What Retirees Wish They'd Known 10 Years Ago (SB1758)

Summary

Podcast Summary: The Stacking Benjamins Show

Episode: What Retirees Wish They'd Known 10 Years Ago (SB1758)
Date: November 7, 2025
Hosts: Joe Saul-Sehi, OG (absent), Doug (Joe’s Mom’s neighbor)
Guests: Jesse Kramer (Personal Finance for Long Term Investors), Jill Sirianni (Frugal Friends Podcast), Dr. Jordan “Doc G” Grumman (Earn & Invest Podcast)
Theme: The top five retirement planning “regrets” as seen by professional financial planners—what retirees wish they’d done a decade earlier, with a blend of practical advice, personal anecdotes, and trademark humor.

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Episode Overview

This lively roundtable episode dives into the five most common regrets retirees have about their retirement planning, according to financial planners. The hosts and guests break down these pitfalls, share personal stories, and offer actionable insights with Stacking Benjamins’ signature mix of friendly banter, relatable language, and practical wisdom. Along the way, Jill, Jesse, and Doc G share both professional expertise and personal experience, ensuring valuable takeaways for listeners of any age.

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Key Discussion Points and Insights

1. Choosing the Wrong Investment Allocation

• [14:56] Doc G admits: Even seasoned planners can get it wrong. He describes how his wife’s surprise early retirement left them too aggressively invested in equities:

  "We were way too equities heavy. Our bond allocation was much lower than I probably would’ve wanted… Ideally, we would’ve had much more safe assets, things like bonds."

• [16:29] Jill’s struggle: She admits feeling more conservative, despite having decades before retirement, and highlights the confusion and fear many non-experts face.
  • Actionable Tip: Know your time horizon and risk tolerance. If unsure, seek a second opinion from a fee-only, fiduciary planner.
• [18:24] Jesse's observation: More often, people are too conservative, often leaving large sums in cash and bonds because “the idea of losing money scares me more than the idea of growing my money compels me.”
  • Memorable Quote [19:47]:
    “The idea of losing money scares me more than the idea of growing my money compels me.” – Jesse Kramer

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2. Not Optimizing for Taxes in Retirement

• [23:28] Jill’s perspective: Recognizes that most are “so accustomed to a simple tax structure as W2 employees,” but retirement taxes are a very different world—each account is taxed differently and strategies are essential.
• [24:54] Doc G’s warning:

  “We let the tax tail wag the wealth dog too often… You can defer taxes, but you can’t escape them. Don’t spend decades worrying about tax optimization; get to the best 80%, hire the right people, then have some peace.”

  • HSAs (Health Savings Accounts) are cited as a rare clear tax win.
• [28:01] Jesse on unpredictability:

  "You plan based on today's assumptions. Financial planning is nothing more than making a set of assumptions… slowly realizing how wrong your assumptions are over time and adjusting."

  • Pragmatic Advice: Focus less on extremes (“Didn’t convert everything to Roth!”) and more on tax diversification – have pre-tax, Roth, and taxable resources for flexibility.
• [30:48] Doc G adds:

  "Tax status diversification is probably the best risk modification...That's probably the best risk modification for when you get to retirement."

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3. Not Updating Your Estate Plan

• [44:01] Doc G underscores:

  “I can’t tell you how much stress people carry around for years because they haven’t updated their estate plan, and yet they don't do it...Basic estate planning is easy.”

  • Hire a lawyer, even if it’s just for peace of mind.
• [44:53] Jill confesses: Has life insurance but hasn’t updated the estate documents yet, echoing how common it is to delay.
• [46:20] Jesse’s pragmatic explanation:

  “You can probably get away without having a fully-fledged estate plan if you don’t have kids...but the state has an estate plan for you, and it might not be what you want."

  • Pro Tip: Once the main work is done, updates are easy—just revisit every 3-5 years, check beneficiaries, and add new accounts if needed.

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4. Not Creating a Retirement Spending Plan (Budget)

• [49:27] Jill’s take:

  “Money is not going to be unlimited in retirement...if we've not become accustomed to living within certain spending parameters, it can be a huge adjustment.”

  • She connects budgeting to life transitions, routines, and ultimately, well-being.
• [51:13] Doc G’s insight:

  “You actually might spend more at the start of retirement...then slower from mid to late retirement. People who are nerdy like us may consider a higher withdrawal rate early and then pull back. It should be variable.”

• [53:07] Jesse on real-world planning:

  “Every good retirement plan starts with a conversation about dynamism… Life is dynamic.”

  • Key Takeaway: Don’t treat your retirement budget as a static number for decades—adjust it based on actual life events and needs.
• [55:39] Jill on Values-Based Spending:

  “It’s not just about looking at your cash flow, but examining the pieces… What do I feel really good about spending money on? Don’t start with deprivation. Be mindful and start with easy yes/no areas.”

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5. Waiting Too Long to Spend Their Money (Over-Accumulating)

• [57:43] Doc G draws on his book ‘Taking Stock’:

  “Many people who listen to shows like this will probably die with excess money...It’s really hard to die with zero."

  • He stresses intentional spending on experiences and self-betterment over “things.”
• [59:28] Jill, from the ‘frugal’ side:

  “This is the frugal person’s problem...I’d rather keep [money] hoarded in my freezer than pull it out and use it.”

  • She recommends getting clarity on what is “enough” and intentionally using savings for meaningful pursuits.
• [63:41] Jesse notes:

  “If you find joy in a very frugal lifestyle, more power to you. But if you’re spending too much, are you sure you’re getting joy out of that extra spending?”

• [63:51] Doc G reveals a subtle regret:

  “It's not that people aren't spending enough; it’s that they’re accumulating too much… losing years of freedom working at jobs they don’t like, just to accumulate more.”

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Notable Quotes & Memorable Moments

• On rules and flexibility in financial planning:
  “Only a Sith deals in absolutes. Dave Ramsey’s all about… no debt… But some people need that rigidity to get started.” (Jesse, [13:19])
• On over-complicating investing:
  “Having a ton of stuff just makes it worse. I've seen people with like 30 different things, and they come in asking, ‘What the hell am I doing?’” (Joe, [29:58])
• On the emotional benefits of estate planning:
  “Forget all the bad things that could happen. Just from the stress relief—feeling good about it—it’s totally worthwhile.” (Doc G, [44:48])
• Jill’s “values-based” budget:
  “Don’t start with deprivation… begin with the things that are easiest to cut. There’s a skill to knowing how to spend money well.” ([55:39])
• Doc G on oversaving:
  “They're accumulating too much. They lose years of freedom… instead of being home doing things they love, they're working at a job they don't like.” ([63:51])

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Key Timestamps

• Start of main content/banter: [01:04]
• Beginning of discussion – retirement regrets: [09:59]
• Discussion of investment allocation regret: [14:56]
• Tax optimization discussion: [23:28]
• Estate planning, updating wills: [44:01]
• Retirement budgeting/spending regrets: [49:27]
• Regret: Not spending/over-accumulation: [57:43]

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Tone and Style

• Friendly, approachable, and witty, with plenty of personal anecdotes, self-deprecating humor, and digressions.
• Hosts and guests regularly poke gentle fun at themselves, each other, and the seriousness of “expert” advice.
• Practical, non-judgmental, and highly relatable—clear that everyone, even professionals, makes mistakes.

