Freelancing: it’s not for the faint-hearted

At the heart of this boundless life style of living and working on the road is the work. Obviously, there are many employment situations that involve constant travel, and that is a great way to test out whether you are cut out for this vagabond life. If you love your work, so much the better. You can keep it up until you retire, switch to being a consultant (a freelancing situation), or cash out. However, unless you are retired, freelancing is about the only way to bring in the money needed to live, whilst still deciding where you want to go. 

I wrote long ago that this is not specifically a blog about freelancing, but if you want to look into the freelancing life, here are some places to start:

The Freelancery: Walt Kania writes one of my favorite blogs. He includes much wisdom and helps you get a perspective.

Freelancer’s Union: This organization, under the leadership of Sara Horowitz, is rewriting the map of labor as we know it in the US. Even without your joining, the pithy lists and little articles linked to the homepage can be helpful and entertaining.

The Write Life: clearly, writing is one of the best-suited occupations for working and living on the road, and this resource is devoted to helping writers.

The Society for Technical Communication: those who write “copy” for others, whether it’s marketing, or technical manuals, might want to look into the professional association for writers, translators, editors, designers, and others. There is an empathy for freelancers in this group, whose members are often term contract employees or independent contractors.

Jobs you can do anywhere: from Ducky Xo’s blog (, comes this handy list:

Best Accounting Software is a review service that publishes short comparisons and reviews of different tools for accounting and tax preparation. It makes it money by affiliate links, but their lists included resources that don’t have such links. Focused on small businesses and freelancers.

Freshbooks is a cloud-based accounting service. Their website includes a helpful list of 17 other websites with resources for freelancers. Expand your research at

The American Translators Association: if you are competent in more than one language, you owe it to yourself to check out how I make my living. There are translation and interpreting organizations in many countries, all under the International Federation of Translators (FIT). From their website, you can find the association in your country (click on “members”).

Elance and Upwork (formerly O-Desk): these are job-matching sites, and you will find them advertising on other sites devoted to freelancing. Both services participate in the business end, by handling the invoices, paying you, and generally simplifying your life on the road. They may or may not be for beginners, depending on the specialty that you have to offer, but there is plenty of information on the sites. Just checking out the categories will give you some ideas. and

Trip update: this week I have accumulated more mileage running last-minute errands than actually doing training rides. As the date for my departure gets closer, the details mount. On Thursday, I rode my trusty Bianchi Volpe for the last time, on a one-way trip to Charlottesville Community Bikes. It will be a wonderful city bike for someone who probably could not afford it, but really needs one. After eight years and 38,000 km, walking away from the Bianchi put a lump in my throat. Back at the house, the footlocker is packed, and I am trying to choose a shipper to get it to the new apartment.

Next week, another sea story. Until then,

Smooth roads and tailwinds,


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