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. Continue reading
Tag Archives: freelance word working
How I have changed: communications and the cloud
The air was cool, with a gentle tailwind from the coast. Up ahead, we spied a Sobey’s in a shopping center on the right-hand side of the road. She wheeled into the parking lot, and I followed her. A few minutes later, we were sitting at a picnic table outside, checking our smart phones and swapping a half-gallon carton of orange juice between us.
The Freewheeling Freelancer Stands Alone!
A big shoutout and a public thank you to you all for following this blog. After more than one year, it is clear that this blog is here to stay. This week, I purchased a domain name for it.
Tell your friends to remember this simple URL: freewheelingfreelancer.com.
Stay tuned as the adventure continues and we continue to learn together.
Smooth roads and tailwinds,
Jonathan
Are we home yet? More pros and cons of living on the road.
Trip update. Still living in Pinecrest, Florida, with my colleague Giovanna and her family. This week has been devoted to preparing for the presentation today at Florida International University. It is called Getting down to business: Management accounting for T&I Professionals. I designed the course to teach break-even analysis and basic organizational skills to any kind of freelancer. I will be presenting on this topic again in Philadelphia in April. Today’s program is an all-day workshop with hands-on exercises. Continue reading
Are We Home Yet? Pros and cons of the freewheeling freelance life.
Trip update: I am in Pinecrest, Florida, a village south of Coral Gables. My host is also a freelance translator, so her family and I have had plenty of time to work in our respective spaces around the house.

A bicycle kit may get stares in fine restaurants, but it still gets service. Seasons 52 in Coral Gables.
On Saturday, I had dinner with Stefano, another colleague, and his wife Lucia, at Seasons 52 on the Miracle Mile. He has been freelancing on the road for more than 20 years, because his principal activity is missionary work – for which he is not paid. His translation work is their family income. Even without a bicycle, he has certainly proven that he can make a living while travelling to churches and missions all over the world, with and without his family.
Tuesday, another translation job came in, which kept me off my bicycle for two days. As I worked indoors, heavy rain beat on the roof. While I was working, ATIF, the local association of language mediators, invited me to present an all-day workshop at Florida International University, so I will be staying in the Miami area for an extra week. Considering the weather that awaits me up north, I cannot complain!
It is time to take stock of this idea. After four months on the road, how do I feel about it? Continue reading
Money talks: louder, please (or softer).
Trip update: I hated to leave Tampa, but I have people to see and appointments to keep in other cities. Tampa will remain a pleasant memory for the good company and the smooth roads. I really enjoyed running errands and meeting friends. Covering 100 km in a day just seemed so normal in a flat place like Tampa Bay. Continue reading
Money talks: can I afford this?
Trip update: Saturday night I pulled into a cheap motel in Land o Lakes, exhausted from pushing against a stiff headwind all day. The first place to stay was so far down US 41, that I only had 30 km to my hotel in Tampa the next day. I am staying at the Suburban Extended Stay Hotel Airport in Tampa all week, enjoying a cozy little efficiency that has everything I need and nothing that I don’t.
The bounce box arrived in good condition (to my surprise), so I can reuse it. I will replace it with two smaller boxes at the next mail stop.
This week marks the end of the planned part of the Southern Swing 2013. I have spent the week assessing the first four months of the trip, and laying out the next three months in broad strokes.
I have not finished closing out the financial year for my company, but I analyzed the cash flow in the last quarter. That includes the three months that I spent bicycling from Keller, Texas, to Gainesville, Florida. The data should be adequate to determine if I am making enough to keep this up indefinitely.
The short answer is yes. Continue reading
Office support on the road
Trip update: Last weekend, I rode from Gainesville to Ocala, Florida, through the vast horse country in Marion County. Marion is one of the largest counties in Florida and has more horses than any other county in the USA. What I found surprising was that the oldest horse farm in Marion is only 50 years old, so the equine industry made a massive impact on Central Florida in a very short time. We are talking racehorses here, and the animals staring proudly at me across the fences were some of the most beautiful horses I have ever seen.
I spent four days with my high school classmate Tom and his wife Marcia. It has been a special pleasure of this trip to connect with people whom I have not seen for decades. I felt so very much at home, that I hated to leave on Wednesday, to continue my trip. I stayed with George and Susan in Inverness, thanks to the Warm Showers organization (www.warmshowers.org). They rode the Withlacoochie Trail with me, and showed me where to shop, eat and even get my bike fixed. They ride Cat-trikes, which are high-end recumbents made of aluminum. Very cool and very lightweight (www.catrike.com).
Now I am on my way to connect with the bounce box that I mailed from Gainesville. I am also looking forward to a mail shipment at the next stop, which brings me to the subject of this week’s article.
No card, no service: insurance on the road
Trip update: Staying with Rich and Mary in Southport allowed my blister to heal nicely. Sunday, we went to lunch in Panama City, getting there in Rich’s Grand Banks Trawler, Calypso.
On Monday, I let them give me another day off the bike by taking me to my next stop, Port St. Joe. It was one of Mary’s favorite shopping destinations, so we made it an outing.
Staying out of trouble: confidential and classified material
Trip update: It has been a quiet week, although I have gotten much physical exercise loading furniture and boxes from the storage area in our carport and porch into the house, so that the contractor can close out the renovation project. I finally finished on Thursday, so I am almost ready to resume the Southern Swing 2013.
This week I would like to share some thoughts about what to do on the road with confidential material and classified material. These comments may apply mainly to technical writers, translators, and others who work off-site for agencies or companies for whom document security is a concern. Continue reading