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Final Takeaway

Start early, stay flexible, and focus on what matters most to you—not on rules, but on your real needs, values, and goals.
The biggest regrets? Not getting started sooner, not asking for help when you need it, and not taking the time to define “enough.”
Remember: You can’t shrink your way to greatness. Spend intentionally, plan for flexibility, and don’t let perfectionism (or tax panic) rob you of a happy life.

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Further Resources & Guest Plugs

• Jill Sirianni: Frugal Friends Podcast, “Buy What You Love Without Going Broke” (book), YouTube content
• Jesse Kramer: Personal Finance for Long Term Investors podcast and blog
• Doc G: Earn & Invest podcast, books including “Taking Stock”

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"The real regret retirees have isn’t missing some magic bullet—it’s missing the chance to align their money with their life and values years earlier." — Stacking Benjamins Roundtable

Transcript

[Joe Saul Sehi]

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[Jesse Kramer]

I mean, you're living in your mother's.

[Joe Saul Sehi]

Basement writing a blog on finance.

[Jesse Kramer]

Really, you should stay off the computer, son, and get a job. Seriously.

[Doug (Joe's mom's neighbor)]

Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor Doug. And remember that guy with a tattoo that said no regerts? What are the five things that would make you regirt your retirement plan? We'll dive into all of them. But that's not all. We're coming down to crunch time in my year long trivia contest between our frequent contributors. Will Jesse pull further ahead in his quest to end oh geez. Three year reign of terror? Let's find out. And now a guy who's on a huge winning streak. Mostly because he gets to spend so much time with me. It's Joe Saul Sehi.

[Joe Saul Sehi]

Hey there stackers. And Happy Friday to you. Welcome back to the Stacky Benjamin Show. I am Joe Saul Sehigh. Welcome to a show that is way, way, way way better than the how to Money podcast. And that's because you're raising so much more money than those guys are for financial education. Our 501c3 that we're helping is called Gifting Sense. Helping middle skate, middle skage, middle school age children learn how to make better money choices. All part of the Voices for Good charity challenge. We'll have a link in the show notes. And you know what? We're open to raise a lot of money. Way more. Way more than Joel and Matt are. And it's so fun talking about those great guys affectionately. Like we're going to all month be picking on our friends Joel and Matt, but let's pick on this guy. Neighbor Doug did the intro today. How are you, my friend?

[Doug (Joe's mom's neighbor)]

Joel and Matt suck. I mean, do we have to. Do we even have to say affectionately?

[Joe Saul Sehi]

Horrible.

[Doug (Joe's mom's neighbor)]

I mean, come on.

[Joe Saul Sehi]

Our stackers are way better than those how to Money fans. Way, way way.

[Doug (Joe's mom's neighbor)]

We don't even have a cool name.

[Joe Saul Sehi]

No.

[Doug (Joe's mom's neighbor)]

For their fans.

[Joe Saul Sehi]

How to Moneyers.

[Jesse Kramer]

Money.

[Joe Saul Sehi]

Ish.

[Doug (Joe's mom's neighbor)]

Yeah.

[Joe Saul Sehi]

But we got some cool people here with us. We want to meet those people.

[Doug (Joe's mom's neighbor)]

Probably should do that soon.

[Joe Saul Sehi]

Let's start off with a guy in upstate New York where summer just ended and now we're in the throes of winner. Jesse Kramer is here. How are you, man?

[Jesse Kramer]

I think this is becoming every single intro. Every single intro is just about what. What season we're in. You're right. So they're still in the middle of roadwork season, though, and they're still working on the roads, but they have another couple of weeks because then we'll be under a couple feet of snow.

[Joe Saul Sehi]

Yeah, snow season. Roadwork season.

[Jesse Kramer]

Yeah, exactly. But I'm doing well. I hope everyone's well on your end, too. But thank you for asking. I'm excited to be here today.

[Joe Saul Sehi]

That is the weather report from upstate New York.

[Doug (Joe's mom's neighbor)]

It has been pounding your chest like you're in a helicopter while you give that.

[Joe Saul Sehi]

And a gentleman joining us from the northern suburbs of Chicago, Mr. Jordan Grumman, aka Doc G, joins us. How are you, brother?

[Jordan Grumman (Doc G)]

Good, man. You're talking crap about Matt and Joe, but if we're playing basketball, I'm picking Joel over you any day.

[Joe Saul Sehi]

Pick a Joel over me as well when it comes but raising money. I mean, stacking. Benjamin's fans are way more philanthropic than how to money people. I mean.

[Jordan Grumman (Doc G)]

Yeah, for those of you who don't know, Joel's quite tall.

[Joe Saul Sehi]

He is quite tall. Yes, Jesse, you're quite tall. Every time I see Jesse, I'm like, I forget how tall you are. How tall are you, Jesse?

[Jesse Kramer]

6:3 if I'm wearing, like, basketball shoes. 6:2 if I'm wearing no shoes at all. And then some basketball back in my day, not. Not good enough play in any meaningful way. But I was pretty serious about it at one point.

[Doug (Joe's mom's neighbor)]

I mean, hold on here. I mean, I'm six one with heels. Joe, you're six six one. Jesse's six three. I mean, I think we got a team here.

[Joe Saul Sehi]

Yeah, that's right. We. We do. And you know what, Doug? We've got a ringer today. Who'd be the best player on this team? By far. Easily by far. She is the co host of the Frugal Friends podcast. It's about time. She's been on a round table. Jill Ceriani's here. How are you?

[Jill Ceriani]

I'm doing well. I am ready to bring all five, six of myself into that court.

[Jordan Grumman (Doc G)]

I'd say I'm not much taller than that. So I think she'd probably hoop on me.

[Doug (Joe's mom's neighbor)]

She would be the mugsy bogues of this team. She'd be a powerhouse under the boards, boxing out.

[Joe Saul Sehi]

Every team needs a point card grit. That's right. What's going on over at Frugal Friends? You sold your house and you've been making waves online because apparently people think that's baloney. Jill.

[Jill Ceriani]

Yeah, it's been wild to see all of the different opinions, but it was my choice, my decision. It was I believe, the best financial decision for me. I've just been loving life, doing the apartment life. Who knows if I'm going to rent for forever but right now it's been really great.

[Joe Saul Sehi]

Let's take just a second. Why did you make that decision?

[Jill Ceriani]

Multiple reasons but honestly one of the ones was realizing that I would not pay capital gains tax. I'm sure this is old news for the rest of you but it was newer news for me to like wait, what?

[Jordan Grumman (Doc G)]

Uh huh.

[Jill Ceriani]

I thought that I'd have to reinvest the money. You know, we live in a flood risk area and so after the hurricanes that happened last year, it just kind of rose, raised awareness for me of the level of risk and liability we're taking on every year. But I'm like, I love my house. They never want to leave it. Until I realized. Yeah, but I still, I have a lot of equity. Build a lot of equity in five years and I'd be able to keep that and not need to roll it into another house and invest it for retirement. So funny that we're talking about retirement today.

[Doug (Joe's mom's neighbor)]

That's not nearly as exciting as I hoped it would be. Jill. I was looking for like a haunting. Maybe like smells you just could not get rid of. I mean some completely pragmatic practical reason. Snore.

[Jesse Kramer]

Are you projecting, Doug? Are you projecting at all right now?

[Doug (Joe's mom's neighbor)]

There might be smells.

