The Biggest Financial Regrets of High Earners

Speaker 1 – 00:00
Creating a big net worth, that’s fine as a goal, but I think it has to have the right reasons behind it or else it’s going
to do more bad than good.
Speaker 2 – 00:07
We spend our money on things that give us status, which is the house, the car, the clothes. If you get to a point
where you have millions and millions of dollars saved, 60s, 70s, and your health goes, you never get to enjoy it,
then it’s like, why did you do all that?
Speaker 3 – 00:19
They’re like, oh, I saved 20 grand on my taxes this year. But they don’t know that they’re building like a snowball.
They’re kind of a bigger problem later.
Speaker 1 – 00:25
How do we live a life without regret? The biggest financial regret of super high net worth people is like, Welcome
everybody. Today, joined by Jameson and Chris. We’re talking about one of the perspectives we have with working
in financial planning for so long is, you know, talking to people that have accumulated a lot of wealth and
preserving it. And I think perspective can lead to a lot of good framework for decision making on what to do or
what not to do, you know, for younger clients and then also for some people that are struggling with like the adage
of the best savers are the worst spenders. So kind of giving yourself permission to start spending and enjoying life.
So, Chris, what’s the first one? What do you.
Speaker 1 – 01:08
So we’re talking, and specifically the biggest financial regrets of people that have accumulated a lot of wealth.
What do you see as most common?
Speaker 3 – 01:17
Yeah, I’d say the first one would be maybe delaying or balancing enjoyment or doing things that you really truly like
to do, whether that’s stuff that requires health and energy, like prioritizing those things when you’re younger versus
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waiting later in life. I think a lot of career trajectories, they require a lot upfront in those younger years. And a lot of
people will get to the finish line at retirement and wish that they spent more time doing extra, you know, whatever it
is now that they have all that money, but, you know, now they don’t have the energy or whatever it is. So just trying
to balance what you need to do at work and then the other things that are also important to you.
Speaker 1 – 01:56
No question. And what are some strategies that you’ve utilized to coach clients into actually taking action on
those?
Speaker 3 – 02:03
Yeah, I think it’s simply just listening and asking them what, like what, how do you like to spend your time simply?
And we do. It’s called a values exercise with a lot of clients where we give them a list of, you know, maybe one of
them says family or meaningful activity. Like all these different values, we have them, rank them and then we ask
how fulfilled they are, scale of 1 to 10, if it’s not a 10, what do they have to change to get to a 10? And it just sparks
good conversation on what matters most to them. And we kind of reframe like, how are you? So how are you
spending your time now? What would I have to change to get more in line with what you’re saying is important to
you?
Speaker 1 – 02:39
Awesome. Awesome. Okay. Well Jameson, what do you think number two would be?
Speaker 2 – 02:43
Yeah, I’d say understanding just like the importance of time and how fast time goes. Time’s, you know, your only
non renewable resource. And we hear a lot that people say they spent too much time working or on things that
weren’t as important in their life and they’ve, they put things to the side that you know, were most important to
them and get, you know, sure they’ve accumulated a lot of wealth but they look back and have a lot of regrets with
how they spent their time.
Speaker 1 – 03:10
What advice would you give to like a younger client that has like huge aspirations of building wealth and having a
successful career? And how would you know, frame that?
Speaker 2 – 03:19
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I guess first thing would be figure out what’s most important to you. If it’s, you know, family, your health, working,
whatever it is, spend your time on that. Don’t, don’t just don’t build it with sacrificing the other things are important
to you.
Speaker 1 – 03:34
You gotta balance the secure in the future with having no regrets. You know, looking now and living a present life.
So it’s a tough one. I think everyone, every successful person struggles with for sure.
Speaker 3 – 03:44
For people with kids, I’ve heard you share a statistic like a ruler.
Speaker 1 – 03:48
80% of your time, they say 80% of your time spent by the time the kids are 18 with the time you have with your kids
is basically 80% of it’s time by the time they’re outta the house and into college. So, and a lot of people are so
focused on legacy for their kids or building up their career, but then they spend so much time in their career and
accumulating money and then they basically never saw their kids and then it’s tough to see them after the fact
because the relationship’s not strong enough. So that’s one that you definitely don’t want to mess up. Yeah,
thought that was relevant with the time.
