When Is "Good Enough" Actually Good Enough With Money? SB1884

Summary

The Stacking Benjamins Show

Episode: When Is "Good Enough" Actually Good Enough With Money? (SB1884)

Date: August 14, 2026
Hosts: Joe Saul-Sehy & Josh ‘OG’ Bannerman
Guests:

• Jesse Kramer (Personal Finance for Long Term Investors Podcast)
• Carol Ann Desiderio (Boston “Benjamins After Dark” Meetup Coordinator)
• Maya Corbic (Wealthy Kids Club)
• Joe’s Mom’s Neighbor Doug (Trivia/Panelist)

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Episode Overview

This episode dives deep into the question: “When is ‘good enough’ actually good enough with your money?” With a focus on the dangers of over-optimizing (or hyper-optimizing) in personal finance, career, investing, and family life, the panelists bring relatable stories and practical advice about getting the balance right between managing, optimizing, and simply living your life. Drawing inspiration from a viral podcast clip about a third glass of wine “ruining a week,” the episode explores when striving for perfection becomes counterproductive.

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Key Discussion Points and Insights

The Dangers of Over-Optimization

Panelist Stories on Over-Optimization

• Maya Corbic (15:45):

  • Over-budgeted due to upbringing in poverty and industry messaging, leading to prioritizing saving over health (e.g., skipping vitamins to stay “on budget”).

    “We don't need to budget this tightly. It’s sucking out every joy and fun out of life.” – Maya (16:22)

  • Realized she could relax as her financial position improved.

• Carol Ann Desiderio (17:48):

  • Had a “scarcity mentality” from raising kids as a single parent, later shifted to aggressively catching up on retirement—at one point saving 67% of her salary, but sacrificing current quality of life.

    “I got to the point where I had, like, a 67% savings rate...There was never any money to do anything because I felt like I was catching up.” – Carol Ann (18:43)

  • Eventually decided to “slow down,” recognizing the need for balance and to not postpone joy.

• Jesse Kramer (20:10):

  • Detailed tracking of car mileage and fuel usage—tracking for “optimization’s sake” led to elaborate spreadsheet work and “drafting” behind trucks on highways to save gas.

    “Some people think about credit card points; I'm just all about mileage, baby.” – Jesse (21:21)

How Optimizing Affects Different Types of People

• Numbers People & Over-Optimization (23:32):

  • Jesse (engineer): Numbers-oriented people struggle more with “good enough” because there’s always a mathematically better answer—but real life is about “mushy” variables like happiness and fulfillment, not just math.

    “The act of optimizing breaks down when it collides with the soft, mushy stuff between our ears.” – Jesse (24:08)

• Is Optimization Taught or Inherent? (25:27):

  • Carol Ann shared that kids often learn optimization from watching parents—sometimes to their detriment by making life a rushed checklist.

Game: The Optimization Olympics

A rapid-fire debate on whether certain optimization efforts are worth it:

• Driving 15 minutes to save 8 cents on gas:

  • Unanimous: Not worth it due to wasted time and effort.

• Choosing between two stations on your usual route:

  • Carol Ann: Yes, it's worth it.
  • Jesse: Not paying enough attention to bother.
  • Doug: Not willing to go out of his way.

• Opening credit cards for $500 bonuses:

  • Jesse: Maybe, if strings are minimal.
  • Carol Ann & Maya: Usually not worth the hassle/strings attached.

• Moving $20,000 to a bank for 0.2% higher interest (31:09):

  • Maya & Carol Ann: Only if it’s a permanent rate and low hassle.
  • Jesse calculated the gain ($40/year); not worth the trouble unless dissatisfied with the current bank.

• Taking a four-hour longer flight connection to save $112 (32:39):

  • All: Not worth it—time with family and comfort are more valuable than small, incremental savings.

Teaching Kids About Optimization (49:00)

• Scenario: Your 12-year-old wants to use saved money ($200) to buy $150 sneakers.
  • Jesse & Carol Ann: Let them spend it—it’s not “harmful,” and there’s a lesson to be learned (either joy or regret).
  • Maya: Agrees—kids have to learn from experience, and parents should follow up after the fact for meaningful conversations.

    “Personal finance is called ‘personal’ for a reason...kids know when they've made a mistake.” – Maya (51:28)

The Five More Years Syndrome—When to Stop Optimizing Retirement (52:09)

• Question: You’re financially ready to retire, but hanging on would give a bigger safety margin. Is it worth it?
  • Carol Ann: Struggling with exactly this—her numbers work, but it’s hard to actually “pull the trigger” due to desire for professional fulfillment and lingering caution.

    “How much Russian roulette do you really want to play with the time you've got left?” – Carol Ann (52:53)

  • Maya: Facing the same question—created a career she loves but is conscious of not deferring “fun” and shared time with her husband.
  • Jesse: Flip “one more year syndrome” into “one less year syndrome”—remember that every extra year working is potentially one less year of health, family, or freedom.

    “Once your numbers say you’re good enough, pivot your thinking to what you are sacrificing by working more years.” – Jesse (56:39)

Can Optimizing Investments Make You Worse Off? (57:37)

• Jesse: Emphasizes John Bogle’s research—broad asset allocation is 90% of returns; people waste time optimizing minutiae (e.g., stock picking, minor bond tweaks).

  “Lose sight of the forest for the trees...you’re really getting a lot less bang for your buck.” – Jesse (58:53)

• Carol Ann: Index fund investing is best; “My money is too important for me to bet.”

  “To me, when you get to this point, it feels like you're gambling...I just don't want to risk it.” – Carol Ann (59:57)

Over-Optimization Beyond Money

• Health:

  • Carol Ann: Investing in health is vital, but you can get obsessive (“third glass of wine isn’t going to ruin your life!”). The point is overall health and “health span,” not step counts or going overboard.

    “If you're spending money on your health—vitamins, gym membership—that's an investment in the bigger picture.” – Carol Ann (61:11)

• Productivity:

  • Jesse: Productivity hacks often have diminishing returns; work expands/contracts to fill the time, so optimization might just be an illusion.

    “These optimization productivity hacks don’t always seem to work for me.” – Jesse (62:58)

• Procrastination in Disguise:

  • Maya: Over-optimization becomes procrastination. Many consume loads of personal finance content but never take action (“just open the account!”).

    “Let’s just get the move on—rather than optimizing everything, start with something.” – Maya (64:56)

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Notable Quotes & Memorable Moments (w/ Timestamps)

• “It’s sucking out every joy and fun out of life.”—Maya (16:22)
• “I had a 67% savings rate...there was never any money to do anything.”—Carol Ann (18:43)
• “Some people think about credit card points; I’m just all about mileage, baby.”—Jesse (21:21)
• “These optimization hacks don’t always seem to work for me...it just leads me to the conclusion that maybe it’s less about the hack and more about some other factors.” – Jesse (62:58)
• “If you’re spending money on your health...that’s an investment in the bigger picture.”—Carol Ann (61:11)
• “My money is too important for me to bet.”—Carol Ann (59:57)
• “Let's just get the move on—rather than optimizing, start with something.”—Maya (64:56)
• “Once your numbers say you're good enough, really pivot into thinking about what you are sacrificing by working more and more years.” – Jesse (56:58)

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Timestamps for Important Segments

• (15:45) – Maya’s story of over-budgeting & “optimization gone too far”
• (17:48) – Carol Ann’s journey from scarcity to excessive saving, to balance
• (20:10) – Jesse’s account of extreme fuel and mileage tracking
• (23:32) – Numbers-oriented people and difficulty with “good enough”
• (27:44) – Optimization Olympics: Debating everyday optimization choices
• (49:00) – Should kids be allowed to “waste” their own money?
• (52:09) – Five More Years Syndrome: When to stop optimizing retirement
• (57:37) – Over-optimizing investments: does it help or hurt?
• (61:11) – Health optimization: when does self-improvement backfire?
• (62:58) – Productivity optimization: diminishing returns and illusion
• (64:56) – Procrastination disguised as optimizing

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Conclusion & Takeaways

• Over-optimization can suck the joy out of life, whether about money, health, or productivity; “good enough” is usually better than perfect.
• For children and adults, experience and small mistakes are valuable for learning—don’t shield yourself (or your kids) from every bump in the road.
• Know when to value time and fulfillment over incremental financial gains.
• Taking action beats endless optimization—start, adjust, and enjoy the ride.

