Over the course of your life, would you prefer to feel special or happy? If you can only choose one in your life, which one would you choose and feel like you made the most of it? That’s the topic for our roundtable discussion today. We’re joined by our very special guest Dana Anspach, CFP®, RMA®, Kolbe Certified™ Consultant, and Founder & CEO of Sensible Money, LLC. She’s joined by our in-house sourpuss OG and Len Penzo, creator of the award-winning blog lenpenzo.com.
Our panel discusses whether achieving “happy” or “special” is necessarily an either/or decision, or if there’s some middle ground between the two. Joe goes on to clarify that the author’s definition of “special” centers around addiction to professional success: addicted to being hardworking, successful, and wealthy. We tackle why many success-focused people are actually “miserably rich.” Do you have to sacrifice your happiness in order to achieve professional success, or is there a way to have the best of both worlds?
In the second half of the discussion, sponsored by DepositAccounts.com, we dive into how to overcome workaholism, so you avoid being miserable and wealthy. Is shedding materialism in favor of simplicity the secret to maintaining a healthy balance between success and happiness?
Stay tuned for Doug’s amazing big-money question. Will Dana propel Paula into a 3-way tie for first place or will OG or Len take sole possession of the lead?
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Watch On Our YouTube Channel:
Our Topic: A Few Word Description
How To Avoid Becoming Miserably Rich (Tony Isola)
During our conversation you’ll hear us mention:
- Living by your own rules, in accordance with your values.
- The correlation between education/socioeconomic status and the probability of drinking alcohol.
- The potential consequences that often come with high levels of professional success.
- The correlation between some vices and professional success.
- The dangers of overworking.
- “Workaholism”: the compulsion or the uncontrollable need to work incessantly.
- “Work-life balance.”
- Responsibly balance living for today with saving for tomorrow.
- How to visualize yourself beyond work.
- How to plan your escape from the corporate world.
- Disconnecting your identity from your work.
- Concept of “free days” during the week.
Dana Anspach
A big thanks to our contributors! You can check out more links for our guests below.
Dana Anspach

Another thanks to Dana Anspach for joining our contributors this week! Learn more about Dana by visiting her bio page on her business’s website at Dana Anspach · Founder & CEO – Sensible Money
Check out her book Control Your Retirement Destiny: Achieving Financial Security Before The Big Transition.
Len Penzo

Visit Len Penzo dot Com for the off-beat personal finance blog for responsible people.
Follow Len on Twitter: @LenPenzo
OG

For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- What is the highest lottery jackpot in U.S. history?
DepositAccounts

Thanks to DepositAccounts.com for sponsoring Stacking Benjamins. DepositsAccounts.com is the #1 place to go when you’re looking to see if your rate is the BEST rate on savings, CDs, money markets, and even checking accounts! Check out ALL of the rates ranked from best to worst (and see the national averages) at DepositAccounts.com.
Mentioned in today’s show
- The “Ben Franklin close” (LinkedIn definition)
- From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life, by Arthur C. Brooks
- Premier Business Coach For Entrepreneurs | Strategic Coach
- 5 Things You Should Know Before You Retire (SB1472) » The Stacking Benjamins Show (featuring Wess Moss)
- Free Online Retirement Class – Sensible Money (Webinar on March 28, 2024, with Fritz Gilbert)
- My Teenage Son, His Cell Phone, and the Bill for $1,055.20 (lenpenzo.com)
Join Us Monday!
Tune in on Monday as we kick off Rewind Week!
Miss our last show? Check it out here: How to Become a Supercommunicator (SB1480).
Written by: Kevin Bailey
Episode transcript
They’re dogs
and they’re playing
poker.
Live from Joe’s mom’s basement. It’s the Stacking
Benjamin Show.
I’m Joe’s mom’s neighbor, Doug, and on today’s show, you’ll learn how to avoid becoming miserably rich with founder and CEO of sensible money. Dana Ock, then Stacking Benjamins, very own Scrooge. It’s og and finally the richest man in the world. It’s, oh God, I’m sorry. That was a typo. It’s just Len Penso. But that’s not all.
Halfway through the show, I’ll share my filthy rich trivia question. And now a guy who hit the jackpot when he hired me, it’s Joe. See? Hi.
Wow.
Hey, welcome to the, uh, humble is our middle name podcast. I am Joe Saul-Sehy. Average show Money on Twitter. Welcome to another episode of the Stacky Benjamin Show, brought to you on Fridays by State Farm.
State Farm agents, or small business owners too, so they know how to help you choose personalized policies that fit your needs like a good neighbor. State Farm is there. Talk to your local agent today. We’re not just gonna talk to our local agent, we’re gonna talk to the people at this round table ’cause man, we got a great one.
On this episode we’re gonna talk about, uh, avoiding becoming miserably rich. And let’s start with the guy across the cart table from me. Who feels wealthy every minute he spends with me Doug. It’s, uh, Mr. og. How are you? Dude? You
know, like a, uh, one-arm paper hanger as grandpa used to say, like a, he was in the paper business, apparently doing it.
One-handed was a pain in the butt, so you were
really busy. Some of those old phrases, you’re just like, yep, whatever. Uhhuh don’t
take any wooden nickels, right? Like a
three-legged dog and a flea scratch
and contest.
No idea. Yes. All that and, and more. And the guy who is deep under Los Angeles, again, joining us, Mr.
Lin Penso is here. Len, how are you my friend? I’m feeling
wealthier. I’ll tell you that. I got an email today from. And this is hilarious. I, it came across my inbox from the len penso.com HR department, which, uh oh, I find really interesting. No, those are never good. ’cause I know I’m gonna, I’m an employee of one at, at this company, so, but somebody from the HR department sent me an email telling me that I had a raise and my raise, it was in the attachment, in the email.
I just opened the attachment. I could see how much my raise was. So, uh, I’ll be opening that right after the show here, so I can’t wait. So can we hurry do it
live? Make sure you click
on the links that are in there too.
Yeah.
Oh, absolutely. Yeah. I can’t wait. This is, I’m excited.
Never do you had a Mr.
Employee, did you?
No, I didn’t. But the HR department, I guess, exists, so they
always do. I thought, Len, you were beginning this with a joke as always. Like, everybody’s waiting for the Len Penso joke. This really happened. It really happened.
Yeah, it sure did.
So great. Cheryl last week came into the room and she’s like, what do you got coming from UPS?
I’m like, what are you talking about? She’s like, I just got a text that you got this UPS package we got. I’m like, do not click that dude. Not please. Do you
ever get the emails from your body parts? Like, I got one the other day said From your colon, and it was about, you know, blockages and, you know, it’s like, well, you know, that’s okay Mr.
Colon, but, uh,
ai, AI is outta control. You
know, it’s a bad day when you’re cold.
That’s link thing that, uh, what’s his name?
I got one from my ovaries. I tell oh boy. And
the woman who’s wondering again, why she came back. She is sauntering towards success. We’re watching her on the walking, uh, the walking platform right now.
Dana’s Fox back. How are you?
I am doing great and, uh, I’m feeling wealthy because I got to take an hour off in the middle of the day to actually run a personal errand, which is very rare. So that was
pretty cool. Was the personal errand coming to be with us? Is that what you’re talking about?
But, you know, then I had to get here early enough to check on my sound system and make sure it was
working.
Uh, Dana’s got the new sound system up and running. She sounds great. Also, uh, the, the, how many, how many steps are we gonna log during today’s show?
Um, at my speed
it’s having over, under, at the pace she’s at now. Seven. Don’t tell us. Don’t us.
Oh, is this gonna be a trivia question? Yeah.
Don’t
tell us. We
should bet on it.
Oh, okay. Oh, gee. How many steps you think she’s gonna get starting now?
Okay. Uh, I’m gonna say, well that is a pretty tepid pace. Um, wow. I’m gonna say 6,000. That seems like a lot. No, I’m gonna say 4,000. 4,000. 4,000. 4,000. I changed my mind. 4,000 when.