Speaker 2 – 04:21
When I heard this thing, I didn’t really understand it, but so like time gets faster as you age. Cause like think about
the first 25 years of your life. 25 is like a hundred percent of your life. But then like when you’re 50, 25 years is 50%
of your time. So like it’s, it like technically speeds up.
Speaker 1 – 04:38
I’ve always heard that time goes by quicker when you’re older. I feel that, yeah, time flies by in my 30s a lot quicker
than it did in my 20s.
Speaker 3 – 04:44
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Flies by when you’re having fun.
Speaker 1 – 04:46
Exactly. Okay, well what’s next? I would say tax planning would be a big one. So a lot of people are so focused on,
you know, throughout their accumulation years, saving taxes, saving taxes. A lot of times they let the tax, you know,
lead the way. And so you know, you get to retirement and priorities change. If you start spending money like
unwinding income out of a portfolio at a set of a paycheck, like it can put you right back in the highest tax bracket
if you don’t have a, a strong at least a third of your net worth. Be saying something that’s tax free, whether that’s
Roth or basis on that brokerage account or tax last harvest you’ve done in a direct index account.
Speaker 1 – 05:23
So I would say that’s a huge regret we’ve seen in people that have over accumulated in pre tax money is not doing
tax planning along the way that’s forward thinking, not just like how do we save the most on this year’s tax return.
Speaker 3 – 05:38
I think that one’s tricky because sometimes the intention’s right. Like we’ll sometimes be working with outside tax
preparers or CPAs. And a lot of people are just looking at the here and now and so they think they’re doing the right
things. They’re like, oh, I saved 20 grand on my taxes this year. But they don’t know that they’re building like a
snowball that’s gonna at some point left unwind it and there’s kind of a bigger problem later.
Speaker 1 – 06:02
No question, no question. Okay, well what’s next? Chris?
Speaker 3 – 06:06
I don’t know if it’s necessarily hand in hand with what you were saying about like the time that you get with kids,
but this is more speaking to what I feel is like if you have, if you’re financially independent and you know that you’re
going to leave money to the next generation, they probably need you could probably use the help when they’re
raising their own families rather than when they’re in their 50s or 60s and they’re retiring themselves. So I Think
trying to look at the family plan. Is there a way that you can achieve your retirement goals and help the next
generation to just live a better life?
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Speaker 2 – 06:41
I guess it’d be transitioning values and wisdom and knowledge versus just accumulating wealth.
Speaker 3 – 06:49
Right. Or efficiently, like, using everything. Like, if you know you’re going to gift this money, like, why. Why wait? You
know, like, if there’s going to be a sizable legacy, like, why are you waiting 30 years whenever.
Speaker 2 – 07:00
If you have the kid when you’re 30 and then you’re. You die when you’re 90, your kid’s 60.
Speaker 3 – 07:07
Yeah, right.
Speaker 2 – 07:08
Whereas they probably need the money more.
Speaker 3 – 07:10
When they’re also a fine line, I guess, with, like, helping versus enabling.
Speaker 1 – 07:14
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There’s a lot of families we work with like that. Like, let’s say doctors or kids become doctors, and there’s like, no
question of motivation. They go through college and the parents have done a good job. Like, they’ve lived a good
life, but they’ve also accumulated a good net worth. But, like, statistically, like, they’re probably in the top 25% of
where they should be based upon what their income was and what they saved. They were disciplined, but not, like,
obsessed with, like, achieving this high net worth. They just, like they secured the future, secured their kids college.
We see their kids have successful careers because that usually means they put a lot of work on their job. They put
a lot of work in at home with their kids and like, taught their kids accountability, discipline, whatnot. But then what.
