As someone who is clinging by a thin thin thread to success at Retirement 4.0.......
A few of thoughts:
A) I view my role in life and my life's work as protecting and providing for my family and those I love. In our society and during this era that means money. While money most certainly doesn't buy happiness, it does buy protection from many things which are genuinely awful. As a result, before we started giving money away to strangers and buying old schooners to fix up I had to be certain that everyone was inside the walls of the fortress and that it was sturdy and well guarded. Without doubt, this is the biggest reason I can't step away from money making pursuits and just rent ELEONORA for a year

(Thanks Keith, the big schooner was a big hit with the Admiral. If things go right on one deal, we might be organizing something along these lines.)
B) Secondly, my family keeps expanding. Marrying the Admiral brought in two more kids and now three grand daughters (will 2.7) as one is still in the oven. The fortress needed expanding and the price of real estate means that building the fortress has become vastly more expensive.
C) Bill Gates went from flying in coach to flying in his own gigantic jet. I have the distinct advantage of only being 5'7" and 150 lbs, so a "coach" seat (if you can call those things seats) fits me far better than it does my tall friend Kim. But I think we just use flying coach as an abbreviation for "spending for comfort" and I have distinct views on that. For example, while here in LA I stay at the Best Western in Wilmington. The rate is $98/night and includes breakfast, which I eat - I paid for it. When the Admiral is with me we stay at the Doubletree at a rate of $270/night and no breakfast. She's worth it and it matters to her. When I'm asleep, I have no idea what room I'm in. Also the ladies at the Best Western are helping me with my Spanish. I joke about being cheap, but that's not it. I really HATE waste and for me a room at the St. Regis in NY is a complete waste. For the same reason, I am not made happier by wearing expensive cloths and other baubles. I'm much happier concentrating my spending on buying things that make those I love happy, where I spend like a drunken sailor. (How did sailors get so maligned?)
D) Ultimately, I can't stand the idea of intellectual death by boredom. So, I continue to find "projects" to work on and have joined a number of not for profit boards, I'm on the cusp of joining a late stage start up. What happens is, those organizations start to become part of the family and I feel strongly that one does everything possible to protect the family, maybe tribe is a better word for it. I was on a board when the CEO had a devastating personal catastrophe, he couldn't work. The board members discussed what to do with the company, which represented the CEO's total net worth. I stepped in, ran the company, got it sold, and the CEO's family has been well taken care of. This isn't because I wanted a job in Charlotte, NC, it's because that's what you do for your family/tribe if your a protection oriented guy like me. Frankly, that's what I do because it makes me happy to get it done.
All of the above is why #1 daughter once said: "Dad, of course you like German Shepherd dogs. You are just like them." She then reminded me of a story I'd told her when she was small: There are are three kinds of people in the world. Most are sheep and happy to munch the grass, a few are evil and they are the wolves preying on the sheep. Then there are the sheep dogs whose true join in life is kicking the tar out of the wolves and protecting the sheep.
Eric, from what I've seen there is far more of the sheep dog in you that you acknowledge. Your actions to help my son when he had a medical problem is something I will never forget. Thank you!! Only sheep dogs do this. You may find that what you need to do is find an extended family/tribe/flock to patrol and protect. So far, that is working for me.
Good luck - retirement is HARD to maintain for many of us. It was easy to go to work.