Well, I, you know, I was gonna say 6,000, so I’m gonna say, yeah, well you can have six.
No, I, I, you know what? Uh, yeah. Okay then I’ll keep six. I’m gonna keep 6,000.
Oh, Doug, you get to bet on
this one. Yeah, this is, I’m a professional walker. 6,000 steps is three miles, and there ain’t no way she’s covering three miles in an hour at that pace. I’m gonna go with, well, og, where did you, you went down to 4,000, right?
Four. I went down to four. Yeah. You went to four. So I’m gonna go, uh, 39 99. Oh, well
I’m, I’m going 2000. Oh, you’re in this. I should have gone 39 98 og. I should have gone 39 98 is what I should have done. And that’s the way you were in it, way you self solve Doug trivia question. You know, I think I’m gonna do that.
I am gonna do that.
Yes. You are. 39 98. I’m 39 98.
There you go. Doug. So I gotta be dead on at 39 99 to win it. Dana, I better see you hustling.
Do I get a guess in this trivia? Oh,
well, but you’ve got the controls. Dana’s
like I, yeah, I was just gonna ask like, do I have to stay at this pace or could I be subtly adjusting the
pace?
You wouldn’t know. All a sudden she’s jogging
and the show’s about to add and Dana’s in
a huge
sprint, dead sprint. Don’t forget, Dana. I control the real trivia. I can make this worth your while. If you can nail it to 39 99.
This is not the real trivia question, but D Dana, how many think you’re gonna walk?
Well, I, I have an advantage. I know how many I normally walk, but I, I’ll guess, you know, 24 70, God
damnit.
Yeah, there it is. That’s why I was gonna say 2000 Dug
right there. I was, I was gonna say 26 initially, and I thought, why be specific?
If I wasn’t so interested in blocking you, it would’ve gone much better. We’ve got SPAC here, we’ve got lead, we’ve got og, we’re talking about getting miserably rich on today’s show.
But before that, uh, Dana, what’s the motor that runs that thing?
Well, let me tell you all about,
wow, that’s fascinating.
Wait, you didn’t just play a commercial while I was telling you about it, did you?
Well, we wouldn’t do that. Keep explaining what else is cool about the
motor. Well, as I was saying, the motor is so quiet.
It’s like a whisper.
That is
amazing. Does it take unleaded or leaded gasoline? Dana,
you know, good old fashioned electricity.
Oh, wow. If you’d have been listening Doug during that whole thing, you would’ve known. All right, we got, uh, Dana here, Len og. Let’s dive in.
Our piece today comes to us from the blog of Tony Isola. Tony is a certified financial planner working at this little company called Ritz Holt Wealth Management. Never heard of it. No idea. That’s a joke for people who, who don’t know big, uh, firm, uh, respected firm. And Tony has written this piece about how to avoid becoming miserably rich.
The good news stackers, you don’t have to have read this piece. We’re actually gonna just kind of use this as a jumping off point. But when Tony talks about becoming miserably rich, he starts off here. He asks, would you prefer being special rather than happy? And before you read this, Dana, we’ll start with you.
How would you describe yourself going for special or going for happy?
I’d say going for happy.
How come? Why not special? When I
think about the decisions I’ve made in my life, they were always things that made me light up, if you wanna think of it that way, right? Like what are the activities that engage me that I have energy for that I wanna do more of?
We call ’em shiny. So you know, you’re going along and y’all have the boring stuff you need to do, but then sometimes there’s those shiny things. So I’ve always pursued those shiny things and so to me that would really fall under the, the happy category.
But you never find, like in your job serving clients like you find that you wanna be the the special snowflake financial planner that nobody else can get anywhere else.
I don’t think that’s ever what I set out to be. Now, maybe I think I’m not today. I don’t know. But I, I mean, it was never my goal. It was always around, you know, I started in this business back when there were really pat answers to things, and it was very much a sales culture and, and so I always wanted to quantify things.
I wanted real answers. I wanted spreadsheets that would actually show people if they should pay off their mortgage or not pay off the mortgage. And so for me it was all around like, how do you find real answers to these things? It was, it was never about being special, although at the time that approach was special.
You know, unfortunately you start off in the early nineties, right? That wasn’t the way financial planning was
done. No, I learned sales funnels in the early nineties. Like it was exactly all about How do you do the Ben Franklin close with people? Wow. I don’t,
I don’t know that one. Ben
Franklin close. Oh, you draw this line and you got all the positives and on one side and the negatives on the other, and you say, Dana.
This is a tough decision, right? To buy permanent life insurance or loaded mutual fund. And, and you’d say, we’ll, put all the reasons you should have life insurance here. And, and by the way, I would phrase the question, I learned how to phrase the question very one sided. So we’ll put all the decisions that are for having life insurance on one side and all the reasons against on the other.
And this is Ben Franklin said, this is how he made decisions, right? He just, you, you make it not emotional. So what do you think all the reasons are? You should do the right thing and have insurance versus all the, you know, loser things where you don’t have insurance. Which, which, which one should
you go
with?
It was horrible. Hold on. You used that shtick on me. Look at the time. I remember that. Look,
look at the time. Yeah. Len, how about you? Special or happy?
When I was younger, it was special and it took a little bit of life experience to realize that was for me the wrong path. And uh, when I was in my early thirties, I, I finally realized, you know, happiness much better to be happy than special.
And, uh, you know, ironically, once I did that, the part about being special kind of, uh, came later after I decided that’s I wanna be happy.
Special took care of itself. Yeah. Special took care of itself. Yep. That’s wild. og how
about you? I’m still probably where, uh, Len was in his early thirties in my, uh, mid forties.
Like, like the transition, I think to doing and being the thing that you want to do and be and become as opposed to just focusing on all of the other stuff. And, and it’s hard for me to kind of think of the word special and happy. Like those two things to me don’t look like parallels or, you know what I mean?
Like either are deciding between those two things. But the way that Len explained it. Having to actually choose it. That’s, for me, that’s an active, that’s an active struggle, I think, to want to focus on the happiness part of it. ’cause I’m not generally a very happy person. Wow. Fooled
me. We, we, we. But what’s funny is, is that, uh, you and I get coaching from Strategic Coach and it really is this, this thing here really focusing on happy versus being special.
Yeah. It’s not to say I’m not
happy, I mean I’m, I’m much more pragmatic, I think.
Yeah. But I think, don’t you think that the lessons you and I have learned through the coaching we’ve gotten has led us toward the happy bucket?
Yes. And like Glen said, the, those two things kind of merge together. If you’re doing all the stuff that you enjoy, then you’re not gonna be in the space.
That’s the not happy space, I guess. I don’t know. You know, and that’s, and that’s kind of around unique
ability, stacker. If you’re sitting here with us going, I don’t understand why this is important, what this has to do with anything I. Tony opens this up by saying, people who choose to be special gravitate toward addiction.
There’s actually studies that have shown this. These aren’t the poor souls sleeping in cardboard boxes on a San Francisco street. They’re not down and out consuming drugs to avoid the reality of mental illness or a miserable life. Quite the opposite. These are people that are addicted to hardworking, being hardworking, being successful, and being wealthy.
He points to Arthur C. Brooks, who, uh, dives into the weeds in his book From Strength to Strength. If any of you read this book, I haven’t read it, Brooks says, according to the organization for economic cooperation and development, the likelihood of drinking rises with education level and socioeconomic status.
Meaning, as we get wealthier and as we have more, uh, high ranking positions in a workplace, we end up self-medicating with alcohol, including drinking hazardous levels, which can turn off the sensation of anxiety like a switch temporarily. Have you guys seen this in, in your own life, Dana? Have you seen this with people?
I’ve
definitely seen this. You know, I don’t think I ever had a drinking problem, but I don’t drink at all anymore. I certainly used to drink more and it’s night and day difference in the way I feel, have more energy, and I, you know, when I think about in my thirties probably drinking was somewhat of a, you know, way to turn off the anxiety in social situations.
