Thanks for your thoughtful reply. I like your method of saying that it's *my* concern, not questioning her. I have tried that approach with her before and always gotten the brush-off ("I'm fine, I have plenty of money," with no details), but maybe if I press a little harder I can get more concrete information to ease my mind. That's the only reason I'm thinking of bringing up her spending, since she has shown reluctance to divulge specifics. Maybe if I can say that I see her spending a lot of money, without judgement, and I just want to make sure she has enough to cover it.
The thing is, she *does* have a financial planner. I think that's part of the reason she doesn't want to tell me even a whisper of how much money she has - she thinks she has that covered. I'm concerned she may have seen how much $$$ she has and think, wow! I can spend all of this! She really seems resistant to me helping her out in any way, shape, or form, and I think it's because if I help, in her mind that means she can't do it herself. That's not it at all - it's more that I know I benefit from having my DH be a second set of eyes on all financial matters, but she doesn't have that luxury anymore. Typing that out now, that might be another way to approach it with her..
So, yeah, there's no way you can actually say the bolded *without* judgment. Because it sounds like you guys have a history of you questioning her spending and her justifying it, so she is going to hear any mention of her spending as an attack.
This is really almost impossible to do "right," and the hardest lesson is that even if you do all the right things, she is a grown-ass human with the inalienable right to be stupid if she wants to. So start off with the expectation that you will likely fail, and that you're giving it a shot because you love her and want what's best for her, not because you think you can actually control the outcome.
Personally, I would try to inject as much empathy into the conversation as possible. You are concerned, because you know your dad's death put a huge burden on her to figure out all these things that he managed for years. You see that she has jumped in and taken charge, and you are really impressed by her ability to pick up so much so quickly. But you are concerned, because that must have been extremely difficult, and you just want to make sure that she is getting the support she needs. Is she comfortable with the planner? Is he responsive, is he available to answer her questions, does he take the time to explain things to her when she needs it? Is she comfortable with how he is managing her money? Has he given her an idea of how much she can afford to withdraw every year in order to make sure the money lasts for as long as she will need it? Does she feel like she can live comfortably on that amount? Etc. etc.
And then, whatever she says,
do not interject your own opinion. Seriously. This is one of the few situations where "I" statements are usually counterproductive, because it asks your parent to acknowledge that you have the right to be up in their business -- "I worry" -- ok, any normal parent is going to say "don't worry, I have it covered"; after all, they are the parent, so it's
their job to worry about
you, not the other way around. For someone who is approaching the short tail end from life, being the watched-over instead of the watcher-overer is a huge adjustment. So you need to find a way in that allows her to retain her longstanding role as The Boss of Her and You.
Your goal instead is to become the trusted advisor and sounding board -- i.e., that you are there for help
if she decides she wants it [of course, your whole goal is to get her to want it, but the best way to achieve that goal is to let her come to you -- there's a reason therapists listen way more than they talk]. And that starts by putting aside your own worries and listening, really listening, to what she is feeling and thinking. You honestly have no idea what her life was like, as a mom and a wife; heck, maybe your dad was a miser and she's been waiting 30 years to remodel the house and buy herself a damn new car. Or maybe she's lonely and adrift and is salving the loneliness by throwing money at it. Or not -- who knows? [A: not you] So you need to just get her talking -- without voicing your own opinion, which will clam her up instantly -- so you can hear what her needs are, what her feelings are. Because you can't help her get what she wants if you don't know what that is; instead, you are focusing on what
you want
for her.
Once you guys have established that rapport, where she feels like she can ask you questions and you will listen, you can start to slip in advice. But softly, softly, on little cat feet. Think Jeopardy: not "mom, you can't afford that car!" but "hmm, mom, are you comfortable you can afford that car? What did [financial advisor] say?" And then when she pushes back, let it go, preferably with something positive -- e.g., "ok! You know, I'm really glad you talked to [financial advisor] about this, it's good he's looking out for you." The more open and supportive you are, and the less you attempt to interject your own opinions, the more likely she is to open up the books and give you that information you need to feel comfortable that she's ok, or determine whether a more serious intervention is required.