"Twenty years from now you will be more disappointed by the things you didn't do than the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sales. Explore. Dream. Discover." - Mark Twain


In late 2015 my employer of nearly a decade outsourced many of its technology functions. My entire team was surplussed. Some of us were faced with a choice: relocate to the Pacific Northwest and wait for what would likely be the next round of layoffs, or take a severance payment and leave the company. I chose the latter. 

You don't realize how much the 9-5 grind prevents you from living a full life until you are forced to leave the corporate hustle. I took on freelancing projects, and in between jobs had time to visit family, do some traveling, and even take a cruise! I'll admit to missing the guaranteed paycheck that came with the Fortune 100 life, but I certainly loved the work and the flexibility! 

As my savings decreased and it came time to seriously consider what to do with my severance, my eyes kept wandering to internet. I'd long dreamed of living on the water - a dream I'd had since my childhood, really. I'd spend entire evenings online looking at used boats. I'd get insurance quotes and look at marina rates. I'd add it all up and realize, it all seemed out of reach. 

Still, people were out there doing it. Somehow. 

I could take another corporate job and spend years deferring my dream. Or I could act on it. 

Acting on it being easier said than done, I continued to window shop. 

In July, as I do every summer, I traveled to the Finger Lakes region of New York for a vacation. During fleeting moments not surrounded by family and friends I drove to marina parking lots and dreamed. I'd sit in my car, scrolling through YachtWorld.com and Craigslist, looking to see what was available in the area. I knew I'd be returning to Orlando in a few weeks, but it was fun to fantasize - and it all seemed so affordable

With just days left of my vacation a boat I'd had my eye on since day one in New York suddenly showed a price drop. Out of curiosity, I went online and got an insurance quote. Hmm. Just for fun, I called a few marinas in the area - did any have slips large enough for the boat in question? One did - and they had just one left. 

That, to me, seemed to be a sign. 

On August 1, 2016 I purchased a used cabin cruiser. It was a bit bigger than I thought I could handle, and a bit older than I was comfortable with, but it was, in essence, a two-bedroom, two-bathroom, home on the water.

I moved back to New York because I have a plethora of friends and family in the area. But I also did the math. Living on a boat is much, much cheaper in upstate New York than it is in almost any other area I looked at. Seven months on the water, followed by winterization and five months on land, makes for a very reasonable monthly rent.

What's more, the Finger Lakes is filled with summer lakefront cottages that fetch pricey sums in spring, summer, and fall - and, during the winter, aren't really rented at all. Finding a place to stay for the five months of snowy weather is not much of a challenge - and, if I was lucky, I'd be able to spend all twelve months each year with a waterfront view. 

Still, the job front would be challenging. Orlando has a booming job market, and many of the companies advertising to freelancers in central Florida don't want to talk to freelancers in central New York. Would I be able to cobble enough work together to get by? 

I wasn't sure. 

And I'd be lying if I said I wasn't nervous. 

A friend, knowing that I might be spending my severance on this dream of mine, sent me the Mark Twain quote in italics above. I'd heard it before, more than once, but it was especially relevant now. 

So I made my purchase, and then set about learning to drive this behemoth of a boat. I made it my home for the remainder of summer 2016. The nights were freezing cold before I was ready to give up waterfront living. I was the second-to-last boat to leave the marina. 

I am now inside a cozy cabin surfing the web and exploring the job market in upstate New York. The Finger Lakes is a world-renowned area for wineries, and is beginning to receive acclaim for its cuisine - and it's always been something of a tourist mecca. Social media, I'm finding, is inconsistent, at best, across the region.

So while I continue to freelance and seek flex-work opportunities on a national scale, I hope to bring my brand of digital marketing and social media customer service to my new home. If you know of opportunities here (or, really, anywhere), I look forward to hearing from you.