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In late 2016, I joined the all-remote team at Zapier as their SEO & Growth Manager. Before I took the job I had set a personal goal to travel the world. Being a full-time Zapier employee meant I had the means and flexibility to work from anywhere. So in early 2017, I packed my bag (yes, just one bag!) and took off for Lima, Peru.

I might not have chosen Lima if I was traveling alone, but I had decided that I wanted to try one of the many remote work-travel programs that have sprung up to serve people like me. Yes, traveling alone is much cheaper. But there are some real benefits to traveling with a group, and I strongly feel that joining a remote work program is something every digital nomad should try at least once.

A colleague at Zapier introduced me to Hacker Paradise, a remote work and travel group. After doing my research I applied to several programs, but I heard back from Spencer at HP first. Later I traveled with Hacker Paradise again, joining them in Chiang Mai, Phnom Penh, Bali, Mexico City and Playa Del Carmen.

Let Someone Else Take Care of the Details

If you travel on your own, you can save money by booking your own accommodations and co-working space. (Or, save even more money and forgo a co-working space altogether. Just make sure your Airbnb has good WiFi!) This is definitely possible, but it can be hard – especially if you’re traveling to a country where you don’t speak the language.

When I first started out as a digital nomad I decided to travel with a group in part so I could let someone else deal with these details. It let me focus on work, and have fun traveling and with a community of like-minded people.

The details vary from company to company, but with Hacker Paradise, I did have to arrange my own flights to and from destinations. But they provide you with a lot of support, before during and even after your trip. For example, HP sends you information beforehand on the safest/cheapest way to get a taxi or other public transportation from the airport. One of the trip facilitators meets you at your housing and helps get you checked into the apartment.

If you have any issues with the accommodations – such as an appliance not working, HP will help coordinate with the property manager to get it fixed. Same goes for the co-working space (which is included in the cost of HP trips) – if the WiFi goes out or there are any other issues, the facilitators handle all that.

Built-In Travel Buddies

Before your trip begins, you are invited to join a Slack workspace with the other trip participants. People use this to get to know each other and pretty soon everyone is sharing information about the destination. Before the Mexico City trip last summer, people were sharing articles on where to find the best street food, and even set up reservations at restaurants like Pujol.

I found this particularly helpful when I went to Lima. I knew I wanted to go to Machu Picchu, and luckily I was able to get tons of info about permits, accommodations and tours from other people in my group.

You can also meet people to travel with later. It's not uncommon for people to make friends within these groups, and then go do their own trip with a a few friends. Being part of the group sort of teaches you how to do it, and then you can go do it on your own and save money that way.

Community of Remote Workers

Before I joined HP, I had been working from home and I was slowly going crazy. I wasn’t talking to people, and it started to wear on my well-being. I eventually got really sick. Having people around to connect with helps you in a lot of ways.

And the people you meet on these trips will be from all different professions and backgrounds. It's really incredible who you can meet. I have found clients this way, and hired people to help me with my business. It's such a great community because we are all remote workers and we understand each other's way of life and the challenges that are involved. Also, people who choose to travel and work remotely tend to have a unique mindset. Many of them are very entrepreneurial or adventurous. You are just bound to connect with a really interesting group of people this way.

And one of the best things about HP is how active the alumni network is. We have our own Slack workspace for Alumns and people are always networking for jobs, sharing advice advice, making connections and talking about travel. To me, this is the best part of the whole experience. Being part of the HP alumni network is like being in a secret society. I’ve gotten a lot of opportunities this way, met new people and been involved in some really cool projects. All just by having access to their Alumni Slack Workspace.

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Picking a Program

It took a few weeks of research and planning to look for the right travel program. There are quite a few, and it’s definitely a growing industry. After my time in Peru, I flew to Barcelona to join another travel program, the now-defunct We Roam. I'm omitting that experience from my review. Because the company is no longer functioning, I don't think it's really helpful for people to know what it was like. But I did travel around Europe with them, visiting Barcelona, Prague, Berlin and Split.

One thing I found when researching different companies is that they are more similar than they are different. So often it comes down to which group has the trip and dates that you want, or who gets back to you the soonest! Sometimes people complain that one group or another is just people who are there to party. I think HP does a pretty good job of screening applicants and picking people who will actually be working while traveling.

To learn more about the different programs that are available, I'd recommend the following:

  1. Ask friends and colleagues for suggestions;
  2. Take advantage of Google – there's tons of info out there and;
  3. Check out Coworkations for reviews.
  4. Also, Spencer at HP wrote a great blog post (on my recommendation!) about 10 Questions to Ask Before Signing Up for a Remote Work & Travel Program.

Have you ever traveled with a remote work group? What was it like? I'd love to hear about your experience – please share in the comments!


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