Speaker 1 – 07:49
What we see is an interesting dynamic is the clients have achieved, like, top 1% net worths have probably gone way
out of their way. Tons of sacrifices. But the time involved with building, that usually means less involvement, you
know, maybe with the. With the kids and like, the. The values or the wisdom. And so then what we see play out is
that sometimes, not always, is that those kids, you know, they. They don’t necessarily have as much motivation. So
then the kids, the parents created this wealth saying, I just want to take care of the legacy of my kids. But then
what that did was it created this kind of pathway for the kids and not have to work. And so they don’t have
successful careers. And then they kind of become dependent on that money.
Speaker 1 – 08:32
And then what happens is you think, like, the parents think, oh, I’m. The money’s gonna fix it all. That actually
creates a much bigger issue on the table. And then kind of introducing this concept of, like, the drama triangle.
Very interesting concept. Like, basically, like, savior, persecutor, victim. It’s like maybe the parents kind of played
like the savior role. Like they built this like huge amount of net worth, saying I’m just gonna like take care of
everybody. And then when the kids, you know, maybe they’re 30 and the parents are sick of them. They funded
college, they funded like the first house, they funded all this stuff. And then the parent, the kids are like kind of like
failure to launch, like they’re 30 and asking like for the 15th time for more money.
Speaker 1 – 09:12
Then the parents have to shift from like maybe some accountability. But to the kids who’ve gotten this free ride the
whole time, they sh. They, the parents then shift from the savior role to like persecutor because the kids aren’t used
to that accountability. And then it puts the kids in a victim and then everyone kind of bounces between those three
roles. So I found that’s a very interesting concept, highly applicable to like the high net worth family dynamics a lot
that we work with. And so I think the goal is like avoiding being on that triangle at all costs. So like yeah, work hard,
create a net worth but like don’t play a savior. Like provide but don’t enable, keep accountable, don’t purse, don’t like
over correct.
Speaker 1 – 09:49
And so to do that like it takes a lot of work and calibration I think along the way to accumulate all your financial
goals, but also to keep the kids accountable. And you know, how do you, how can they handle adversity by
themselves? That can be a gift as well, you know, letting them learn that from a young age as well. A very
interesting concept. I think the higher net worth, the higher applicability, that concept comes into play that we see
on a day to day basis. And now that we’re moving into, we just introduce it, introduce trust services. So we’re going
to be, you know, part of those conversations more often. And so we’ve started to see that play out a lot more. But if
you’re already on that triangle, like how do you get off as quickly as possible?
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Speaker 1 – 10:29
Maybe it’s some uncomfortable 6 to 12 month pathway to kind of recalibrate the boundaries of a relationship
between parents and kids. But I think it’s a very important one because we saw a lot of people kind of float through
that maybe for 20 or 30 years and then that’s, I would say the biggest financial regret of like super high net worth
people is like they just wish they, you know, they can’t take the money with them. They just wish they had a better
family. I think that triangle fits pretty squarely into that. So not questioning, like creating a big net worth, that’s fine
as a goal, but I think it has to have the right reasons behind it or else it’s gonna, it’s going to do more bad than
good. And a lot of people think that it will just fix everything.
Speaker 1 – 11:10
And it’s really just going to create the problems you already have is just going to magnify them even greater. So,
okay, what’s the next one?
Speaker 2 – 11:17
Letting your health deteriorate.
Speaker 1 – 11:19
How do you see that play out from a financial planning perspective?
Speaker 2 – 11:23
Everything gets in front of their health. So they just kind of put exercise. I mean, it’s easy to work a lot and say, I
don’t have time to exercise or work a lot, you’re busy, you don’t have time to eat healthy, or it’s not possible to get
eight hours of sleep in. And so all these things take precedent over health. And then, sure, you probably end up
accumulating a lot of wealth, but then if you get to a point where you have millions and millions of dollars saved
and your health goes, you’re in your 60s, 70s, and your health goes, you never get to enjoy it. Then it’s like, why did
you do all that?
Speaker 1 – 12:04
Any ways that you plan for that proactively with younger or even clients that are retired can’t just say, hey, you’re
not healthy. But like, how do you navigate those conversations?
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Speaker 2 – 12:13
You gotta ask the right questions to figure out like, what’s important to them and what they’re. You can, you can
kind of figure out what their stressors are. If. Yeah, I mean, you just ask people things and they’ll start talking, you
know, so if they tell you that they’re. They wish they were, like, it’s pretty easy to figure out if health is not a priority
and it should be. So if they tell it to you and then you know, okay, well, you have enough money and we’re talking
about how you can spend more money and you’re not. So how do we deploy that to.