It just, so I agree with that sentiment and I’ve certainly seen it with clients. You know, I had one client we actually terminated because he showed up visibly not sober for several meetings. And so Wow. We were, you know, it became almost dangerous to my staff. And so we said politely, we had to find a way to say, you know, we can’t serve you anymore.
So, yeah, I, I do think that there’s a lot of truth to that, but
I think Dana, how prevalent this is, I just remember you talk about starting in the early nineties, I mean, I remember that song in the late eighties, the Loverboy song. Everybody’s working for the weekend, right? Like Friday, you’ve had so much stress.
What do you do? You go get loaded because you’re getting rid of the stress of having a high pressure job.
Yeah. You wanna turn it all off. It’s the end of the day and you know, you’ve got a bajillion things running through your head. You’re still thinking about it, and that makes it easy. You know, gimme a glass of wine, give me a vodka.
Red Bull was my drink of choice if I was going out. Yes.
I still have those days from time to time, by the way, where I’m like, I just want a, I just want a glass of wine. The self medication. Uh, Len, how about you?
Early in my career, I saw a couple people who were alcoholics at, at the job office, but, uh, they were older gentlemen and they weren’t, they weren’t management types, they were just rank and file.
I don’t know what the cause of that
was. But you didn’t see this people, people high up in your organization that were big drinkers. What? I’m
Oh, no. So what I, I was gonna continue on throughout the rest of my career. Usually the people, you know, high up the, the c-suite people, they were definitely workaholics, there’s no doubt about that.
But all of them, I never saw any of them really have a drinking issue. But they had lots of ma locks on their desk, almost all of them from the stress. And I would say, what’s Malac? Malos? Like antacid, like Tums stuff for Tums.
Okay. I
never heard that before. Before
people use, yeah. Oh yeah. They almost all of them had it on their desk, a bottle of it, sitting on their desk.
Because like they probably had ulcers. They had, yes, because it was high stress. And I would say of the ones that I would aware of, I would say. Two out of three of them had broken families where they were married and they were divorced or they were, you know, they had marital problems or they were mo married multiple times just because their family life suffered greatly from all the work that, that they were putting in, which was insane.
And you know, a lot of them expected us to do the same when we were working with them. And it is, it’s very, that was stressful on me as well. But uh, I didn’t follow them
over the cliff. Oh gee. There was a guy who had a really big practice where you and I began our career that we both knew really well. I don’t know if you ever knew that he was just a raging alcoholic, but he definitely was when I got closer to him.
But did you see many people during your career that were self-medicating?
The short answer is yes, and I knew about many people and I. It’s weird because it’s, I was gonna say it was part of the culture, but then I was just thinking about the stuff at the Waste Management Open a couple weeks ago. Oh yeah.
I, I don’t know if you guys followed any of that, but it got crazy. I mean, it’s always kind of the party thing anyway, but it got to the point where they had to shut down alcohol sales completely across the golf course. People were running on the course and doing Snow Angels and the bunkers during the, you know, while the pros were playing it, it went from being like this fun party atmosphere to somebody tipped it over the edge and then the whole group followed that.
You know, obviously in retrospect, people are talking about it like, okay, that was a bridge too far. And, but leading up to that was very acceptable of all of the behavior and largely it’s done because it’s fueled by, whether it’s alcohol or drugs or trying to be famous on TV or whatever it is. But all of that comes with that liquid courage.
There’s nothing good that came from it on the back end. I. I, the phrase that I heard recently was, there’s nothing good that happens at a nightclub after midnight. You know that it’s all downhill
from there. You know, gee, the, the waste management open, it was so bad that they’ve already changed the name of it for, for next year it’s going to be called The Wasted Management Open.
Yes.
That was coming. Oh, and that’s right in Dana’s backyard, I think it is. 10
minutes from my
house. Were you participating? I, no, I wasn’t there. You know, I, I used to go, I stopped going years ago, you know, if I’m not,
this just got crazy. Yeah. It’s outta outta control. This
year it was kind of an accepted thing, and I think when, you know, in the industry or in many industries, you know, our experiences on the financial planning side, but, you know, the finance, wealth management, the, the, like, it’s frowned upon to not do those things.
Len, like you were talking about, you know, and the bosses is staying late and says, Hey, well let’s, let’s run out real quick and have a drink. And you’re like, dude, it’s eight 30, man. Like, I gotta, I gotta go home and say hi to my, my kids and get to bed. ’cause I gotta do this crap again tomorrow at seven.
That just kind of as a self-fulfilling prophecy back to the Malos or Tums or whatever it is. So sadly it was pretty, well, look at
Wolf of Wall Street, right? If you grew up in this business in the nineties, I, I, you know, I worked at a big brokerage firm in the late nineties, and that culture was insanity.
But it was exactly how you just described it. ot, I mean, you know, it was all about the party. It was nuts. The party.
Yeah. More, more, more
M-O-A-R-O. More, more, more. Make as much money as you can, more and, and party your way around it. Well, and I remember having a conversation, Joe, just to have a, kind of put a point on this in terms of the, from a culture standpoint, I remember having a conversation with, with one of our sales leaders who legitimately said.
You need to go buy something you can’t afford right now so that you’re motivated to sell this month and not like go buy. You know, don’t go buy like a nice watch, buy, buy, buy a high end car. Yeah, go buy a Porsche because that thing’s gonna have a thousand dollars payment every single month. You’re gonna have to work your tail off to afford it.
And it’s like, well that doesn’t make any sense to me. I
had a regional vice president that came in for my brokerage firm who slammed his fist down on the table. There was three of us that were in our first few months and he said, I want you all to know, no matter what you do here, it will never be enough.
And that was, you know that more and more, more exactly like you’re
describing, calling Gary Glenn Ross. Right. Always be closing coffee is for
closers. Yeah. Well, and that gets to the point, Len, what you were talking about was not seeing the alcoholism, but seeing the thing that Tony’s really focusing in on here because when he is talking about being miserably rich.
Sure there’s signs of it with alcoholism. There’s signs of it with excessive partying after hours because of the self-medication, but heap goes right to the heart of it. With workaholism, he calls it workaholism, is defined as the compulsion or the uncontrollable need to work incessantly. It is a potential to ruin families without the stigma of cocaine or booze.
Many high power business leaders conclude they have no choice but to maintain their grueling schedules. Many can’t distinguish their perceived obligations from being caught in infinite labor loop. And the dilemma here is that on one hand you feel like you have to run after this thing to meet the goal to be special, right?
You’re clearly not happy. You’re chasing special. I need to hit the number to make Dana’s boss think I am enough. I, you know, I’m, I’m closer than anybody else to enough. And he says that workaholism feeds fear and loneliness and fear and loneliness than feed workaholism. It’s this, it’s this circular loop.
Uh, Len you must have seen working for a big company, people that are just workaholics. Oh
yeah. Like I said, the guys in the c-suites especially, and I worked with them a lot, especially when we did proposals and talk about high pressure and, um, when you got put on a proposal. You were expected to put in at least 12 to 16 hours a day.
You are working shoulder to shoulder with, in many cases the vice president of the company or presidents of the company. Sometimes the CEO would be, in reviewing your work, you were on a 60 day deadline usually, and you had to do this massive proposal and costing and it was brutal and you were expected work weekends, the holidays be damned and the pressure was you had to win, so you had to win the proposal and you, after you do all that work, if you don’t win, then it really comes down on you.
So, I mean, it was just brutal. I, there were many vacations that I work, I think I’ve brought this up before I’ve gone, I went to Hawaii and brought my work with me because, you know, it was the only way I could. Yes, I had vacation time. I had to use it before it went away, but I was still working in my hotel while everybody, you know, when
my family’s out, you know, wait a minute, you’re taking the vacation day because you
have to Because it expired.
