SEVEN YEARS AGO, I set out on my bicycle to see if I could support myself exclusively from my work (translation) while living on the road. For the last quarter of 2013, I rode the Southern Swing 2013, which you can read about by choosing that category in this blog. A lot has changed since then, and today I want to discuss those changes.

The experiment proved the hypothesis. Indeed, it was more than successful. My business model included losing money in the last quarter of each year: 1) because it included cost of the annual conference of the American Translators Association (ATA); and 2) I would buy expensive items at the end of the year, which helped lower my tax liability for the year. Well, I made a profit in the last quarter of 2013, because the cycling lifestyle had such a low overhead that I easily made more money than I spent, even with the conference and staying in hotels and motels rather than camping.

I wrote five posts that quarter, with lessons learned about preparing to live and work on the road. Here they are, updated to 2020.

Cutting the umbilical cord

Snail mail. No matter where I travel, my company (Scriptor Services LLC) and I need a legal address and home of record. That said, professional mail forwarding services will sort, scan and forward your mail as you travel. They can scan the mail and email PDFs, so you can choose what to forward and what to trash/recycle/shred. Especially if you go abroad, the scanning option can save a lot in postage costs. Some services handle only mail, while others provide a full office presence (answering service, business address, etc.). Just Google “mail forwarding services” to see the wide range. If any of you have specific knowledge of these services, feel free to comment. (Thanks to cruising cousin Jack in Houston for reminding me of these services.)  I meant to try out one or more of these services, but in the end, I used the support of my team in Charlottesville instead.

The boxes of my stuff. This was an experiment, so it was not realistic to burn my bridges and dispose of all my belongings in Charlottesville. As a compromise, I put everything I could conceivably want again in boxes, numbered and ready to ship. I sent for them as I needed them and sent them back if necessary. There were two scenarios I foresaw for ending this kind of support:

1. 1. I find someplace where I want to live more than Charlottesville, and I send for everything. Presumably, I would make a final run back to Charlottesville to arrange for shipment, but maybe not.
   2. I decide to stay on the road permanently, and I don’t want my stuff to clutter the house. Some storage and moving companies could perform the services that Daniel does now, shipping the numbered boxes to me on request and storing them when I send them back. Or maybe I develop a “super bounce box” paradigm – a single large shipment that I send for safekeeping to a pied-à-terre in the next major region where I will travel.

I found myself doing both of the above, in a way. I am preparing to leave Charlottesville when travel restrictions are lifted and I sell the house. I have moved into a small room with all my stuff, so I can vacate the house quickly when it sells. Back in 2015, I emigrated to Italy so I could ride around Europe without the time limits of a tourist visa. For that, I shipped my belongings to the small flat that I had rented (the super bounce-box). When I came back to the USA two years later, I mailed what I was not carrying on tour to Charlottesville.

Medical records. Before I set out, I confirmed that my health team could electronically transmit my full medical records to anywhere that I needed them. This included medical and dental x-rays, medical imaging, hospital and lab records, and notes from office visits. I just needed to pick a new health care provider in the location where I needed the records and let them know. Similarly, if I were hospitalized on the road, this material would be available electronically as well. The number on my military ID tags can lead Emergency Medical personnel (EMT) to the records and my emergency contact if I am unconscious. For civilians, the Road ID Tag service provides wristbands and “dog tags” with both a toll-free number and a website, which the EMT can use to get your medical information. These arrangements should work world-wide, so I don’t expect to need anything different.

Order fulfillment. The booklets that we sold on our website were physical books, which Tracy would put in an envelope and mail when we received notification from PayPal that an order had come in. When I returned to Charlottesville in 2017, I took over fulfillment. This year (2020), I published two novels and in the process learned how to switch my booklets to Amazon KDP for fulfillment. For the freewheeling freelancer on the road, there is nothing better than Amazon and IngramSpark for your paper books. Amazon, Smashwords and a host of other sites will publish your eBooks for you. Mine are all available in your favorite format through my author website.

The PO Box. The company business address is a box at the local post office. Every week, Tracy emptied the box and gave the mail to Daniel to ship to me. The experiment was a success, but I have kept the PO Box, because that address is almost thirty years old. Changing it will require notifying thousands of clients, vendors, colleagues and others of a change of address, so it will take some time. I could integrate this move with the choice of a mail-forwarding supplier or let Daniel, who will be staying behind in Charlottesville, help me transition to the new location, then close the box.

Confidential and classified material

In another post, I shared 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.

