Taking My Freelance Writing Career on the "Road"


Some of my earliest memories hold clues to my affliction. I used to call it “my 6-month curse.” That primal desire to pick up and leave wherever I was and seek out a new view. As a kid, I didn’t mind moving schools. In fact, I loved it. By age 11, I wanted to run away from home and join an America’s Cup race team. (Because joining an elite team of sailors is as simple as that, right?) Anyway, that lust for change has never subsided, though I am glad to know that there are others in this world that share my torment.

So what is a professional wanderer to do? One cannot very well leave a corporate job every six months, lest ye be deemed a wretched “job-hopper” and tagged “unemployable.” The answer is to seek out the unconventional. The freelancer, once code for “in between jobs” is a properly unconventional métier for the itinerant. So a freelancer is what I became.

I began building my freelance writing career when it became clear to me that being an attorney was not my soul’s calling. The stress. The games. The clothes. Ugh. Why in the world did I ever believe that my dream occupation involved wearing (gasp) shoes? Well, the truth is, being attorney was never my dream, but that’s an article for another day.

Long story short (“too late”) I pivoted my legal career into writing legal web content for attorneys and businesses around the world. My goal was to create a stream of income from something I could do just about anywhere. Over the course of three years, I’ve done just that. All I need is a computer and a decent internet connection and I can research and craft content at my leisure.

Lately though, I’ve been having some real anxiety over whether I’ll be able to truly pull this off while cruising on Rhea. I sometimes lie awake at night imagining the things I do now in one hour taking me two or three hours. The thought of having to work seven days a week while in paradise is, frankly, a nightmare. This anxiety frequently crops up when I’m working from the boat situated safely in a first world, metropolitan city in Northern California. We currently pay over $13 dollars a foot for a slip that includes wireless internet. It works. Sometimes. Painfully slowly, when it does. Cell service is also dismal when sitting below the water line in an inch-thick fiberglass tub.

As a result of this anxiety, we’ve purchased a Solis, by Skyroam, which can pick up cellphone signals in just about every country on the planet for $9 a day. I’m also debating on the purchase of a wifi extender, which would allow us to access wifi access points up to a mile away from the boat, if we have the password. I’ve heard though, that many cruisers don’t end up using the extenders, or they don’t work as advertised. So, the debate continues. I had high hopes a few years back that satellite internet would have advanced much further than it has by now, allowing for fast internet access without spending 4-figures a month. Elon Musk, if you’re reading this, apparently you can do anything you set your mind to, so consider this a personal challenge.

Ironically, I just found out during our recent trip to Los Cabos, that I can get free internet in Baja that works faster and more reliably than what I have access to in Berkeley, California. As long as I am in proximity to a cell tower, I should be able to carry on with business-as-usual during our exploration of Baja, the Sea of Cortez, and surrounding areas. And, I know that if I am truly desperate, there are plenty of resorts I can dinghy over to and enjoy a cocktail by the pool while I borrow wifi ;-).

So, for at least the first season of our watery wanderings, I should have the freelance gig well in hand. Once we decide on our next destination, I’m sure another wave of anxiety will rise like an Atlantic squall. But for now, as one of my favorite people in the world likes to say…I’ll just shoot the alligators closest to the boat.

RiverWork, Freelance, WritingComment