Freelancing on the road: a summary

He was riding his bicycle. That was about the only good thing about the scene right now. The slick, coastal road wound up and around the promontories, so that the wind and rain was as often in his face as blowing him sideways. The cold rain ran off his Arc’teryx rain jacket, soaking his crotch and running down his legs. He pedaled on, one stroke after the other. At the top of the hill, he pulled alongside the other rider, and matched her pedal cadence. Her face was set in a stony expression. The rain was dripping off her nose, and he knew that she was soaked everywhere that he was.

“Are we having fun yet?” He quipped.

She scowled at him. “You call this fun?”

“Fun isn’t always about laughing,” he said. “I would rather be here slugging along this coast with you than sitting still on the motorway, waiting for some crash up ahead to be cleared away.”

Her expression thawed. She looked at him quickly, and smiled. They sped down into the village where they would spend the night. While they checked in, cleaned up and changed, the storm blew over. The sun was low in the sky over the Tyrrhenian Sea as they walked to a trattoria for supper. The air was fresh and warm, as it always was after a heavy summer rain. Sparrows and swallows emerged from the eaves of the village buildings, eager to feast on the insects that came out near sundown.

Like so many villages on the coasts of Italy, this one was awash with tourists. They found a restaurant with more Italians than the other places, but half-way through their meal, a wandering musician appeared and proceeded to make his way among the foreigners. The couple broke off their conversation to smile when the musician came to serenade their table. It was all part of the atmosphere of the place, though the cyclist was less impressed by the strained notes than the tourists from Michigan at the next table. After a coda long enough to wrap around his ample waist, the singer moved on with a deep bow. The couple faced each other again, their faces glowing in the light of the candle on the table.

“I get it that you don’t have a definite time for this trip,” she said, twisting a strand of brown hair and tucking it behind her ear. “You’ve been doing this for more than two years now. Haven’t you found ‘home’ yet?”

“Yes and no,” he said. “I’m not sure. I think of home as where I am now, and where I’m going next.”

“That doesn’t make sense. Home is where you come from; where you want to go back to.”

“Who says so?” He topped off her water glass from the carafe on the table and filled his own.

“I do and everyone else.”

“I don’t, so it can’t be everyone,” he said, with a smile.

“OK, wise guy, but where are you from? That should be home.”

“I could list four or five different places, and each would be home for a different reason.” He took a sip of wine. She noticed that unlike most men, his eyes did not wander from her face when he was talking. “Where are you from?”

“You know. Minneapolis.”

“That’s a place,” he said.

“Of course. Home is a place.”

“If you want a place, then my home – where I came from – could be where I was born, where I grew up, where I went to school, where I made the best memories, or where I lived the longest. Would you agree with that?”

“Sure,” she said. “So where?”

“Each of those is a different place for me. Norfolk, Rome, Annapolis, Honolulu, or Charlottesville.”

“Which one are you going back to?” And why?”

“Whichever one calls me next. Maybe Minneapolis.”

She smiled and turned her head. A group at the other end of the room had burst into a discordant chorus of “Happy Birthday” in French, accompanied by the singer and his guitar. Servers were coming out of the kitchen door with trays of porchetta, bucatini alla romana, carciofi alla Giudecca, and even some desserts for the early arrivals.

She turned back to see that he was still looking at her.

“But what if home is a feeling?” He shifted closer to her so that if he bent his head, the candle might catch his sandy hair. “Can you understand that maybe I feel at home in many places?”

“I guess, but don’t you have a base?”

“Maybe more than one. I have my new pied-à-terre here in Italy, and the house in Virginia. Is that enough?”

“Could you settle into either one?”

“Probably, but I’d rather find a new place after I have checked out the places that I haven’t been. Like the West Coast of North America. Someplace where it doesn’t snow in the winter, I think.”

“But you’ve kept riding for three winters now,” she said with a wry smile. “Why stop?”

They laughed.

“So what does home feel like?” She asked.

