This might sound obvious, but you have to start being retired to learn how to be retired successfully.
Like most things worth doing well, it takes discovery, experimentation, and practice.
Seth Godin (possibly the most quoted blogger on the planet) stimulated this thought with a recent post titled, Learning Without Doing.
All projections we might make about retirement before we do it — empty, lonely, sad, full, connecting, deeply satisfying — are just stories until we find out for ourselves.
The skills of retirement are like all skills: they have to be learned. You might already have a bunch of them. There are many more to make your own.
My goal is to be a skilled retiree, like a skilled cook or fisherman or mountain guide. Imagine the help one might give. “Talk to him. He knows the terrain. He knows where to find the fish."