[Joe Saul Sehi]

Might be smells. Which is why Doug is at the far end of the card table. Jesse. The far far end of the card table. We got a great show today guys. We're going to talk about what one CFP says are the five regerts that people have if they don't do enough planning for retirement. We're going to dive into these. You don't need to have this open in front of you stackers, but if you want to, you can head to our show notes page@stacking benjamins.com and bring it up. But we will take care of all the heavy lifting. We'll tell you what all five of these are and we will dive in with Jill, Jesse, Doc G, Doug and I. First though, we have a couple of sponsors to make sure we can keep on keeping on. And you don't pay for any of this goodness on this amazing first Friday of November. So sit back and relax. We're going to hear from them and then Jill, Jesse, Doc G, Doug and I gonna dive into the five regerts of inadequate retirement planning. This message is sponsored by Navy Federal Credit Union. As the holiday season rolls around, we know that you strive to do everything you can to bring cheer and joy to your loved ones. And as a credit union dedicated to serving all veterans, active duty and their families, we understand that every little bit counts. That's why for a limited time, you could earn a 250 cash bonus when you spend $2,500 with Navy Federal's cash rewards and cash rewards plus cards in the first 90 days. Of course, Stackers, this is part of a big financial plan, right? Don't get yourself into debt. Make sure that you are spending and saving with a plan. But you know what? The giving doesn't stop there. You could also earn up to 2% unlimited cash back with these cards. So saving up for whatever the season brings just got a little easier. Give joy, get joy. Join now@navy federal.org Navy Federal Credit Union Our members are the mission. Navy Federal is insured by NCUA. Visit Navy federal.org cashrewards for details. Cash Back terms and conditions apply. Offer ends January 1, 2026.

[Jordan Grumman (Doc G)]

The holidays mean more travel, more shopping.

[Jesse Kramer]

More time online and more personal info in more places that could expose you.

[Joe Saul Sehi]

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[Jesse Kramer]

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[Jordan Grumman (Doc G)]

All right.

[Joe Saul Sehi]

Today'S piece came to us from Go Banking Rates, the CFP that wrote okay. Does anybody else grow when they read these pieces that say I'm a financial planner? Colon 5 Retirement moves I'm like, did I need to know you're a financial planner before all that? Anybody? Just me. Jesse.

[Jesse Kramer]

Blame the editor.

[Jordan Grumman (Doc G)]

Joe. They never say, I'm a podcaster.

[Doug (Joe's mom's neighbor)]

I'm a podcaster.

[Jordan Grumman (Doc G)]

These are five retirement.

[Jesse Kramer]

I live in my mom's basement. Here are five of my regrets.

[Joe Saul Sehi]

Yeah, how come they never ask me? I work in mom's basement. Here's where's what I regret. This is five retirement moves that you'll regret in 10 years. I don't want to get into specifically what these five are, but what I do want to do is this. There's people listening to this that are in their 20s, that are in their 30s, and they're like, really? We're going to talk retirement today. This is an hour that I might not need. But Doc G, when do you think, you know, people need to start making some of these good decisions and building some of these habits that we're going to be talking about the next hour?

[Jordan Grumman (Doc G)]

I mean, I think you need to start right away. A lot of us make the mistake of concentrating on retirement as this defined moment where you leave work and every everything is good. But I think we more need to look at it as we're continuously building a better life, which may or may not include work, it may or may not include hobbies and other things. We need to start thinking kind of early in our career. What are the kind of big things we want to do? How do we want to keep ourselves busy? Some of that's going to be work, some of that's going to be other stuff. And the hope is that when you do eventually get to retirement, in a sense where you're not working, especially for an employer anymore, you've got this well defined sense of things you like to do, and then you just gently move into doing more of that.

[Joe Saul Sehi]

Jill, one of the things we're going to talk about here, I'll preview just a little bit. Is focusing on your budget a little bit something you guys have talked about. But what's funny is just watching you and your co host Jen, from afar, your opinions of budgeting over the years have changed. I feel like if you start thinking about retirement early, maybe your feelings will change the same way that your feelings about budgeting have changed.

[Jill Ceriani]

Yeah, I think we've transitioned from calling a budget a spending plan. We still use the terms interchangeably, but I think it's important to know that there is flexibility in all of it and to kind of remain a little bit agile for that. I think certainly learning how to create a spending plan that Works now will only follow us into retirement. But also learning some of those different flexibilities, learning how to spend around the things that we value, can be really important for us down the road as well.

[Joe Saul Sehi]

Well, yeah, we're going to talk a lot about values today, Jesse. It's funny, Jill brought in flexibility. It kind of strikes me that when people are new to any of these topics, they're like, so what are the rules? And we tend to think in terms of hard and fast rules, which I think is good. Like, if you're trying to bake a cake for the first time, following the recipe step by step by step makes sense. But later on, because you studied it for so long, you know what to break. So I don't know, what do you think you're. You're in there talking to people in the financial planning trenches every day.

[Jesse Kramer]

I am as you were just asking me that question. Joe, you're reminding me of this conversation I've had before about our friend and colleague Dave Ramsey, who some people have heard of him, good friend, big fan.

[Joe Saul Sehi]

Of the show, by the way.

[Jordan Grumman (Doc G)]

Big fan.

[Jesse Kramer]

He's been compared to a Sith Lord before. You know, Darth Vader, Darth Maul, Darth Sidious, because he deals in absolutes, right? Only a Sith deals in absolutes, as the Jedi would say. And Dave Ramsey's all about dealing these absolutes. No debt, right? No debt. No debt, no debt. And not that I want to be a Dave Ramsey defender, because most of the time I'm not. But there's a certain subset of the population, whether it's just because they just work better inside of very strict frameworks or because this is totally undiscovered territory, unexplored territory for them. They need some rigidity, they need some rules, as you just asked about, Joe. So I think for some people, there's nothing wrong with hard and fast rules to get them going on the journey. And then once they learn more and learn more, that's where maybe some of the flexibility can start to come into play. But I think there's a place for both.

[Joe Saul Sehi]

You know what's funny is where we do this live on YouTube, and if you want to hang out with us, we generally record these on Monday. We're not here on Monday this week, but normally Monday afternoons. And B. Wayne hanging out with us says, leave work and then everything is good. Talking about retirement, just. Just leave work and everything is good. And back when I was a financial planner, B. Wayne, it's interesting, people would kind of treat it that way. And because of that they go, oh, wait, wait a minute. There's all this planning that maybe I should have done 10 years before I decided to leave work that I could have gotten done. And leaving work would have been a lot more fun than it ended up being. So let's dive into these. Number one is choosing the wrong investment allocation. Let's start with you, Jordan, choosing the wrong investment allocation.

[Jordan Grumman (Doc G)]

Oh, and I'm totally guilty of this. So my wife wasn't sure when she was going to retire, and I thought we had more time. And then earlier this year, she decided to retire within a few months. The issue with that is actually my asset allocation wasn't really in a place that it should have been for retirement. So we were way too equities heavy. Our bond allocation was much lower than I probably would have wanted. Some of it was laziness. Some of it wasn't come to terms that she was going to make the decision that fast. And, and so we went from accumulation to accumulation very quickly. And ideally we would have had much more safe assets, things like bonds that weren't moving up and down as much with the market. We ended up being okay. Right. The timing actually worked out. Equities were high. We were able to sell at the appropriate time. But I think a lot of people make this mistake of not planning five to 10 years ahead and slowly moving to the asset allocation you think is going to be appropriate for retirement as opposed to trying to do it last minute when all of a sudden you're making the decision.

[Joe Saul Sehi]

So you're saying that would have been better had you done it slowly.

[Jordan Grumman (Doc G)]

Yeah.

