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Travel, Freelancing, and Six Lessons Learned

travel writers most important accessoryby Joe Wallace

I’ve been back from my Chicago to NYC trip for a while now, looking back over the journey and adding up the lessons I learned about freelancing on the road.

To recap–I went on a blogging road trip to New York and decided to experiment with my freelance work–could I maintain my existing clients while traveling? Make all my deadlines?

In the end, the answer was yes, but there were a few things I will do better next time. Looking back, here’s a list of things that went well and things that could have gone better with a bit of extra preparation.


  • I let my clients know in advance that I’d be traveling and that some deliverables might come in at odd hours, but still on deadline.
  • I worked ahead where possible to pre-position some of my freelance writing and blogging. This wasn’t possible in many cases because of time-sensitive material, but some of the evergreen content I did manage to write in advance.
  • I got up early and put in freelance hours before hitting the road, then hit the freelance writing trail again over lunch and dinner. This gave me an advantage over simply trying to cram it all in after stopping for the day, tired from driving and reviewing record stores, restaurants and hotels.


  • Buy into the iPhone tethering option rather than hoping to find a Starbucks for free wi-fi. “Tethering” lets you get an Internet connection by hooking your iPhone to your laptop, in case you didn’t know.
  • Planning my overnight stays better–I spent more money than I needed to because I didn’t book ANY of my hotels ahead. On a trip that requires as much spontaneity as this one did, that was a necessary evil, but having a few well-researched oasis-style stops with wi-fi and known amenities would have been a big help–even if I didn’t end up actually using them due to time issues.
  • Posting more from the road–I was doing a lot of blogging about the trip, but I really could have saved myself some additional work post-journey if I had found a bit more time to squeeze in a few extra blog posts, reviews and other details while still on the road. Also, I should have archived the 1000 + photos I took on the road as I went instead of doing it only twice, 500 images at a time, spending too much time sorting and sifting.

Travel writing, blogging, and managing freelance clients at the same time is NOT impossible from the road. It does require you to be a bit of a “type A” personality, but that’s the nature of the beast. Continue reading Travel, Freelancing, and Six Lessons Learned