I'm in that winding down process now and know exactly what you mean. I'm a physician in the same state as you. From the fear of loss of prestige to the transition from saving the paycheck to withdrawing from assets, from getting up at 5:00 and being worthless after 7PM it is all strange and very new.... There are days of boredom and restlessness....
Francis: EastWest Gal hits the nail on the head for me. I'm a professional from Pennsylvania who is about to give notice that I am retiring, and that I will consider a part-time gig so long as it's mutually at will. That part-time work could smooth the transition for both me and my firm. My partners will accept it, or I will walk after a reasonable notice. 19 work days till I enter the phase in which I will give my notice. Scary, scary.
But I think you need to get to the point where you just conclude that you have to push through the fear and get on with it. We both are facing the siren song of OMY. (In my case, for example, my net worth goes up by around a quarter mill a year on average for every year I stay chained to my desk.) But it's at the point where I (and apparently, you) have enough money, and are probably using OMY as a crutch to avoid taking a psychologically risky leap.
You are on a board with a bunch of smart and capable people, and they (especially those engineers! ) can really analyze every aspect of their finances and life to the Nth degree. But while I can't hold a candle to the engineers and their deep analysis, I know that I'm spending too much time analyzing all the angles, and I just need to flick the switch and get on with it. It will pan out for me and I will forge a new way of living. It will pan out for you, too. Don't die at your desk, Francis.
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