“I’m not sure. It’s a feeling that I get from a place that is more about the people I find there than the amenities. ‘Home’ makes me feel accepted, respected, and loved in the sense that the people of the place wish me well. Looking at it that way, I think that I’m at home in more places than not.”

“But people can make you feel at home that way, without sharing the feeling. You’d still be a ‘come-here’, a stranger in their midst.”

“Good point. So I have to add that the feeling includes my sensing that they’re glad that I’m there, and they welcome my participation in local life. Because of citizenship issues, nation-states, and the inevitable differences of culture, I know I’ll always be l’americano here, and that the old families in other places will always consider me a newcomer, because I didn’t go to high school with them. I’m OK with that. I still have my place in the local society. I can make my contribution and have it accepted.”

She considered his face for a silent moment. Then she sat back.

“You’ll never put down roots, will you?”

“Probably not. I’ve never lived anywhere long enough to do that, so, like a bromeliad, I draw my nourishment from the air around me. I only put out enough root to know my way around the pineapple patch.”

“That’s why you’re not a tourist. You’re always at home, but never going back home.”

“Kind of.”

“Will you ever stop riding like this?”

“Oh, yes. I can’t keep this up forever. One day I won’t be able to ride.” He sat back and spread his hands. “Then I’ll stay ‘home’ – wherever that happens to be.”

“I can’t believe that. I see you finding some place to rest between trips. Some place you want to go back to.”

“Like you do?”

“Kind of.”

He smiled and caught the eye of a server two tables down. He scribbled an imaginary line across the air to signal for the bill.

After he paid, they rose and walked along the lungomare. He bought a carnation from a woman on the sidewalk and gave it to her.

“Where will I put this?”

“You’ll find a glass or a vase when we get home.”

“You mean the B&B?”

“Home, sweet home,” he said with a smile.

The next day was sunny. It was still windy, but the air was warm and dry. By mid-morning, he was in a pleasant rhythm, enjoying the moment, which included taking in the scenery, listening to the wind and the birds, smelling the trees and the detritus from the beach, and matching his pace to hers. They stopped for lunch in a park by the side of the road, then continued up the coast.

He had been living on the road for almost three years – more if you count the tours in 2012 and 2013. He thought about what he had written more than a year ago, “The most significant emotional drawback of all the things against living and working on the road is the fact that one cannot build a personal relationship that was not already there, if one must keep moving on. Of course, if I go back to places that I have been, I can sustain and even grow relationships by correspondence. However, I have not gone back to any place – yet. Nor have any of my new friends jumped on their bicycles to ride with me, although that is not as unlikely as it may sound.”

He was not always alone any more. At least in the summer, she would join him for a few months. They had both ridden alone until last year, when they discovered that riding was much more enjoyable with a friend. Now he looked forward to the summer rides more for the company than the better weather and the longer days.

As he rode, he considered the question that she and so many others had asked him “How long do you expect this to go on?” He never had an answer.

The coast road was still winding. The crosswind became a headwind. He geared down one step and increased speed, until he was drafting her a safe meter behind. When he settled into her slipstream, he changed gears back up and matched her cadence again.

He knew that he could not live on his bicycle forever. But if his riding is not cut short by a collision or a sudden illness, how will he know when it is time to stop wandering? Would he ever? Would it be gradual or sudden?

They came to the top of a promontory, and she slowed to stop. The beach below traced a white-pink line between the dark woods and the dark sea, as the low sun stretched across the water and the sand.

“Photo op?” he asked, as they dismounted. She smiled and nodded. “I’ll hold the bikes,” he said, grabbing the top tube of her bicycle. She gathered her SLR camera from the pannier and walked out to the edge of the cliff. He watched her from the opposite side of the road. She walked back and forth, considered different angles and what she would shoot. He continued his thought.

He had two places that he used as bases, one in Italy and one in Virginia. Right now, each served mainly to store what he did not need on the road. Taking advantage of off-season rates and early booking, he could fly from one to the other for about the same as it cost to travel the same distance in North America by car, plane or train. Maybe he would simply find himself spending more time in each place, and less time riding. Already he had plans to hole up in one or the other to work on his writing some day.

