Always know what you are getting into, how to get where you need to be, and ALWAYS have a backup plan.

In 1983 I was stationed in Pensacola, Florida.  I was a Navy Medic – an E-4.  I think I made about $560/month.

I went to the beach and saw all of these beautiful sailboats with the rainbow colored sails, and the girls flocking around.

Two days later I bought an 18 foot Prindle Catameran.  The trailer was included.  I think I paid $6500 for it, used.

Forget the fact I had no car, much less one that could tow a trailer (I had a motorcycle as my only mode of transport at the time).

Forget the fact I had never even sailed a sailboat, much less owned one.

Forget the fact that I had a previous near-death experience on a catamaran in Coronado Bay off the coast of San Diego.

Forget the fact I couldn’t afford the damn thing.

I bought it.  Because the girls liked it – and I liked the girls.  My mental process at the time was that this would natuarally bridge my like of girls with their like of boats and I would get “oh-so-lucky”.

Part of my plan worked – the girls DID love the boat, and eventually, once I learned how to use it (and the boat) the girls started liking me.

But I made a LOT of mistakes.  I bought a boat and trailer and didn’t own a car.  This made me completely dependant on other people to get me to the water – which generally meant they came with me whenever I sailed.

I didn’t know how to sail – I basically taught myself while driving circles off the coast for hours – until the tide and winds mercifully pushed me back to shore – usually a long distance from my launching point.  This created either long walks from me and/or total bitching from the “friends” that towed my boat and trailer for me.  A complete failure to pre-plan on my part.

But the worse failure of all was when I DID learn to sail – I took off down the coast on an absolutely wonderful Friday afternoon – sailing with the wind down the coast and generally showing off for whatever girl I had on the boat at the time.  It was only four hours later that I realized what failure to plan for failure was about.  I had no backup plan – I was now four hours down the coast, it was dark, the wind had died down, and I didn’t know how to tack for shit.

It took eleven hours to get back to where we launched from.  It was, I believe, the last time I ever sailed to this day.  I sold the boat to a guy with a car, and a trailer hitch, and a fucking clue.

Yes, I was that stupid.  Yes, I did learn from it.  I learned to always have an exit strategy and to plan for both success AND failure.  That night I only planned for success, and today I can’t even remember her name.