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Closing Challenge

Doug’s recap advice:

“Don’t lose sight of the fact that a big part of the goal is happiness.” (68:43)

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For more info on featured guests, resources mentioned, and meetups, see the show notes at stackingbenjamins.com.

Transcript

[A]

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[B]

Oh, good morning, Winnie the Pooh.

[C]

Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show. Foreign I'm Joe's mom's neighbor Doug, and on today's show, I got my stopwatch rolling because I'm gonna time out this introduction to see how it goes. Seriously, in this world of optimization, do you think optimizing this intro is a bridge too far or should I tweak it even more? That's right. Today we're asking when is good enough good enough? But that's not all, because we'll optimize today's show around my incredible trivia question. This going to amaze your friends, so have them gather around. And now a guy who loves impressing his friends by talking about just how old his car is. It's Joe. Oh, Saul. See, I. Dang it. I double tapped the watch at the beginning and now I got to do it all over again.

[A]

Don't you hate that when a good plan goes awry? Hey, everybody, I am Joe Salce High. Happy Friday to you. We have a phenomenal, phenomenal show today. We have a fantastic cast. We're going to talk about how do we actually pay attention to stuff. Should we optimize every little piece of our life or when is good enough good enough, in fact, And I'll get into this in a minute. I wrote a Fast Company piece on this, which kind of made me think about a broader topic on this and around your money. Because so often in the financial community we see people optimizing and a guy who's always optimizing who you just heard. And we're going to hear again. Mom's neighbor Doug is here. How are you, man?

[C]

Fantastic.

[A]

Today, Joe, optimizing the front end of the show. Feeling good?

[C]

Well, we're still working on it. I've still got a team of researchers working on it. But you know, there's, I've been. I try to optimize a lot in my life. Here's an example. You know, sometimes Late at night, you just need something cold and crunchy. Like you just. And usually the answer to that is cereal, right? Like, it's tough to beat a bowl of cereal. Like 10 o' clock at night and you just.

[A]

It's like the best worst decision ever.

[C]

Well, I mean, I do it healthy. I do cinnamon toast crunch.

[A]

Oh.

[C]

So I thought, well, we could do this better, right? There's a way to optimize this. You want cold? How about we make it colder? Throw the ice cream in there.

[A]

Oh, really?

[C]

Turns out that's over optimization. That does not. Doesn't work.

[A]

Maybe not enough. And a guy who. Speaking of ice, it is mid August and they're waiting for the first snowfall in Rochester, New York. It's Jesse Krabers here. How are you, man?

[D]

Man, I'm doing well. I'm doing well. It's still beautiful and summer up here. But I will say, a friend of mine, we were talking about trying to make maybe a hiking trip to the Adirondacks in like mid October, which is upstate New York, Beautiful mountains. But up at those elevations, mid October, you are flirting with snow and ice season. And who wants to hike on an icy mountain? So it's coming sooner than we want it to come, Joe.

[A]

Well, not here. It's 95 degrees still in Texas, so bring it this way, please, God. Upgrade. Even in mom's basement where it should be nice and cool, down here, it's still a crisp 85. Hey, question. Are you a Buffalo Bills fan?

[D]

Oh, yeah, I am.

[A]

Speaking of winter coming, let's talk about this before we introduce the rest of our cast. Your bills have a brand new football stadium and apparently it's already getting ripped for bad sight lines. And have you seen this?

[C]

Doug loves it. Tiny little screen. Yeah. As big as your iPhone. Yeah, the jumbo.

[D]

I take the summers off from following football. I'm a fair weather football fan, which is pretty funny to us speaking about the weather, but I'll have to look that up. It doesn't surprise me that people are already complaining about the nice new thing, though.

[A]

I know already, already. You can't have anything good there. You can't have anything good. You know what is good though? It's good when you can teach your kids about money. Also. And I'm super happy this woman's here. We have known her for a long time. She was one of the coordinators of our Benjamin's After Dark group in Boston. Carol Ann Desidero joins us. Carol Ann.

[B]

Joe, that was so awesome the way you botched my last Name like that. Thank you.

[A]

So it's desiderio.

[B]

It's desiderio.

[A]

Desiderio. What is a desidero? Desiderio. Among friends. Carolyn, I.

[B]

Hey, listen, I had to nail you on something, so there we go. I thank you for having me. Nice to see everybody. I'm happy to be here.

[D]

Carol Ann, I think. Didn't the Eagles write a song about your last name? Does it do desperado?

[B]

Desperado. Never mind.

[D]

Wrong word. We all make mistakes.

[A]

But, Caroline, you have had somebody say a desiderio. Why don't you come to your senses? Have you had somebody say that line before?

[B]

Not until this very moment.

[A]

So that's awesome.

[B]

Thank you for that. I'm never gonna not hear that now. Every time I hear that song.

[A]

You're welcome. Well, you're married to a musician, right? So that's true.

[B]

Yes, I am. Yeah. I'm sure Kevin can do something with that.

[A]

Well, let's chat about that for just a moment. You are one of the members of our bad group in Benjamin's After Dark group in Boston. So tell us about getting together with some other stackers in Boston. How's that?

[B]

It's been so great. We've been going a few months now. We are playing with times and dates just to kind of make things a little more accommodating for everybody. So we used to do it 6 to 7pm now we do it 6:30 to 7:30. It gives people a little more time to get there after work. And we also have changed it to the third Wednesday every month instead of the second to make it a little more accommodating for people's work schedules. So we're new and we're trying to get up and running and. And be a little more flexible. We're five months in, but we've had some great conversations and some repeat customers, including your own beautiful daughter who comes to our groups.

[A]

I gotta tell you, I love the young people that come. There's another awesome young lady who we can give a shout out, or first name maybe, who I just met at our quarterly meetup, our national meetup. And I'm trying to remember her first name.

[B]

Talking about Sue.

[A]

No.

[C]

Well.

[A]

Well, Sue's very young, but this is a woman in her twenties who.

[D]

This is great radio.

[A]

Great radio.

[E]

Yes.

[C]

Yes.

[A]

I'm not gonna remember her name because I only met her once. But she came to our quarterly meetup. She had come to your meeting maybe the month before. Maybe it was one that you missed.

[B]

Oh, was she the school teacher? Yes, I Can't remember her name. Oh, my God, this is terrible.

[D]

What does she teach?

[B]

Children. What? Elementary. Ish children.

[D]

Good answer.

[B]

She's one of the reasons why we're changing the scheduling of the meeting because during the school year it just doesn't work for her and we're trying to make it accommodating for people to be able to come out. And we meet at Hannah's Brewery on Main street in Melrose, which is an awesome place. They've been so accommodating to us. We love it there. It's a great space.

[A]

Awesome. Close to public transportation.

[B]

Close to public transportation. Close to the commuter rail. If you're in the Boston area, you can get anywhere you need to be. We are on the Orange Line, but also the commuter rail. Boston people will know what that means.

[A]

Yes, I was going to say, if you're in the Boston area, come on out. Take the Orange Line, the commuter rail, whatever it takes. Just come hang out with Carol Ann and everyone else. All right. This woman not only runs the Wealthy Kids Club, she has only about a quarter of a million people following her on Instagram. Our friend Maya Corbeck is back. How are you?

[E]

I'm good. I'm very good. Thank you for having me.

[A]

You just got back from a nice vacation someplace warm or cold?

[E]

Well, I live in Canada, so it. I guess it was warm, but it was up north even further than where I normally live. So in the cottage country. It was lovely.

[A]

Nice. Beautiful. Fantastic. Let's talk about Wealthy Kids Club. How does it work? What do you do?

[E]

The Wealthy Kids Investment Club actually helps families budget their money, manage their money better, and pursue their financial goals. Originally it was Kids only club, but then I started noticing because it's been operational for the last four years, I started noticing that parents were just kind of sticking their kids in the club, but they themselves did not really understand finances. And so it became a family oriented club where other families can meet families like them. It's this lovely experience where families get together and learn about finances and get their money better.

[A]

It's really fun. And that's what you lead to also, I think in your Instagram videos.

