I first took out a small sailboat on the Charles River in Boston a couple of times, then 10 years later took up scuba, discovered my love of the sea, particularly after taking a 7 day dive trip to the Bahamas on a beamy 40' sailboat, and decided that I'd like to live aboard a boat someday. Then 15 years later, I had the opportunity to do so, and took the money from my half of the house and bought my Corsair 36 trimaran.
I did do a lot of reading, talking to sailors and research prior to taking the leap, but I do not regret it and wish I did it sooner. That said, I have a lot to learn (this site is a great resource) and I am still discovering the full implications of the saying, "Boating is hours of enjoyment mixed with moments of sheer terror,"
particularly in regard to docking.