First of all, my office has to be password-protected. This means having security (at least a PIN) on the smartphone and the computer so if someone picks them up, they can’t easily access the content. I also don’t set any files on the computer to be shared, reducing the likelihood of someone on a public network getting into my files. Security on my Surface 3 is actually easier that on the old Toshiba Portege in one respect. It is small and light enough to carry conveniently anywhere I need to go, which reduces the temptation to walk away from it to go to the bathroom, or to refill my tumbler at the bar at a Starbucks.

The freewheeling freelancer does not have a lockable office, so the basic rule is: never walk away from your computer or your smart phone. Ever.

When getting ready to take your work on the road, it would be wise to review any security requirements or restrictions that your clients may have.  Some of these requirements may be buried in non-disclosure agreements or contracts that you signed years ago.

Some of my clients did not want any of their files stored on the cloud at any time. This was why I traveled with a small terabyte hard drive for backup. Some of my government clients wanted to be sure that I was not working on the road at all, and insisted that my entire hard drive be secured by special software. Fortunately for me, those clients accounted for so little of my annual revenues, that it was easy to leave them behind. Still other clients wanted to know that I was performing my services in the United States. That was another small group that was easy to leave behind when I moved abroad.

I share this information simply to illustrate the variety of issues that a freelancer’s clients may have. You may have ones that I have never seen.

Almost all the requirements for document confidentiality that I have seen concern deleting material from media storage after the job is completed, and shredding any paper documents. Sometimes I must certify that I have done this; more often than not it is part of the contractor agreement with the client. Now that I’m on the road, this is actually easier for me. I don’t keep paper unless I absolutely have to, and if I am in a place where I can print something, I’m usually also near a shredder (business center, friend’s office, etc.).

Classified material means material that has received a government classification (confidential, secret, top secret, etc.). Working on classified material may seem out of the question for the freewheeling freelancer. However, this work paradigm emphasizes flexibility. I am available to travel to a secure location if the client wants me to work on classified material. This is no different than my availability when I was working back in Charlottesville. The travel costs to go to the classified location are part of the estimate.

In 2017, I retired from commercial translation to focus on writing my own books. I still translate at least one book each year, but they are neither confidential nor classified.

Sickness or injury

Sooner or later, I would take ill or be injured. It might not have been on my bicycle, but the bike was where my life was centered, so that is where I focused my preparations. I was glad that I did, because I needed dental work and an ultrasound in Italy, and I rode to the ER at St. Joseph Hospital in Regensburg with haematuria, which required an operation in Landstuhl. Total out of pocket expenses: less than $250. And I’m still riding.

This is not a discussion of the current pandemic. Let me assume that travel restrictions have been lifted and that you are preparing to travel (again?). It is likely that an uneven patchwork of restrictions are in place as you cross borders (even within one country). The need for safe behavior and common sense will never go away.

Getting sick. If I am staying with friends or family, I can ask them for recommendations. If I take sick, they will help by contacting their physician or other health care provider(s).

If I am by myself, I may have to consult local directories or the tourist office, ask the reception desk at the hotel, or locate a local doctor online. As I mentioned above, I checked before I began travelling to ensure that my health care providers back home could transmit my medical records as needed. If the sickness is going to require staying put or follow-up referrals, I may have to send for those records.

Accidents or injury. Regardless of your insurance situation or location, the process during an accident is similar almost everywhere. The victim or a bystander calls emergency responders (ambulance, fire, police) and the responders take charge. If I am conscious, then the procedures for accidents are similar to those for sickness.

An accident is the most likely reason that I may be unconscious and unable to inform the health team of my situation. This is why I wear my ID tags at all times, and why I recommend that anyone travelling alone have some alert ID system like Road ID to allow emergency responders to obtain medical information quickly.

In addition to some kind of ID tag, it would be a good idea to have a card with pertinent information on your vehicle. Name, address, blood type, a point of contact for emergencies and a list of prescriptions, if you take any, would be the minimum information I would include.

I also have business cards in luggage tags on all the panniers and bags on my bike, which would give responders my name and website, and get them on the path to contacting those who know about me.

Preparing to be injured or sick includes a discussion of insurance.

Insurance on the road 

So, who covers the freewheeling freelancer in the rain, the cold and the sun?

Getting ready for a trip that is not by plane or automobile, there are three main areas of insurance that distinguish the freewheeling freelancer from her colleagues flying scheduled airlines or driving an automobile: medical insurance, business-related insurance and personal insurance. Let me say first that I am neither an insurance expert nor a lawyer. This is what I have found out so far. Please comment if you have a perspective that might help others.

