Digital Nomad

The good, the bad, and the unknowns of making a living on the road.

Words and photos by Cotopaxi Ambassador Erin Sullivan

In the summer of 2015, I got fired from my office job and wanted to give freelance a try. I didn’t know what that actually looked like, so I tried to find people who did. I became an intern, an assistant, and a coworker for a year before I quit to pursue solo endeavors as a writer and photographer in the outdoor, travel, and personal development industries.

Generally speaking, there are a range of jobs that offer the freedom to work remotely. Some of them come in the form of a flexible company or boss, and many more involve working for yourself. Whatever the circumstance, having the flexibility to work wherever there is Wi-Fi is a major perk, but it also comes with some very valid challenges.

Here’s what you should know:


You work for yourself

With no one person to report to, you have the freedom to decide when you are working. You’re more productive at night? No prob—sleep late and nobody will notice. Want to take some time off? You make your own schedule, boss. You decide when you work and when you play.

You are location independent

As long as there is Wi-Fi, you can work there, so this gives you major freedom. Live cheaply abroad, or split your time in multiple places. It doesn’t matter where you are as long as you have solid internet.

You can travel on your terms

Because you can work from anywhere, you can spend weeks in Thailand or Colombia if you want to. It is also often cheaper to live halfway across the world when compared to North America. Wherever you are, as long as you’re getting your work done, you can easily spend your weekends exploring places you’d have to take major time off to see if you had a typical 9-5 gig.

You will grow

Working for yourself and being location independent teaches you some serious decision-making and prioritization skills, and accelerates the learning process. It turns on your entrepreneurial side, and will show you if you’ve got what it takes to jump into a new endeavor. It gives you more experience as a self-starter.

You meet like-minded people

As these types of jobs become more common, communities form, especially in places known to attract the digital nomad type. These are people who understand your lifestyle, and most likely, people who share your values because they’re doing it for a similar reason you are—usually something to do with having the freedom to explore and enjoy life on your terms with more freedom.


You work for yourself

Working for yourself can also be… really challenging! It can be a total pain in the ass to be your own boss, to be your own accountability partner, your own cheerleader, and your own secretary. Unless you hire someone, finishing your work is all on you. Sometimes it feels like it would be nice to have someone consistently giving direction and deadlines, but that’s your job, too.

You can’t travel without strings

When you choose to work from the road, you’ll most likely have to plan on working wherever you go, unless you plan around a vacation. Your emails chase you and your creative pursuits follow you around. It’s a trade-off, but you’ll most likely end up setting aside a few days to work even when you’re supposed to be on a trip.

Your work-life balance is confusing

Because your lifestyle is a bit unconventional, and the backdrop for it might be somewhere pretty awesome, it can be confusing to know how much you should be working. You don’t have the 9-5 container of knowing how much time you have to get your work done. Your time is endless, so it’s easy to overwork or get overwhelmed. This stuff takes major discipline.

Lack of routine/uncertainty

Life can feel chaotic without some sense of routine. If you move around a lot, you need to find your own routine and experiment with what that looks like for you. Depending on your job, you are also often responsible for your income—knowing where your next paycheck is coming from and getting the next job after that. It can feel like a major hustle.

Long-term community can be hard to find

Since people who work location-independent jobs move around so much, it can be hard to lock down a core group of friends. But it depends. If you live in one place and hold yourself to normal working hours, your community won’t be much different from someone with an office gig.

It is easy to glamorize this job because it allows you to live a more adventurous and flexible life. But know that like any job, there is a lot to consider. And even though there are a lot of benefits, know that what I’m talking about here is still work. It’s still hard. And it still feels like work, even when you love it.

Getting or creating a job like this is not rocket science, but it’s not easy or simple either. To pull this off, you need to stay flexible, positive, and patient, and go easy on yourself if you happen to discover that it might not be for you.

So how to start? You just do. You start somewhere, and you try out new ways to do things, and you learn as you go.

Top photo by BC Serna.