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You schedule a time to discuss the tough stuff. My family never talks about anything so I had to suddenly fly home when my brother became at the end of his rope living with my elderly mom and moved out and my sisters were at each other’s throats about her care. Better to talk about this stuff on a schedule. Annually. What better time than Christmas when everybody is together? Yes, it’s easier to ignore the elephant in the room. But actually, it is better to discuss. Say open the conversation and let it run for an hour, then table it.

Very true.

Every time I bring up my will or my wishes about death, dying, etc., my daughter goes crazy. Every time I try to gift her with something I want her to have, she refuses denying reality that I am getting older and need to have my affairs in order.

My father was a very proud person who never wanted to discuss these things with his children. He handled the family finances singlehandedly and even kept everything from my mother, who to be fair to my father, wanted nothing to do with it. Also, he never used a computer for anything. Everything was done on paper and all his transactions were by check or cash.

Well my Dad passed away this past summer and it's been a bit of a nightmare organizing the finances. My mother has been no help at all. I've had to jimmy open strongboxes and go through file cabinets in order to piece together what he had and what bills needed to get paid.

For example, he had an IRA that none of us even knew he had. I realized that he had to take an RMD by the end of this year (or get a 50% excise tax). Because my mother is unable to articulate anything invoving finances, I had to call the IRA, convince them I was my father's son (and not a scammer), fill out forms and get them notarized at a bank along with copies of the death certificate, affadavit of domicile and all that, just to find out the beneficiary (which was my mother). Who will not cooperate at all. She just tells me to leave the money in my father's name and I cannot make her understand the consequences of not taking an RMD distribution.

That is just tip of iceberg of what I am dealing with.

So yes, my advice is to have that conversation with your parents, unpleasant as it might be, before they die, so that things can get sorted out much quicker.