[Joe Saul Sehi]

You think would have been a much better move.

[Jordan Grumman (Doc G)]

And if we were really stuck in that place and let's say equities were at all time lows and we decided to change our asset allocation at the time, we would have, again, it would have been the wrong time to do it. It wouldn't have been appropriate economically.

[Joe Saul Sehi]

Jill. Jordan talks about being too aggressive in his allocation, and yet in this piece they talk about the opposite, which is people get way too conservative. Like, they stay way, way too conservative. They should have their assets working harder than they really are.

[Jill Ceriani]

Yeah. When I read this first one, you know, choosing the wrong investment allocation, I think I freaked out a little bit, like, oh, no, what do I need to know? And I think that can be one of the fears for most people who don't have a solid grasp on investing strategies. But I think we can overcomplicate it too. I mean, I think it's important to talk about how we can find ourselves in both extremes. But I think it's most important to understand both our time horizon and our risk tolerance and then be able to make the decisions that are necessary within that. But I mean, for me, I can absolutely relate. I think I'm a little bit more on the conservative end, even though I do still have, like, decades before I end up retiring. And so that. That is one of my own personal concerns of how do I make sure that I am being risky enough, given the fact that, you know, I've got a time horizon of about 25 years to go. And this is where we really like to recommend seeking out those certified financial planners that you apparently do not like.

[Joe Saul Sehi]

Joe, I like the advice in the piece. I just don't like the I'm a financial planner colon.

[Jill Ceriani]

I can appreciate that. But I do appreciate the credibility and the credentialing. And so I think if we are finding ourselves unsure, having that second opinion from somebody who does know what they're talking about, who is a fiduciary, I personally prefer fee only would be recommended. You can just consult. You don't have to be handing over your whole portfolio to somebody.

[Joe Saul Sehi]

No. Well, and that's. That's an important distinction because I think just getting that second opinion by somebody that at least has been there and they know that, you know, this is kind of the road ahead makes. Makes a ton of sense to me. Jesse, I gotta believe that in your career, when you see people, because you get to look kind of behind the curtain, right? And see people that are too aggressive versus people that are too conservative, which one do you see more often?

[Jesse Kramer]

Which one have I seen more often? I don't know. I guess I've seen both. Probably people who are more too conservative would be the. I think that's a little more frequent. Someone who comes in, maybe they're still working at the very. Or if not, they're kind of in the early years of retirement and something like 60 or 70% of their portfolio is in cash and bonds, something like that. I know everyone's unique and yada, yada, yada, all the things you're supposed to say there. But most of the time, right, if you have someone who's still working, if you have someone who's in the early first years of their retirement, to have that much of a portfolio in a conservative asset is probably means you're too conservative overall. But one thought I do have.

[Joe Saul Sehi]

Why do you think that. Wait a minute. Before we get to your thought. Why do you think that is? Do you think it's that we just don't know what to do. So we put it in a place that we think is safe.

[Jordan Grumman (Doc G)]

Right.

[Joe Saul Sehi]

Air quotes safe. Because frankly, there's no safety in putting your money in a savings account. Long term, you're safely going to earn no money.

[Jordan Grumman (Doc G)]

Yeah, I also think the. Fine. I was going to say, I also think the financial media sells this kind of 70, 30, 60, 40 thing. And a lot of people don't realize that's not probably appropriate for a young person who's just starting to invest. So we're starting to talk about retirement portfolios. So some people don't recognize the fact that your portfolio is going to look different at different parts of your career and different parts of your trajectory.

[Jesse Kramer]

Yeah, yep, that's. That's true. But yeah, going back to your question, Joe, I do think a lot of time there's that I know I can screw myself up if I put money in the stock market. I know that I can potentially lose it. And the idea of. Lou, it's loss aversion. Right. This is Behavioral Finance 101. The idea of losing money scares me more than the idea of, of growing my money compels me. And therefore I'm. I don't really like the idea of stocks because that loss is too real. Putting it in cash or some sort of bond or some sort of certificate of deposit, like, okay, all else being equal, I don't want this is going to sound a little bit mean or rude and I don't intend it to. But when someone comes to me with a large portion of their net worth and certificates of deposit, that tells me something about the way that they see the world, about the way that they understand or don't understand the stock market. And maybe, you know, there's an opportunity for education there, but I do think that's what it is. At the end of the day, Joe.

[Joe Saul Sehi]

I think it's the way we just look at risk. Yeah, we think about the risk of loss aversion, but we don't think about loss of goal aversion, which is. Can be every bit as big if we leave the money in a, quote, safe place forever. By the way, I felt like I did a pretty. I'm giving myself a pat on the back. I feel like I did a great job of introducing this topic, but I did a horrible job. Is the other side of introducing why I picked this for the three of our contributors today. And it's because while Jesse does this full time and meets with people, Jill does the podcast full Time. But Jill, you're not a cfp, you're not a financial planner. So you kind of are living this along with a lot of people. And Doc G is more on the philosophical side, I think. Jill, when it comes to the budgeting, spending and some of the tech stuff, I feel like that's like the fact that you woke up to Texas kind of cracks me up.

[Jill Ceriani]

Yeah, I'm actually studying to become a cfp, so a lot of this is top of mind for me. But yeah, I will represent the every girl today.

[Joe Saul Sehi]

Yeah, no, and that's exactly what I am glad that you said that because that's specifically why I like having you on. Because we're having a lot of the same feelings that a lot of our stackers are having as they broach all of these topics. So that's number one is that we have the wrong investment allocation. So you know, we're not going to solve investment allocation today. But Doc G, when you went looking for that better allocation, where's, where's a good place for our stackers to start?

[Jordan Grumman (Doc G)]

I think there are a lot of good retirement books out there, podcasts, blogs. I mean I think you've as well as getting financial advice, right? You don't have to have financial advisor who charges an aum, but you can get one time financial advice, et cetera. And I think if you're looking. So if you were kind of been steadily accumulating and you're not sure where your asset allocation should be, especially as you're five or 10 years out of retirement, that's the time to pay for some financial advice. Sit down with an expert and say, okay, these are my long term goals. This is when I'd like to retire and really try to figure out what looks like a good asset allocation for you. That should allow you to transition gently into retirement as well as have your cash needs fulfilled. But of course we're in retirement so we need cash flow and we need growth. And that's why I think getting some professional help, especially at that time, well before you're actually leaving the workplace is important.

[Joe Saul Sehi]

Let's move into the second one of these five which is on their list not optimizing for taxes in retirement. And Jill, you're studying for the CFP like you said. But I want to go to you just because what you said about taxes earlier when you read this not optimizing for taxes in retirement. What was your first thought?

[Jill Ceriani]

Realizing that there is so much to know about what is tax in retirement. I think for a lot of us we are so accustomed to, at least even the audience that we talk to, they're W2 employees. They are accustomed to a pretty simple tax structure year over year. And so I think the transition into retirement can be a little bit surprising that, oh, there are new things for me to know and realize and recognize as I'm now in retirement, what these different retirement accounts are going to be doing for me, how they are taxed differently, and that there are strategies to be implemented to be as tax optimized, tax efficient as possible. And so I don't think that we have to be experts on this. I don't think that all of us have to be studying for the CFP to do this well. But I think it's important to realize that there is strategy to be implementing here to have a, a good generalized understanding of that. Again, seek out those professionals, read the books, listen to the podcast. But recognizing that there are different stipulations for each one was an important one for me.