[E]

Yes, and it's funny actually, because the Instagram videos are done in a way that kids can understand them. But I find that a lot of parents are learning from them too, because they didn't learn this stuff when they were younger.

[A]

It is funny. I found that Maya just with Stacking Benjamins, is that we try to keep stuff 101 as often as we can because we often think that people understand what up in Canada like a tax free savings account is or a Roth ira. Here we just take that for granted and many people don't. They're afraid to ask which the more we do this, the more we find out. Well, I'm super happy you're here and the Carol Ann's here, Jesse's here. We're going to talk about optimizing your life. I read a wonderful piece at Fast Company about the power of good enough. When is good enough good enough? And I wonder that around specifically that was around your whole life, but specifically with your money and with your work life. Like when is it enough? And then Maya will ask you specifically as well about, you know, teaching kids, about, you know, when we teach kids, are we teaching kids optimization? When should we teach them to optimize? And when is enough maybe enough? So I can't wait to get into it. We've got Maya here, we got Carol Ann, we got Jesse, we got Doug. We are going to dive into this in a moment. We got a couple sponsors though who help us keep on keeping on. We're going to hear from them and then we're going to talk optimization and maybe over optimization. How many meetings a day do you take notes in? Or how many different just events where you have to jot something down? Here's a hill I will die on. Granola AI is the best, the best note taking software that is available. I've used a ton and it is by far the best. It's an AI powered notepad built for the way real people actually meet. Here's how it works. You take rough notes like you normally would and in the background Granola is securely transcribing the entire meeting. It turns it all into a clean, structured, actually useful group of notes when the meeting ends. And the best part, it works through your audio's device which means you don't have to have any setup. There's no awkward bots. It integrates seamlessly into the stuff that you already use. It's just your normal meeting with superpowers. I absolutely love the output of my meetings and if you want to know how it looks, just either try it for free or write me [e-mail] because if meetings are eating up your day, Granola is a no brainer. You can try it totally free by heading to Granola AI sb. That's Granola AI SB and get your time back. Here it is again. Try it for free. Granola AI sb. Back in my early days of financial planning. Buying life insurance was so difficult and frankly, for a lot of people it still is difficult. But the funny thing is, and not funny haha, but just, I guess, ironic, we all know that we need life insurance and we don't want to overpay for it. We want to get on with our life. We want it to protect us and then we want to do other things.

[B]

Well.

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[E]

What comes to mind is budgeting and over budgeting. So I grew up in poverty. We had very little money. And when I was becoming who I am today, I had some very low income jobs and so I had to budget every penny. That sort of stuck with me. But also being in this industry as a financial educator, you know, we're constantly told that, you know, we need to budget and allocate every cent. And some people even say, like, budget until it hurts, which I completely disagree with. Now I remember my kids were very little and I needed to buy some multivitamins. I remember going into a health food store and not buying the multivitamins because I was going to go, I don't know, maybe $5 over the budget. It was ridiculous. I remember coming home and my husband asking, where are the vitamins? And I said, well, you know, we were going to go over the budget. And he just looked at me and he was like, are you kidding me? Like there is enough money like you can, you know, we don't need to budget this tightly. This is ridiculous. Like we are optimizing for every cent and there is no need for that. It's sucking out every joy and fun out of life. That was the moment when I realized I wasn't really enjoying doing that. I mean, I did that for many, many years because I had to. But we were in a good financial place where that didn't need to be done. Anymore.

[A]

And it's so wild that budgeting can be either a wonderful tool or just this absolutely rotten thing. And so much like a money nerd, Maya, that you would. You're prioritizing wealth over health. You know when you say that, like, who cares if my kids are healthy? We need more money.

[E]

Yeah. It sounded absolutely crazy. And I remember reflecting on it and I thought, okay, this is nuts. Like, we need to change things.

[A]

I love that you started with that one, because we often optimize saving money, but we don't think about time. We don't think about health that much in our personal finance community. Carol Ann, what's one where you maybe went a little off the deep end?

[B]

Yeah, I actually can relate a lot to the story Maya just told. Thank you for sharing that part of your background with us. I came from a similar kind of situation where divorced at a very young age, raised two kids on my own. Money was always tight. It was always so hard to make ends meet that you really did have to watch for every penny. But then what I did with my kids, once they were in college and out of the house or whatever, I ended up having to then turn around. And every spare cent that I used to spend on the children now got reallocated to making up for lost time. What I thought was lost time catching up with retirement and savings and things like that. And I optimized. That's my vitamin alarm. Sorry about that.

[A]

Time to take your multivitamin.

[B]

Yeah, that was my multivitamin. But I optimized so much that I got to the point where I had, like, a 67% savings rate from my salary.

[A]

Oh, my goodness.

[B]

It was such forced scarcity that there was never any money to do anything because I felt like I was catching up for lost time for all those years in retirement that I couldn't afford to save. And so I did have to get to the point where I was like, I gotta slow down. Why am I doing this? I've caught up to where I need to be. I'm in a good place. It's okay to have a little extra money so that I'm not counting every penny. I can afford to go food shopping now without using a calculator. Like, it's okay. And so it's a different mindset that you really, really have to wrap your mind around when. When does enough become enough? And you can slow down a little bit to just make the other areas of your life a little more enjoyable as well. Because I'm at the point now where I've Got more money than time. And that now becomes the problem or the concern.

[A]

Yeah, time becomes, becomes. And then you think about the time that you may have, I don't want to say wasted, but spent the time that you spent on accumulating money living this lifestyle far below, you know, what you could have done if it was more moderated. And I'm glad you brought up that story, because that's also prevalent in the personal finance community, Carol Ann, with people, you know, especially in the fire community, where they're like, no, no, I have fun tomorrow. Today we're going to make sure that we ring every penny out of this. Jesse, you've never over optimized anything, never overthought anything. Like, as a guy that was an engineer, there's no way you overthought a thing. I'd never meet any overthinking engineers.

[D]

I was trying to think of the funniest one, but there was a time where probably for like a couple years where I tracked all the mileage on my 2012 Toyota RAV4. And I also tracked every single time I filled up at the gas pump and how many. Wait a minute.

[A]

Okay, the first part. Tracking your mileage. Doesn't your Toyota RAV4 do that for you?

[D]

Well, yeah, yeah, but, but, but my

[A]

point is questioning the distance it was giving you.

[D]

It says 200 spreadsheet for specific dates, Joe, for specific dates. This month, this month, this month. And then simultaneous to that, I was tracking how much gas I would add and how much I would spend on gas. So that way I could calculate the running miles per gallon at any given point in the, in the life of that Toyota. And you know, how much I was spending on gas, I would be going down the Thruway. And they say what? That which gets measured gets managed. Like in order to improve on something, you ought to measure it. And so sure enough, the act of throwing all this useless data into a spreadsheet meant that as I'm going down the Thruway, I would be like, okay, that tractor trailer is going 68 miles an hour. And I'm pretty happy with 68. I'll just tuck in behind him to draft off draft. Yeah, because I'm tracking this data, I need to improve my mileage. So that was a miler as a hypermiler. Exactly. Some people think about credit card points. I'm just all about mileage, baby. And so that was a couple of years of my life that I probably won't get back.

[A]

Yeah, but you've seen the back end of a lot of nice tractor trailers.

[D]

Oh, my gosh, I know so many 1, 800 numbers you can call if someone's driving erratically.

[A]

Did you ever calculate how much money you saved by drafting off of tractor trailers?

[D]

I mean, I will say for my little RAV4, my mileage in the moment, like, you know, RAV4 gets 26 miles to the gallon or something like that, on average. But when you're there drafting, you're getting, like, 45, which, again, what does that mean? It means that your. We'll say it doubles your fuel efficiency, which would cut your gas cost in half.

[C]

You must have saved tens of dollars.

[D]

I bet you I saved hundreds. Maybe even. Maybe even a thousand a year if I was doing it. Well.

[C]

Wow.

[A]

Before we go any further, I want to know exactly who I'm talking to. Who we have on a scale of 1 to 10, 10 being that you are always thinking about optimizing and you got to force yourself not to optimize. Zero being you have to remind yourself once in a while that maybe a little optimization might help your life. On a scale of one to ten, Jesse, who are you?

[D]

Probably a seven.

