How to become a digital nomad

Dana Vines

3 min read

This was maybe a search I performed a few dozen (if we’re being honest a few hundred) times before I actually started living this lifestyle. The memories are vivid, walking out of my bedroom as a small-town, 15 year old version of myself and announcing that I would be moving to Costa Rica that year. Had I made good on that threat it would have been 2003 and it would have actually been an ideal time to visit as CR was still a “value destination”. When I did finally visit 20 years later, I found hyper tourism and inflated prices beyond belief. ***Side note: let that be a lesson, don't sleep on your dreams otherwise time will take its toll on what you thought you wanted to begin with.

ANYWAY…..The dream of living abroad while working for an income is not far away in the context of a post covid era where an increasing amount of jobs are available in the remote capacity. In 2003, the concept of being able to travel full time in any form of comfort was far and away from my realm of plausibility. Today, it's not so far of a reach for anyone that has a laptop and a will to change their stars.

My personal path started with simply setting the intention to not accept any jobs that didn’t allow me to work remotely. I had just come off of 8 months of living in a bus full time surviving off of savings earned. Once we reached the end of our last $500, I realized it was time to find work. During those first couple months of earning a new position, I was living on the streets of Portland, Oregon in a renovated skoolie…bathing in the local community center and using public transportation strategically to get around town for little to no expense.

Eventually, that position ended and I was faced with a choice. As you’re likely faced with choice now. There was a very clear concept in my mind of what I wanted in life and you might be grappling with that presently. The dissonance between what you think will be great and what your present reality is. I will tell you now, beware all ye who enter here……It’s not all sunset selfies and delicious dinners of an international variety. It's just like anything else in life, there will be challenges and downfalls, and times that you look around and think “what the hell am I doing” the end of the day I can recommend this life for anyone who truly has a fluid and adaptable understanding of comfort. If you have the capacity to see Home as a subjective term then you’re a green flag. If you are able to be flexible in the face of circumstance, not in theory but in practice, then you’re a green flag. If you’re able to travel for 32 hours straight only to arrive in a place that has whole fish and strange pickled items on the menu as your only food option and you can happily swallow that down because #nutrients then maybe, just maybe, you can hang with those who claim “nomad status”.

Finally though, the HOW becomes less complex once you make that decision. In the words of the great Jeff Goldblum ``Life…somehow…finds a way” will attract what you set out to accomplish so don't get discouraged by the delay in hiring. Expect it to take at least 3-6 months before you even get an interview. The key is to stay persistent and utilize the resources we identify on the HOW page of this website.

So here I will break it you into simple steps, the only ones you need to fully enter a digital nomad lifestyle and they are as follows:

  1. Commit to making a change

  2. Get a remote job

  3. Book a plane ticket somewhere else (we’ll talk a lot more about this soon)

  4. Go to that place

  5. Prepare for calamity and beauty

  6. Stick with it

In the following articles I'll dive deeper into each of these concepts but for now, this can service as a high level roadmap for a clear path to achieving your goals. Obviously these are broad concepts but I just wanted to present the reality of becoming in this format. It's easy to idealize what you’re getting into but if you stay with me, I’ll break this down step by step for anyone interested in adopting the lifestyle of a digital nomad in the following articles. Stay tuned.