He is making poor decisions and my sister and I are cleaning up his messes. When is the right time to tell them we need to make the decisions not them

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Garden Artists advice is very good. I have a similar situation except it's Dad with dementia and Mom who is getting a little forgetful. In my case it took a combination of honest, gentle discussions with Mom and some behind the scenes actions. As I realized things were going down hill I quietly began collecting all the info, financial stuff, copies of files, contact info for docs, utility bills etc. now, a couple years late rim very glad I did as I handle all the bills and work with mom on keeping meds and appointments straight. We don't even attempt to reason with Dad. He's stuck in 1968, everything is just fine. I'm currently trying to get them to accept some in home help. They say they don't need any help, I know better but can't force it. They've met the cargivers and liked them but it will takes crisis to get them in the house on any regular basis.
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This is always a difficult task because it's a reminder that they're losing the ability to manage their lives. Start gradually by asking how you can help them...such as whether making a list of monthly and quarterly bills, general dates received, dates due, account numbers, payable data, etc. would help them.

The secondary value of this is that you also have an inventory of their bills so you can call the creditor if some bills don't appear to have been received (when in reality they're stuck inbetween the cushions on the sofa or hiding under some junk mail).

The goal is to make sure they're paid, whether it's by you or your parents. You could even make an "event" of it, fixing hot chocolate or something for your parents, sitting down together on a weekly or monthly basis, and making sure that all the bills are paid.

Take the same gentle approach for their financial and real property assets, as well as other items of value. If they don't have their legal decisions documented, find an elder law or estate planning attorney and get wills created (assuming they're both still capable of understanding the nature of what they're doing), as well as medical advanced directives.

In my experience, it's basically a step by step, issue by issue approach rather than a takeover like a military junta. You need to gain their confidence, while also finding a way to make them still feel worthwhile and valuable as people.

For the issues that are more emotional or difficult, plan them to coincide with, precede or follow something your parents enjoy. For us it's a Dairy Queen treat in the summer. That always seems to provide some relaxation after a tough day, and the sugar high makes them feel good.
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