Speaker 1 – 12:44
So if Chris was your client, you wouldn’t be asking him what his blood pressure review 2 max is?
Speaker 2 – 12:48
No, I’d refer him to a doctor to do that.
Speaker 1 – 12:50
Oh, okay. So there are boundaries in place. Okay.
Speaker 2 – 12:53
I just, you know, try to be like, well, you know, you ask them what they’re, figure out what their stressors are and if
health is one of them. Well, I mean, yeah. And then, yeah, we’ll. Yeah, yeah.
Speaker 1 – 13:03
Give a Quick intro. Cause I think that’s a good representation of someone’s health, right.
Speaker 2 – 13:06
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The older you get, the lower percentile of VO2 max that you’re in, it, like, is like a multiplier of your mortality risk. So,
like, if you’re in the top 1% of VO2 max or something, as you age, you have, like, a. 10 times. 10 times less likely
chance of dying the next year or something. I can’t remember the exact statistic, but it’s like one of the. One of the
biggest metrics that, like, can show you, hey, what’s your probability of dying the next year as you get older? But
basically, essentially what it is, like, you’re the max that you’re. The test is you go run on a treadmill to, like,
exhaustion, and you have a heart rate monitor on it sees how hard, how. How high your, like, heart and your
cardiovascular you can push.
Speaker 1 – 13:56
So it’s like your top, when I did it was the bike with, like, a mask.
Speaker 2 – 13:59
You do that too? Yeah, anything that works too. Yeah, Bike, treadmill.
Speaker 1 – 14:02
The whoop tracks it too. So what’s checking? Mine’s in the top 25. Top 1%, top 25. I think it’s a top 10. Been
slacking on the cardio recently.
Speaker 2 – 14:10
I gotta find that statistic that.
Speaker 1 – 14:13
No, but it’s good. I think in general, like, some of those are good metrics for. Obviously, we’re not doctors, but, like,
we. We are very passionate about health.
Speaker 3 – 14:22
Do you track VO2 max for the families you work with?
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Speaker 2 – 14:26
And I don’t. I should, though.
Speaker 1 – 14:28
That’s not bad. I mean, that’s a new service offering.
Speaker 2 – 14:30
Maybe we could do VO2 max testing.
Speaker 1 – 14:33
All right, enough of a. Enough of a tangent here.
Speaker 2 – 14:37
You were talking about bringing stethoscopes into meetings, or you just do?
Speaker 3 – 14:42
I don’t know. I don’t know if that was me.
Speaker 2 – 14:44
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A quick wellness check.
Speaker 3 – 14:45
Maybe I. Maybe I said that at one point.
Speaker 1 – 14:47
Okay, Chris, what’s next? You get back on track here.
Speaker 3 – 14:52
The last one I had was lifestyle creep in comparison. So I think with. We work with a lot of physicians and people in
medicine that, like, the path is delayed gratification. Like, you put all this time into your undergrad, your med school
residency. If you do a fellowship, it’s a lot of years. And then over that timeframe, your income 10x is, you know, or
a big jump at least, and you have a new social circle. And I think, Jameson, you’ve spoke to this, like, people, like,
ultimately, you want to fit in with the Crowd and maybe you can speak to this a little more. But like, you see your
friends, your colleagues, like they have big houses, nice cars, country clubs, like whatever it is, you know, maybe
they delay a meeting with a team early and they just want to get settled.
Speaker 3 – 15:40
But getting settled means like filling their budget up with all these big ticket items. So you meet a year later and
there’s nothing left and you’re making 6, 7, $800,000 and you feel like you’re paycheck to paycheck.
Speaker 2 – 15:52
Yeah. For thousands of years, humans have, you’ve wanted to fit into a tribe. So you’re doing everything to, let’s
think like thousands of years ago, if the people in your community didn’t like you would literally die. You’d like, you
know, get mauled by a bear or like something because you were the. And so we’re wired to fit into the tribe. And
you want status. Status before money status was how you were like, you know, you were important. And so that’s
hardwired in our DNA. So we spend our money on things that give us status and give us, want people to like us,
which is the house, the car, the clothes.
