“Hey, do you want to watch our dog?” For the last few years my Chicagoan friends Greg and Dave had talked about me staying with them in Chicago or possibly to do a house swap. And when they needed someone to watch their dog while they were away in June, it seemed like an opportune time. But I had my reservations about going.
The thing was that I would be busy traveling in May. I’d be in San Jose for a conference, then to Hawaii for a family vacation.
I’d then spend over a month in the Midwest, in Chicago and then in the Midwest. I only had four days in between each trip to get my ish together, pack, do laundry, see friends, and what have you. It was fun, it was exciting—and it was also exhausting.
While it may seem like a dream to some, I dreaded it. I am a creature of habit, and actually *gasp* like my life in Los Angeles. You can say I was a reluctant digital nomad.
Ideally I would’ve had more space in between my travels. I was hoping to have more space in between my travels, but when I realized I may not the opportunity to get a taste of this digital nomadism most freelancers have been talking about.
Here’s what I learned about staying productive while hopping cities:
Have your productivity pack in tow
You know what you need. I personally try to pack as little as possible. On the trip I brought the following:
– My Samsung Chromebook
– Chromebook case
– Cell phone charger
– Backup! I was terrified of losing my files. A lot of my stuff is stored on the Cloud, but I do have some documents on my hard drive. I use Carbonite, which is about $60 a year.
Come up with a new work schedule: and stick to it
I really wanted not to work while traveling in Hawaii, as it was a family vacation. But I had work deadlines, so after talking to my friend and mentor Alan, I figured out a schedule for me. I did the 2/6 schedule, where I work for 2-3 hours a day while on vacation. There was a Starbucks around the corner, so I made a pact with myself to work from 6 a.m. – 9 a.m. while on vacation. That way I’d be back at the hotel to grab breakfast with my family.
I felt bad because I was supposed to be on vacation, and not working. My family has been extremely supportive of me when I have a deadline. Creating more structure is something I’ve been struggling with.
When I was in Chicago I spent a week at Grind, a lovely coworking space downtown. I worked a lot at a local coffee shop, which worked out just fine. Since I was in Chicago for a solid month, I had time to squeeze in sightseeing and then figure out a routine that worked for me.
Allow for flexibility
There were plenty of times when things didn’t go as planned. I got lost, or the train was behind schedule, or my friends invited me on a bike ride or something fun that I simply could not pass up. So yea, you can’t remain rigid all the time. I did my best and got my stuff done.
Plan for periods where you can’t work
I was in three different places, hoping via train and plane And there’s absolutely nothing you can do about it. The Southwest Chief, which is the route I took on Amtrak from L.A. to Chicago, had no WiFi. I resorted to writing a blog post on my freakin’ smartphone, which I don’t recommend doing to anyone.
So check ahead of time if the plane or train you’ll be on offers WiFi. Amtrak offers WiFi on select routes, and you can check out availability there. You’ll also want to check if airport terminals offer WiFi, either for free or for a small cost. Airfare Watchdog has a pretty decent Airport WiFi access chart. And of course, check if the airline you’ll be traveling on offers WiFi, what it costs, and how reliable it is.
If you can’t work, use it as a time to relax, do nothing, read a book, or what have you. You’ll just need to plan around it, of course.
It was definitely challenging to stay productive while in transit, and as I prep for FinCon this week, I’ll be working 1-2 hours a day to stay on task. Wish me luck!
What kind of tricks have you learned to stay productive while traveling?
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