Yeah, it goes away. Right? If you don’t use it, you lose it after, but
you’re still working during that time, so you’re just, yeah, you’re still working, but you’re looking out the window and you see palm trees.
Oh yeah. As a matter of fact, I remember me and another coworker, we both had Hawaii trips that we had made before this proposal came down, but it was too bad.
We were stuck, so they allowed us each to go to Hawaii. He was on one island. I was in the other, and we were on a conference call. You know, in Hawaii working on this proposal? Well, it was just, it’s just absolutely, we were both like, can you believe that this is happening to us? But I mean, that’s the way it goes.
Thank God I didn’t do that 365 days a year. Whereas most of the c-suite people, that’s what they did a lot. That was their whole life. For me, that would be maybe two months outta the year, but it was just a living hell every year.
We had a guest on January 1st, the amazing Eric Alman talking about balance and focus in your life and about having a client 6:00 PM on Christmas Eve, and he and his family celebrate Christmas, 6:00 PM Christmas Eve.
Client says, I need this tomorrow
morning. Yeah. I just, oh, that, yeah, that, that happens. One
of my favorite Christmas movies is Family Man, have you se I mean this pretty, the Cage, pretty quiet movie that, uh, didn’t really receive a lot of press, but, uh, the one with Nicholas Cage, where it’s like the ghost of Christmas Pass, right?
Where he gets to peek into the life that he could have had, had he just not followed the. The hustle culture or you know, whatever kind of the road less traveled type thing and he hates it and then he finally likes it. Yeah. You know, at the end basically.
Well, that’s a funny thing. Workaholics think this is the only way, like I have to achieve this thing at the top of the mountain, top 10 traits, I’m just gonna read a few of these.
54% of workaholics prioritize work over personal life. 51% worry about work on days off. 50% have it hard to switch off. 48% check emails during the night. 46% of the first to arrive at work and the last to leave. 46% feel too pressured or busy to take their annual leave at all. 45% skip the lunch break after work.
Oh gee, you gotta see this among your clients that as people, I think as people tend to get wealthier, you tend to see these people that can’t spend their money because they’re so busy in this circular loop.
I think the challenge for that is it stops at one point or another. It either stops because there’s a health issue, it stops because there’s a family issue.
Len was talking about divorce and you know, all that other stuff that can happen. It stops because they just like glitch out. You know, like, I’m out, I can’t do it anymore. And then that just slams the brakes on all of the other stuff that’s going on from a long-term financial goal standpoint. And I think our job is to remind people as they go through their life, as they are accumulating things and being successful money-wise, that they’re on the right path and, and they don’t have to do more.
You know, it’s great to have extra money and it’s great to, you know, save it and invest it and that sort of stuff. It’s fine. What’s the point of, you know, living to be a hundred, having 20 million bucks in the bank and never have gone to Disney? It’s ridiculously expensive to take your kids to Disney. We went for one day to Disneyland.
And you know, it was like 1200 bucks. For what I mean, that didn’t include the churros, which are like $7 a piece,
which were good, by the way. You know, that’s funny. ’cause speaking of Disney, real quick, Audrey, my family got the, you know, here in Southern California, we got the, we used to get an annual pass for Disneyland, right.
For the family. And it was 99 bucks for an annual pass, you know? Yeah. Per person. And I think that included parking
200 each, or
1 75. More story about the good all day Uncle
Len. Yeah, exactly. The first time I went to Disney World, it was 1250 a ticket, $12 and 50 cents. But that was a long time ago. But my point is, is that the financial piece of the world would go, that’s ridiculous.
That’s a waste of money. You’re, you know, you should invest that and compounded that money that you spent turns into, you know, blah, blah, blah, blah, blah. It’s like, right. I got that. I got to hang out with my kids. Yes. At a cool theme park. Ride some cool rides, eat churros for lunch, you know, and ice cream sandwiches.
Like, you don’t get to do that all the time. And I would rather trade that and not have as much money. Like, ’cause there’s not, there’s, there’s no point in having there $10 million or $5 million, whatever the number is, and not have enjoyed it along the way.
It’s silly. Dana, have you seen this with your clients?
’cause I would think that at some point, based on what OGs saying. It’s gotta be hard for some of these successful people to visualize the future. And I know how important we’ve talked when you’ve been on the show before about, you know, you kinda gotta visualize yourself beyond this work. And I think that pe a lot of these people had struggle with their planning because they’re such workaholics.
Yeah. You know, I’ve probably been lucky to not have seen too much of it because, you know, the nature of people that we attract are getting ready for that transition to retirement. And oftentimes they are in the corporate world and they’re, they know they’re ready to get out. So they’re looking for that plan out.
Where I’ve seen it more is actually with people who are entrepreneurs. Uh, and a few times when I’ve seen it with my clients, you know, I remember a, a doctor client who, like he said to me once, you know, I’m a doctor, that’s who I am. I do this and I do that, and if I retire then what will I be? And that was the.
In his mind, right? He, he goes to work and he, and he is explaining this to me. They call me doctor this, they call me doctor, that I get to train the residents. I get to do this. And, and so he just couldn’t separate his identity from that. But at the same time, I, I don’t think he was unhappy, you know, he and his wife seemed happy.
That’s where his joy came from. And so he slowly scaled down to four days, three days, two days a week, one day, and then eventually retired, passed away not too long after, uh, he totally retired. I was reading this article, thinking through some of the workaholic things, going, oh my gosh, is that me? Is that me?
I spent the whole thing saying that. I’m like, wait a minute.
Hold on. Yeah. So I, where I struggle and as strategic coach, I, I’ve been a part of that in the past also. Right? I, I love their concept of free days. I think it’s super important to have time to refresh and recharge, and I. I absolutely have to do that.
At the same time, if you do love your work, there can be things like, if I have a free day and I don’t have something special planned, like an activity that I’m really looking forward to doing, I might get up and think, man, I actually can’t wait to go write this article. Now. Maybe that sounds weird, right?
But you know, so would that be workaholic or is it That’s where I, I like to be creative and that’s where my joy comes from and all of those other things. So I think there can be the healthy aspect of it and some of the unhealthy aspect of it that is referred to
in the article. I think it’s funny, Dana, because I think it can also, I, I think it can be both.
West Moss joined us recently talking again. He’s been on a, a few times, but talking again about what the happiest retirees know and the fact that they have at least four of these, what did he call them? Len, these super, not not hobbies, but super pursuits or life pursuits beyond what they do. I think those free days help you stay a little bit more
well-rounded so that for people like you who clearly love what you do, me, I love doing this. Those free days allow me to remember that it’s a marathon, you know? And, and these other things kind of make me more well-rounded. Do you have to remind yourself that
Me, do I have to? Yeah. Yeah. I mean, I agree with you, but for me it’s like I have to have something I’m passionate enough about on those free days.
And so, you know, it’s really interesting. It’s, it’s like, okay, if that’s a free day, then I need to go find something I’m passionate enough about to. That I’m gonna be engaged and not think, yeah, I don’t really feel like doing that. I used to ride motocross and absolutely loved it. Like no problem taking a free day.
I’d go out on the trail with my dirt bike any day. That was something that was completely engaging for me. I’ve taken up pickleball and I enjoy it. It’s not same as motocross, and so
I just say a lot of people. The opposite of you. Yeah. You know, it’s almost like CrossFit. How do you know somebody plays pickleball?
Don’t worry. They’ll tell you. Don’t worry. They’ll tell you. Coming up in the second half of this, Tony actually talks about the solution to work a holism. We’re gonna get to that and talk about on our end, how do we avoid being miserably rich? But before that, at the halfway point of every show. We have this phenomenal contest between our three, uh, frequent contributors, Mr.
Len Penso, og, and Paula Pant. And Dana, every time you’re here, you’re playing on behalf of Paula Pan. I think. I don’t know if you’ve ever been on with Paula. You’re always playing the part of Paula, aren’t you? I think
one time I was on with Paula one
time. Well, you’re on team Paula again, which as usual, Dana has good means, good news and bad news.
