Welcome to the Freewheeling Freelancer

Why, who, what, and where:

The stated purpose of this blog is to share my experiences riding my bicycle indefinitely while continuing to work and conducting an otherwise normal life. The point is not the bicycle, but the word “indefinitely.” Together, you and I will explore how a freelancer could truly live on the road. Only backpackers have greater issues of time, distance, weight, and logistic support than bicyclists. A freelancer in an RV (caravan), a boat or a car could easily apply the lessons here, perhaps with more slack about what to take and less stress about what to leave behind.

This is not the place to learn how to become a freelancer or why. There are hundreds of blogs on that and many of them are excellent. I will link to some of them as they touch on our journey.

This is also not a blog about long-distance cycling. There are many excellent blogs on that, too. And, yes, we will link to them as I share the things I learned getting ready for this journey.

This blog is about what is different about freelancing on the road. What to pack, what to leave behind, what support you need at first, how to outgrow that support – and, of course, what I wish I had not left behind and how I dealt with that. Every week we will discuss issues that come up in either endurance cycling or freelancing, but only as they help us make this journey together.

I do hope that we make this journey together. Your feedback will let me know what you want to know and, more often than you think, solve problems that I had not foreseen.

Let me introduce myself.

I am a writer. I make my living as a freelance translator (Italian into English). Translating involves writing somebody else’s material in a new language, so one has to be a writer first. I own a car (to carpool to Church on Sunday), but my bicycle has always been my primary means of transportation.

Other essential ingredients of “me”: Christian (Episcopal), father, widower, sailor (retired naval officer) and traveler. Physical details: 175 cm tall, 74.7 kg, body fat: 21%.

2013-08-21 14.21.12

At work in my old office.

You can read the formal résumé on my website (www.scriptorservices.com) and LinkedIn profile (http://www.linkedin.com/in/jonathanhinelanguagemediator), so I won’t bore you with it here. Similarly, you can get lots of pictures of me on Facebook (http://facebook.com/tradux).

The itinerary (more or less).

I plan to leave Charlottesville, Virginia and visit friends and family on a long loop which will include the Atlanta Association of Interpreters and Translators (AAIT) conference in Roswell, Georgia on 28 September, and the annual conference of the American Translators Association (ATA) in San Antonio, Texas, in early November. From there, I will make my way across Texas and around the Gulf Coast to Tampa, Florida. At that point, I will decide whether to go back to Charlottesville, and whether to do so quickly (train or bus) or slowly (visiting friends and family up the coast).

One of the key features of this trip is that it is not carefully laid out. Already, my departure has slipped six weeks, because our house renovation is running late. A bus trip to Chicago, Illinois, has been replaced by a more-or-less direct run to Roswell, Georgia, to make a presentation to the AAIT.

Where could this go?

As I set out on this odyssey, I don’t know. I have an idea that together we will find out how to live and work on the road, or we will know how and why it did not work. Of course, a personal emergency could stop the whole experiment. But I am focusing my efforts on a larger goal: becoming a true cycling nomad. If the Southern Swing 2013 is successful, then we will look beyond my present context of being an American freelancer bicycling around the United States.

Next week, I will explain how my cycling and freelancing lives came together – unless you have something more interesting for me in your comments and questions.

Smooth roads & tailwinds,


14 thoughts on “Welcome to the Freewheeling Freelancer

  1. What an inspiring idea, Jonathan!! I can’t wait to follow your adventures! As a fellow long-distance cyclist (two 600-mile trips but nothing compared to what you’re doing), I take my inspiration from the Tyrolean mountaineer Reinhold Messner, who was the first person to climb all of the 8,000 meter peaks. Although he was most famous as a speed climber in the Dolomites, when a reporter asked him how he managed to climb all of the 8,000’ers, he said “Always slowly.” That’s what I always think of when I’m pedaling up and down and up and down and up and down some series of passes: always slowly; just keep turning the cranks and the destination will take care of itself. See you at ATA!

    Liked by 1 person

      • Oh, that Surly! I should have noticed the capital letters. You’ll get more on the bike later, but it’s a Bianchi Volpe. I had forgotten about the Surly, which I have seen at REI in Boston. The two bicycles are very similar, except for the shifters (bar-end on the Surly; Shimano integrated brakes/shifters on the Bianchi). The MSRP is extremely close, too.


    • Grazie, Riccardo —
      Conte has a lousy voice, but the song is great. Although not as fast as Bartali, I climb hills the same way, seated going up, resting my butt once in a while on the way down. I rarely stand on the pedals.
      SR&T, Jonathan.


  2. This is very exciting, and I look forward to living vicariously on the road through you. Freelancing while bike touring is something I considered when I lived in the USA, and I may still do in one day, most likely in smaller amounts than what you are planning.

    Liked by 1 person

  3. Sounds like an exciting, and vigorous journey! As a freelance translator that has to move a lot, your journey particularly interests me, so I look forward to following you on the road! The very best of luck to you 🙂 .

    Liked by 1 person

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