[Joe Saul Sehi]

Yeah, I think it is for a lot of people. It even says in the piece CFP Matthew Borsten says many retirees are used to being W2 employees. So the tax thing's already handled right? And we get to retirement, doc, and it's the very first time that we go, oh, wait a minute, there's some tax strategy. You might be in your 60s and it's the first time that you've needed a real quote tax strategy in your entire life.

[Jordan Grumman (Doc G)]

I agree with that. But I also want to go against the grain with this one a little bit.

[Joe Saul Sehi]

Oh boy.

[Jordan Grumman (Doc G)]

I think we let the tax tail wag the wealth dog too often. I know people who endlessly argue about traditional IRA versus Roth IRA and they spend years going back and forth with this. And the truth of the matter is, especially because we don't know the future, we don't know what tax rates are going to be in the future. We don't know what legislation is going to happen in the future. There is a point where you can go too far with tax optimization. And a lot of times people pretend like tax trade offs are for free and they're not. Let me give you a perfect example of that. People talk about real estate and they say, well, I can buy real estate, rent it out, which is its own thing. And let's say it wasn't a pain and you could do it easily. And then they're like, well, then I can take depreciation, which means I'm gonna pay very little tax. And then whenever I wanna sell that building, I can buy A new one. And we can do, you know, a 1031 exchange. And they talk about all this as if you're escaping the tax man. And it is true. If you hold that real estate till you die, you will escape the tax man. But most people will eventually sell the real estate. They'll have depreciation, recapture, they're eventually gonna have to pay capital gains. You can defer taxes and you can be smart with your taxes, but you don't escape the tax man. So my only warning is it's not worth spending decades complaining, worrying and being concerned with taxes. It makes sense to get about the best 80%. You can hire the right people, but then have some peace that, you know, if you converted tons to your Roth IRA or if you didn't, it'll probably all be fine. I think sometimes we have to let go of some of this tax optimization fear. There are consequences to all the moves you make. And generally it's really hard to totally escape taxes. You can die. You can. HSA is a win.

[Joe Saul Sehi]

Are you saying you win by dying?

[Jordan Grumman (Doc G)]

You win by dying, right basis for the people who inherit. And if you happen to have some real estate, you're never going to have to pay those taxes. If it's inherited to your children, they won't have to pay the depreciation, recapture, et cetera. You can do an HSA. It's a small win, but HSAs are clear wins in our tax system, but the rest is a lot less clear. And so even tax gain and tax loss harvesting, there are consequences to all this. And it's just something you have to think about.

[Joe Saul Sehi]

The HSA is a great one. I'm glad you brought that up because I know people hear us money nerds go on and on about how kick ass the HSA is. And I know there's stackers out there that I've talked to one on one, and they freak out because they don't have an HSA available to them. And you know what the the lesson is? You're going to be okay. You'll be okay. Even if you don't have an hsa, you'll be fine. By the way, Dave in South Carolina hanging out with us on YouTube, who is on the same boat as you, Doc says be smart, but don't let the text. As you were saying it, he was putting it on the screen. By the way, this is Dave Ramsey in South Carolina.

[Jordan Grumman (Doc G)]

Great mind. Yeah, great mind.

[Joe Saul Sehi]

Dave Ramsey hanging out with us here on the YouTube machine. Jesse, let's bring you into this tax discussion because this idea of tax optimization anyway, how do we know where the hell we're going to be so we know what we're optimizing for?

[Jesse Kramer]

The short answer is you don't. And I think the best practice that I've learned from folks who I work with and that I've seen multiple times from smart people in this community is you plan based on today's assumptions. Meaning, like Jordan brought up a really good point, which is that we don't know what tax rates are going to be in the future, but general financial planning practices, you assume today's rates in someone's retirement plan as you're doing those kind of projections. Financial planning is nothing more than making a set of assumptions, making the best assumptions that you can based on today's knowledge, but then slowly but surely realizing how wrong your assumptions have been over time and adjusting those assumptions as you go along. It's about understanding the range of outcomes, right? It's not about firing a bullet at the one single outcome that your retirement will be, but it's about defining the range of possible outcomes there. But I just, taking a step back, I think this is kind of funny. Only the, you know, the article was written in saying these are the top five regrets that I've seen from retirees 10 years in. I'll be honest, I've never seen, read, spoken to or heard a retiree saying, you know what's really stuck in my craw? Goddamn tax optimization. Just saying, I will. However, that being said, that being said, the work that I do, it's like tax optimization is a bigger value add for almost every single client than something like investment allocation. Like investment allocation is kind of easy, it's been solved or it doesn't take that much work to optimize someone's investment allocation. Whereas, boy, the kind of things you can do on a long term tax planning point of view, there's a lot of work there, some of it's a little complex and there's a lot of low hanging fruit that I'd say the average retiree probably isn't aware of.

[Joe Saul Sehi]

Well, with investment allocation, Jesse, I mean, Jill, you said this earlier. With investment allocation, sometimes having a ton of stuff, Jesse, just makes it worse. It doesn't make it better.

[Jesse Kramer]

A ton of stuff. Sorry, say that again.

[Joe Saul Sehi]

What do you mean different investments? If you make, I think.

[Jesse Kramer]

Right, right.

[Joe Saul Sehi]

I think, Jill, you said like, it doesn't need to be super complicated your investment allocation to be good. I've seen people with like 30 different things and they used to come into my office and go, what the hell am I doing? I'm like, I don't know. I was wondering the same thing. You've got so much junk all over the place. What's the plan? So, so difficult. All right, let's come back to this piece. I think this is why I don't like tax optimization stackers as much as I like tax flexibility where we have a little bit of everything because we, you know, take some today with pre tax, have some on the shelf for later by going with a Roth or after tax strategy and some money that's flexible because we just don't know where we're going to be. We don't know where tax rates are going to be. I'm kind of with Eddie who's in the comments saying that he thinks that we're going to be in higher tax brackets later. But who knows? Jordan?

[Jordan Grumman (Doc G)]

Yeah, I was just going to say one of my points I was thinking of as we were talking about this and we really give short shrift, but I think we should talk more about it. It's actually tax status diversification, which is exactly what you were just talking about. It's having some money in your brokerage account. It's having some money in your totally tax deferred traditional ira. It's having some money in your Roth. That's probably the best risk modification for when you get to retirement.

[Joe Saul Sehi]

For me, it's just so much, so much better planning. But speaking of better, we'd better at the halfway point of this show have our year long competition. Was I kind of shoehorning that, Doug?

[Doug (Joe's mom's neighbor)]

Yeah, not your finest moment there, Joe.

[Joe Saul Sehi]

Speaking of bad transitions, let's do one. Now we have this year long trivia competition between our three frequent contributors. OG. OG's not here, but we do have a G. We got Doc G here. So he's gonna be playing for OG. Mr. Jesse Kramer, who's here in person. And team Paula Pant and Jill. You get to be Team Paula Pant. So we keep the GS together and keep the cool people together. Jill and Paula. Jill as the guest here because Jordan's kind of a frequent flyer when it comes to this competition we're having. We have some good news and some bad news for you when it comes to being on team Paula. Do you want the good news or the bad news?

[Jill Ceriani]

Bad news first. Bad news first.

[Joe Saul Sehi]

Well, the bad news is you're in last place. So Doug, tell Jill and all our.

[Jill Ceriani]

Stuff only up from here.

[Joe Saul Sehi]

That's right. Tell Jill and our stackers what the score is. So far this year.