Which one do you want first?
I’ll take the, uh, good news
first. Well, the good news is you’re gonna get to guess last because Paula is re assumed her normal place in last place. Paula has one, OG has two, and Len has to, and because Len is our champion. That means yes. Hey, did you see
my, my trophy back here?
Oh. Oh wait, I haven’t got the trophy yet. og. Still waiting.
Oh, that was good. I knew exactly where you were going. And by the way, I’m so glad that like three days ago I finally set you the, the milk bar certificate. Yes,
yes. I got it. Thank you. I can’t wait
to try it out. Only a month after you won. It’s delightful.
I
tasted it, it kind of tasted like paper though. I thought it would taste a little better. That’s bad. The certificate, that’s Yeah.
Yes. No, there’s, there’s, there’s intermediate step led. Oh, okay. One step. But Len goes first, og, second, and, uh, and data. You’re gonna guess last, which means we just need a question.
Doug.
Hey there, stackers. I’m Joe’s mom’s neighbor, Doug. I don’t usually play the lottery, but I picked up a couple of tickets this week just in case. My motto has always been, you can’t win if you don’t play. And I figured I’d finally start applying that to things other than dating. I’ve heard that most people who win the lottery end up miserable, but there’s no way I would let that happen to me.
I’d be responsible with my money and only buy the things I’ve always wanted. Already made a list of things to stick to, just in case wanna be disciplined about this. Of course, I’ll add to the list depending on how much I win, but don’t worry, I don’t want anything crazy for myself. I’ve kept it modest.
You know, only a rotating bed with pink chiffon and zebra stripes, and a bathtub shaped like a clam. And for entertaining something basic like an all red billiard room and a 24 seat dining room with an original oil painting by Michelangelo or Rembrandt. Well, actually, probably both. And of course the backyard’s gonna need a makeover.
I’m gonna add little touches like Grecian statues and S-shaped hedges and just three swimming pools. Not gonna go crazy. Maybe add in something, you know, common man, like starting an annual carnival with rides and games and a beer garden in an Eagles cover band. Then I’ll make the news for being the lottery winner to be responsible and down to earth with their winnings.
Publishing houses will fight for the right for my story. Joe’s gonna have me on as a guest to teach all of you stackers, how to be responsible with your lottery winnings, and my memoir will probably become a bestseller. I can’t wait. I can already see it all happening. I got an outfit picked out for when I cash in my ticket and everything.
Oh God, yeah. Again, something small. I’m gonna wear a Canadian tuxedo with a bow tie just like James Bond. Here’s today’s question. Really? Yeah,
it’s, I didn’t know there was a question attached to this. I think we’re outta time, aren’t we?
You probably guessed the question by now, but just in case you haven’t, what is the highest lottery jackpot in US history?
Oh, I’ll be back. I’ll be back right after. I see how much it’ll cost to add an extension on my house for a video arcade and like a pony training room or something. This is
something small, something common man like that. Uh, this is interesting because Dana, this might be the time, this is recent enough.
That maybe going last isn’t great. We’ll see. Len, do you remember, do you remember when you won the biggest lottery?
Yeah, I, you know what, right down the street from me, there was a, one of the, was it Powerball winners? This was maybe four years ago, three years ago. It was huge and it was over a billion. Uh, and it was like right down, this was the seven 11 right down the street from you here.
So that was where the winner was. And the owner of the seven 11 only got, I think, a million bucks for, for still selling that. But still it’s pretty cool. That’s pretty cool though, knowing that the, uh, winning ticket was right down the street from me. I’m not giving anything way by saying, I know it’s over a billion dollars.
Did you say us or, or just in the world? Doug. I
said SI actually believe it may be in the world though.
Okay. Uh, I can’t, but we will say us. It could be the world. Okay.
But the question is us. I know it’s over a billion. I know that for a fact, but did it get over 2 billion recently? I don’t know. I have two numbers in my head that it’s one on, uh, I don’t know if it, if one got over 2 billion.
I think it probably did. I’m gonna say two. I’m just gonna say $2 billion and I’ll let OG and Dana, uh, figure out which side they want to go.
Well, OG you’re first. Which side of that are you taking? Well,
as a matter of fact, happen to have the winning tickets right here.
Can’t win if you don’t play. I too remember this. And just for clarification purposes, this is the advertised jackpot, not the after payout. And Yes, right. Advertising. The billboard number, not the gross, not net, not the, uh, present value number. And
this scheme is so big. By the way, it was gross Doug. It was
totally gross.
Super gross. Um, I think it’s slightly less, 1700000001.7. Billion dollars going
a little south of it. Dana, what do you think? Ooh,
this is tough because, but even before Len said anything, my initial reaction was, I think it was over a billion, but I don’t remember it being, oh, it’s over a billion. Close to two.
Well, I’m gonna go with 1.6
goes for the under. It’s going for the under. We’ve got Dana 1.60 G 1.7. Len is at 2 billion, rounded to 2 billion. We’ll see who’s right in just a minute. Len, you kicked it off with 2 billion and you had a thought.
Well, my thought was, ’cause remember I said I had two numbers and, and I have to be careful when I do this because you know I’m going first.
So it’s always, you have to kind of, my first number was 1.75 billion, which I think is the actual number, but I was trying to play the game. I, I, I think OGs got this one. Ah, og. Do
you think you got it? Uh,
I’ve, you know, confidence is what a man feels before he learns all the facts. So,
um, and we get reminded that every week here on the trivia
question.
Very confident right now, but we’ll see. I was pretty confident last week and got hosed,
so we’ll see. Dana feeling good?
I’m feeling pretty good. 1.7 is a lot, but maybe that was
it. Maybe we’re about to find out Doug, who wins this shindig. Well, I’ll get
to it eventually. Joe, you just gotta sit back and relax and just listen.
Just get on the ride
and see. And we thought Uncle Glenn was bad.
I know. He always chastises
me, huh? Hey there stackers. I’m Daydreamer and future lottery winner. Joe’s mom’s neighbor, Doug. During the break, I went out and got a new safe to keep my lottery tickets in until the drawing. I can’t risk someone breaking in rifling through the freezer and finding the empty ice cream container that I hide all my valuables in.
Dammit. Anyways, today’s trivia question is what is the highest lottery jackpot in US history? The answer. Of all the lottery tickets you can buy, Powerball is by far the most popular with nearly 200 million people playing each year. Most people opt for choosing their own numbers, picking everything from lucky numbers to numbers from fortune cookies and even numbers that came to them.
In a dream, the average jackpot hovers around the $140 million mark. I mean, why bother at that point? But the highest jackpot in US history went to a single winner down the street from Len who hit it
big. Oh, it was, it was the one for me.
How big did he hit it? Well, he hit it for uh, 0.44 billion more than what Dana guessed, 0.34 billion.
More than what OG guessed. And just 0.04 billion more than what Len guessed, because the jackpot was $2.04 billion. And that means Uncle Lenny is our winner.
Wow. Wow. Alright. It was over two bills, some
cash. Wow. It was two
bills. It’s a nice start, but too bad you can’t retire on it. That
one wasn’t the one down the street from me though.
The one down the street from me was like 1.4 billion.
I thought,
Joe, do you remember the person that we knew that won the Powerball that worked with
us? Uh, I remember my client that won. Oh, how much? Wow. Wasn’t that person. I don’t remember how much they won because most of it was gone by the time they became my client.
And by the time
they got to you
Yes, they pulled a dunk. It is actually the only time in my entire career. I advocated that my client sue their former advisor because the advisor had put all of their money into annuities, which were right at the break point of how much. So there’s this commission that Dana, you were alluding to earlier about all these sales techniques, and instead of having one annuity, they had like 35 annuities so that the advisor could maximize the amount of money to them and get this.
Then before the surrender charges were over, ’cause these annuities had surrender charges. The advisor was advocating they take streams of income they didn’t need out of the annuity, triggering the surrender fees and taking the proceeds and putting them in new annuities so that they got commissions on that.
