How to Not Quit Your Job and Travel for a Year

Analyze your job situation.

Could you technically do your work remotely? Are other people at your company already working from home? There are a lot of jobs that could easily transition into remote employment, and more companies are becoming flexible when it comes to allowing for remote employees. At the time, I was working with a tech company in Denver. My fiance was a renewable energy consultant with a firm based in Boulder. We were confident that these jobs would translate to remote work, but unsure if our companies would support the move. Regardless, it was certainly worth having the conversation.

Plan it out.

Before you ask your boss consider answers to a few questions that will indirectly come up. What is the benefit for the company? Would there be any disadvantages to you working remotely? How can you ensure that you will be able to maintain the same quality of work from an off-site location? Acknowledge these objections in advance so you can provide thoughtful answers when your boss brings these topics up. You want to make this transition as seamless as possible. Going in with an action plan shows that you are serious about continuing to do your best work, and that is the goal of this conversation.

Have the conversation, be to the point.

When the day came for me to approach my boss, I was horribly nervous. I honestly had no idea what the answer would be, but I felt totally prepared to at least have the conversation. I asked her for a meeting, we chatted for about five minutes in which I laid out the proposition of working from Mexico. I explained that it would be just for a year, I would travel back to the States to visit the office for our big trade show, and would be completely available through Google chat and web conferencing. She was pretty surprised by the idea, mentioned that she had to discuss with the CEO and told me she’d let me know as soon as possible. I went back to my desk, heart racing, to wait for an answer. Ten minutes later we were back in my boss’s office and the answer was yes. I couldn’t believe it. Being given the freedom to work remotely gave me such an appreciation and feeling of loyalty towards my team and my company.

Set up your remote office before you leave.

Let me tell you, arriving in Tulum to find out that the Wifi download speed was not fast enough to hold a conference call sent me into a quick panic. Have you ever had to hold a client call at a restaurant while the DJ is practicing his set for the night? This is the exact scenario you want to avoid and can do so by planning out your work situation just as you would plan out any trip.

What are the tools that you need to do your job perfectly? For me, these included:

• A reliable wifi signal with a minimum speed of 3mbs down, 1.5 mbs upload. In order to ensure this would be available before arriving at a new location, I would always ask the landlord to run a speed test and send me a screenshot of the results.
• A way for clients to call my office extension and reach me. To do this, I set up a Google voice account that connected to my computer. Then I had our IT guy port my office line to that new Google voice number. I had several people test out this new method and was totally delighted when my Google chat showed an incoming call from my office extension.
• Video and web conferencing ability. I made sure these tools were installed on my computer and working correctly.
• Work in the same time zone as your coworkers. If your office is in San Francisco and you are living in Hawaii, plan on scheduling your day to match Pacific Standard Time. When your coworkers are working, you generally should be too. In Mexico, I was on Central time. This actually was a benefit — I could schedule meetings with clients on the East coast earlier than when I was on Mountain time. But I still made a point to end the day when my office closed.

Here is the most important piece of advice I can give for setting up your mobile office. Always have a backup plan. Learn where you can repair your computer, or buy a new one if needed. Research where you can find reliable wifi in town if it suddenly disconnects at your house. Join nomadic remote worker chat groups for the new area you’re traveling to and ask for advice. Find the coworking space in your town (if there is one) and pop in to see if it’s a good place to work. There are so many great resources available, take advantage of these and set yourself with an alternate plan in case you need it. Remember, if your coworkers in New York are able to work, you need to be able to as well. Faulty wifi can be an excuse once or twice, but it’s better to avoid this situation altogether.

Check-in frequently.

Make sure you are visible and available. Establish a daily or weekly check-in with your boss and your team. Set a recurring event on your calendar so that these meetings become routine. Even if you previously had monthly meetings, you want to show your coworkers that you are here and easily accessible, even if you are not physically in the office. Often, employees use internal chat tools to communicate while in the office. This makes location independence even easier and less of an issue.

Become the best at what you’re doing.

It goes without saying that this should be the objective with anything you’re working with, but when you’re working out of the office, it’s even more important. Work to improve your skill set. Prove your value.

Think outside the cube.

Even for those adventure-seekers with a seemingly more stationary career path, there are options. The key is to look at your skill set, not necessarily your current occupation. You might find that these skills easily translate into a job that might allow travel. For example, if you’re a nurse, consider transitioning to travel nursing. If you’re a teacher, you might explore the idea of working with an international school abroad. Once you start thinking creatively with travel as the end goal, you’ll be surprised at the number of options that begin to surface.