[Doug (Joe's mom's neighbor)]

Well, Jill, right now Jesse is out to a moderate lead. Used to be commanding, but he's at 13 and a half points, just ahead of fellow substitute teacher here today, doc Garrett slash OG, who's sitting on 12 points. You have the unenviable position of having just nine and a half points.

[Jill Ceriani]

Okay?

[Joe Saul Sehi]

But if you get to ten and a half, there's still two months left, Jill. So team Jill slash Paula could be in the race. Who knows? That also means the good news is you get to go last because you're in last place, so you don't have to guess first. Jesse's going to guess first, then Doc gave. But we need a trivia question to get us there. So Doug, what's on your mind today, man?

[Doug (Joe's mom's neighbor)]

Well, hey there, Stackers. I'm Joe's mom's neighbor, Doug, and it was on today's date, way back in 1492, that the biggest news from that year happened. What was it, you ask? Well, I'll tell you. Yeah, but I'm sure you already know. A boy witnessed a fireball falling from the sky near the town of Ensisheim, France. They gotta change the name of that town. Wait, what were, what were you thinking of? Anywho, I'm sure that kid immediately saw dolla dollar bills, yo, once that rock hit the turf. Reminds me of that time back when I was a young boy. I thought I saw a dollar bill, but turned out to be on a duck. I mean, how, how can a duck bill and a dollar bill be so different? Well, speaking of $, I also saw a buck, but that, that was on a deer. It's so confusing. Fine. All right, getting back to the trivia.

[Joe Saul Sehi]

Geez.

[Doug (Joe's mom's neighbor)]

Thinking that something filled with radiation falling out of the sky was good luck because that would be my first thought. Villagers began breaking the meteor apart to grab a piece of it until town officials stopped them. Not because of the radiation, but because they wanted to put gates around it and charge everyone five bucks to see it. And by bucks, I don't mean deer.

[Joe Saul Sehi]

Oh my goodness.

[Doug (Joe's mom's neighbor)]

Fine, I'll get back to it. Here's today's question. Let's say that the meteor, instead of landing in a field, had landed on a house. If the homeowner filed a claim and it had happened today and not been the biggest news from 1492, as has been well established, how much would that homeowner, on average, expect their annual homeowners insurance cost to rise? This has got to be the clearest question. Easiest question I've ever. I'll be back right after I go see if I can find some cold hard cash. I found some last winner. It was just pennies frozen in the old mill pond.

[Joe Saul Sehi]

Oh, wait.

[Doug (Joe's mom's neighbor)]

Cold cash.

[Joe Saul Sehi]

Hard, cold cash.

[Doug (Joe's mom's neighbor)]

Cold cash.

[Joe Saul Sehi]

Whoops, there it is. All right, thank you.

[Doug (Joe's mom's neighbor)]

Jesse. Shaking his head.

[Jesse Kramer]

So hold on.

[Joe Saul Sehi]

Jesse's like, I gave up my afternoon for this.

[Jesse Kramer]

The last one I remember that was like, this was all about Joe Louis. Like, all the preamble was about Joe Louis. And then the question ended up being, if Joe Louis had a title fight today, what would the Ticketmaster fees be?

[Doug (Joe's mom's neighbor)]

Yes.

[Jesse Kramer]

And it's like the preamble. The question is, what are Ticketmaster fees? This question was so convoluted that I'm not even sure I know what the question. The question was, if a meteor hit your house today.

[Joe Saul Sehi]

Brilliant. That's what you mean, is brilliant.

[Jordan Grumman (Doc G)]

So if it took out your house completely. Right.

[Joe Saul Sehi]

It had.

[Jordan Grumman (Doc G)]

The meteor has to like, take out your house.

[Joe Saul Sehi]

No, the core of the question is if you filed a homeowner's insurance claim this year, how much can you expect on average in the U.S. by the way, your homeowners policy cost to go up high after that, is that a.

[Jordan Grumman (Doc G)]

Percentage or a dollar?

[Joe Saul Sehi]

How many dollars on average, today's dollars do you expect? Your filter, the average homeowner in America.

[Jill Ceriani]

Monthly or annually?

[Joe Saul Sehi]

Annually.

[Doug (Joe's mom's neighbor)]

Annually.

[Jill Ceriani]

Okay.

[Doug (Joe's mom's neighbor)]

It's Jill. Oh, she's going last.

[Joe Saul Sehi]

Jill's going last.

[Doug (Joe's mom's neighbor)]

I just wanted to scare her for a minute. Jill, you're up. It's your turn.

[Jesse Kramer]

It works.

[Jill Ceriani]

I mean, I got an answer, but I'm gonna wait it out.

[Jesse Kramer]

I'm gonna say $622.

[Joe Saul Sehi]

Average person sees their cost go up by 622 bucks after their first claim. Doc, what are you going to do with that?

[Jordan Grumman (Doc G)]

I. I think it's a little bit lower. The question is. Yeah, I'm gonna say. I'm gonna say 550.

[Joe Saul Sehi]

$550.

[Jill Ceriani]

So, Jill, are we the closest without going over? How does the start?

[Joe Saul Sehi]

Just the closest. Yeah, we used to do not going over. But I got to tell you, the Stackers got very angry about that. They wanted to just be closest. We worry about the big things here at Stacking Benjamin's, whether whether we're doing closest without going over or just closest.

[Doug (Joe's mom's neighbor)]

We don't even worry about if the trivia is right.

[Jill Ceriani]

I'm going to say $470 annually.

[Joe Saul Sehi]

Now that sounds like you carefully research that.

[Jill Ceriani]

I've had an insurance claim recently.

[Joe Saul Sehi]

Darn it.

[Jordan Grumman (Doc G)]

You brought in a ringer it's like.

[Joe Saul Sehi]

I might know something about this. All right, Jill says $470. Doc says 550. Jesse, let it off with 622. Who's closest? We're going to let you know in just a second.

[Jordan Grumman (Doc G)]

November is heating up for U.S. soccer.

[Joe Saul Sehi]

United States need to be a little more nasty. Make international friendlies for the men. Oh, Callum, that was nasty.

[Jordan Grumman (Doc G)]

And a Black Friday friendly for the women. Expectations have always been here for this team.

[Jill Ceriani]

We understand that.

[Jordan Grumman (Doc G)]

Listen anywhere on the go with the Westwood One sports app. And for behind the scenes stories, catch the U.S. soccer Podcast.

[Joe Saul Sehi]

Boy, do we have an episode for you.

[Jordan Grumman (Doc G)]

Follow and listen on your favorite platform.

[Joe Saul Sehi]

Jesse, you kick this off by saying you thought the average homeowner's claim set your costs skyrocketing by 622 bucks. Now that all of the guesses are in, how you feeling?

[Jesse Kramer]

Well, I borrowed OG's protractor, and I was measuring the angle of a meteorite streaking across the sky as it impacted my roof, and it was 6.22 degrees. So if I'm wrong, I think that's probably a Joe Salsi High problem, because I think I have to be right. Wow.

[Joe Saul Sehi]

By the way, Doug, if he's right and the answer is $622. Jesse, I'm coming through the screen at you. Yeah, I'll be coming through.

[Doug (Joe's mom's neighbor)]

That's a bad day, Doc.

[Joe Saul Sehi]

G, you followed up with 550, which put you squarely in the middle. How you feeling now?