It’s a gift that keeps on
giving. Wow. Wow. It’s
the gift that keeps on giving. It was criminal, it, it was completely
criminal. I had one more with my coworkers. There was a, this was right before I got hired into the company, but the coworkers went in, it was right after California had, its started its lottery up and there was like 20 of ’em went in and they won.
And after taxes and everything, they, each one got like $8,000 a year for 20 years or something like that. Eight or $9,000 a year for 20 years. So it didn’t make ’em rich, but they had fun with it, you know? Yeah. That’s
OGs bar tab.
I had a client at a CPA firm I worked at, and they had won a lottery. They had a 20 year, they chose a 20 year payout.
It was over a hundred grand a year, but they came in three years from their last payment. All of a sudden they had nothing. Right? Oh, no. They had three more years of payments and now they were trying to figure out what to do and, and so it just, it stuck with me as like,
wow. Always take the lump sum. Yeah.
Yes. That way if you’re gonna blow it, you blow it all right away. I have a, there’s never a doubt that’s what I would do.
I have a
cousin who won before the multi-state, uh, lotteries became a thing. So it was an individual state, and I can’t remember if it was Florida or Michigan, but they won 9 million. To me, the funny part of the story, and I’ve told this story in the show before, but it’s been a while, was that I was right in the middle of a three day offsite with a, with senior leadership team of a large company doing a three day total quality management seminar.
Um, it was kind
of all the rage. tq Oh my gosh. Yeah, it remember that Len,
remember that was all the rage in the ear, like early to mid nineties. Yep. So we’d all go to offsite, we’re in a hotel room and on, and inevitably when I, when I was doing these things, inevitably by the end of day one, there were always a couple of doubters who were just grumpy to be there, and they hated all of it.
And at the end of day one, somebody just got pissed and like, I’m so tired of this. It’s all bs. There’s no such thing as total quality. It can’t be achieved. This is a waste of all of our times. And it just, it always brings the room down. And I’d done it enough by then to know it was coming. And he said, it’s like winning the lottery.
Sure it’s possible, but does anybody in this room actually know anybody who’s won the lottery? And I had no answer. I go home that night and on my drive home I get a call from my mom saying, your cousin just won the lottery serendipity. I walked in the next day like a badass. I. And I’m like, yeah, I know somebody.
It was a, it was a great thing. Hey,
uh, one more
thing that always gets me with the lottery. People who play the lottery, especially when it’s getting up there to like a billion dollars and people will buy a hundred tickets or 50 tickets. I’m thinking, do you even do statistics? I mean the difference between, you know, your chance of winning is one in a billion or 10 in a billion.
It’s still infinitesimal. So why waste all just buy one ticket and see if you’re gonna hit it And there you go. Buying an extra 10 or a hundred of ’em doesn’t really
Yeah. You don’t feel 10 times the excitement. No,
no. Buy a ticket and maybe you’ll
get lucky. Yeah, we’ll get lucky if we get to the second half of the show.
The second half that reminds me of a carnival I went to in Arkansas. Once. Second
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deposit accounts.com.
Uh, Dana, you know what happens when you go to deposit accounts.com. I
don’t know, but I think you’re gonna tell me.
I am. It’s amazing how this works. And I will tell you, Dana, you can compare more than 275,000 deposit rates from over 11,000 banks at credit unions all for free.
And I have it, uh, open right now. If you go to deposit accounts.com, you’ll see what it is on the day this is released. We record this a little bit ahead of time, but today the National average savings account has ticked up to 0.52%. So just over half a percent. That is up to 100 since, uh, last week when we looked.
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He also presents a solution and he says. How can one avoid being miserable and wealthy? It turns out that redefining the game-winning trophies is a great start. And Dana, he begins with the difference between Western society and eastern society. Western society says more things when I die equals more goodness.
Eastern society says, shedding your things to find your true self is a better way to go. Sounds like he’s siding with Eastern philosophy. You agree?
I agree a hundred percent. I think simplifying, whether it be your finances or the actual stuff around you is huge. It’s, I don’t know you, we’ve all probably known people, whether you see the hoarder shows.
I don’t know if you’ve ever known any personally. I have. And, and they have an unhealthy relationship with their stuff, right? There’s it’s emotional baggage that’s coming along with all of this stuff. And so I think it’s, it’s huge to simplify, you know, with clothes, I have a one in, one out rule. I probably have the most streamlined closet, the out of event, most females.
It’s just crazy. Like, I’m like, no, if I can’t see it, I won’t know I own it, you know? That’s it. One in, one out.
Mine’s not streamlined yet, but it’s much, much better than it was just a couple. I just said, this is madness.
I don’t know, Joe. I’ve seen that sweater now three weeks in a row. I think you’ve got,
that’s
because it’s winter and Texarkana two streamlined.
It’s a two streamlined. This is my favorite sweater. That’s why Doug put the T-shirt under it, which today it’s Moxy Cola. Is a different, uh, different T-shirt every time Len, after retirement, have you found yourself streamlining or going bigger?
Oh, no, I’m streamlined. I’ve always been streamlined and I’m still streamlined.
And yeah, I probably, if anything I’m getting more streamlined even, even more. It’s, it’s, I’ve always been about minimalism, living far below your means, not having a lot of stuff. And, uh, it’s just, you know, it’s great. I, I know people that used to have, I’ll, I’ll use my late grandma for example, God rest her soul, great woman, but she had, she must have had 200 pairs of shoes in her closet and I used to think, grandma.
You don’t even get out of the house.
Why do you have 200 pairs of shoes? But, you know, I, I, you know, how do you manage that on top of everything else in your life? I mean, you got the shoes to manage and everything else. It’s like, it’s, isn’t it, it better just to have three or four pairs of shoes and be done with it?
I mean, that’s just. It’s so easy, you don’t have to worry about it. It’s when you have large amounts of things that you have to, there’s a management component in there that just complicates things, you know? So, I dunno, I
remember Sha Mullaney talking about that at a campfire. Sha Mullaney, who is, uh, describes the tax code very, very well for frugal people and talked about the, the tax upside to being frugal and said that, A, you’re not buying things at this top tax bracket, right?
As you earn more and more money, your tax bracket goes up and that last thing you buy at the end that you really didn’t need is something that’s being taxed in the, you know, 30% plus range, where things down, those original things, your essentials are taxed much, much less. But he said something even more dire, which was if you go into any shopping mall, then you go into any store.
No matter whether, whether somebody takes care of the stuff or not, someday, every single thing in this store is gonna be in a landfill. And now I think that every time I go to any mall, I’m like, it’s, it doesn’t, it’s 10 years, 20 years, 30 years, 40 years from now, every single thing in this mall is gonna be in a landfill.
And you’re like, what’s the point? Like, why do I have all this stuff? Oh, gee, I know in your life, the time that we’ve known each other, you’ve turned, you’ve turned really much more toward experiences. I remember Tracy McCubbin, the great organizational expert, talking about how stuff depreciates, but experiences appreciate over time.
It’s a constant struggle because I like, I like stuff my, my only addiction is collecting wine. Right now, which is,
uh, so you’re working hard to consume it. Make sure that
it’s kind of unhealthy on all fronts from the, from the monetary aspect and, and also the cons consumption aspect of it. But we’ve started to spend a lot more attention on this in terms of where we’re spending our time and where we’re spending our money.
I went through a thing a couple of weeks ago where I went through all my drawers. You were talking about your closet cleaned, all that stuff out, and then I took all the hanging clothes and I got this trick from, I don’t know, some show or something, but flip the hangers around backwards, which annoys the hell outta me, by the way.
And you set a timer. So basically six months from now, whatever, you go back into the closet, everything that’s still facing the wrong direction, you can take off and send away, donate, or, you know, give away. Because if the hangar hasn’t switched, you haven’t worn it yet. And if you haven’t worn it in six months, you’re not gonna wear it in the next six months.
