I always dreamed about having a boat when I was a child. My grand parents bought a piece of land for building a boat house, and I had a grand-uncle that had a rowing boat, but except for that I'm from a land-lobber-family.
One day I found myself getting old and decided I either had to realize my childhood dreams or forget about them.
First I bought a rowing boat. Then I used that boat for building a mooring bouy, and bought a small, cheap sail boat that I had anchored up by the mooring bouy. I'm very happy that my first boat was an old, small and cheap boat, because I did all the mistakes in the book and then some during my first two years as a sailor - but I learned a lot! I moved, got rid of that boat and got another old, cheap and small (though a little bit bigger) boat here in Oslo.
As my family grew bigger (we're five now - three children) we found that we needed a bigger boat - and eventually we bought a much bigger boat.