But before he slowed down, he had routes that he wanted to ride: The Pacific Coast Highway and the Katy Trail, Eurovelo Routes 5 and 7 (at least), and US Highway 89. He wanted to ride all the way around Sardinia.

She came back to the bikes and stowed her camera kit.

“Ready?” she asked.

“Yes. At this rate, we should be at Stefania’s house in just another hour.” Staying with friends and colleagues along the way was one of the special features of the route that they had designed this summer.

He blew down the hill in his highest gear, revelling in the speed and the clear, empty road below. She was more cautious, but soon they were both riding the flat beach road. She overtook him, and he settled in behind her again. That’s it, he thought.

“I figured it out,” he shouted, and sped up to come alongside her.


“What we were talking about last night at supper. When I will know it’s time to quit and settle down in one place.”

She kept looking ahead. “Well?”

“I remembered what Admiral Gerry Miller used to tell his ships’ captains when they checked into the US Sixth Fleet. ‘If you’re not having fun, you’re not doing it right.’”

“I don’t see you not enjoying the bicycle – ever.”

“You’re right, but maybe my riding will change. I may find myself staying longer and longer in one place, along the way. One day, I’ll realize that I’ve settled down. As long as I’m still having fun, I’ll know that I’m doing it right.”

“But you still don’t know when that will be.”

“Nope. No idea,” he said, grinning, “but it will be fun.”


Being a freelance translator is one of many occupations that can lend itself to a nomadic lifestyle. While it may sound romantic, it is not a lifestyle that suits everyone. It also requires planning and commitment. I prepared for two years before I set out. In no particular order, here are some thoughts:

Touring vs. working on the road: Touring is all about the journey and the sights along the way. Working on the road is about continuing to work while travelling. The fictional vignette above paints a fairly accurate picture of my life on the bicycle when I tour. When I travel by myself, I need to balance my travelling and my working. I try to arrive wherever I will spend the night well before dark, so that I can work and still get a good night’s sleep. In the winter, camping becomes problematic, so I favor hostels and B&B’s, which are cheaper in the off-season. In particular, hostels often allow me to cook my own food. I have to eat out enough as it is. Overall, paying for accommodations like this is the same or cheaper than a decent flat in a major city.

When I ride by myself, I only tour when I have time off, for example, to take a side trip to Ravenna to see the mosaics on a weekend. Those who live and work at home probably do the same thing on their weekends: go visit someone or something.

Vacations: I had only taken three true holidays in my adult life before my computer broke down in a remote area of the Gaspé Peninsula in the summer of 2014. I was off-line for eight weeks and discovered what a holiday can be. I have learned that I cannot tour with a friend and work at the same time. However, I also learned that I can earn enough when I am riding by myself not to need to work when I am touring. My annual budget lets me take a summer holiday like other workers. I notify my clients when I go on holiday, at least the ones who have availability calendars on their websites. I also put an auto-responder on my email and my telephone voicemail. The rest of the year, I am as close to my clients as the smartphone on my handlebars.

Client relations: Almost all my clients are language service companies. They neither know nor care where I am, as long as I take in their work and deliver it on time. My few direct clients have grown so close that we are like teammates on their respective projects. As for the people in those language service companies who know me, some of them follow my blog or Facebook postings, but their interest in my whereabouts is personal, not professional. Others are pleased or envious, but no one has expressed anything negative about it to me. I make a point of visiting clients when I pass through their cities, and I meet them at translator conferences. Many have become friends.

Thanks to modern media, I am still acquiring new clients. My profile in the Directory of Translating and Interpreting Services of the American Translators Association (ATA) accounts for more new business than any other source. Referrals from colleagues still occupy a significant second place. I also maintain a presence on LinkedIn (professional) and Facebook (mostly personal); that networking has yielded some interesting assignments, including one of the recent book translations.

I only offer my professional services as an employee of my company, Scriptor Services LLC, never in my own name. This is a winning arrangement for my clients, most of whom are in the USA, and subject to conflicting laws about employees vs. independent contractors (freelancers). Having another business as their vendor simplifies their lives.

