How I Went from Working a Desk Job to Traveling the World
Every hairbrained idea has to start somewhere, and for as long as I can remember, I’ve wanted to go to far away places, experience every culture, and I loved the feeling of life on the road. You probably feel similarly, since you love Nalgene Outdoor just as much as I do.
But once I started my career, it felt like I’d never be able to take time off to travel, as I always dreamed of. So I fit in travel when I could, and considered myself something of a connoisseur when it came to long-weekend adventures, travel hacking to save money, and making the absolute most of my annual two weeks of vacation. But after a few years of working in television news, I still felt that indescribable feeling that I was eventually going to chase – I just needed to take the time away from my career to travel.
It was certainly a scary thing to consider, for a whole host of reasons. I was entrenched in my career, and wasn’t sure what it would be like to take time “away,” to try something different. But ultimately, I saved money, booked a one-way ticket, gave plenty of notice to my employer, and with not much more than a backpack and a Nalgene bottle, I boarded a flight.
Steps I Took To Create This Lifestyle
Before leaving my stable job to travel, money was my biggest concern, and what I believed to be the biggest obstacle. Despite having a healthy career under my belt, I rarely managed to save more than a few bucks week after week. So in order to travel, I first had to save some money. I did this by scooping ice cream on the weekends at a gourmet treats shop, and by moving in with a roommate to save money on rent. That combined with living frugally for more than a year left me with a small pool of money I could use to travel, and a tiny cushion for when I returned and needed to restart a life.
But after traveling for a few months on that humble “travel fund” I had put together, I realized I was at a crossroads: I could return to my home country and start applying for jobs again, or I could figure out how to sustain my lifestyle by making money on the road. I had no desire to pull the plug on my travels just yet, but I wasn’t quite sure how to work for myself, or how to make money in a legitimate way from anywhere.
In order to create a lifestyle where I could basically travel forever, I would say I definitely learned things the hard way. As I mentioned, I didn’t have a ton of in-person guidance, and very much had to figure things out on my own. But after some stumbling, I finally figured out a system for earning money from anywhere as a digital nomad, and realized that there were also steps I could take to make the process easier along the way.
Here are steps I personally took to create this lifestyle:
I tapped into my professional background
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.
I did research
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.
I traveled slow and steady
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.
I did work-trades to meet people and save money
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.
I was okay with doing things alone
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.
Tips for Traveling While Working a Full-Time Job
As I mentioned earlier, before I picked up and started living life as a full-time traveler, I scratched my travel itch by becoming an avid small-trip traveler. This meant taking trips whenever I could, wherever I could, with my meager two weeks of allotted vacation time a year. I lived my life like this for several years, while building up my career, and before I realized my digital nomad dreams.
If you’re in this position now, it’s a great place to be, because as I’ve learned, you can do a lot with a little bit of time.
Here are some tips for traveling while working a full-time job:
Look for weekend and long-weekend trips
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.
Regional travel can get you far
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).
Learn the basics of airline perks
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.
Have the right gear
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.
Becoming a digital nomad for me was never necessarily my end goal, and it was not always my dream. What I dreamed of was a life where I had uninhibited freedom, where I was able to spend more time outside and on adventures, and I had the means to support myself. This ultimately translated into life as a digital nomad.
Before I started living this lifestyle, I always wondered what happened “after” someone took time off to travel, or what they did next. I now see that for myself, there is no “after,” because I am still “here.” Maybe there will one day be a moment when I hang up my trusty backpack for good, and return to life as a Weekend Warrior. But that day is certainly not today.