Guy is in early 60s, and “can’t afford to retire”… makes about 300k maybe 50% bonus… Owns 3 apartments in New York just bougth a $4m one in Manhattan… For the past year he has had some serious health conditions… not terminal right now but needs treatment and it seems serious… The situation where for normal people would accelerate retirement and refocus life on things that are importantnt…
I sit next to the man and yesterday he was on the phone for 1 hour arguing and trying to get an adjustment from a car rental… He says they charged him $5 dollars more than the quoted price!! Five fucking dollars.
My boss may or may not have Asperger’s. He’s very competent, but he’s extremely awkward with social interaction and is a strict literalist. My favorite example:
A third party application that we use went down. He contacted the vendor and they said it would be down for around 3 hours. This was at 9:17 AM. My boss immediately sent out an email to the team that indicated the platform was down and would be available again at 12:17 PM.
My boss is awesome. He’s 75 years old. I’m not sure if he ever gave a flying flip and he certainly doesn’t now. The things he says in executive meetings are simply spectacular. He will also just walk out of a meeting if he loses interest. He also happens to have a great sence of humor and is one of the smartest people I’ve ever met.
Penny pinching is just a symptom of a larger mentality. If your boss is obsessive over $5, he is probably even more obsessive over larger sums. My friend is launching a venture that is funded by a top 3 person in the world in terms of wealth, and has face-to-face meetings to talk about funding. I am told that this guy will spend an hour arguing about amounts of money that he makes in like 5 minutes. It’s just in his nature, and his nature is what makes him rich, not any action individually.
Your boss would probably be happier if he retired. However, I can understand how someone who has spend most of their life in a certain lifestyle would find it hard to let go. Maybe you would be happier if you packed up your things and lived the rest of your life on a beach in Thailand, but you still won’t do it.