Nov 10, 2015

Working while traveling (or the other way around)

Set sail around the world, laptop in tow, plop yourself on a nice sandy beach and settle in for some work - isn’t that the dream? The truth is, this isn’t how working while traveling always goes down, but it is totally possible to churn out quality work while exploring the world. The key? Keep things realistic.

This post was originally posted on the Hummings blog.


First of all, find work that can be done remotely. This can be anything from being a virtual assistant, designer, developer, project manager, etc. I’m an engineer so as long as I have a laptop, wifi, and an outlet I’m good to go. There are tons of possibilities, and you don’t always have to be a freelancer to do it. Many companies ( allow their employees to work remotely, as long as they get their stuff done.


Ultimately, when you’re traveling, you’re not working, and when you’re working, you’re not traveling. When you’re exploring the maze of small cobblestone streets of Fez, it’s unlikely you’re going to be getting any meaningful work done. Likewise, if you’re focused on your laptop screen, you’re not going to be taking in your surroundings or connecting with local culture. It’s unrealistic to expect you will, and trying to do so will only make you stressed out and unhappy.

You need to give yourself the space to work without distraction. When I went to Mexico City and Oaxaca, I worked full time and got quite a bit done while traveling because I made time for both work and travel. It doesn’t matter where you decide to work, whether you’re in your hotel or on a sandy beach. In fact, it’s probably better in your hotel – where there’s electricity, a strong wifi signal, and most importantly – a quiet place to focus. Then, when your work is completed, you can go explore without worrying about whether you’re working or handling your responsibilities. Finding time to separate work and exploration/travel is extremely important. Set aside days where you know you’ll be working that day, and don’t expect to go check out that local market that you’ve heard about. Instead, set aside time tomorrow, over the weekend, or next week when you know you can go explore without feeling guilty.

Doing things this way also means you need to be in places for longer than you would if you were there on a 10 day vacation. My favorite place to travel was Morocco. I didn’t work full time while I was there, but it was an amazing place. A one month trip to Morocco (if you’re planning on working full time) isn’t really enough to explore the country on a deep level. In a one month trip, if you’re working until the evenings and exploring on weekends, that only gives you about 8 full days of exploring, not counting evenings. In the evenings, there may be times where you’re tired from working all day, and just want to relax – and that’s OK.

I’ve found that it works best if you have at least three months in a place. That gives you enough auxiliary days to explore and you won’t feel the pressure of having to maximize every single second so that you don’t miss anything. Trying to do too much in too little time can be extremely stressful and will undoubtedly lead to burnout. You can have downtime, you can explore things, and still have enough time to work as you’re expected.


Stay connected. I can’t emphasize this enough. Most countries will allow you to buy a sim card with data. This will, at the very least, provide you with access to email and instant messaging if you need to stay in touch with your clients and coworkers. In a pinch you can even use the data access to turn your phone into a hotspot so you can access the data with your computer. You never know if a cafe is going to have reliable internet before you arrive – having a backup plan in place is a great way to mitigate that.

Do your research beforehand. In Mexico, the coworking spots had amazingly fast internet, but unfortunately in Oaxaca they did not – I ended up going to cafes a lot there. If you’re going to a city, try to find where you’d be able to work, and make sure to reach out to the hostel, hotel, or Airbnb and ask them about internet speeds. Tell people you need to work from your room and will need high-speed internet – people are usually pretty up front about whether that’d be feasible from their hotels or not.

Sometimes you need to arrive in a place a few days before you start work just so that you can explore cafes or coworking spaces to find the ones that make for a good working environment.


The biggest concern for clients, employers, or anyone else you work with is that when you finally get off that plane and start exploring the Guatemalan mountains, you’ll be impossible to reach. Something goes wrong and someone has a question, and they’ll just get your auto response email or your voicemail and things will all go awry. Regularly checking email, responding to messaging, and returning calls can instill confidence in those that work with you, and assuage their concerns about you being on a different continent.

If you know you’re going to be offline for a few days – tell people. Let them know that it’s only for a short time and you’ll be back on the case soon – people are usually very understanding about such things. I like being transparent about all aspects of my business so when I told my clients that I would be working while traveling, they all took it pretty well because I’ve established a habit of regular communication with them. I’ve been working remotely with all of them for a long time now. Ultimately it’s a matter of trust – you need to promise to stay in touch and work hard, and they need to believe you. You also need to follow through on that promise.


Try an alternate schedule. I find I work best in the mornings before lunch. This is my focused, uncluttered time since my mind is fresh and hasn’t been inundated with emails, stresses, and other things that seep into one’s brain on a daily basis. Then, I like to explore for a few hours in the afternoon while it’s still light out, and then I continue to work in the evening/nighttime.

Try alternating the days you explore – spend Sunday working and go to the touristy location on a Tuesday when it’s less crowded. Maybe waking up really early in the morning and working until 2 PM is the way you want to go, giving you the remainder of the day to explore without worrying about work.

Try different things and see which one works for you.


Try approaching things from the perspective of living instead of traveling. Go to the local markets, buy groceries, and cook at home (eating out adds up FAST when you’re traveling). Find out where you can do laundry. Know the cafes that are good to work from. Meet your neighbors. Try to enjoy the environment you’re in, rather than frantically trying to check items off of a list and just really soak in your surroundings.

Obviously exploring the tourist attractions is fun and you should balance that with everything else. However, living instead of traveling will save you money, lower your stress levels, and allow for a deeper connection with the local culture.