Traveling with the intention of working full time is a bit different than traveling for vacation. In this case not only is the purpose of the trip different, but also the duration. Being gone for a month or more is quite different than visiting London for a week. Assuming you have a house or apartment, you’ll need someone to look in on it, you’ll need plants watered, fish fed, mail put on hold or taken in by a friend. You’ll need to be sure you have your bills taken care of.
Luckily a good friend of mine needed a place to stay during this time period so I ended up with free house-sitting while we are gone, so I don’t need to worry about the house or anything. Most of our bills are either on auto-pay or I get ebills via email, so that’s easily handled remotely. So most of the day-to-day life stuff back home is just handled.
You will need to ensure wherever you are going has internet access, ideally free and ideally at the location you are staying. You may need a quiet place where you can take con-calls or concentrate. Working from the local coffee shop every day just isn’t practical for many people. Cell coverage is also important, and be aware of your roaming rates! While on vacation we’ll often move from one city to another, I can’t be spending my days here packing, driving/flying, and unpacking, I need to work (and relax when I’m not working), so we’re staying in a rental house for the entire month long stay. We arrive, unpack, and we’re done. In the future I could envision moving locations on the weekends, trading some relaxation for some additional locales. But not this time.
You need to set expectations and a schedule with not only yourself, but also anyone else you are traveling with. It would be easy for my wife to get wholly into the vacation mindset, and not understand why I couldn’t walk down to the beach with her just now, and why I was spending all my time on the computer. The flip side is to make sure you limit the work somewhat, so you aren’t wasting your exotic surroundings. I’ve committed to working as close to 40 hours a week as possible. The risk for me is working too much, not too little.
I’m also starting the day much easier than usual, in order to buy myself some nice daylight hours in the afternoon and evening to be able to enjoy the beach, the ocean, the town, and everything that this place has to offer. I’m working from about 7 AM to about 3 PM local time. I would shift even earlier, however Sayulita is oddly positioned for it’s timezone, so the sun rises late and stays up late so I’m really getting a very good block of daylight after I’m done working. If it was a different location maybe I’d swing the other way, and explore in the mornings and work from the afternoon onward. Or possibly I’d do a split-shift type of thing, working a few hours, running around for a bit, and then working more. In this case though the early shift makes the most sense and keeps me aligned with our East Coast office North of Boston (where I typically work). Its important to me that for this trial run, that my remote location has as little impact on my work and my coworkers as possible. If I’m shirking my duties, or MIA during most of the business day, then the rest of the team will be put out having to cover for me – which is obviously no good.