[A]

I'm gonna say Carol Ann, how about you?

[B]

I. I don't know. I might be like a 9 or 10. Because every time I try to pull back on one area, it makes me realize I'm. Or think at least that I'm not doing enough in another area. And so I'm always biting off more than I can chew.

[A]

Always, always overthinking it.

[B]

Always. Yes, because there's always something more I can be doing.

[A]

My. Where would you put yourself on a scale of 1 to 10?

[E]

1 is where I have to remind myself. Probably say I'm five. Like I'm really in the middle.

[A]

Right in the middle.

[E]

I do realize the importance of it, but. All right, yeah, I do realize the importance of it, but I actually thrive sometimes on just going along and doing the main things that are important, but not really focusing too much on optimizing. As long as I see some progress.

[A]

Well, let's talk about kind of the cost of optimizing for a minute. Jesse, do numbers people have an especially difficult time accepting good enough because there's always a mathematically better answer.

[D]

Could you rephrase that question for me, Joe? I think I understand what you're asking, but I just say it one more

[A]

time, like a lot of our stackers are mathematically oriented. Okay, yeah, let's say that they are the 10. Like Carol Ann, do you think because you see a lot of people when you're talking about financial planning, that numbers people have this difficulty accepting that being a five, like Maya said, is okay sometimes.

[E]

Yes.

[D]

Yes, I see.

[A]

Yes.

[D]

Excellent question. I love the question. I come from a world of numbers, right? I've got two degrees in engineering, and I spent seven years working as an engineer. And the thing that math and the hard sciences tell you is that every equation can be optimized, right? Calculus. Every. Every curve has a maximum or a minimum menu. Anytime you're trying to design something in engineering, there's a certain way to get the strength to weight ratio as high as possible.

[E]

And.

[D]

Right. You can kind of keep on squeezing for more and more efficiency. And I think that a lot of people who maybe have that mathematical bent to them naturally want to come into the world of money and apply the same exact thought process I did for many, many years. And maybe you could argue that I still do. It's just that when that world of money collides with that soft, mushy stuff between our ears, you realize that you're no longer. You're no longer optimizing a mathematical equation. You're now trying to optimize mushy psychology and feelings and emotions, and it just breaks down. It doesn't work the same way. So I think. I suspect that a lot of this optimization tension that we're here talking about today has to do with where the mass and the mushy brain start to collide. And it just. It's gray. It's a gray area. It's gray matter. You could say

[A]

you have a way with words, Kramer. Maya, I know that all kids are different, right? But do kids naturally begin as optimizers for the most part, or they learn optimization from watching us? And she's gone again. We're having trouble keeping Maya. Carol Ann, you've had kids. Same question. Same question. Did your kids learn optimization from you?

[B]

I feel like I've been a bad influence in this area on my daughter because what I noticed with her, she grew up always trying to. You've spoken to her before? Megan, she's wonderful. She's 30 years old, smart and successful, and she's a great kid, but she always grew up thinking, I got to do more, I got to do more. And I think she'd learned that from watching me. And so when she was in high school, she kind of was like, well, now I've done this. Now I need to get my first job. And I got my first job, and I got to stop picking out college, and I picked a college. Now I got to do the next, the next best thing. The next best thing. And at some point I had to tell her like, slow down, it's okay. It's life is not a checklist. You can enjoy the successes, take your time. There's no rush to do anything. And she's a young married couple. I've got a wonderful son in law, Jesse. They're a great couple together. They were like oh, automatically now the next thing we have to do is buy a house. And I was like, well, we had to have that talk. You're not necessarily ready for a house. Just because you think that's the next adult thing that you're supposed to do. To kind of check that box doesn't necessarily mean that's what comes next. And I had to like slow her down and help her to really like live in the moment and enjoy it instead of just going on to the next thing.

[D]

Just real quick. I don't think you should question Jesse so much, Carol Ann. I just, eh.

[B]

Just.

[D]

You had. Yeah, I was following your story just fine and then. Yeah, you lost me there.

[B]

Don't ever underestimate a Jesse. They know what they're talking about.

[A]

We've learned that the hard way here at Stacky. Benjamin's too underestimating Jesse a couple times. Guys, let's do a little game called the Optimization Olympics. You're going to choose. Is this worth it? Is the optimization worth it? Is it good enough or should you stop? All right, let's take turns until we get Maya back. We will just go back and forth. Jesse, we'll start with you. Drive 15 minutes to a gas station where the gas is 8 cents cheaper.

[D]

I despise this one. I, I despise this one with everything in my being. It's never worth it. It's never worth it unless the gas station has made one of those mistakes where like they accidentally hang up a one instead of a three and it's like dollar gas instead of $3 gas. The time that you waste and the gas that you waste to get there, never do it.

[A]

Let's see if that's the difference between a 7 and a 10. Optimizer. Carol Ann, is the 108 cents cheaper, 15 minutes out of your way?

[B]

You going, I got to say no for the amount of time and money that you're spending in gas to get to that gas station. I'm not doing that.

[A]

All right, Carolyn, let's change it then. Let's say that you've got two gas stations along the same route and both are on your way you optimizing for the one that's 8 cents cheaper?

[B]

Oh, yeah, absolutely, Jesse.

[D]

Probably not paying attention to it is my honest answer.

[A]

Not paying attention. That sounds like an OG answer, by the way.

[D]

Not for gas prices. I just think gas is that commodity that is so similar from station to station that, you know, I just. I probably wouldn't notice.

[A]

I'm on the Carol Ann end of this, Doug.

[C]

If I see gas is cheaper across the street, but it means I have to take two lefts and a right to get there, I'm still not going to get the cheaper gas.

[A]

Go.

[C]

They have to be giving out free tasty freezes over there before I'm make my way to the cheaper gas.

[A]

Let's go to the next one. Open another credit card for a $500 signing bonus, Jesse.

[D]

Probably worth it. I have to admit, I don't do a lot of the credit card game and because usually I find Joe, there's some strings attached. But if it's just like, hey, open this credit card, we give you 500 bucks and three months from now you can close it again, I would certainly consider it. And that sounds like pretty easy free money.

[A]

Okay, Carol Ann, I struggle with the

[B]

whole credit card hacking thing. I feel like it's a waste on me. So, no, I don't do that. I. You know why? Because in the past, I've done these things where I've opened a credit card, but I don't spend enough money to really take advantage of points and stuff on credit cards. And there's always strings attached. You have to spend X amount of money in the first six months that you open the card or things like that. And I don't know. I don't benefit from those things.

[A]

You and I are direct opposites because I don't do it because of the fact that I would open it and I wouldn't get rid of it. I would start using it, and next thing you know, it's a. It's a bad deal. I had to rein that in when I was getting my financial act together. Maya, 500. You're offered for a new credit card. Would you. Would you do it or not?

[E]

No, I side with Carol Ann on this one unless it was significant amount of money. But $100 or $500 right now is not enough to motivate me. Maybe years ago, but not now.

[A]

Let's do another one. You've got $20,000 in savings. We'll stick with you, Maya. And you are offered at another bank point 2% more. So 2, 10 of 1% more. Do you take it for a point 2 difference?

[E]

If it's one of those offers where, you know, that only applies for the next three months or six months, it's a no for me.

[A]

Okay.

[E]

It's too much work. I guess I'd have to calculate exactly. You know, I'm trying to do calculations in my head right now, but if it's only for three months or something like that, then gotcha.

[A]

So bonus offer? No. But if they're consistently 0.2 higher, you'd do it?

[E]

Yeah, I do it.

[A]

Carol Ann?

[B]

Yeah, I've opened accounts at different banks. Not my main bank, though. I've never changed my main bank because it is too much trouble to change your auto, your mortgage payments and all that kind of stuff coming out of the banks. I'm not going to put that much work into it if it's only for like 0.2%. But I have done in my brokerage account CD Lattice, just to get that little tiny bit of optimization. Even though it was more work to have to make sure I re upped every three months or six months or nine months, depending on the term of the cd. I have done that. Which may or may not be worth

[A]

the time calculating the time benefit. It's like hypothetically maybe driving behind a semi to get just a little bit more mileage.

[B]

Who's crazy enough to do that?

[A]

Jesse, how about you?

