be sure to include your plan for handling your work responsibilities while abroad.

My six-page proposal listed everything from my remote work schedule to monthly meetings (my boss made it clear that I could not cancel meetings and would be expected to continue conducting meetings while overseas). If your office does not have updated equipment like webcams installed, you can use apps/software like GoTo Meeting and Skype to conduct meetings.

Want to impress your boss? Include a plan for every meeting in your proposal. This shows them how serious you are about doing your job while you're gone.

Step 4: Communication is Key

Clear communication is non-negotiable for remote work. In your office, your boss can stop by your desk or pop into your office to ask a quick question. Your coworker can stop you in passing to ask about a project deadline. There's also the traditional last-minute meeting you're told you'll have to attend thirty minutes before it is scheduled to begin. You won't have these luxuries while working abroad.

Your boss will want to know that you can be contacted at any time during your assigned work schedule even though you're not physically in the office. Be sure to explain how you plan to communicate with staff in your proposal. Fortunately, technology is so advanced that there isn't a limit to what you can do from wherever you are.

Step 5: Be Transparent About Footing the Bill

Understanding that your employer is probably not going to pay for your flight, housing, and other expenses that come along with your new remote work lifestyle will help you stay focused on your ultimate goal. The only thing you should expect your employer to pay for is your paycheck.

If you cannot afford to pay for everything, you may want to abort the mission until you're able to save enough money to do so. Remember, you want your boss to take your proposal seriously. Expecting them to pay for the whole experience could make it easier for them to deny your proposal. Letting your boss know upfront that you will be paying for everything lets them know how committed you are to working remotely.

Step 6: Let Them Know What's in It for Them

Companies will want to know how they can benefit from you working remotely. As an employee, you will never get anywhere if you only pitch personal benefits to your boss.

Focus less on personal benefits and more on benefits from the company's perspective in your proposal. What can you promise them? Leave no stone unturned. Look at your company's mission statement closely.

For example, something as simple as wearing your company's T-shirt while volunteering abroad could be the marketing strategy that gets your proposal approved – especially if your company is big on making a social impact.

Step 7: Wait for the Perfect Time to Pitch

I'm not a fan of baseball but I know it's easy to strike out if you don't wait for the perfect pitch. Not sure how one can easily equate the importance of a great pitch in baseball to pitching a proposal to your boss but it's there...somewhere.

The pitch is almost as important as the proposal. Have you double-checked your proposal to make sure you have your plan for communication, work schedule, and expenses included? If your proposal is complete, it's time to pitch your proposal. Be prepared to answer any questions your boss or senior management may have.

Include a letter of intent with your proposal that briefly summarizes why you are interested in working remotely and what you hope to gain professionally. Instead of emailing the proposal to your boss, print out a copy and hand it to them personally.