Life as a Digital Nomad: Part 1 (Testing the Waters)

By Mike Huber

In 2010 the company I worked for gave me my pink slip due to budgetary cuts.  I was feeling distraught and lost because I had been working there for 8 years. Fortunately, I had a great director who helped by transferring me from a management position into a project manager slot that would be fully remote.

Remote positions at the time were called working from home.  It didn’t take long for me to ask myself a question:  What if I didn’t have a home? This mostly was bar talk amongst friends and I didn’t expect the crazy scenarios we discussed to ever become a reality.  Well…it seems planting those seeds in my mind was all it took for them to nurture, and then to grow into 13 years of almost nonstop travel.

The first two years were mostly spent learning to excel in my new position as a project manager along with clumsily discovering how to adjust my work/life balance in creative ways.  This involved motorcycling throughout New England in between work responsibilities.

Something I learned early is that there are McDonald’s with wi-fi everywhere, and at the time it was one of the better places to stop to respond to emails or for a conference call (this was a life prior to riding a BMW, so I didn’t require Starbucks).  I timed my rides to reach these locations 10 minutes prior to conference calls.  This allowed me time to set up and prepare for them as needed.

The first day as a remote employee I decided to knock out a ride from Boston to Route 17 in northern Vermont.  Route 17 is also known as the “Little Tail of the Dragon.”  It was May and I was literally working off my Ducati Monster M1100 as I tore up Vermont. Since it took so long to reach Route 17 it made sense to ride it twice to ensure the long ride was worth it and regain the curve back in my tires.  It may have been one of the best days I have ever had working and figured this newfound freedom would provide many opportunities to fill in the gaps that I had been missing by going into a regular office day to day.

Riding all the way to Vermont from Boston on your first day in a new position probably was a bit of overkill.  I was missing calls and hadn’t noticed my phone was constantly ringing in my pocket (an easy oversight being so heavily focused on riding).  I was in flight formation and setting the pace for a flock of mallards that happened to be flying down the White River, which ran parallel to Route 100.  Unbeknownst to me the phone continued ringing as the Ducati’s Termignoni exhaust roared through the Green Mountains while I leaned into corners that followed the river.

Shortly after parting ways with the mallards and crossing back into New Hampshire, I saw some lights behind me.  It was a New Hampshire State Trooper.  Dammit! I am sure I was speeding, but the question always is how fast. It was fast. As I began talking to the State Trooper to try to minimize the damage, I could now hear my cell phone ringing.  I picked it up as the Trooper ran my information.  It was my new manager based in Virginia calling to introduce herself and ask if I had noticed that I had missed a call I needed to be on.  I stated I was just out getting a coffee (which was 100% true; it’s just that the coffee was 200 miles away).  This was probably one of my more challenging multitask scenarios (i.e., signing a speeding ticket while on an introductory call with my manager).  To this day I feel I would have been able to get out of that ticket had I not been so distracted by work. Lesson 1 as a remote employee learned.

After that day I knew I should take my work a bit more seriously and slow my pace.  I continued to ride, but always ensured I attended every call (which I did over the next 13 years). My work ethic has always been strong, and I didn’t want to compromise this position and what I could possibly do with it by losing my focus.  Continuing to merge my work responsibilities with riding was something that I honed to an art form.

Once I was comfortable performing my work one or two days a week off the motorcycle, I thought I would step the adventure up a notch: California.  I had relatives in Oakland and there was a Harley rental in San Francisco, a short transit ride away.  It made sense to fly there for two weeks and work remotely in a new environment and time zone to see how I would perform.

The test run couldn’t have gone smoother.  I was on Pacific Time when my team was on Eastern Time.  This ensured that by 1:00 p.m. all my tasks and calls were completed.  Having earlier workdays provided much more time to explore San Francisco and the Bay Area.  A couple of vacation days in the mix allowed time to rent a Harley in San Francisco and take a 3-day trip to Tahoe and Yosemite.  Even though I was on vacation those days I felt obliged to join work calls whenever possible just to stay on top of my projects, while obtaining bonus points from management for doing so on my time off.  I felt this made up for my missed meeting when I had first started this position in New Hampshire.

The California trip had solidified my abilities to work from anywhere.  On the return flight to Boston my thoughts focused on a farfetched mindset:  What if I don’t have a home?  It would take a few months of planning and a solid leap of faith.  As with all leaps of faith you never know where or how it will end, but I felt sure I could make this dream a reality. What I didn’t realize is how far I would take this and the new experiences my decision would deliver.  I turned my life into Ferris Bueller’s Day Off on steroids over the next 13 years.