[D]

I know, man. Ridiculous things people do to save money. I had the benefit of. I pulled up a calculator, I calculated it's a $40 a year difference in the interest rate.

[A]

There it is. 40 bucks.

[D]

That's 2% on 20 grand was 40 bucks a year difference. I would not make that particular change. That feels like over optimization to me unless I had some sort of ulterior motive to be like, this bank sucks. They've screwed me over one reason or another. Something I just don't like. Their online portal stinks. The new bank I'm going to seems really, really slick. Like, okay, maybe then I'd change, but not.

[A]

You're going to look at surrounding features.

[D]

Correct. Correct. It's other factors would weigh in my decision.

[A]

All right, let's stick with you for one more here. I like this one. Let's not make it $40. Make it $112. You can save $112 instead of flying direct to take a connecting flight, but it adds four hours.

[D]

Okay. Slightly longer answer than it needs to be, but certainly not an OG answer. In today's modern age, you can sit at an airport for hours. And in the PRE. In 30 years ago, you're like wasting your time. But today so much work occurs like on a laptop that I could probably be really, really productive sitting there for that four hour layover, like totally wasting my time. But I still don't think I would do it. It would have to be a much, much, much bigger dollar amount for me to accept that, because if I can be home four hours earlier and in my own environment, hanging out with the family, that there's no way I'd do that for $112 to.

[A]

You're valuing the time more than the money. There it is, Maya.

[E]

Yeah, I side with Jesse on that one for sure. I definitely value my time more than the money and it's not enough. I feel like it have to be a larger amount of money and I'd rather be home with my kids, get home sooner or wherever I'm going.

[A]

I was going to ask you, Maya, if you had said yes, I'd do it. I'd say, but you're traveling with two kids,

[D]

right?

[A]

No.

[E]

Then especially not. It would have to be significantly larger amount of money.

[A]

It is different if I'm doing it myself because I've taken this deal before where I have plenty of work that I have to do anyway and I'm traveling to a place. It's also different if I'm traveling to the place versus coming home.

[C]

Yes.

[A]

If I'm coming home, I want the direct flight.

[C]

Yeah. Joe. When my kids were young, I would find overnight layovers just to delay getting home.

[A]

Carol Ann, there was a time in

[B]

my life when I would have said yes to this question, but I got to give credit to my husband. We don't do that anymore. We don't have to. First of all, we don't have to live that way anymore. We don't have to optimize for every single thing. Kevin's much better at this than I am. So he keeps me. He keeps me. He's the fun and I'm the money. He's. He figures out how. What we want to do to have fun, and I figure out how we're going to pay for it and stuff like that. But no, I don't do those kind of things anymore because we can afford the extra $112 not to have to wait three hours in a, in an airport someplace for a layover.

[A]

You call him the fun. He's very fun. But I think you're fun too.

[B]

Oh, thanks, Joe.

[A]

Even though you're the money and keep dragging him to the Boston Benjamin's after dark groups so that he becomes the money, too. All right, in the second half, we're going to ask you questions that are a lot more serious. We're going to bring it with some of the bigger questions, which are five more year syndrome for people that are maybe hanging on to work for too long just to optimize their money situation. That one. And then we're going to give a money test for people that have kids teaching your kids about money. And I'll be curious to hear what all of you have to say because you all, all three of our participants have kids. But we'll get Maya's take on that one. But halfway through our episodes on Friday, we have this phenomenal year long competition between our three frequent contributors. Jesse, who's here, OG who is now being played by Carol Ann. And then Paula Pant, who is being played by Maya. Maya, you want the good news or the bad news about how this is going to go?

[E]

Let's do the bad news first.

[A]

Well, the bad news for you is the good news for Carol Ann because Paula is in last place. That's the bad news for you. That's the good news for Carol Ann. But that also, Maya, means there's some good news for you because Paula's in last place. You get to guess last, Carol Ann. That's the bad news for you because. Oh, geez. In first place. You have to guess first. And Jesse, no news is good news for you because you're in the middle, buddy. What's the score, Doug, so far this year?

[C]

Well, last week Paula made it really, really interesting and fun by scoring a point all by herself. So she's up to seven points now. That leaves Jesse as the forgotten middle child. He's at 8 points and OG is in the lead, but not by much at 10 points.

[A]

7, 8 and 10. It is fairly close, so let's see if it's going to get closer or if we're going to break it apart. Doug, what's today's question?

[C]

Hey there, Stackers. I'm Joe's mom's neighbor, Doug, and it was on today's date, back in 1964, that an incident known as the Great Plymouth Truck Robbery occurred. Seriously, it was nearly as big as Joe's mom's ATM incident of 09 that we aren't allowed to talk about. But I just did. Oh, I did it again.

[A]

There you go.

[C]

Okay. Anywho, two men dressed as police officers stopped a US Mail truck delivering small bills from Cape Cod to the federal Reserve bank in Boston. They tied up the driver and the guard and drove off, stopping to drop off money in various places. The truck, and it's too tied up. Occupants were later abandoned. This was the biggest cash heist ever. It was huge at the time. So let's ask this question. Just how big was it? How much money in small bills did these bandits make off with? I'll be back right after I see if I can heist a few of the chocolate chip cookies I hear coming out of the oven upstairs. Listen, folks, if you've got the phone number for Joe's mom's house, call her right now because I need a distraction.

[A]

I can't wait to hear the phone calls upstairs while we're waiting for those. Carol Ann, that's actually close to home for you. It was a long, long time ago. Long, long time ago. But maybe you know some of the. The history of the area. How much money was stolen?

[B]

Did David Doug say what year this was?

[C]

I did. It was 1964.

[B]

Thank you. Okay. I don't know the answer to this question. I feel like I should, because I think they made a movie out of it.

[A]

I don't know. You talk about the one with Ben Affleck. Yeah, that was where they held something up. I don't know if that's the town.

[C]

Are you talking about the town?

[B]

I don't know if it was the same. Doesn't help me to answer the question. Anyway, so at this point, I'm just stalling for no good reason.

[C]

It was not about this.

[B]

So 1964, there was a lot of money. It's obviously going to be. I don't know. I'm going to go with $10 million.

[A]

$10 million, Jesse, what are you going to do with that number?

[D]

That's a good guess, Carol Ann. Interesting guess. I liked how the movie angle helped you answer the question in the form and fashion of og, you know, telling a story, weaving in outside details. That was very well done.

[C]

And this really did almost happen in her hometown. Correct.

[B]

Listen, Kevin's not going to be happy when I get home tonight, I can tell you that.

[D]

I'm going to go lower. And is a million. Is that too high or too low? I'll go with a million. I'll go with 1 million.

[A]

Even 1 million. So much, much, much lower. So, Maya, you've got 10 million from Carol Ann, a million from Jesse. What are you thinking?

[E]

I was originally going to go with a million, but since Jesse picked that number, I was also thinking, how far is Cape Cod from Boston? Because they were stopping and distributing all this money or hiding it along the way. So I thought, okay, it does not have anything to do with anything. And it really doesn't. I mean, they could have put away as much money or as little money

[A]

along $10 here, $10 there, right?

