What you do when you are about to retire is to plan for your future. I don't mean what you'll have to do to keep yourself from going crazy that first Monday. I mean WHAT you'll be in 15 years, and WHERE you'll be. Read that sentence again, with the emph ASS is on the right syl AB bels. What you'll be. Where you'll be.
Will you be healthy enough to live where you plan on being in 15 years. Or will you be better of closer to kids, or closer to a hospital, closer to shops, entertainment, parks, roads outta town if you need to be more outdoorsy? As, or shortly after you retire, you should be taking a stark look at what you may have to contend with if your health begins to sour at 75, and not at 85 like you'd hoped. Will you need to be in 'the home'? Nearer your kids two cities over? Do you have lifelong friends with whom you have exceedingly important and intense friendships, or maybe you each have skills that, when shared between you, you can all hope to live a long life in retirement?
Retirement is the time to have fun, but first you need to maybe broaden that definition. For example, are you a caring type, empathetic? Could you do home sitting, home care, even on a voluntary basis, says for shut-ins and the elderly? Could you volunteer to shop at a grocery chain that allows customers who are immobile to phone in orders? Maybe take calls somewhere, or do repairs, say for motorized chairs and scooters for people with mobility problems? Coaching, financial counseling, teach ESL...volunteering is one of the most rewarding things you can do with your skills and time, and it's virtually never an impediment or an imposition when retired.
You should have a hobby, even if it's returning to classes. They have Elder Colleges in several large centers. Or take up fly tying, or model railroading, or build unique kites, or take up cross country skying, bicycle repair, learn a new CAD program and design stuff. Learn! Can you run a 3D printer? I cannot, buy maybe you should!
Generally, to wrap this up, you should feel you have a purpose of some kind. You needn't have each hour of each day meticulously entered in a spread sheet three months before hand. Nay nay! But you should be committed one or two sessions each week where you place yourself before an organization that provides services, or that makes you contend with an environment that you weren't heretofore entirely comfortable with. Make yourself useful, even if it is to yourself!
Did I say have fun? I play with toy trains, and I am an amateur astronomer. That means I play with telescopes until the wee hours when I crawl into bed exhausted and cold. I also sing in a choral society. You'd be amazed how healthful it is to take up choral singing. If you can't read music, but can hold a tune, you can learn how to 'sight read' sheet music. I did, and I haven't got the fastest chip upstairs, if you knowhaddamean.
'Ah, but a man's reach should exceed his grasp, or what's a heaven for?'
Hi! I think you should do a TED talk on this subject. Thank you for this thought provoking response...actually from all of the responders!