[Jordan Grumman (Doc G)]

I'm feeling like I won't be in last place, which is very comforting. I'm not going to be the worst guesser, which for me is a step up. I think this one's tight. You know, anyone could win. You know, Jesse took away all options because he guessed first last time and hit it on the dot, which means that I had no responsibility for being wrong because I lost right out the gate.

[Joe Saul Sehi]

Then if he does that two weeks in a row, Doc, I'd still feel.

[Jordan Grumman (Doc G)]

Justified because then I had no choice.

[Joe Saul Sehi]

Then you're still.

[Jordan Grumman (Doc G)]

As long as I'm off the hook, it doesn't really matter.

[Joe Saul Sehi]

Yeah, Trey has a great question here that says insurance now goes up every year anyway, so how can you differentiate if it's from a claim cost of homeowners insurance going up so quickly? Well, people policy genius did it for you, Trey, so we're taking their word for it. And Jill, you came in with $470. Put you on the low end. You feeling good?

[Jill Ceriani]

Oh, yeah. Unrealistically optimistic. I'M about to take this w. Listen to that.

[Jordan Grumman (Doc G)]

I like the confidence, Joe. I like the where. Where has she been this whole time? I like the confidence.

[Joe Saul Sehi]

Yeah, but this is Paula.

[Jill Ceriani]

Every week, like I'm bringing the Paula energy.

[Doug (Joe's mom's neighbor)]

I don't know if Paula has that kind of swagger. I mean, that is Jill's walking funny. She's got so much swagger.

[Jordan Grumman (Doc G)]

It's big pe. Big Paula energy.

[Doug (Joe's mom's neighbor)]

Right?

[Joe Saul Sehi]

That is true. But we have asked Paula though, Jill. We're like, how can your gut be wrong 10 years in a row? I have no idea. We're going to find out which one of you is right. Is Jill swagger deserved? Is Jesse going to get it on the head? Is Doc G going to finish second? Doug, who's taking the homeless prize?

[Doug (Joe's mom's neighbor)]

Hey there, stackers. I'm cold hard cash collector and guy who unintentionally went ice fishing, Joe's mom's neighbor, Doug. Back in 1492, the biggest news of the year by far was that a young boy watched a meteor fall from the sky and bury itself a meter deep in a field near the walled town of Ensisheim, France.

[Jordan Grumman (Doc G)]

A meter deep.

[Doug (Joe's mom's neighbor)]

Nobody even knows how far up. Nobody knows how far a meter is anyways. Maybe that should have been our trivia question. Had that meteor landed on a house and the owner had filed a claim and it had happened this year, how much would the lucky person's homeowners insurance have risked? Lucky.

[Joe Saul Sehi]

So lucky.

[Doug (Joe's mom's neighbor)]

I mean, I'll take the insurance premium increase because you know how much money you're making if a meteor falls on your house. That is a no brainer charge an entrance. Anyway, what I can tell you is that that premium would have increased 400 fewer dollars than what Jesse guessed. $382 fewer than what Doc G guessed. Just $302 less than what Jill guessed. Because according to policy genius, the correct answer is $168 per year. Making Jill it. More importantly, making Paula our winner today.

[Joe Saul Sehi]

Jill with the swagger.

[Doug (Joe's mom's neighbor)]

Damn, girl.

[Jordan Grumman (Doc G)]

You're welcome. Paula, did you see?

[Jill Ceriani]

Yes.

[Joe Saul Sehi]

Yes.

[Jill Ceriani]

You weren't wrong, Jordan.

[Doug (Joe's mom's neighbor)]

The real winner today.

[Joe Saul Sehi]

Jill, you have an acceptance speech. Because Paula wins so rarely, I think we need an acceptance speech.

[Jill Ceriani]

I want to thank my fans. I want to thank the tree that fell on my own garage that prepared me for today. I'm feeling on top of the world.

[Joe Saul Sehi]

Oh, congratulations listeners.

[Doug (Joe's mom's neighbor)]

I would encourage you to go to Google Maps, look up NSA Shime France and you'll see on the map is labeled the meteor impact. Like there is a spot it is the saddest, saddest thing you'll ever see. It's the worst monument that, I mean, I'm just like as a town, if that's what you're bringing. You just need to invite Euro Disney there because there's, there's just nothing, nothing to look at. It's a rock on a tree stump. Swear to God.

[Joe Saul Sehi]

B Wayne hanging out with us says it's comeback time. It is comeback time. It's the fourth quarter. Jill's here for team Paula.

[Jordan Grumman (Doc G)]

Nice job.

[Jill Ceriani]

You can expect this in my basketball skills too.

[Jordan Grumman (Doc G)]

Let's go.

[Joe Saul Sehi]

And Trey says, great job, Jill. So you're saying Paula's got a chance.

[Doug (Joe's mom's neighbor)]

She is three full points behind cheater Jesse.

[Joe Saul Sehi]

All right, let's dive into the second half of this. We actually have three to go, but this one I think we can do fairly quickly. The third regurt people have when it comes to their estate plan. Ten years later, they regret Jordan not updating their estate plan.

[Jordan Grumman (Doc G)]

Yeah, I mean, this is a big one. This is a big one. We don't know what's going to happen. And I have to tell you, anyone who understands this stuff, like we all listen to the podcast, et cetera, I can't tell you how much stress people carry around for years because they haven't updated their estate plan and yet they don't do it. And so I think we carry a lot of stress with it. Basic estate planning is easy. Some people try to do it on your own. I think your best thing to do is hire a lawyer. My wife had one of those companies where she paid a little extra every year to have legal coverage. And so we did it twice in the last five years right before she left her current job. And I think it's a huge relief. So just from the forget all the bad things that had happened, just from the stress relief of getting it done and feeling good about it, it's totally worthwhile.

[Joe Saul Sehi]

I felt so good when I got my estate plan done. Jill, have you had time to do yours?

[Jill Ceriani]

Oh, no, I'm sitting here like, yeah, gotta do it, gotta do it. The best that I have is life insurance. That was a big one for me. But this is next on my list. I do view it as one of those financial self care pieces that is so important. I think one of the reasons that I've been slow going with it is just not having kids. But I think recognizing that there's still my husband who would be left behind and there's so many important aspects to an estate plan that this Is a good reminder, a good little nudge for me.

[Joe Saul Sehi]

But you did one great piece of this that they even mentioned in the piece, which is putting beneficiaries on your stuff and getting life insurance. Those are two big things. So you've covered two thirds of it.

[Jill Ceriani]

Thank you.

[Jesse Kramer]

You're.

[Joe Saul Sehi]

Well, you're welcome, Jesse. I don't know. When I was a financial planner, I saw people avoid this so often and I think it's. It's just. It's not going to happen to me, Syndro. Yeah.

[Jesse Kramer]

Yeah, it is. Sorry, I was distracted by Eddie's comment in the chat. No offense, Jill, but Eddie, she's not too young.

[Jordan Grumman (Doc G)]

But she's not too young.

[Jesse Kramer]

She's young. Yes, totally, but. But not too young. And Jill, I do actually think you made an incredibly important point.

[Joe Saul Sehi]

And by the way, let's read. Let's read the full comment here so people know what the hell we're even talking about. Eddie says she's too young to worry about staying place.

[Jill Ceriani]

Too young. Stop. Stop doing what you're doing to her.

[Jordan Grumman (Doc G)]

She's not 22. She's a little older than that. Appearances. This can be deceiving.

[Jill Ceriani]

Yes. Slightly older. Yes.