[E]

I'm just gonna go, yeah. I mean, really. So I'm gonna go with 5 million. It's completely unrelated, but just kind of

[A]

split the difference guesses. All right, we got Carolan at 10 million. Jesse at 1 million. Maya halfway. Well, almost halfway between them at 5 million. Who's going to take this home? We're going to find out in a minute. We'll be right back. We spend a lot of time making smart financial decisions. But here's one that doesn't get nearly enough attention. Your water. Think about it. We obsess about the ingredients in our food. We compare investment fees down to the tiniest fraction of a percent. And then a lot of us just assume whatever comes out of the tap. Well, I'm just gonna drink it. Here's a surprising statistic. 3 out of 4 US homes a potentially harmful contaminants in their tap water. And even when water looks perfectly clear, it can contain things like chlorine, lead forever, chemicals and even microplastics. When I was in college, I worked for a group that would go out and do water testing. And the different things we'd find even in city waters just blew me away back then. And the sad news is in many cities, we haven't had any change to our infrastructure. It's safe enough to pass quality standards. But is it what you really want to drink? This is why I was interested when I learned about Aqua True. Aqua True is a countertop water purifier that's been tested, certified to remove 84 contaminants. It's patented four stage reverse osmosis system goes way beyond standard pitcher and refrigeration filters. The best part, no plumbing, no installation. Just cleaner water from a system sits right on your counter. Aquatrue has been featured in Business Insider and Popular Science. Good Housekeeping named it the best countertop water filter. Plus 98 of customers say their drinking water is cleaner, safer and healthier. Go to aquatrue.com now for 20 off your purifier using promo code stacking. Aquatrue even comes with a 30 day best tasting water guarantee. That's aquatrue.com spelled a Q U a T R U promo code stacking. It's incredible at a small company like stacking Benjamin's how one one hire makes all the difference in the world. If you're a small business, the right hire can be make or break Hoping the right people see your job posting isn't the best growth strategy. When the pressure's on, you need the right hire. This is a job for Sponsored Jobs Indeed Sponsored Jobs is a boost whenever you need to find quality talent. When workplace chaos hits and you need the right hire, this is a job for Sponsored Jobs. Hiring Indeed is all you need. Stop struggling to get your job post even seen at other sites. Get matched with and higher quality candidates who can drive the results you need. Reach candidates that meet your specific criteria like skills, certifications or locations. Sponsor Jobs Boost your job post on search results so you can reach the people that can help your business thrive. Plus, with Indeed Sponsored Jobs, you only pay for results. People are finding quality hires on Indeed right now in the minute I've been talking to you. Listen to this. Companies like yours have made 27 hires on Indeed according to Indeed Data worldwide. And Sponsored Jobs posted directly on indeed are 95% more likely to report a hire than non sponsored jobs. So spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results. When you need the right person to cut through the chaos, that's a job for Indeed Sponsored Jobs. And guess what? Our stackers are going to get a 75 sponsored job credit. That's you to help get your job the premium status it deserves@ Indeed.com podcast just go to Indeed.com podcast right now and support Stacking Benjamins by saying you heard about Indeed in mom's basement. Indeed.com podcast terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs in business, there is no room for guesswork. Every shipment matters, every deadline counts. And when you're trying to keep operations running smoothly, the last thing you need is uncertainty. That's why reliability is at the core of USPS Ground Advantage. From the moment your package is first scanned in, it moves through a secure nationwide network, aiding in a timely and accurate delivery. You get near real time tracking so you can keep up with your shipments and with affordable upfront pricing, there are no hidden fees or surprise surcharges to throw off your cost sheets. It all adds up to predictable deliveries you can depend on, because knowing your logistics are handled lets you focus on everything else your customers, your team, and the future you're building. Visit USPS.com ground advantage to start shipping with confidence. USPS Ground Advantage we mean business

[B]

all

[A]

right Carol Ann, you started at 10 million, and these two thought that maybe that was a little high. But listen, if it was 50 million, you're going to bring this home. Feeling good?

[B]

Feeling good about my answer, Joe?

[A]

Excellent. Jesse, you got the lowball answer at a million. It was 1964, so it could have been, you know, what's a million then versus a million today, Right?

[D]

Exactly. I don't really have a good feel for how much these trucks have in them. I mean, even today, if you ask me, how much does that truck going by on the highway have in it? I have no idea. So, anyway, I'm pretty pleased.

[A]

Pull one over and find out one time while you're tailing it. While you're tailing it down the freeway. That might not end well. Maya, you're right in the middle at 5. So you've got, like, from what, 3 million to 7ish feeling good?

[E]

Yeah, I think so.

[A]

All right. Maya thinks she's bringing it home. But only one person knows who's taking this home. Is Maya helping Paula get back into a tie with Jesse? Is Carol Ann helping OG Pull ahead again like he was earlier in the year? Or is Jesse creeping up right behind OG Man, I can't wait to find out. Doug.

[C]

Hey there, Stackers. I'm Chocolate Chip appreciator and guy who needs better henchmen. Joe's mom's neighbor, Doug. Nobody called. You know, good work usually boils down to having a good team. And I gotta say, phone didn't ring. Stackers. So when I say my hand was caught in the cookie jar, it's not a euphemism. She literally caught me with my hand in the cookie jar. Like it was all up to the elbow. It was all the way in there. Well, unlike me, back in 1964, some bandits got away with a ton of cash. Most of the money was never recovered. And while some people were indicted, most fear that the true criminals may have gotten away, that Carol Ann knows who they are. But how much money did they get away with? Well, it was eight and a half million less than what killed Carol Ann guessed. Three and a half million less than what Maya guessed. Just 500, 000 more than what Jesse guessed. Because the correct answer is $1.5 million, making Jesse our winner, who is now just one point out of the tie for the lead.

[A]

Jesse Kramer with the big win.

[D]

I'm drafting OG that's what it is. I'm drafting him. I'm gonna say, like, one point behind him right until the end.

[A]

You kind of Figured out that if you draft him all season, like, that's optimizing this whole stacking Benjamin thing.

[D]

That's the goal. That's the goal.

[E]

Yeah.

[D]

I'm sorry for taking the 1 million guests before you got to it. That. That's my bad.

[A]

You would think going last would be a benefit, but Paula goes last every week.

[C]

And if she'd only said a million and one dollar.

[A]

A million and one.

[E]

Yeah, that's like Price is Right.

[A]

Yeah, that's what. When she first said, well, my first guess was a million, I thought she was going a million one. I thought, oh, maybe, maybe she's doing it. All right, let's get back to the real questions because we're talking about optimization. Let's start off with kids in a conundrum with kids. And then let's talk about one for adults. All right. Your 12 year old has saved 200. They want 150 sneakers. It's their money. Is it worth it? Is it good enough? They should do it or do you stop it. Let's have Maya answer last. Jesse, you've got kids too young for this so far. So put your dad hat on. What are you thinking?

[D]

My first instinct is to let them spend that money the way they want to. And then, I mean, right. As long as it's not like truly harming them, you know, but like.

[B]

Right.

[D]

I think spending money on shoes is a perfectly reasonable way to spend money. And then there's always that lesson, if there even needs to be a lesson. Maybe they love the shoes and it's the best thing they've ever spent money on. Or maybe there's an opportunity down the line to be like, oh, you see, like, you know, when you spend money, sometimes you don't exactly get the fulfillment that you thought you would. And it's an interesting lesson to carry forward, but I don't see any issue with it.

[A]

Carol Ann, I'm sure you've been through this. Issue.

[D]

Issue. Buying the shoes.

[A]

Sorry, issue. Oh, just not an issue.

[D]

Me.

[A]

Hold on, hold on. There it is. Yeah. Carol Ann, you maybe have been through this before.

[B]

Yes, I'm actually in agreement with Jesse on this one. If they put their mind on something, they saved up for it, they worked for it, let them buy it. It's not harmful to them. I'm hoping that they do see that once they have $200 sneakers on their feet, it's not all it's cracked up to be. And maybe that's the first and last time they do that. But you can't teach that kind of lesson. I think people have to spend their money and waste it sometimes to learn that. I'm in agreement with Jesse on that. I'm buy the shoes.

[A]

Okay. Sometimes, even if it's a bad decision, might be the right decision. What does our Kids of Money expert say? Maya?

[E]

Yeah, I agree with both Carol Ann and Jesse. One thing that I frequently talk with parents about is about letting kids make their own mistakes. Personal finance is called personal for a reason. And so as long as we are responsible in terms of, you know, we save, we invest, we pay our bills, the rest of the money should be used to give us some fulfillment and joy, in my opinion. And a lot of times I like to use an example of, you know, how there are some things that I like to spend my money on that my teenage son would find very wasteful. Some things that give me joy are like my manicures. To him, that's absolutely ridiculous. But he likes spending money on video games. And as Carol Ann said, these are the lessons that they can only learn by spending that money. And maybe they will have. They will enjoy those sneakers and have the best time ever wearing them. Or maybe they will be like, well, this really wasn't worth the money. I could have done something better with it.

[A]

It sounds like it takes some strength. I mean, you really got to circle back a few weeks later and have a conversation.

[E]

Yes, absolutely. And I always suggest that. And I've done that with my own kids. I remember sometimes the hardest lesson or hardest thing for parents to do is to watch their kids spend the money on silly things. They're silly to us, but they're meaningful to the kids. And so I've done that with my own children. And I would always follow up a week or so later and gently ask, hey, how was that? Would you do that again? Would you recommend that purchase to your friend? And kids know. They know when they've made a mistake. They know when they should have done something different. Or once in a while they're like, no, this was really great. I would do it again.