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Speaker 1 – 16:33
What’s interesting is you’re going to have all this way too high of a net worth than you need potential in retirement.
And without a purpose behind that, it could lead to a lot of other issues as well. So I don’t think, I think the purpose
of this is there’s always life’s hard. Like no one escapes the human experience. I think the concept of like, you have
to choose your hard. So your hard could be working your butt off now to like accumulate this high net worth. The
hard could be, you know, starting a business, going through medical school, whatever it is. But you have to choose
it. Because no matter what you do, if your kids have a free ride, like, they’re gonna have a hard life later. Cause
they’re gonna lack the motivation you have to choose like which hard.
Speaker 1 – 17:19
And the hard that you do choose needs to have a purpose behind it. So it’s worth it. But I think the biggest solution
to all of this is having really like in depth conversations of like, what is your purpose? What’s your mission? What
are the values for your family and letting that lead the way? Because without those conversations, like, life can just
kind of call a shotgun for you. And before you know it, you’re. You’re in the situation in her life that like, you know,
you’re not really, you’re not happy. So I think a Good part of a financial plan can help address as. I mean and the
reality is like we’re not psychologists here, but we do see money is one of the, if not the biggest stressor in
America. And so a good financial plan, it should reframe that.
Speaker 1 – 18:10
So your money is supporting your life by design, which is removing stress, removing regret and making sure you’re
living a present life and secure in the future. Right. If you hit all those goals but you can’t put that, something like
that cannot be put on autopilot is what we found. It’s not like here’s a plan, follow this 10% increase, 1% every day.
It’s, it’s not going to do it because humans are emotional, different relationships, ebb and flow, it’s gotta be
calibrated consistently. But you have to have all these like parts of it dialed in to make sure that you do reach those
goals. No regret, future secured, et cetera. But yeah, I mean our biggest goal for all of our clients is like obviously
security now and in the future.
Speaker 1 – 18:52
But the other balance I think is not talked about in financial planning is how do we live a life without regret. And
that is challenging people not just to save, but how they should be designing lifestyle today. So those are my
closing remarks, but Jameson, Chris, any other thoughts?
Speaker 2 – 19:09
I’m trying to find this VO2 max stat real quick. It’s like if you’re in the top 20, I’ve read this. If you’re in the top 25% it
reduces your all cause mortality by 50%.
Speaker 1 – 19:18
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You’re in the 25, right Matt? Yeah. What does that mean?
Speaker 2 – 19:21
All cause mortality is death of any cause, like for any reason. You’re reducing it by 50%.
Speaker 1 – 19:28
I’m good for 12 months is what you’re saying.
Speaker 2 – 19:30
50% higher chance of or lower chance of dying.
Speaker 1 – 19:34
Yeah.
Speaker 2 – 19:35
And then it’s like multiplies as you get older. So like the older you are that I think this is what it is. The older you are,
the higher your risk of one year. All cause mortality. So like us, the risk, the probability that we die in the next 12
months is low. The probability that someone is 90 years old dies in the next 12 months is very high.
Speaker 1 – 19:57
So someone at 990 with a high VO2 max, it’s a, it’s like a.
Speaker 2 – 20:00
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Multiplier because like if you’re, is it.
Speaker 1 – 20:03
One of those things where if you put it, have a good VO2 max that’s going to be easier to Carry kind of like muscle
mass in your 20s carries with you for the rest of your life.
Speaker 2 – 20:09
I’m not sure. I don’t know the answer to that.
Speaker 3 – 20:11
I feel like the VO2, the test is pretty intensive. So they get a 90 year old.
Speaker 2 – 20:16
Yeah, I don’t know. But the 90 year old probably doesn’t have to get to full on exhaustion. Right?
Speaker 1 – 20:22
Cause like as you mean 90 on that bike.
Speaker 2 – 20:25
That’s what I’m saying. Like you getting to full on exhaustion versus them or maybe they just can and that puts
them in like the 25th percent. I don’t know.
