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John Stillman

Financial advisor and founder of Rosewood Wealth Management in Durham, NC, host of the Mr. Stillman's Opus retirement-planning podcast.

Oct 30, 2026

0:36
Definitely not foolish of them, right?
0:38
No, I think a lot of people feel guilty because they've been conditioned for so long that I'm supposed to aggressively grow my investments.
0:49
But I've had some version of this question asked to me a hundred different times or maybe not even in question form.
0:57
They're just stating, hey, you know what? We don't care about making any more money.
1:02
We just don't want to lose what we have.
1:04
And I think a lot of that is, you know, a lot of the folks we deal with never had massive incomes necessarily.
1:13
They were just diligent at spending less than they made.
4:29
So that's the other part of this conversation too, is just knowing that you are in the position where you can start pulling back and actually, you know, being a little bit more conservative potentially.
1:52
And every person needs a plan of how they're going to tackle that.
1:55
That's exactly right.
1:56
I mean, the way I always try to frame it to people is You absolutely 100% need a plan for how you're going to pay for long-term care if you need it.
2:05
That doesn't necessarily mean that you need long-term care insurance per se.
2:10
It might, that might be the best solution for you, especially if you already have a policy that you've been paying on for a lot of years, it could very well be best to just keep that.
2:19
But if you find yourself wondering, should I go buy a policy or should I tackle this problem a different way? That's when we really want to explore the options and see what's going to make the most sense for you.
2:31
You know, we don't have to get into the costs of helping people understand what long-term care can actually cost.

9 MINS LATER

11:41
So knowing your options is super important.
1:30
It's when do you do a Roth conversion and all questions that that relate to Roth conversions should link back to the under-arching question, which is between now and the time I die, how do I pay the least amount of taxes? And when do I pay those taxes? It's not whether you will pay taxes, but rather what are the efforts either before retirement through contributions or conversions technically, or after retirement through conversions from pre-tax to Roth, when do i pay them so that i have overall all time paid the least so that means you can't be deterred from paying more taxes up front so you pay less later but conversely you also shouldn't only pay taxes up front because sometimes it does make sense to delay john why don't you take it
2:18
from there so i like the way that you phrased it when you said there are philosophical considerations which I think a lot of people wouldn't necessarily consider that there are philosophical considerations related to their financial plan.
2:31
But in this case, there are, because what we really have to determine is, are you looking at your money solely as your money? Or are we looking at it as generational wealth? And people hear the term generational wealth and they think, you know, people with multi billions of dollars that are passing money down in trusts to their grandkids and great grandkids.
2:57
That's not what I mean when I say generational wealth.
2:59
I just mean, if you're passing money to the next generation, that is by definition, generational wealth.
3:08
So if you're thinking about this money in terms of only my lifetime, how do I pay the least amount in taxes? It's a little bit more of a toss up.
3:19
Do you do Roth conversions or not? But if we're extending the view of that money to also your children's lifetimes and say, how do we as a family pay the least amount of taxes on this money? Once we add that second generation to it, In nearly every case, not every, but in nearly every case, we're going to be better off to do the Roth conversions because we have this very long timeline for the money to grow tax-free in the Roths.

8 MINS LATER

11:30
Does it matter timing wise kind of what age you are when you do this? And if you do it all at once, are those things you should also be kind of figuring out when you work with your financial advisor?
3:13
What other things or misnomers about Social Security have you heard about?
3:17
Well, so on the same lines of waiting till 70, if you think you're going to live a long time, the other thing I would say is if you have no other money, If you have nothing saved for retirement, then it's an easy solution.
3:31
You need to work as long as you can and start social security as late as possible.
3:36
The more money you have, the more complicated the question becomes because we're trying to make all of these pieces fit together.
3:45
And so often people are thinking about social security from the standpoint of how do I maximize what I get out of the system? which of course the system is set up based on actuarial tables, right? So the breakeven age, no matter when you start it, the breakeven age is going to be in your early 80s.
4:04
If you start it at 62, you're going to get less.
4:07
You get that for 20 years.

6 MINS LATER

10:32
So how much should you factor that in to making this decision? Because I know a lot of people do think about that and say, maybe I want to go a little bit earlier than maybe I would have otherwise, because I'm afraid I'm not going to get these benefits.

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