How To Work Remotely While Traveling The World
Workin' Girl

How To Work Remotely While Traveling The World

As an adult, one must accept bills as a constant part of life, so a stable income is important. But what would you do if you could have a job that offers flexibility, financial stability, and the opportunity to indulge your travel bug?

Let's face it: We expect more out of life than our parents, or their parents, ever did and the old-fashioned "work for the same company until you retire or die" thing isn't going to cut it for us anymore. The thought of working remotely would often pop into my head but I never really considered remote work as an option until I had a conversation with a young lady I met while dog sledding in Wyoming. She had talked her boss into letting her work remotely from a different country for a month every year. I was inspired and, on August 7, 2017, I submitted my proposal for working remotely to my boss!

Working remotely would be a dream come true for many people (like yours truly) who force themselves out of bed every morning just to make it to the office in time. So why haven't you asked your boss yet? The question is rhetorical. You're still young and you just want to try something different without having to give up your stable position to pursue it.

If only you knew the power you have, especially at work.

Once you've decided to take a leap of faith and ask about working remotely, you'll want to be very strategic in how you present your proposal. Though I'd like to believe my reputation for being a hard worker was the reason I was approved to work from Thailand for a month, it was actually my ability to develop a well-structured work plan that proved to my management team that it could be done. You definitely want to work out the logistics before presenting the idea to your boss if you want them to take your proposal seriously.

If you're considering pitching the idea of working remotely to your boss, here are a few steps to help you with preparing a proposal prior to the conversation. My hope is that you are not only inspired to work remotely but are given some helpful tips to make your work-and-travel dreams a reality.

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

Getty Images

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

Getty Images

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

Getty Images

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.

Whether you work remotely for a week, three months, or an entire year, the benefits are all-encompassing. The experience itself can be life-changing.

Hopefully, you now feel encouraged and inspired to begin writing a proposal of your own to work abroad. Taking the leap to talk to your boss about working remotely can also be very challenging – especially if your company has never approved anyone working remotely before. Though you will serve as a guinea pig for the company, you are not alone!


Thousands of young professionals have dreamed of leaving their office space for new experiences, but they are also nervous about pitching the idea of working remotely to their bosses. Employers know the 21st century workplace is slowly evolving and making small changes to allow young employees to develop professionally through nontraditional work-life experiences.

They also know they'll need to evolve to remain competitive and keep young professionals engaged. Remember, you are the star employee. You have more power than you think you have when it comes to your employer. Now, what are you waiting for?Write the proposal and go for it!

Need help getting started? Click here to download my free Remote Work Proposal Resource Guide.

*This article was originally published on BucketlistMemoirs.com and has been shortened for clarity.

Featured image by Getty Images.

15 Women Share Their Personal Hacks For Better Orgasms (And Sex Overall)

I’m pretty sure that I’m basically being redundant when I say that I write about sex quite a bit which means that I spend quite a bit of time doing research when it comes to sex-related intel, tips, and hacks. Yet I have to say that when it comes to getting some much-needed information in the realm of coitus, it’s been my clients (along with random interviews that I do with people because I don’t mind talking to complete strangers about intimate ish) who have garnered me some of the best takeaways.