7 months in, 7 cities later, what have I learned as a digital nomad?

Chicago river and skyline

Being a digital nomad is hard. That’s probably the simplest way to put it.

Though I’ve worked in some amazing cities, the reality of it is a bit different. Still, I’m not giving it up. Here are my takeaways after seven months and seven cities:

  • I didn’t pick inexpensive cities. Toronto, NYC, Boston, Denver, Pittsburgh, Nashville and Detroit are not cheap, though I was happy to see that the dollar was strong in Canada (for once!). Still, these trips cost $700-1200+ to stay and eat for a week each, even with two star hotels and economizing. My ultimate still is an Italian city, and even though this or even Bangkok will set me back, I feel they’ll be cheaper than major (and even the second tier cities) in the U.S.
  • Scheduling time to work is essential. I knew this regardless, but I found that working mornings—usually at a nearby cafe as hotel coffee and wifi is generally inferior—and touring during afternoons and evenings worked out well. I sometimes work evenings too, depending on my workload. It’s a balance that kept me on the road longer, but I still got to see almost everything. My exceptions are Toronto and (of course) NYC, and Denver with a car.
  • Clients are adjusting—slowly. Most of my clients are completely onboard (and excited to read about it) and we still work as we always did, but a couple still want to meet in person and don’t want to (or cannot) use Skype or Google Hangouts. I don’t have a remedy for this, though we’ve been working through it, usually meeting when I’m back in town.
  • I up my data plan every time I leave. It’s sort of surprising how many places still have mediocre wifi, and I do the majority of my work online. I’ve only hit the limit of my 10GB data plan once, and am looking at mifi devices as they may be the better solution.
  • O’Hare is the worst airport for electricity and wifi. I know it’s the largest, but outlets are in short supply and wifi is still pay. Toronto remains my gold standard so far, with many gorgeous little stations with multiple outlets and fast, free wifi. And you can buy drinks and food at the same spots.
  • Denver has ridiculous airport taxi fees. While Chicago remains around $45 to get into the city, Denver tops out around $75—as much as NYC to New Jersey! SuperShuttle became my new best friend, at $42 roundtrip.
  • Keep everything charged. It’s startling how often I deplete my phone and laptop, and even with three chargers for my phone, one’s always being recharged.
  • Looking forward to more cities. I’m still planning on future trips southeast, and certainly the west coast and abroad but I’m playing it by ear.

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