How I Went from Working a Desk Job to Traveling the World

I used to have big fears that taking a leave from full-time work would be a big ding in my resume. Coming out the other side, I now have this working theory that this is a very “old school” mentality when it comes to most careers, and that employers these days actually understand (and are impressed by) candidates who do things differently. In order to succeed as a digital nomad, I leaned into my professional experience to build up a new career. I started writing as a freelancer online, began creating video content, and took a course to improve my skills. To this day, I still get job interview requests in my LinkedIn inbox.

While no one in my personal life was living this lifestyle, there are plenty of online communities and resources that helped me realize that tons of people live like this. Get this: the number of digital nomads in the U.S. has exploded over the past couple years- from 4.8 million in 2018 to 10.9 million in 2020. In order to answer my own questions and become confident as a digital nomad, I did tons of research, read the websites and blogs of people who were living similar lives, and connected with people in Facebook groups.

Since money was obviously one of the most important elements of maintaining life as a digital nomad, I looked for ways to reduce my overhead costs, especially while first starting out. One big way of reducing spending was by traveling slowly, instead of country-hopping every weekend. With long-term travel, I’ve found that the quicker you go, the more expensive it is, because you take more plane rides and spend more money in transit on things like food. Especially when I was first building up my own income, it was important to reduce overhead costs, and traveling slowly helped greatly.

Yes, at first saving money was a big focus of mine, so I discovered another way to reduce costs: work trades. This is where you work in exchange for your accommodation, and typically for some meals. You can do work trades on farms in Italy, vineyards in France, schools in Asia, and just about anywhere and doing anything. I personally found a wonderful work-trade arrangement at a hostel, and worked about 20 hours per week for free accommodation. Not only did I not have to pay rent for several months, but I made incredible friends, and learned a lot about the local culture.

One of the challenges of traveling full time is that it can be difficult to match up your plans with the plans of others. I’ve also found that if you’re waiting around for others to come along, you’ll spend most of your time waiting. So, I got comfortable buying plane tickets and making plans on my own, even if I was a little nervous about taking some big trips alone. Every single time, a friend would either end up tagging along, or I’d make brand-new friends along the way, if I didn’t want to be alone. But I also really learned that I loved having the alone time out there in the world to have my own adventures.

I found that I could get a lot done with a weekend trip, or even an “extended weekend” trip, such as a four or five-day adventure. I once went to Costa Rica on a long weekend (using credit card miles to get the flights nearly for free, which we’ll talk about in a little bit). That might have been a little excessive, but yes, you can get a lot done in a short amount of time. Look for weekend adventures within driving distance of your area, set up flight alerts to find airfare deals, and find adventure buddies who are eager to also become Weekend Warriors.

While I was daydreaming of visiting far-away places and exotic beaches, I tried to focus on amazing places I could travel to in my area (or in my part of the world, at least). Regional travel makes a lot more sense for those shorter trips, and also can lead to more cost-effective travel. I found that this practical mentality led me to really explore the area around me, and develop a deep love for it.

Saving money as a traveler was always important to me, so I learned ways to travel cheaper, even for shorter trips. One of my favorite hacks to this day? Staying at hostels, especially in more expensive cities and locations. If a shared dorm room isn’t your thing, most hostels have private rooms, which can still be cheaper than other types of accommodation, such as a hotel. Other ways I travel cheaper? I try to minimize the amount I eat out while on a trip (hostels and guest houses usually have kitchens), and I look for ways to be smart about transportation (taking buses instead of cabs in some cases, for example).

Airlines have tons of benefits and perks, but you need to learn how to use them to your advantage. I learned how to take advantage of airline credit cards in a fiscally responsible way to earn a ton of miles on purchases I was already making. Read the websites of reputable airline experts to learn the basics. When I did that, I started earning free flights (helping out greatly with the whole saving-money thing), and got other perks, such as passes to lounges around the world.

What makes a trip more costly and complicated? When you don’t have the right stuff, and you need to make expensive purchases right before your trip. When I started traveling more, I slowly built up an arsenal of vital high-quality travel gear. This includes a quality backpacking backpack, portable charger, my 32oz Wide Mouth Sustain Nalgene bottle, and excellent walking shoes. Now, whenever I plan a trip, I just need to pack and I’m ready to go.