How NOT to be a digital nomad

When I started my business at the age of 22, I had one overarching goal in mind: geographic autonomy. I figured that if I could achieve the autonomy to work where I want, then that means I would also have the freedom to choose when I worked and even what I worked on and whom I worked with. To the dismay of my mother who always wanted me to stay in my hometown of DC (sorry, sending me on a semester abroad to Europe forever planted the movement seed), I decided to test out digital nomadism in 2019 just under 5 years into running my shop. Here’s what I did wrong:

I wasn’t thorough enough

Before moving anywhere, research and analysis are absolutely necessary. What’s the typical cost of living for someone in their late 20s? Does my dollar stretch as far there as it does in my current situation? Are there other digital nomads there? What kinds of professionals are in that community to network with, and what industries and subject matters do they represent? Is there even a professional network to mingle with at all? How affordable is housing? Is that housing sustainable for as long as I need it to be? What happens if I need to go to the doctor or the dentist, or if my car breaks down? Etc, etc.?

My assessment did not define these with any depth. I said, “maybe I’ll try Tahoe!” Found an Airbnb that cost the same monthly as my apartment in my hometown, and booked it for 3 months under the entrepreneurial ethos “screw it, let’s do it and figure it out as we go.” This lack of thorough assessment is the root of all the mistakes I made as a digital nomad, and it would end up costing me precious time, resources, and money.?

I wasn’t patient enough

I had wanted to relocate from my hometown for years at that point, so my personal narrative was that I had already been patient enough with waiting to move. But the real patience should’ve begun when I finally made the decision to pull the trigger. Only 35 days passed between the time I booked my first Airbnb and the day I hit the road. Essentially, I was thinking I’d just keep my current operations flowing the same way at the same pace despite a massive change in my location and thus my routine, my accessibility, etc. This lack of patience made things that did not feel fragile at the time extremely delicate once I made the move. I didn’t give myself enough time to appropriately budget, plan, coordinate and overall ease into the process. To analogize, instead of landing the plane softly on the runway after a calculated, strategic flight, I ripped open the emergency hatch and jumped out with a parachute.

Be a steadier pilot, choose the softer landing whenever possible. In my case, it would’ve been possible, feasible, and much more realistic to take my time and execute more methodically.?

I wasn’t nimble enough

The lack of thorough assessment combined with my impatience meant that my business wasn’t very nimble on the road. To use another vehicle analogy, I didn’t batten down the hatches to my boat before sailing it into rougher, uncharted waters. I prepared for the trip as if I’d be sailing through the same currents, and that was shortsighted. I didn’t make the necessary adjustments to my operating model to remain at the same level of efficiency and efficacy. And given that I was going into unfamiliar territory, there was so much unexpected that occurred both personally and professionally that I wasn’t prepped for so it all came completely out of the blue and made a heavy impact when it did.?

I should’ve been more strategic before making this move. If I had been more thorough and patient, I could’ve done a test run for 30 days and gone home to evaluate how it went. Instead, I went all in on my first try, and it always felt like I was playing catchup the minute I took off. I was off balance before I even got to Tahoe.?

I wasn’t budgeted enough

This is a pretty simple section given the lapses in my overall strategy. I didn’t have enough money. At the time, I had plenty of money coming into the business and thought I had at least a few safety nets to catch me if things started to unravel. Only, this assumption was made under the guise that things wouldn’t unravel all at once. Queue the lack of nimbleness… My experience was rampant with unexpected challenges, and unfortunately, when it rained it poured. Couple that harsh reality with significantly underestimating the cost of living in a rural mountain community and you get a recipe for cash flow issues.?

I made the mistake of assuming, not proving, that the cushion built up in a big city would be more than enough to withstand even a flurry of setbacks in my nomad destination. Remember the lack of thorough research? I didn’t anticipate the difference in cost of living to the extent that I should’ve, and so every trip to the grocery store for the bare necessities bit into my flexible spending, and that then bit into my reserves, and so on. If I had to go back, I would’ve left with a certain budgeted amount that I could use for, let’s say, 3 months without worrying about drawing from my current cash flow. Instead, I was biting into my cash flow the minute it arrived, and that meant that I just gradually shortened my runway before I eventually hit a dead end.?

I wasn’t balanced enough

All of these factors equated to one all-encompassing feeling: imbalance. To continue with the analogies, it’s like going into a final exam in a pass/fail class having only studied a fraction of the material. Not exactly a foolproof strategy to pass the test. Perhaps my biggest blunder of it all - and I’ll tack this up to 20-something naivete - is heading out on this quest assuming near-flawless execution, and not truly expecting life to throw some serious curveballs at me and my journey even if I didn’t have any idea what those curveballs could look like. When life did in fact present me with some serious obstacles - personally, professionally, and spiritually - I was swinging at them without confidence, poise, and perspective.

More homework, more patience, better strategy, and better budgeting would’ve all yielded a sturdier balance to operate from and could’ve ultimately helped not only extend my stay but also improve the quality of my stay in such a heavenly place for a bit longer.

All things considered

I mustered 6 months in Tahoe, and it wasn’t all for not. I learned a tremendous amount about myself, responsibility, business, and lifestyle design. I met some incredible people and had some memorable moments that I still hold dear to this day. I swam in that extraordinary lake every day that I could, bagged a few 10,000-foot mountain peaks, and got to experience 3 seasons of outdoor activities including 26 days of deep powder skiing at Heavenly. Finally, that trip set me on the course for the life I have now, where I am happily settled in southern California, a place I had always dreamed of living.?

Would I do it again? Absolu-freaking-lutely. Would I do it differently? Maybe just a little bit…