So it’s okay to make it go away. We’re definitely trying to think about it much more in a simplifier instead of a multiplier type of type of thinking. And that’s, I mean, I think that’s what I do for work is simplify things. You know, we try to do that for the show. I try to do that for clients, but for some reason in our, uh, in our personal lives, it’s been a little bit more of a struggle for sure.
But, um. But at least I’m conscious of it now. Hey Joe, real quick. Yeah. Len,
every week I have a poll on my blog that I ask the readers and, and just outta coincidentally, two weeks ago I asked him this question, do you believe it’s better to direct most of your spending towards experiences rather than material possessions?
And there were 1800 responses. Do you want to care to guess how many people said, uh, it’s better to spend the money on experiences? 80, 20, 80, 20? No, it was 50. I had 52%. Said only 52%. I thought this was low. Only 52 is low. 52. Wow. Yeah. And 21 said no, and then the other 27 said they weren’t sure. Wow. Isn’t that interesting?
I really thought the number would be about 80 20 as well. Yes. I was really shocked at
that. And maybe it’s ’cause I’ve bought into that. I bought into happy more and more where I’m like, no, it’s all about happy, not about, uh, special. And, and, and buying things has never made me much happier. Dana. I.
Oh, I was gonna say, I wonder if they interpreted that question material things more like art or collectibles or, I mean, for 27%, you know, it just makes me wonder like, wow, did they understand really what
you were getting at?
I. I, yeah, I don’t know Dana. It was really surprising though. I
was really
shocked. Retail therapy is powerful, man. You’re sitting there on the couch and you’ve got an opportunity to buy like a weighted blanket or an automatic cheese straightener and that
stuff. I love my weighted blanket, by
the way. I mean, you get instant gratification versus having to wait for nine months and schedule it and then work gets in the way.
And next thing you know, you’re working when you’re on vacation in, you know, Thailand, but you get your little thing in Amazon and you’re happy. I don’t know. I kind of get
it. I do love when it comes to experiences. What, uh, we did a piece from Jonathan Clements, the former Wall Street Journal personal finance columnist, where he talked about Doug.
Remember this, talked about booking trips way before you go, because part of the deliciousness of the experience is also the anticipation of it happening. I know on your mind a lot, you’re about to go on a trip and, uh, uh, several in just in just a couple days. And I know you’ve been thinking about it more and more.
’cause I’ve been hearing about it the last few weeks. I’m worried
about it because it, like, it’s almost like New Year’s Eve. This trip can’t possibly be as good as what I’ve built it up in my mind over the last three months. I’m so excited about it. But, uh, yeah, there’s a lot of endorphins to be had.
Endorphin harvesting is what I’m doing right now. Are you going to Bali? Uh, yeah, I know it. ’cause that’s what Stacking Benjamins people do is go to Bali. I know the bar’s high
Doug, the bar’s high.
They, they don’t let me go there. I, you know where I go, Len, instead of Bali, Idaho.
Oh, well that’s a, yeah, that’s a good place.
Too close.
Have you ever been to Bali, Idaho? It’s a great town. It’s like Paris, Michigan. Can’t even be Paris, Texas, which is the second most, uh, popular Texas out there. There’s a second piece to this that he has, by the way, which is accolades and pleasing Strangers were influential to me a few years ago, like drinking seawater.
This desire can never be satisfied. I gotta assume, Dana, when your boss said that in the nineties, it will never be enough. There was a piece of you, I mean, these bosses say this by design that wanted to go, oh yeah, I’m gonna prove you wrong. When did you make the switch from? No. You’re, you’re, you’re like, Nope.
Were you out right away? No, I
had, I remember thinking, oh my God, what have I done? This is not the place for me. I just knew it wasn’t the place for me. And so, yeah, that for me was just like an instant sinking feeling in my stomach. Like I’m very culture oriented. Like this is like, I wanna be happy coming to work every day.
Think about how much time we spend at work. It’s a lot of time. It’s a lot of our energy and effort and so, you know, I wanna be happy doing it every day and, and happy showing up there and have people that are feel supported around me. And so for me that was innate. I mean, I sent myself a postcard when I was like 20 saying, remember, spread a little sunshine everywhere you go.
I think it’s like my nature, right? It is just like, yeah, that’s my nature. Yeah. And so for me it was instant. Like, this place is
not for me. So what do you do to make sure that you chase happy?
I don’t even know if the word chase is right, but like today, I mean, I started this off saying, you know, I got to run an errand in the middle of the day actually prepping for this podcast.
Help me think about that. Like, yeah, you know what, it’s okay. Take an hour off in the middle of the day and go get this done. And, and so those are the things of, you know, scheduling time to go play pickleball. We just went up to Colorado and took a few days off and you know, you have to schedule those things in.
I have never been what I call a workaholic. You know, I probably work on average more than 40 hours a week, but rarely more than 50. And so to me, you know, of course there’s those times where client stuff comes up and you gotta. Dig in and get it done. That’s what they pay us for. You know, you might be working all weekend on a big decision that a client has to make, but there’s other times where it’s like, all right, I’m done at three, I’m going home.
So finding that balance and for us, we encourage our staff to have that balance or very supportive. No one has to clock in and answer where they had to be for the last two hours if they need to take their kid to a doctor, you know, run an errand or take the car in. Those are the things that I, I think are super important.
Having autonomy.
I’m still stuck on the fact that she said she prepped for this,
for this podcast. I thought the same thing.
Damn.
Well, I read the article. I’ve realized too, Dana, that this is that, that I love what I do, but it’s a marathon and I really despise being here past five o’clock. Past five o’clock I am.
I want nothing to do with it until 7 30, 8 o’clock the next morning that I’m back. But it’s gotta be that. And I don’t work hardly at all on Tuesdays, like four days a week and then take Tuesday to go have that free day and do something else is magic for me. Len, how do you chase happy? And once again, chase might not be the right word.
Yeah, the
big revelation for me was to stop pleasing others and, and please yourself first. I mean, that’s what turned everything around for me in my early thirties. It took me until I was about 32 to figure out everything I did was to please others until around 32, the switch one off. And I said, this is, you know what?
It’s my life. I’m gonna do what’s good for me and what makes me happy And everything changed when I changed that mindset. For me, that was huge. Now, the one thing I do wanna say about working along, it takes experience to know what’s really important, what’s not important. So I know when you’re first starting off at work.
You might not know when it’s for staying extra, uh, at work. You know, do I have to stay two or three extra hours at work today? Sometimes that takes experience to know whether you really do. If you’re not sure, stay at work. But over time it won’t take too long. But within a year or two you’ll start figuring out, is it really important?
Do they really need me today to stay an extra three hours or can it wait till tomorrow? Just spend some time. You will learn the longer you work, what’s truly important. Most of the time, I would say in my job, I’d say 85% of the time if somebody said, Hey, we need you to stay an extra hour or two, I realize, no, that’s not true.
The place is not gonna come crashing to the ground if we wait till tomorrow morning to pick it up. So, um, try and figure out discerning what’s truly important. Most of the time it’s very rare that you actually have to be there for an extra hour or two. It can wait.
It’s so funny, Len, same for me, early on in my career it was what goes on the task list.
And now increasingly it’s what comes off. Yeah. Like what is the, what is the thing that just, I, I don’t, I don’t need to do og How about you fencing off happy.
Ultimately, I think that there’s a lot of truth to the phrase of, you know, if you’re doing what you like to do, then you’re not actually working at all.
You know, you’re not working a day in your life type of thing. I think we all know people that just continue to do what they want to do, and there is no end of that because they’re doing the things that they wanna do. You know, Dana, you were talking about your doctor client who was doing what he wanted to do, and you’re telling that story, Joe, I was thinking about the physician that you and I knew who worked well into his nineties.
I don’t know if he was doing it because he financially had to or not, but he, when we interacted with him, it certainly looked like he was, he clearly loved it. He was doing what he wanted to do. He was a pediatrician to our kids when he was 95 years old, and he just loved doing, my grandfather worked when he was.