Medical insurance. That anyone traveling should have medical insurance of some kind is obvious. To the weaknesses of our own bodies, we have to add the risks inherent in straying from home.

This subject is easier in most of the world, where national health care is the norm, than it is in the United States of America, where I am right now (as are most of the readers of this blog). For example, in the USA, medical insurance is regulated at the state level, and individual coverage may vary if you leave the state. On the other hand, the large Federal programs (Medicare/Medicaid, military Tricare, Railroad employee and Civil Service insurance) are the same all over the country.

The Affordable Care Act (ACA) introduced major changes in the way that health care is paid for. Regardless of how you are affected by the ACA (or not), be sure to travel with the Proof of Insurance cards that your insurer can provide you, so you can prove that you are covered.

You may be insured through your spouse’s employer. Make sure that it covers you away from home, and carry that proof of insurance.

If you are based in the New York and New Jersey area, the Freelancers Union has made medical coverage possible for freelancers. Writers, translators and interpreters may want to affiliate with TTIG, the AFL-CIO Union for translators and interpreters. It is part of the Newspaper Guild – CWA, and comes with group health and dental insurance.

Freelancers can also join the National Association for the Self-Employed (NASE), which has group insurance plans for its members. This may be the most “portable” of the various options that I have learned about.

I should disclose that I have not needed these options myself, because I am a retired naval officer. I found out about them researching the subject for others (NASE, TTIG), or joining the organizations for other reasons (Freelancers Union).

If you are close to 65 years of age, remember to check into Medicare, how it will affect your current insurance setup, and how you are covered on the road.

Business-related insurance for freelancers has always been a little weird, and a lot depends on the field in which one is freelancing. For word workers (writers, translators, tech writers, columnists, editors, proofreaders, etc.), the major concern is professional liability (also known as “errors and omissions”). Much has been written about this (e.g., the freelancery blog), so I need not dwell on it here. Some freelancers elect to rely on the liability of their homeowners insurance, and if they are leaving home for an extended time, they need to check with the insurance company, just to make sure that there are no limitations. Others rely on the shield provided by incorporating their business; the idea being that only the assets of the business are open to attack. Such a business, riding on a bicycle with only a laptop and a smartphone, might not be worth taking to court. However, it helps to review one’s vulnerability periodically and to look into professional insurance just to be sure.

There is a professional association for almost every field of work, and these groups have often looked into insurance issues for their members. Some even sponsor or offer appropriate insurance; other have at least helpful guidelines. For example, I have had E&O insurance through the American Translators Association. I also belong to the Freelancers Union, which has done a lot of work in this area.

Personal insurance is something we don’t think about living in a house and driving a car. But if you don’t own a home, your renter’s insurance (if you have it) will need to do more than pay for your losing your bicycle and your things to a thief. Renter’s insurance today includes liability insurance. Make sure it covers you anywhere, not just in the apartment.

If you have a car and a house, check into the liability coverage and the medical payments coverage of both your home policy and your auto policy. My homeowner policy, for example, covers me for liability, as long as my bicycle is not motorized in any way. Medical Payments coverage pays the medical costs of anyone that I injure with my bicycle – but not my costs. I have medical insurance for that. The auto policy covers me when renting or borrowing a car (so far not needed). There is also non-owner’s auto insurance, if you are planning to sell the car you won’t need on the road. I have that, and I will acquire renter’s insurance when I sell the house.

The key is to remember that you can get into trouble on a bicycle as easily as in any other vehicle, and insurance keeps you from going broke if you do. 

If your travels will take you abroad, as mine did, there is an added level to check on. You may have to notify your insurance company and get a special card to carry overseas. Some countries will include visitors under their National Health Service, and some will not. Travelling internationally will affect the coverage from your homeowner, renter and auto policies (if you have them), as well as your medical insurance.

So here we are, with our travels on hold. It’s a great time to reflect on what we wish we had known. It is also a wonderful time for daydreams and planning the next trip. Many of us are evaluating our old lives and seeing that things will not be as they were, ever.

Please take some time to share your thoughts in the comments. Ask questions. Correct my mistakes and omissions. If you are shy about it, please use the contact form, so I can answer you personally.

You may inspire a new post, for which I will gladly give you credit or keep you anonymous if you prefer that.

Be safe. Be well.

Smooth roads & tailwinds,

JT