Communications: This lifestyle definitely belongs to the 21st century. The smartphone on my handlebars and the Surface 3 computer in my pannier make it all possible. Before I bought a Nexus 5 phone in 2014, I worked by stopping at WiFi hotspots along the way, of which there were many in North America. That still works, and I stay in accommodations, including campgrounds, that have WiFi when possible. The smartphone can serve as a WiFi hotspot, and I pay for a 5-GB/month data plan to support that. I use Skype® to call telephones and other Skype® users worldwide – and to check voicemail at the company phone in Virginia.

Place of business: Scriptor Services LLC remains fixed. While I may be wandering who-knows-where, my clients have the same address, email, and phone numbers that they have had for years. Countless immigration issues arise once one crosses the borders of the homeland; I avoid those by not having the company move. I keep no bank accounts outside the USA, and the credit cards are American. The 1% fee that I pay for foreign transactions buys me peace of mind. All my income is in the USA, so I file my taxes there, avoiding issues with the tax authorities of the various countries that I pass through.

Postal mail: A contractor in Charlottesville (Bright Business Solutions LLC) checks the Post Office box of the company and gives the mail to my son, who forwards it with the personal mail. This has worked well. I don’t get that much real mail, and I appreciate having the junk screened out first. Even using mail-order has been smooth. If I need something, I can usually have it shipped to a mail drop up the road. This could be a hotel or a friend. There are service companies that forward mail to world travellers for a very reasonable fee, but I have not had to use them yet.

Base of operations: I am not trying to ride around the world, but simply keep travelling. For the two years that I was riding in North America, I found myself passing back through Charlottesville every six months. The old house was my support base. This allowed me to swap out summer and winter gear and not have to carry it all.

I could not ride around Europe on a three-month tourist visa, so I obtained a residential visa in a Schengen Area country. Having a fixed residence was a prerequisite for such a visa, so I rented a small flat in Italy. There isn’t much in it, but it does allow me to store the off-season gear, much as I did in Charlottesville. And it provides a reliable mail-drop. I have friends and a next-door neighbor collecting the mail while I am away.

Interpreting and training assignments. Almost all my work is translation and revision. However, I do pick up an occasional interpreting assignment, or provide consulting or training on-site. I tested this in North America, and it worked well. When the request came in, I provided an estimate that included the travel from wherever I happened to be and back to my bicycle. The client(s) would have had to pay for me to travel from Charlottesville anyway, so this was not a shock for anyone. I do not expect much of this work in Europe, both for lack of a network of such clients and EU rules about non-EU citizens working.

Deadlines: Deadlines are even easier to handle now than when I worked in a fixed location. My life and my schedule are completely in my hands (no choir rehearsals, weekly meetings, local commitments, or family illness), so I can accept work knowing that I will have the time to complete it properly. Only a collision or sudden illness could affect that, but I ran that same risk in Charlottesville.

Large projects: Translating books (I have done three of them on the road) requires a different routine than the short-deadline projects that were my bread and butter for decades. With a book project, I can accomplish a certain amount every day while travelling and build my time line for delivery accordingly. However, I may stop where I am for a few days or a week and crank out target text until the job is done – then move on. Sometimes, the client will have forgotten something and wants to move up the deadline. Other times, I want to focus on the book or treatise, and finish it without interruption. Still other times, I may “front-load” the project to deliver early, so that I can tour the following week. In any case, I have found that the money earned during these stopovers more than pays for the lodging and dining costs of wherever I have chosen to tarry.

Throughput and the budget: It is a reality that I cannot translate as many words per day on the road as I used to in my home office. The big surprise for me was finding out that I did not need to.