92 years old, he was still at the office. He wasn’t working. He wasn’t, you know, hauling paper around. He was, he was there, he was doing what he wanted to do.
But you know what’s interesting that he did though, at that point? ’cause he was, I mean, I know enough about this guy, oh gee. That he’s well beyond financial independence, not a workaholic.
I mean, he made it, I think, either two or three days a week that he would work. And it was just to get that Yeah. Love and feeling of doing what he loves to do. You know, just continuing to Absolutely. To, yeah.
Yeah. And that’s definitely not workaholic. So many people are focused on like, oh my gosh, you know, you gotta retire when you’re 60 or 65 or 70 or whatever.
It’s like, well, you don’t have to. You can do whatever it is that you wanna do. The nice thing about planning on working until you’re 75, if you’re an entrepreneur and you’re like, I’m gonna keep doing this, is, guess what, you don’t have to save as much money, which means you don’t have to work as hard, which means that you can have fun now too.
You don’t have to. There’s like all these. Great things that come from expanding your time horizon. You know, we’ve learned in Coach, you know, it’s underestimate the stuff that you can get done in 25 years and overestimate the stuff that you do in one year. Just take a longer time horizon to get to do the math and it all works out always.
So I think Lynn said it best. Just make yourself happy. If something’s not right, just fix it for yourself. The world will still continue to turn. Well, what I
found out, gee, was the big, uh, paradox. Um, and this is also, uh, partly from Strategic Coach, but just it has been amazing is the more I put fencing around my work hours and avoid work workaholism, the more stuff gets done when I show up at work.
The more stuff gets done in my family life, the more the important stuff in my life happens. When I focus on better results. Yeah. When I focus on happy versus impressing other people, all the magic just begins to align itself.
What’s the saying? Work expands to fill the time allotted.
It totally does.
Absolutely. And I, and how many of us have known workaholics Dana, that just you, you can feel it, but they’re so wearing the badge of, I work harder than you. That you can’t convince them that there might be a better way. Hopefully it’s convinced a couple of our stackers though, to look a better way. ’cause there’s no sense of being miserably wealthy.
I hope that helped you not become miserably wealthy, but I also hope that the things that each of the three of you are doing outside of here is gonna help people too. Well, og let’s start with you. What do you got going on this weekend? My friend kid
stuff like crazy track meets baseball games. We are elbow deep in spring.
You’re playing dead school sports right now. You’re being dead. Yep. Yep. I’m well. My middle kid plays baseball and not my most favorite, you know,
sport I, you’re gonna say not my most favorite kid.
Not my most favorite kid either tied. They’re all tied for first and last at the same time. That’s really weird.
You
do remind them sometimes they’re tied for last, don’t you?
Yes, I do. Yeah. Who’s your favorite? I’m like, well, you guys are all tied for either first or last. You get to decide today which one that is. But I wheezed myself into being the official team scorekeeper. So I’m learning how to score baseball on an app and I keep all the stats on max preps.
So I’m engaged in the game. I’m watching my kid taking videos of him too. But you know, I gotta watch every ball on strike. And you know,
consequently the, the texting volume from OG to me has skyrocketed since he became
does a baseball gay, gay guy. And I’m like, wait, tell me the difference between a pass ball and a wild pitch because I got three of ’em.
I need to score and I don’t know what to do. So it’s fun times. That’s what’s going on this weekend. Len,
what’s going on@lenpenso.com man?
Well, this week, you know the advantage of having blog for. Gosh, how many years? 16, 17 years is I can go back into the archives score every once in a while and pull out some gems.
And this week I’ve pulled out one of the all time great gems where we discussed the day that we went into the mailbox and we got the phone bill. The, and the phone bill was, normally it comes in a regular little teeny number 10 envelope. This phone bill came in an eight by 11 Manila. Oh no. Uh, envelope.
Oh no. And it was about an inch thick. And we opened it up and we realized that my son went on a phone call Spree. This was before they had a, you know, all you can talk or whatever plans. And, uh, the bill was 140 some pages and Nice. It was a thou over a thousand dollars phone bill. So, uh, I just. Detail, the whole story there@lenpenso.com on my son.
Wow. And the thousand plus dollar phone bill. Wow. Yes. A
cautionary tale.
Not a good day at the Penso Family house.
How soon after that did he end up working at the car wash to cover
that? Yeah.
Dana, thanks for hanging out with us again. But, uh, I have the very important question. How many steps did you walk?
Okay. How many steps? I’ve got my calculator out, so right now I’m at 42 67, but when you asked me, I was at 1457, so Oh, it was 2,810.
Wow. Just over you. But Dana, you, you had inside information. I did. You know how fast you walk, which really means I just beat Doug. That’s all that we really have to focus on.
You guys suck. So what’s going on in sensible money? What are you guys doing? You’re always doing some workshops, some training, some fun thing. I.
We are. So right now I’m getting ready for our next webinar, which is March. I can’t remember the date, maybe the 28th, but it’s with Fritz Gilbert, who is the founder of the Retirement Manifesto blog.
And his work ties into everything we’ve been talking about today in terms of really finding purpose and intentionality in retirement. You know, I’ve never seen anyone write about it as well as he does. I love this, you know, idea of, he set different, I wanna call it like frameworks around how they were gonna approach retirement.
Things like remain curious, you know, be open-minded. And so they had this, that’s where his manifesto came from. And so I get to do some work with him and prepping for our upcoming webinar and we’re gonna be talking about a lot of that kind of stuff. So that’s fun stuff for me.
We did a, uh, a topic of a recent Friday was Fritz, uh, Len, I
think you were in that conversation two weeks ago.
Yeah, two weeks ago. We, we covered it. Yep. Yeah. Talked about
the, uh, planning beyond the numbers. Mm-hmm. Yeah. Planning for all the emotional stuff. Great stuff. And, uh, people can find details though@sensiblemoney.com. I
assume they can. They’ll find the webinar on sensible money.com. Scroll to the bottom left.
You’ll see
it. Awesome. And if you’re walking the dog right now, you know what, just go to our website, stacky Benjamins dot com and hit the, uh, show notes link for today’s show, and you’ll find both what Dana is up to with Fritz and Len Benzo’s, amazing thousand bajillion dollar phone bill story there as well.
All right, that’s gonna do it for today. Let’s put a bow on this. Doug, what should we have, uh, what’s on our to-do list today? Well,
Joe, here’s what’s stacked up on our to-do list today. First, take some advice from our panel, hoping to be special. Maybe happy is a better move. Second, take some advice from me.
If you’re not happy with what you’ve got, you’re not gonna be happy with what you’re gonna have. Happiness comes from within, but what’s the biggest to do? Always make sure you set the code on a new safe before you lock your valuables inside. Otherwise, you’re gonna have to haul your safe down to the seven 11 to claim your millions.
Thanks to Dana Ock for joining us today. You can find out more about dana@sensiblemoney.com. We’ll also include links in our show notes at Stacking Benjamins dot com. Thanks also to Len Penso for joining us today. You can find Len at len penso.com/telephone bills. And thanks also to OG for joining us today.
Looking for good financial planning. Help head to Stacking Benjamins dot com slash OG for his calendar. The show is the Property of SP podcasts LC copyright 2024, and is created by Joe Sulci High. Our producer is Karen Reine. This show is written by Lisa Curry, who’s also the host of the Long Story Long podcast.
With help from me, Joe Kate Yakin, Karen Reine, and Doc G from the Earn and Invest podcast, Kevin Bailey helps us take a deeper dive into all the topics covered on each episode in our newsletter called the 2 0 1. You’ll find the 4 1 1 on All Things Money at the 2 0 1. Just visit Stacking Benjamins dot com slash 2 0 1.
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I’m Joe’s Mom’s Neighbor, Doug, and we’ll see you next time back here at the Stacking Benjamin Show.
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