5 Lessons from a 2-Month Remote Work Experiment

Editor’s note: This guest article is from Tim Leffel, author of The World’s Cheapest Destinations.


I am one of those travel writers who actually makes a living at what I do, so in theory I can work from anywhere, right? So why am I hitting the 10-year mark in a house in the United States, where my money doesn’t go nearly as far as it would if I worked remotely?

There are a lot of good reasons I’ve stayed put.

A kid in school. A working wife. Two of my daughter’s three grandparents within driving distance and one a two-hour flight away.

But we’re ready to cut our expenses in half and lead a more interesting life elsewhere. So this summer we gave it a two-month trial run. First we spent a month in the lovely central Mexican city of Guanajuato. It’s a pedestrian-friendly colonial city that’s not too big, not too small, and it has one of those wonderful highland climates that always feels like spring. Then we spent our second month in the Yucatan and Belize, where I had a number of assignments.

Except for a week at my little no-tech Yucatan beach house, I was still trying to work the whole time. Meanwhile, my wife and daughter were taking Spanish lessons and then just tagging along for the ride. For them it was a very long summer vacation, for me it was two months in a virtual office. Here are the valuable lessons learned for when we make our break for real next year.

  1. Wi-Fi is great, but you still need privacy.
  2. I was pleasantly surprised by how easy it was to be online when I needed to be in Mexico. Even the luxury hotels there now often throw in wireless Internet for free and it was usually a fast connection. Most any coffee shop has open access too. But I still popped out to an Internet cafe fairly often just to get some uninterrupted work time. Otherwise I got stuck in conversations every ten minutes that would break my concentration and it was hard to have a Skype call with my wife and daughter arguing about snacktime in the background.

    Lesson learned: get an apartment with a dedicated office room or somehow carve out some alone time each day. If you’re working remotely from anywhere, you still need your own space to get things done.

  3. Skype is wonderful, but you need a great connection.
  4. I’m a big fan of Skype. With a U.S. number people could call me on and an outbound calling subscription, I could do almost anything I needed to do on the phone. But in the apartment I was renting, the wireless signal had a nagging habit of suddenly fading to a weak level that was okay for surfing but lousy for voice.

    Lesson learned: Don’t sign a six-month or year-long lease before checking out the signal quality if you need to talk on the phone regularly. Otherwise you’ll need to find a good Internet cafe with Skype and headphones nearby.

  5. Slowing down feels good, but don’t expect others to understand.
  6. It’s easy to get into the more healthy pace of a foreign culture with it’s 3-hour lunches, afternoon siestas, weekly festivals, and strolls at dusk. Unfortunately, some of the people you deal with back home have never known any of that and can’t even fathom the idea of not working 10-hour days and toting their crackberry the other times. In their 24/7 connected world, you’re a slacker if you don’t respond to e-mails within the hour.

    Lesson learned: Be prepared for daily apologies and soothing of egos in your business dealings if you “go native.”

  7. Prioritizing is paramount.
  8. I’ve collaborated on a few books with a great business writer and speaker named Steve Little who works part of the year in Merida, Mexico. He says, “Most business owners get up each day and do what they want to do instead of what they have to do.”

    Sure, lifestyle design is about doing what you want to do, but a lot of times it’s the other grunt work and task execution that keeps the bills paid. Over a two-month period, I probably averaged only about two or three hours a day online. When you run several websites that employ freelancers and you need to interface with various business partners and editors, that’s not much time.

    So before I left I took a cold hard look at which activities directly affected income, writing quality, and site traffic. I figured out which tasks led directly to income and made sure those were the ones I attended to first each time I logged on. Things that are fun but produce negligible traffic/earnings/assignments went to the bottom of the list.

    Lesson learned: This was the smartest thing I did up front. If I hadn’t prioritized and stuck to my guns, I would have been pulling my hair out every time I saw hundreds of unopened e-mails piling up.

  9. Virtual assistants are even more important when you are traveling.
  10. If you’re going to scale back your hours of work, there’s an equation that kicks in saying, “Something has to go.” Maybe you work half as much but your expenses are cut in half, so it’s a wash. But if you want to be better off than you were at home while still working less, it makes sense to farm out some time-consuming tasks you don’t need to do yourself. In my case that’s posting HTML content on two websites I run and switching out ads on those pages when necessary.

    I can do that work myself, but if my time is worth $40 an hour and someone else can do the task equally well for 1/4 of that amount or less, why would I? I have two virtual assistants I send assignments to and they do great work. While they were plugging away adding new pages and making my sites look good, I could spend time on the high-value tasks that can’t be duplicated—like writing articles, putting up good blog posts, communicating with freelance contributors, or researching hotels I was reviewing.

    Lesson learned: virtual assistants can be the difference between being super-productive and feeling constantly behind.

tim-leffelTim Leffel is the author of several books including The World’s Cheapest Destinations (now in its 3rd edition). He edits the award-winning narrative webzine Perceptive Travel, dispenses advice on the Cheapest Destinations blog, and heads up the Practical Travel Gear blog. You can follow him @timleffel

Top photo by Refracted Moments

I'm Corbett Barr, founder of Fizzle and Palapa and co-host of The Fizzle Show. This is where I write about building businesses, living the good life, and doing work that matters. More about me »

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