It went really well for him for about 30 years, and then he started to decline into depression. I don't think it was directly related to being retired.
He built a barbecue out of cinder blocks, then rebuilt it out of bricks. He learned to knot in order to make hammocks. He took up painting with acrylics -- I wouldn't say he ever became good at it, but he liked it and that's the point. The same for charcoal -- but he didn't like the mess, so he dropped it quickly.
He took up teaching advanced math to the local elementary school kids. He taught himself programming in BASIC and wrote math games and text adventures about our neighborhood.
He watched a lot of movies, read a lot of books, and kept the house on a schedule. He went from being an adequate cook to a reasonably good one.
He built relationships with the neighbors and went for a walk twice a day when the weather was adequate.