A couple of years ago I went to the annual gathering of the Thoreau Society when the theme was "Simplify, simplify." They were selling t-shirts that said "What would Thoreau do?" It crystalized my desire to simplify my life, but I haven't made very much progress.
I spent an hour or two today going through boxes of John's mail (a longstanding problem) trying to make sure that we found all of his IRA accounts to roll over into an annuity. I found four old accounts in addition to the current retirement savings account. That all five will be consolidated into one account feels to me like a real achievement in making things simpler. The discouraging thing is seeing how much better our situation would be if he had invested his money differently, but that reflects decisions he made 20 years ago and never revisited, not recent problems. He used to listen to the business news and have strong opinions, but he didn't act on them.
There is one other account that can't be consolidated because it isn't pre-tax money. I asked John what he wanted to do with that account and suggested several options, but he didn't show interest in any of them. It startles me to have him not have an opinion.