I plan to talk to my son after I have everything in order (new life insurance and some answers from our retirement guy).
Just having the talk about your assets and where you stand on your own retirement funds is way more than my parents ever did. Good on you for that. I'm learning the hard way from my parents that they are in no way prepared and would never talk about it when I would ask.
Yeah, I don't want him to have to deal with any mess once I'm gone!
My parents didn't talk about much, but they did make sure to teach me to save. I just learned last week that their house has been paid off for a while (so that's great!). However, I think they still have my oldest sister set up as the executor of their estate, and I may have to see if they'll discuss that. She has not responded to any communication from the family for years, so it's just really not the best idea anymore. Not that there will be any inheritance, we'd rather see them enjoy their money themselves(!), but the rest of us (who are still close enough) should not have to deal with the mess it will create, since she may not even respond if one of them dies.