[A]

That's great, guys. Let's go to adults. We see this one all the time, especially in personal finance. Carol Ann, you're financially ready to retire, let's say, but given another five years, you would have a much larger safety margin. Is it worth it going another five years at work when you're ready to go and you're shaking your head now?

[B]

I'm shaking my head because I'm actually struggling with this right now. Oh, yeah. This is a very timely question. For me, my husband retired two years ago and I have a ways to go before I can or planned on retiring. But every time I look at the numbers, they seem to work. But yet I'm still hesitant to pull that trigger and leave. Like I originally planned on working till 65 and that's a long time from now and he's already retired and I'm missing out on time that we could be spending together and like waiting to do the things that we're putting off until retirement, some of the bigger things. And so I'm really having a hard time with the two more year thing.

[A]

Do you enjoy what you do?

[B]

I do, I enjoy what I do. And I do feel like I've got some goals, professional goals that I still want to meet and I'm capable of meeting and I see no reason why I can't meet them within the next two to five years. And that's great. But like I said earlier, I'm also looking at people my age and realizing that we might not have as much time or health as we think that we do. And so how much Russian roulette do you really want to play with the time that you've got left? Because God forbid here I could get sick and maybe that decision is made for us and it doesn't work out the way that we want it to work out. Yeah, so yeah, I'm kind of teetering on that right now. Every time somebody asks me when I'm going to retire, I keep saying it's either going to be somewhere between two and nine years, which is a ridiculous time span. I just, But I can't figure it out.

[A]

I don't know what to do. Get between 1 and 100 for now. But it's interesting. I'm wondering if there's a. I mean, this is a topic for another day, but for a lot of people, maybe there's a halfway on this. Maybe there's a, maybe there's a, there's a mid ground. Amaya, what about for you? Let's say you've got enough money to retire, but staying a couple more years would really help and give you a margin of safety.

[E]

So, you know, it's really interesting because I'm kind of thinking about that as well. It is a timely question for me and my husband as well. Our kids are older, our son is in university right now. The daughter will be going next year. We're at that point now where we could retire, we could downsize. And I feel like, as Carol Ann said, you know, I'm doing the calculations, they seem to be there would be enough money. But I've also created, luckily, I was lucky and I created a life that I love and I enjoy what I do. And part of me always thought I was going to work forever because I like what I do. But I also realized that sometimes I get, I guess, a little bit too obsessed or maybe I'm a little bit of a workaholic. So I tend to forget to have fun. And my husband is also the fun one as well. And the older I get, and as the kids are getting older, too, I realize, like what Carol Ann is saying, our health, you know, we have it now. We're capable. We, we can travel, we can do things that maybe as we get older, we may not be able to. So I think it's about trying to find that balance and maybe retiring part time, maybe not retiring full time.

[A]

Let's go to the pro last. You know what I find fascinating about both Carol Ann and Maya's answers, Jesse, is that, you know, we're kind of, we're going to be talking about this a lot in the fall on the show, kind of questioning the whole premise of this full retirement. What's it all about? Where's the boundaries? It seems to be less about the money for both Maya and Carolyn.

[D]

Yes, I loved both answers. I find this topic endlessly fascinating. Isn't it interesting? Right. So the answers had to do, both your answers had to do with time, had to do with children, had to do with travel. It didn't have to do with the optimization of the numbers themselves. And I forget if this episode is even out or not, but either way, recently I was speaking into a microphone for my podcast and I talked about the idea of let's stop thinking about it as one more year syndrome, one more year of income, one more year of compound interest so that it can feel safer. And let's kind of flip it on its head and think about one less year syndrome. So, right, it's one less year of time where you'd get to really spend a lot of time with your children. It's one less year where you're going to be healthy enough to do things like travel and be an active retiree. And if you think about the pot of available years that you have to spend time with your kids or be active in retirement, it might not be nearly as big as you think. And to take away one of those years to say I'm going to keep on working, you are taking away a very limited resource in terms of that viable time that you have to pursue your passions and life goals. And so that doesn't mean that people need to dive into retirement headfirst when they financially ought not to. But I think what it does mean is that once your numbers say that you're good enough, you really need to pivot into thinking about what you are sacrificing by staying at work for more and more years. If work's not the thing that really fulfills you, and if your goals lie

[A]

elsewhere, I think that fulfillment part's so important because what I didn't like about the way you frame that Jesse was around, what are you sacrificing by staying at work? And I did like what Carol Ann said, where she's like, I got some professional goals, and I think sometimes you might leave work and go, you know, I left some things on the table that I really wanted to get done. If I'm pretty passionate about what I do, I think that may be a big piece of the key. Let's stick with you for a second. Let's talk about optimization, where we see it a lot as financial nerds, investments. Jesse, do you think that optimizing your investments can actually make you a worse investor? Where's that line?

[D]

Yeah, one of the data points that I really like to point to, although it does have some people who criticize it, but I think this particular data point is referred to in a positive manner, much more than it's referred to in a negative manner, comes from John Bogle, and it's research from, like, the late 80s or early 1990s. And it basically says that your broad asset allocation leads to something like 90% of your overall investment returns, meaning your choice of investing 70% in stocks versus 30% in bonds. That's. The broad asset allocation is so much more impactful than which stocks you actually invest in, which would be like the. The micro asset allocation. So when we talk about investment optimization, it often is people really diving into that nitty gritty nuance about which stocks and should I invest in TIPS or Treasuries? Should I invest in municipal bonds in my taxable account to prevent the tax bill? And it's not these, These questions are bad. It's. It's fine to try to squeeze some juice out of that final 10%, but I think it is important. I think some people lose the. They lose sight of the forest for the trees or whatever it might be, and they forget the fact that the biggest decision they can make is that broad asset allocation decision. And everything after that. It just. You're. You're really getting a lot less bang for your buck for the time that you're spending there.

[A]

So you're saying studying and learning asset allocation better could be a great use of time, but picking individual stocks maybe not, correct? Yes. And yet, Maya, I saw a tweet. Do we still call them tweets? I saw a tweet recently from Elon Musk saying all these people betting against SpaceX, they are selling short SpaceX shares, that they are in trouble because if you've bet against him in the past, it's been a losing proposition. And he said, you know what? SpaceX is going to go up. It's going to go up big. And I read that and I'm like, oh, maybe I should put some money in SpaceX. I don't know. I feel like there's always a quicker, better, funner stock that I could own.

[E]

Yeah, I find that a lot of times, like there's that fomo and with fomo.

[B]

Oh, no.

[A]

And we lost her again. Maya's had so much fun with her Internet today. I've been where she's. She's at before. We'll go to you, Carol Ann. Are there times when you think that you just. If I tinker with it a little more, like maybe it'll get a little

[B]

better, you know, when it comes to that kind of stuff? No, because. So I'm like an index fund kind of investor. I just want a piece of everything. To me, when you get to the point of what you're asking about right now, Joe, it feels like you're gambling and my money is too hard come to me. And I've worked too hard to get my portfolio where it is to really gamble. So I don't want to be like, trying to optimize in one area space that as an example, you might be losing out on something else. But if you just kind of go in with ETFs or index funds or things like that, you get a little bit of everything. I feel like I'm hedging my bet in multiple ways as opposed to individual stocks. And fear of missing out is not an issue for me because just like, I could go up, I could go down, and I, I just don't want to risk it.

[A]

I love that quote that my money's too important for me to bet. That is the direct opposite. Thinking of so many people, and I absolutely love it. I want to ask you one more thing. Let's talk about optimization outside of money. You know, you see some people that are really optimizing productivity, optimizing their health a lot. Is there a time, Carol Ann, you find that maybe optimizing productivity or optimizing health can make you less productive or less healthy?

