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.

Rich and his Trawler Yacht, 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.

The extra day was worth it. The 60-km ride to Carrabelle was easy on Tuesday.

The Old Carrabelle Hotel at Christmas

Christmas Eve was spent with the generous folks at Church of the Ascension. I spent Christmas at the Old Carrabelle Hotel, working on a translation I want to deliver at my next mail stop.

Since Thursday, I have been riding 65-80 km every day with a headwind in the rain. Coming in cold and exhausted from the road each night, it has been hard to work in the hotels. But that is part of the package, and part of the format I have chosen for this kind of travel.

What forces me to ride in foul weather is the fact that I must check into the hotel where my bounce box is headed. I know that I could call and delay my reservation if necessary, but personally, I would only do that only if I were seriously ill or injured. I would make sure that I got to the next mail stop on time, even if I had to put my bicycle in a taxi and motor the last leg.

I am on my way from Perry, Florida, to Cross City, travelling along US Highway 19/98/27 (the three routes merge here for a while).

The Big Bend Scenic Highway. After 20 km on a bike, it stops being scenic as it cuts through vast Wildlife Management Areas.

I have left the Big Bend of Florida, finally headed south. Ironically, the weather forecast is for colder temperatures this week!

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 handled 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) is introducing 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.

If you or your partner/spouse does not have insurance through an employer or one of the new ACA health exchanges, there are other ways to obtain medical insurance (note: the realities may change soon, as a new paradigm forms under the ACA).

If you are based in the New York and New Jersey area, the Freelancers Union (www.freelancersunion.org) 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. http://www.newsguild.org/.

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. www.nase.org.

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, and how it will affect both 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., www.thefreelancery.com), 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 (www.atanet.org). I also belong to the Freelancers Union (www.freelancersunion.org), which has done a lot of work in this area, and to the Society for Technical Communications (www.stc.org), which is preparing an affinity program for insurance.

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) probably won’t do anything except pay for your losing your bicycle and your things to a thief. 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, which is worth investigating, if you are planning to sell the car you won’t need on the road. 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 overseas (as mine may well do soon), 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 and auto policies (if you have them), as well as your medical insurance.

Instructions for a rainy day.

Although I have had some wonderful comments back from many of you, on balance, I am not sure whether one of the two parts of each post (trip update and the subject of the week) should be longer or more detailed. Do you have a preference or is the balance about right?

In a bi-lingual pun of the season, let me wish you all a Prosperous New Year (¡Prospero Año Nuevo!).

Smooth roads and tailwinds,

Jonathan