295 Days on the Road: Life as a Digital Nomad

Many of you have either received in the mail or read my annual Christmas letter (if not, head on over here), which tends to detail out the highlights of the year in narrative format. However, after reading my biz wifey (Kyrsten Sherwood)'s incredible "2017 Nomad Year in Review" post, I knew I had to do one too. Kyrsten was actually the inspiration for my nomad year. The Sherwood family went nomad a few months before I did, which was what inspired my nomadic thinking during the famed "PowerSheets revelation" I had in November 2016. 


So here I am, my own 2017 in Review as a Digital Nomad. I officially began my nomad life on December 23rd, 2016 and ended it on October 13th, 2017. 

On December 23rd, I moved out of my apartment in Aurora, IL and into a suitcase. I spent the next 5 days and nights in downtown Chicago with my grandparents as we celebrated Christmas. From there, I spent the next 295 days (or 9 months, 21 days) in...


  • Toronto, Ontario (Canada)
  • Rome, Italy
  • Casablanca, Morocco
  • Marrakesh, Morocco
  • Cancun (Riviera Maya), Mexico
  • Frankfurt, Germany
  • Munich, Germany


  • Durham, NC
  • Atlanta, GA
  • Louisville, KY
  • Dallas, TX
  • Charlotte, NC


  • Chicago, IL (25+ times)
  • San Francisco, CA (4+ times)
  • Los Angeles, CA
  • Portland, OR
  • Phoenix, AZ
  • Lake Geneva, WI
  • Raleigh, NC
  • Washington, DC
  • Nashville, TN
  • New York, NY
  • Columbus, OH
  • New Orleans, LA
  • New York, NY
  • Waco, TX
  • Indianapolis, IN
  • Cupertino, CA
  • Minneapolis, MN
  • Detroit, MI
  • Ann Arbor, MI
  • St Joseph, MI
  • Lexington, MI
  • West Bloomfield, MI

*lists written from memory and I am definitely missing some. Stay tuned for updates.

    by the numbers

    I slept in nearly 25 Airbnb's, 15 friends' couches, 14 "friend of a friend's" guest rooms, 10 different Kimpton Hotels properties (some more than once), and 8 miscellaneous hotels. 

    I flew approximately 300,000 miles and put about 20,000 miles on my car (a lease - not my smartest move). 

    I incurred a whopping $52,000 in travel expenses including meals, fuel, flights, places to sleep, and rental cars where necessary (some paid by brands/conferences/etc and some paid out of pocket). Travel is not cheap, even when you're traveling solo like I was.

    things i ate 

    I discovered amazing places like Voodoo Doughnuts, Glory Hole donuts (sensing a theme?), 405 BBQ, and more street vendors and food trucks than I could ever count. I lived nearly entirely off street vendors while in Morocco and Portland. I fell in love with Gilt Bar (Chicago), Compass Coffee (D.C.), Sightglass Coffee (San Francisco), Besaw's (Portland), Rogue Brewhouse (Portland), The Burger's Priest (Toronto), The Works (Toronto), and just about any other place I've geotagged on Instagram in the past year. I rediscovered my love of Slow's BBQ, In-n-Out, and Buddy's Pizza. 

    lessons learned

    Don't try new (or new-to-you) food the night before a speaking engagement. You WILL get food poisoning or an upset stomach, it's just Murphy's law. 

    Don't always go for the cheapest Airbnb - you'll end up sharing a "one bedroom" loft apartment with six men for 11 days straight. 

    Just because you're traveling doesn't mean you can't hole up and just watch Netflix for an entire day. Even nomads need a break. 

    TSA Pre✓ and Global Entry are mandatory (if you get GE, you get TSA Pre✓ included), no exceptions. So much time is wasted in line for security and I cannot tell you how many times I nearly missed a flight in 2017. 

    Always carry cash. Period. 

    Pack less than you think you need, and then cut what you packed in half again. You'll spend most of your days alone and nobody will notice if you wear a pair of pants twice.

    Speaking of being alone, nomad life is lonely. Co-work in community spaces and create opportunities for chatter and conversation.

    My travel goals for 2018 are still very much a work in progress but I'm curious...

    where do you want to go? 

    Dannie Fountain1 Comment