  • Expenses: This lifestyle has almost no overhead, so my personal budget (what I need to live on) fits well within my means. Consider that I no longer have an automobile (remember insurance and taxes), a mortgage, home operating expenses, or even local property taxes. I feel no temptation to buy things, knowing that I must carry them.
  • Revenue: Before I started out on the road, I had been turning down more work than I could accept for many years. That is still the case. Knowing that I would not have to worry about my clients disappearing meant that I could calculate exactly how much work I needed to support this lifestyle. I tested this in the last quarter of fiscal year 2013 by living exclusively on my translation income for three months. I usually lose money in the last quarter of the year, but I made money instead.
  • Workload: Since setting out, I have been budgeting half as many words per day when estimating jobs. This has worked out well. I just don’t need as much revenue as I used to. Also, if a job is worth stopping for, I am free to do that, work on it until it’s done, then move on.
  • Disclaimer: “Your results may vary.” I have been translating professionally for almost 55 years. It took a long time to establish the collection of clients who send me work, and to develop the subject matter expertise that I offer. However, aspects of what I am doing may apply to anyone who would like to travel more, but still keep working. With careful planning, testing, and preparation, it should be possible, but each person’s situation will be unique.

In the spirit of sharing what may be useful information (or not), here are assorted observations about living on the road. They are organized as PRO’s and CON’s – because it is not all wonderful out here.

Subject PRO CON
General health No doubt about it – exercise boosts the immune system. I have never been guilty of overtraining, and I have managed to get plenty of rest, especially after a difficult day. This life style is a healthy one, leaving me free to sleep in if I work late, and to change my schedule as needed. Daily riding increases alertness, concentration and stamina. I can feel it when I check in and open the file(s) that I am translating. I sleep well, from having exercised both my brain and my body. Not a real CON, but a reality: one must have health coverage, whether public or private. At my age, travel insurance is prohibitively expensive, so I rely on reimbursements from my health insurance back in the USA. That means saving cash to pay for care up front. So far, nothing unaffordable has occurred.
Exercise Riding a bicycle everywhere means that I don’t have to worry about my cardiovascular fitness. I have only been in one place where there was not enough floor space for me to do my daily floor stretches. The morning routine used to include weights, so I had to make up different exercises. When I am stopped for a while (as when working a big project on a tight deadline), I must be careful not to eat too much, and to take training rides locally.
Diet It takes attention, but I think that I have managed to keep my diet balanced, even with the additional eating out that being on the road entails. Eating well has proven easier in Europe than in North America, whether dining out or shopping for groceries.

I have learned that I genuinely enjoy being able to cook in, even if it is just on a cooktop in a rented room. I am not a gifted cook, but I like to control what I eat.

I can’t monitor my weight on the road consistently.

Eating out is most often the only option, and in the USA, the choices were dismal outside major metropolitan areas. Even eating with a host family may not be ideal, although I have been lucky in this regard. With one exception, all the people who hosted me were eating healthfully in various ways.

Clothing Sportswear is comfortable. I can confirm that people generally have taken casual dress about as far as we can. Nowhere have I been completely out of place, and often my bicycle kit was better dress than the attire of other customers. My trekking shirt and slacks work well as “street clothes” off the bike. Boredom. I like my suits and sport coats. I miss wearing my bow ties. Shorts, polo shirts, belts and sport coats entail too much weight and space, but I miss them.
Laundry Living in technical fabrics means that I only have a small load of cold-water wash every three or four days. At EUR 5-6 for both washer and dryer, that is affordable. I carry detergent in my toilet kit for hand laundry. I also have a compact camping clothesline and clothespins. Not every place has laundry facilities. Laundry in the sink is not very convenient in winter, because my clothes don’t always dry overnight.
Personal relations I have learned that I enjoy my own company. I have never spent so much time by myself. I like the simplicity of not having much to own or worry about, the Spartan accommodations along the way, and the lack of responsibility for other people. I plan my travels to visit family, friends, colleagues and clients. Most of the friends and family that I have visited, I had not seen for many years. It gets lonely on the road. What I discovered was not a sad loneliness, as one feels when missing a partner, but the realization that one cannot usually form new, lasting relationships living like this. At best, I can reinforce existing ones. (I have not tried any bicycle dating sites – yet).
Christmas and other holidays I have genuinely enjoyed spending the holidays with new friends in different places. Life on a bicycle took me away from the consumerist society, leaving me free to tap into it on my own terms. I did not send out Christmas cards for two years. Most of my friends have kept the connection alive through loyal adherence to the Christmas card tradition, so my son and I have resumed collaborating on a family Christmas letter, using email.
Managing the calendar Life is simpler now. I don’t have many commitments. What comes up is easily remembered. Keeping up with long-range, repetitive appointments can be tough, for example, I missed one medical follow-up and a dental visit. These things are not insurmountable, but they take more attention and planning when living like this.
Church and social life Everywhere, I have been welcomed in church on Sunday. Often, I have been able to sing in the Choir, and I know that if something were to happen to me, the local Church people would help me. If there ever were a reason to feel part of something bigger than myself, it is my Church life. I can’t stay and become part of the different communities that welcome me. Sometimes, riding to an event (a conference or a book fair) imposes a deadline on me. I might have to leave the week before a beautiful Evensong or miss a really great concert.
Hospitality I have met so many wonderful people that I am humbled by the love and generosity around me. Some were already friends; others strangers. All have enriched my life. I cannot reciprocate while I am on the road. I don’t feel obligated, because I believe in returning favors by passing them on. But it would be nice to host others again.

