Three Years, One Question

As April 2018 fades away, so does the three-year anniversary of my decision to chart a new course by pursuing a life of traveling, sailing, and volunteering, and leaving a successful career in corporate finance behind.

It was April 15, 2015, when I walked out of my office in downtown San Francisco. 

Although I had done some personal financial analysis and made a to-do list, I didn’t have an exact plan when I turned off my computer and handed in my badge.  As I took the elevator to the ground floor, I wondered whether the five-floor descent was a symbolic representation of what I was doing with my life – returning to the ground floor, giving up everything I’d worked so hard for during the last 15 years.  

I’ve come to realize the *actual* symbol appeared when those elevator doors opened:  I had the whole world in front of me and, more importantly, I was free to explore it.  No PTO to record.  No emails to answer.  No deadlines to worry about.  

It’s been three extraordinary years, punctuated by high points and low points, proud moments and doubtful moments. 

I’ve traveled deep not wide, spending more time in fewer countries rather than less time in more countries.  My trips are measured in months, not days or weeks.  I’ve lived with local families, helping them with their daily lives and giving back to the community I’m visiting.  

I’ve sailed across oceans and advanced my sailing certifications.  I now get paid to teach sailing, which makes me smile every time I think about it.  Soon, with a Captain’s license in hand, I might expand this “side hustle” to include skippering vacation charters or crewing on yacht deliveries.

Many people have said, “Dan, you’re living the dream.”  That’s not entirely accurate.  I am living a dream.  My dream.  

But, to be clear, it’s not all sunshine and roses; there are nightmarish moments in my dream.  I’ve been assaulted and robbed.  I’ve slept in some run-down hotels, met some oddball Airbnb hosts, and survived some crazy taxi (and tuk-tuk) rides.  I’ve been lost many times; lonely a few times.  I’ve faced “first world problems” of sacrificing expensive activities like sports events, concerts, and City dinners that'd I'd grown accustomed to attending without a second thought.  (I now meticulously track every dollar I spend - more on that in a subsequent post.)

What began as a trial period of 6-12 months has now become a way of life for me.  I don’t plan on going back to an office environment, or the long hours, politics, and stress that inevitably come with it.  I certainly miss the routine, the paycheck, and the social and intellectual aspects of the office, but I'm slowly figuring out alternative sources for these comforts.  

I may not have everything figured out, but who does anyway?