Speaker 1 – 20:32
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That’s my goal. Make it to 90 and put that mask on and go crazy on that assault bike. We’ll get, we’ll put that as a
podcast episode if I last that long. Just me testing my VO2 max, Jameson cheering me on in the background.
Speaker 2 – 20:45
Yeah, so anyway, takeaway, you know, get your VO2 max tested and.
Speaker 1 – 20:48
No, I, I think this is an important tangent though, because the one thing like when we do those values exercise,
Chris, that you mentioned, we see stuff all over the map. But I would say if went and looked at like 90% of those
conversations, health was part of every one of those.
Speaker 2 – 21:05
Oh yeah.
Speaker 1 – 21:06
And that is probably by far the number one regret is like to have a successful career. It takes a lot of sacrifice and
one of the first things that goes out the door is health. Right. Because like most people, it’s like I want to provide
my family and I also want to spend time with my family. And then your health, like exercise and just like, when do
you have time for that?
Speaker 2 – 21:23
Or Brian Johnson.
Speaker 1 – 21:24
So I watched the documentary, but I was like, it’s a little too much for me.
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Speaker 2 – 21:28
He just, he claims because like he, I don’t know if he’s, he had an exit for like $800 million. And before when he was
doing all that, he wasn’t healthy. Like he was like he like almost committed suicide. Like he was just like very
unhealthy. And he claims now that, and it’s interesting now that he’s like a billionaire. Almost a billionaire. He says
this. I don’t know what the answer is, but he claims now if he would have focused on his sleep, exercise and health,
he would have more money while I was doing all that. It’s hard to tell because like, I.
Speaker 1 – 22:00
Don’T know, I don’t know. But as someone like that he spoke, all he does is focus on health. So it’s like, is he living a
life?
Speaker 2 – 22:06
He claims he’s the most happy he’s ever been.
Speaker 1 – 22:09
Okay. Yeah. I mean, you know, that’s on social media. That’s his highlight reel. We got to get him an interview and
ask him.
Speaker 2 – 22:16
Yeah, he’s real extreme. Like, like you said, it’s all he does. But I just bought his olive oil. We can go. We don’t need
to go on this tangent. But he claims that, like, it’s really hard to get well sourced.
Speaker 1 – 22:26
His marketing is marketing.
Speaker 2 – 22:28
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Yeah, but if you buy. I just did. See, it’s really hard to find. All most olive oil you buy in the store is like garbage. Like,
it’s not like, well sourced. It’s like. And so he looked around and he couldn’t find well sourced olive oil, so he just
made his own. I don’t know. I figured I’d try it.
Speaker 1 – 22:45
Yeah, I got a couple of bottles in this Italy vineyard I went to.
Speaker 2 – 22:48
Yeah, that might be good.
Speaker 1 – 22:50
They show me that, you know, how they grow and stuff.
Speaker 2 – 22:53
Hope it’s legit, but that’s the one thing. Speaking of health is like. Is like the oils that are, like, not well sourced. It
can really. Yeah. Really mess you up.
Speaker 1 – 23:02
Yeah, that’s a good one. I mean, I think that Brian Johnson example is really good though, because it’s like you. A
lot of people think, if I have money, it’s going to solve all these issues. But like, he’s saying, you know, no, in $800
million and like, yeah, so very interesting conversations. But I think that my takeaway for all of this is like, there’s
again, no one escapes emotions. No one escapes human experience. Like, no matter rich, poor, or middle class, it
doesn’t matter. Like you all, Everyone needs to have an intentional thought process behind their plan and make
sure that they’re balancing, like, the most important things in life. Because if you don’t do that and life just the time
kind of fills the gaps and other people’s agendas kind of fill your. Your plan doesn’t become your plan. That’s the
worst thing.
Meeting Title: FinancialRegretsof High earners 3
Episode 2 v4.mp4
Meeting created at: 5th Feb, 2026 – 11:52 AM
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Speaker 1 – 23:49
There’s no intention, I think, is the worst thing when it comes to your finances. So. All right, we’ll catch you next
week.