[B]

I always feel like your health is your number one priority. And if you're spending any money on your health, vitamins, medicine, gym, wellness programs, whatever it is, that's an investment in the larger picture. I suppose you can get a little obsessive about it. A third glass of wine isn't gonna necessarily take 10 years off your life. You can become obsessed by it. I have been that person at certain times in my life where I've looked at the steps on my watch and took another walk around the house before I went to bed. Just because that's a little cuckoo. I don't need to be doing things like that. It's not gonna. It's not going to move the needle all that much. But I do think overall, in the bigger picture of things, optimizing health should be a number one priority, because what good is the money for if you don't have the health and the lifespan and not so much the lifespan, but the health span, to be able to spend it and enjoy it and do all the things.

[C]

So, Carol Ann, I want to clarify something. So three glasses of wine, like, where's the line? Like, where do I need to get worried? Is it that ninth glass? The third bottle? Just for clarification for a friend, when

[B]

you, when you're going from glasses to bottle, as far as a measurement goes, you might want to think about the line being somewhere in there.

[C]

That is that when I kind of check my.

[B]

Okay, that's what I'm taking from that.

[C]

I'll let, I'll let my friend know.

[A]

When you're measuring in bottles. That's awesome. You know what's interesting to me is that when I see people that spend so much time at the gym that it ruins other pieces, their life, like their fa. They don't see their family as much. Same thing as work. And I know people like this that spend so much time. By the way, Carol Ann, to your point, yesterday Cheryl and I went for a walk and we were 110 of a mile away from the next mile marker. So she went and walked a little bit down the street and back to get that last tenth of a mile. Same thing. Jesse, productivity. Can optimizing productivity make it less productive?

[D]

Probably. And I think even what's the. There's some famous business school type guy Hutchinson or something like that, and he's got this law that says work kind of expands or contracts to fill the time allotted to it. I find that to be true in my life. So I guess what I'm saying is optimizations hacks haven't always worked. And what really it comes down to is if I'm working to a deadline, I somehow managed to get it done. And if I sit down at my computer and I'm like, oh, I've got a wide open day, I don't really have anything I need to do, what will I do today? I tend towards dilly dallying and not being very efficient. And maybe that could very well just be a Jesse problem. My point is that these optimization productivity hacks don't always seem to work for me. Or I just had a very mixed bag of reviews and it just leads me to the conclusion that maybe it's just less about the hack and more about some other factors.

[A]

Maya, based on what Jesse said, I want to end on this question. Do you feel like there's a time when this obsession with over optimization really is just procrastination in disguise and maybe we should recognize it as such 100%?

[E]

I think you nailed the problem here. In my line of work, there are a lot of parents that want to start investing for themselves and their kids. And so many of them watch financial literacy content online or they listen to podcasts and they analyze things. And yet I get so many messages on Instagram from parents saying, hey, I've followed you for so many years, but I still haven't opened that investment account and I'm not sure if I should invest in this or that. And it's like, how about we just open that account and we find a nominal amount of money that you invest that lets you sleep at night? It could be $50. You can buy fractional shares. Let's just get the move on. Rather than optimizing for all this, you know what to invest in, what account is better for me in terms of my financial situation and taxes and else.

[A]

I love this so much on our financial action month here at Stacking Benjamin's such a great thing. Just get started. All right, we're going to wrap it up there. I've got 87 more questions, but we're going to call it a day. I love the idea of optimizing, but when I hear about getting behind a. Getting behind a semi to draft the semi, maybe there's too much, that makes me laugh nearly as much as I did when I heard about the three glasses of wine just totally wrecking a podcaster's week. Like, yeah, really, what about that time with friends is that. Are there times when times of friends might be worth the third glass of wine? I don't know. Let's find out what's happening where you all are. So, Carol Ann, let's have you go first next Wednesday night. Let's do the details again. 6:30, if you're in anywhere in New England, come out and visit. You guys. Where are you going to be?

[B]

Come on down to Melrose. We're at Hannah's Brewing Company on Main street in Melrose, and it's the third Wednesday of every month, 6:30pm so next

[A]

week, and if you go to stackingbenjamins.com bad b a d, you'll find our Benjamin. It's after dark groups across the country. Thanks, Carol Ann.

[C]

Who?

[A]

I'm not even gonna mispronounce her last name again. Embarrassing. I've done Carol Ann maybe for what, 10 years maybe.

[B]

And every time you say it, you get it wrong. It's extraordinary.

[A]

I know. I'm wicked smart at pronouncing it horribly bad. Did I get that accent right?

[B]

That was good.

[A]

Yep, I'm coming close. Maya, thanks for hanging out with us. It's so good to have you. We were talking about how we've been in Internet jail before and everybody feels super bad when there's days it just isn't. Isn't working. But I'm so glad you could share your wisdom with us. So tell us what's going on with you. What's coming up next?

[E]

Right now, the Wealthy Kids Investment Club is open for enrollment. And I'm also taking on any opportunities for speaking engagements at this point, schools or events and conferences and things like that.

[A]

People can go to Wealthy Kids Club, right? It's Wealthy Kids Club. You know, if you're a kid or a kid at heart, Right?

[E]

That's correct.

[A]

Jesse Kramer, tell us what's coming up at the Personal Investing for Personal Finance for Long Term Investors podcast. I can't. I can't get Carol Ann's name right. I can't get your podcast name right.

[D]

Well, I mean, Carol Ann's last name, I think is five syllables.

[B]

Well, it's a long name.

[D]

Is that right, Carol Ann?

[B]

Yeah.

[D]

Desiderio.

[B]

Desiderio.

[D]

My podcast title is, I think, 48 syllables. So it's a different magnitude there, different scale factor. It ran out of fingers. Nevertheless, we still create podcast episodes even with all the syllables. And this past Wednesday, we published an episode that is my DIY financial plan working.

[A]

Oh, cool.

[D]

Just kind of a deep dive into. Oh, I think we all know the importance of having a good financial plan, but I would posit that there are plenty of people out there who don't exactly know what a financial plan is. I don't think our industry has done a very good job of even defining what that term means. So we talk about that and then we help listeners understand if their financial plan is kind of working or not and what some of the telltale signs are that it's good or bad or somewhere in between.

[A]

It's always interesting when I see somebody who's like, I think I'm going to fire my financial planner because The S&P 500 is fine. And I'm like, you have no idea what a financial plan is or what a financial planner does. And if your financial planner is somebody that just competes against the S&P 500, it's time to fire them anyway.

[D]

I think that's very well said. Well said.

[A]

We will link to Wealthy Kids Investment Club. We'll link to the Benjamin's After Dark meetup in Boston and elsewhere around the country and a personal Finance for Whoever podcast Personal Finance for Long Term Investors on our show notes [e-mail] all right, Doug, you've got it from here, man. What should we have learned on today's show?

[C]

Well, Joe, first, take some advice from our guest panelist, Maya Corbeck. It's possible to over budget dude, chill out a little. Make sure you don't lose sight of the fact that a big part of the goal is happiness. Second, remember what Carol Ann said about optimizing your career. If you enjoy what you do and you still have goals you want to achieve, maybe it's okay to work a few more years than you absolutely need to.

[A]

Wait a minute.

[C]

What a big lesson. If you're planning the great cookie heist of the 2000s, it's better to formulate a game plan ahead of time. Otherwise you'll be doing time washing windows all weekend, which wouldn't have happened if you were all better at creating diversions. Maybe we'll practice again next week.

[B]

Team.

[C]

Thanks to Carol Ann Desperado for joining us. If you're in the Boston area, you can meet Carol Ann, James, sue, and our great stackers who meet up every month at our Benjamins After Dark meetings. Heck, if you're in other cities, you can also meet up. Head to stackingbenjamins.com bad for details about about our meetup groups so you can hang out with people nearly as cool as Carol Ann. Thanks to Maya Corbic for joining us today. You'll find Maya's work helping kids learn about money at the Wealthy Kids Investment club found at WealthyKids Club. We'll link to it in the show [e-mail] and finally, thanks also to the Jesse Kramer for gracing us with his presence once again. Look for his absolute, absolutely filthy podcast Personal Finance for Long Term Investors. Wherever you're listening to us right now, you'll love it. This show is the property of SP Podcast LLC, Copyright 2026 and is created by Joe Sal Sehei. You'll find out about our awesome [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media screens. Come say hello and oh yeah, before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time back here at the Stacking Benjamin Show.

[A]

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[D]

Support is available 247 with VRBoCare.

[B]

We're here day or night, ready whenever you need help because a great trip

[D]

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