Many people start boating as a luxury pastime; many of the rest are chasing a dream. In my case, it was a decision taken out of simple economic necessity. I needed somewhere I could afford to live and one could buy an older cabin cruiser in reasonable working order (typically a Norman or Dawncraft) for as little as a couple of thousand dollars. As the oldest of 8 children from a family that knew only rural poverty as I grew up (mostly in various parts of Scotland); to become self sufficient and independent after completing secondary education were expectations, not aspirations. Simultaneously a combination of poor employment prospects and rising cost of living made this extremely challenging to achieve.
I was fortunate to have a temporary job working in an office that proved unexpectedly durable; albeit at minimum wage – and from this I gradually saved up to purchase my first boat (pictured below). She was a Dawncraft 25, though the actual interior space was about 15′ long and 6’11” wide (at widest). At slightly under under 100 sq ft living area, it seems fair to claim “tiny home” credentials.

I think it’s a general rule that one never forgets the day you get a new boat. I got behind the wheel with zero boating experience, opened the fuel tank vent, let the engine warm up and then cast off the lines and motored away from the dock, with a younger brother aboard who came to help navigate canal lock gates. I spent the first few hours zig-zagging across the canal as I continually oversteered until I got used to how she handled – boats operate on a delay from control input. It’s perhaps best not to admit to colliding with a lock gate wall when the front was swept out of control by a tricky river current during approach.
I did not have anywhere arranged to moor her (she had been an auction item on Ebay). I brought her back as far as I could that weekend, and left her tied up beside the waterway. Fortunately I found a space in a nearby marina quickly and the following weekend moved her there as an initial solution. Sometime later I took her out on the river and ended up in a marina further down – also unplanned, but with the river in flood returning upriver proved unwise to attempt with the limited power of the 15hp outboard engine – and once again luck (or fate?) turned up a dock space.
I discovered that I liked boat living, and the initially temporary decision became long term – I remained aboard her for the next five years (and have owned a boat most of my adult life). In that time, I got onto the first rung of my career as a software engineer (I taught myself programming as a child, but dropped out of university, so my path to this was rather indirect), met my first wife (an American) – and decided my next boat would be significantly larger, and a sailing boat.
The obvious challenge here was having no idea how to sail, so my second boat was an Enterprise sailing dinghy that I kept at a sailing club for the last couple of years aboard Lisa Jane. This picture isn’t of the one I owned, but apart from the hull colour (mine was yellow) it’s essentially the same boat:

I sailed her at the sailing club for a couple of years, taking part in all the races, learning how to handle her through trial and error (mostly error in the first year, it took me most of that year to troubleshoot my tendency to capsize in stronger winds). Although my motivation had been primarily utilitarian – to learn how to sail – dinghy racing was a lot of fun, especially once I got better at getting her to plane. Sailing is such a variable experience – one day you’re barely drifting along trying to eke out motion from the barest puffs of wind; another your race is cancelled because someone is knocked out by a tree (from the wind tossing his dinghy and him ashore while trying to right a capsize).
Having been living so cheaply on the cabin cruiser, I was able to save up to buy my first large sailing boat – a steel sailing schooner in the US. Her name was Guanahani, she was 48′ on deck (the measurement I usually quoted as 57′ LOA sounded pretentious with the long bowsprit) and displaced 52000 lbs. She was in America, but the plan was to emigrate there, and improve her into a fully operational cruising boat (she needed quite a lot of work done).

The plan did not survive meeting the real world and things got very complicated. Between the end of my first marriage, severely underestimating the challenges of the project (both cost and technical difficulty), and the Georgia climate (heat and humidity without air conditioning) – I had not completed the project even after five years of living aboard and progress was diminishing.
She taught me a lot – I learned many things about boat systems, welding and fabrication, rigging – the list is long. I even learned more about myself and what I’m capable of in the face of adversity. When I met my second wife though, it was time to move to a new chapter of life – living once again in a house and navigating the corporate world and the career game.
For five years, she slowly deteriorated – rust slowly eating into the areas I had not stripped to bare metal and sealed (the deck and bilges, particularly). With her sitting nearly 500 miles away, and seldom finding the time and energy to get work done – it eventually became clear that I could not win with this project – I was going backwards and the economics of sinking yet more resources on top of those already consumed were increasingly foolish.
Accordingly I made the difficult decision that it was time to let her go, and knowing the unfeasibility of the project from the current state – I let her go to become an artificial reef for recreational divers and fish habitat. It seemed a better end for her than being cut up into scrap metal.
It seemed that for the first time in most of my adult life I would be without a boat, which had the flavour of a potential identity crisis. This did not happen though – fate intervened and around the same time I let Guanahani go, I learned another boat I had admired at a distance but assumed I could never afford was both available and affordable. She is the SV Tenacious, an aluminium (she will not rust) hulled monster (large enough to be intimidating to operate solo, significantly larger than Guanahani). What she has is in good shape (and enough for short distance cruising), but she still needs the interior finished and additional systems for long distance cruising.
Thus a new chapter in the story begins…
