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And how do you start and continue conversations about the difficult topics? In my family, health care and medical matters have been easy to talk about, caregiving is kind of difficult, and money is very difficult to talk about, IF there aren't unlimited funds.

Sit down and write out what your goals are for the outcome of the conversations. Put the pros and cons down on paper. People can be in denial and don't want to talk about serious issues, but if it needs to be done, better start now. My mother refused to admit she needed to sell her house and move out. She didn't want to give POA to anyone or let anyone know about her finances. After two hospital stays she lost all control of her life. The job fell to me, thankfully with help from my aunt and cousins when I needed it most. Don't wait.
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If your loved one has a financial planner (my financial planner is free through my credit union, you don’t have to be rich to have one) you can request a planning meeting. Way better than trying to do it yourself as a non-expert family member.
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