So, how do I feel about this life on the bicycle? I like it; I plan to live like this indefinitely. Of course, I am not a retired traveller, but juggling my travelling and work to meet my clients’ needs is part of the adventure.


Long-time readers know that this blog began as an experiment: could I live and work on the road for the long haul? I wrote this vignette and the article in 2016, after the experiment had proven to be a success and I was riding around Europe.

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Until next time,

Smooth roads and tailwinds,



4 thoughts on “Freelancing on the road: a summary

  1. Dear Jonathan, your blog really explained hw you were living and why. It made me feel closer to you. I haven’t gotten back to Emily and Hilda but I will soon. One thing I wondered about was whether there were enough trees along the cornfields of Kansas for Emily to slip on. I have not been to the countryside in Kansas, but in Montana and in parts of Vermont, there are not many tree lined roads next to corn or hay fields simply because the trees would reduce the acreage of the crops. Have you biked in the Kansas countryside? It snowed about 3 inches worth last night and it was a slushy mess this morning. I expected it to melt, but instead it froze and now the wind is howling past the deck at 50 miles an hour. Fortunately I had the large dying maple just to the right of the front walkway (to which the hammock was attached) taken down ten days ago, except for a section for the hammock. The tree threatened the house and I expected any day to wake up to branches in the front entrance. I miss it but I sleep better at night. Keep the blogs coming. Where on this lovely earth are you now?





    • Dear Joan — Thanks for your comment. As for Emily slipping on oak leaves in the middle of a Kansas cornfield, you are right about the lack of tree cover in Kansas. However, even places like that have trees planted around rest areas and other places where humans have left their mark. In this case it was a lone oak that shed its leaves on the road. I don’t know who planted it; their house or picnic table is long gone now.
      I’ll reply to the rest of your comment privately.


  2. I love hearing what motivates other people to take up bicycle travel, and how they make it work. My husband and I spent six months cycling through Europe in 2016. I generally concur with your list of pros and cons. With two years’ perspective on our journey, I can definitively say that the warmth and hospitality of the people we met along the way was extraordinary and filled my emotional cup. We’re taught that the world is a terrifying place; our trip reaffirmed our faith in humanity. On the other hand, never knowing where we were going to sleep from one night to the next was tough. My husband was fine with it, bit it was emotionally difficult for me. At the beginning, the constant newness of everything was exciting. By the end, it was exhausting. I just wanted to take for granted a few of the simple things in life – where I’d be laying my head down that night, and how to read the food labels in the grocery store so I didn’t, for example, mistakenly end up with buttermilk instead of whole milk for my morning coffee. Despite the hardships, it was still such a fun and amazing experience that we’re planning our next cycle trip – it just won’t last six months this time. Calling my bike saddle my permanent “home” isn’t for me, but I sure respect those of you who do. Thank you for sharing your experiences with us all (both through fiction and non-fiction).


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