I was never a courageous swimmer as a child and I've stayed out of open/deep water forever. Now that I am an adult and paying for my own vacations, I like to get my money's worth and have been swimming for longer distances every year.
This year, me and my wife swam to the famous Bled island (about a 1000 feet), which in itself is not all that daunting, but there was wind blowing almost directly in our faces and the swim was quite sketchy out in the open. Lo and behold, the next day had completely calm waters, but we didn't have time to do it again.
Seems like a small thing, but I am very proud to have done it. Next year I'll be buying a safety buoy, just to be on safe side.