[Jesse Kramer]

But Jill raised a really good point, which is that having kids and therefore naming guardians via usually a will is kind of this big threshold that you can probably get away with not having a fully fledged out estate plan if you don't have kids, as we joke, as I've heard you say it, Joe and Og. I've heard Og say it too. It's like the state has an estate plan for you whether you realize it or not.

[Joe Saul Sehi]

And it's not good.

[Jesse Kramer]

Well, it might not be what you want it to be.

[Joe Saul Sehi]

Well, that's. That's what I mean, I guess by not good. Maybe not specific enough.

[Jesse Kramer]

Yeah, it's totally fair, right? Correct. Correct. Google whatever your state is and then the word intestacy laws. Intestacy. If you want to figure out what your state's estate plan for you is. I forget what your exact prompt was, Joe, to send us down this path. As I was listening to Jordan and Jill, my thought was that it's actually kind of nice this, this whole idea. And I was reading the article itself that said you should go back and review your estate plan every three to five years. The really nice thing is that you have to do the lion's share of the work upfront and then all you really have to do every three to five years is review the bare bones basics. Just to say, does the flow of assets after my death still match my current day wishes? Do the beneficiaries I named three or five years ago still match my current day wishes? Are there any new accounts that exist today that didn't exist three to five years ago that now I need to include in my estate plan? My point is that the review process should be pretty simple once you've done the hard work upfront. And I know we talk about the fact that it's no fun thinking about your own death, but it's important nonetheless. And the hard part is getting going. Laughing at another comment. The hard part is getting going in the first place.

[Joe Saul Sehi]

Tony, Tony hanging out in the comments says don't misspell when you're looking up intestacy. I believe that's what he's, what he's talking about.

[Jordan Grumman (Doc G)]

It sounds like something you see the GI doctor for.

[Joe Saul Sehi]

You know, Dave Ramsey hanging out with us says, how is estate planning necessarily linked to retirement planning? I mean truly these are, Jill. I mean these are two different, two different things. But yet people will have regrets if you wait too long.

[Jill Ceriani]

Yeah, I mean I think this can be viewed as financial self care and I think there can be this misconception that this is only for the wealthy. But I think, you know, Jesse, you already outlined kind of who exactly this is for that it's for when we pass on and making life a little easier for the people that we leave behind, those that we love, making sure that we've got peace of mind for ourselves until that time comes, but also for those who are going to need to handle and arrange all of the different aspects that we're leaving behind, which is separate from our own planning for retirement, the money that we're going to be living off of the lifestyle that we're going to be leading. I mean both are necessary and part of retirement, but two kind of separate things.

[Joe Saul Sehi]

Jill, let's stick with you because the next one nails your area of expertise. People regret not creating a budget for their retirement. And so I'm sure the first thing a lot of our stackers are wait a minute, budget and retirement. Like why is that so important?

[Jill Ceriani]

Yeah, money is not going to be unlimited in retirement. I think this is the time of life when our spending is more than our earning.

[Jordan Grumman (Doc G)]

Right.

[Jill Ceriani]

We're not working a job, of course we're living now off of the earnings of all of our investments. But I think there is a level of rigidity, for lack of a better word, that happens in retirement. We kind of have these set constraints that if we've not become accustomed to living within certain spending parameters, it can be a huge adjustment. And retirement just across the board is already a huge transition time. If I can pull in some of my social work mental health background, anytime we go through a big transition, it impacts these very specific areas of our lives. I call them the five Rs. So it's our roles, relationships, routines, reactions and reflections. And I think particularly a spending plan or a budget intersects with really all of those. I think most acutely, probably our routines, the ways that we are accustomed to spending money. So if we don't have a good plan in place that we've been exercising for decades, it's going to be a pretty big shock to us when we come down to this time when here is what I have to spend and how do I want to allocate that? So I think this is one of those pieces that we can be working on now that we're just going to be expert in in retirement.

[Joe Saul Sehi]

Jordan, it strikes me when you were talking earlier about not having the right asset allocation with your investments, like fixing that quickly is easy. Not having a spending plan like Jill talks about going from no spending plan to lock down spending plan. Like you're not going to do that overnight even if you try.

[Jordan Grumman (Doc G)]

Yeah. And if I may add something to the last conversation because I feel like it needs to be said, I think estate planning and retirement planning are very connected because you're very vulnerable in retirement. So you really do want to think about estate planning because once you're in retirement and one spouse dies, you want to make sure that other spouse is taken care of and conversations about things like Social Security. Also, it's very important for legacy planning with Social Security because usually spouses don't die at the same time. Those are actually all very connected. Remember, retirement is a little bit more vulnerable because you don't have income from a job or a business usually. And so I think it's actually very important to plan those together now as it comes to budgeting. I think the thing that people get budgeting wrong in retirement is that actually it should be variable. And in fact, often people spend more at the beginning of retirement and slow down from mid to late retirement. And so people who are nerdy like us and think about things like safe withdrawal rates may consider having a higher safe withdrawal rate in the first early years depending on how the market does so they can take those extra vacations. Like what does ha. What happens when you retire? Everyone fixes up their house and they all go on a lot of vacations, which means Your spending actually might go up early in retirement, but that also can be offset by the fact that after you settle in and do that house repair and get a little bit older and aren't as mobile, you actually might spend a lot less than you were planning on spending. You can actually have a variable budget in retirement. You can vary that based on how early and how young you are in retirement, as well as you can pay attention to things like how's the market doing? And how much do I want to withdraw this year? And if you're careful about those things, you can probably maximize your spending better.

[Joe Saul Sehi]

When you're trying to help somebody come up with their retirement number. Jesse, do you model what Doc G. Is talking about? Like, do you model the fact that you may, and this piece even talks about it, that you may spend less later in years in retirement than you do up front?

[Jesse Kramer]

Oh, a hundred percent. Every time I see in one of the DIY forums or Facebook pages, I see someone saying, I have $1 million. I'm using a 3.5% withdrawal rate that is $35,000 per year, and I will now live on $35,000 per year for the next 50 years, no matter what. You know, my mind melts and my heart breaks a little bit because it's dynamic. It has to be dynamic. Life is dynamic. And every good retirement plan, I think, starts with a conversation about that dynamism, whether it's vacations, whether it's home improvements, whether it's, you know, I've got four daughters and they're all going to reach marriage age in the next 10 years, and we're going to be spending on weddings. Every single one. I guess when I look at the retirement planning software we use at the, it's kind of like a spreadsheet, but it looks much nicer. And the bottom row of every output page ends up being what that column's withdrawal rate is. Each column is a year. And I just like looking at that particular row sometimes because you'll see as high as 6 or 7% in some years and then in the twos or threes other years. And over time, hopefully it does average out to some sub withdrawal rate that maybe the listeners today are more familiar with. But I guess my point is that you have to start with that cash flow, which is another way of saying a budget. You have to start with that budget or cash flow. That's the foundation of all financial planning, whether you're in retirement or not. Again, I'm not sure I've heard anybody really voice the regret that they didn't have a budget. I would say that CFPs will go to their clients and say, if you don't have a budget, I'm not exactly sure how I can do my job for you. That's definitely true. And for any DIYers out there, if you don't have a really good understanding of your cash flow or your budget, I'm not sure how you're going to plan your own retirement.

[Joe Saul Sehi]

I think it doesn't come out as I regret not having a budget, Jesse, as much as it comes out that I wish I could do more, I wish there were more things I could do which speaks, I think, a lot to budget.

[Jesse Kramer]

Yeah. Yeah.

[Joe Saul Sehi]

I don't think they use these terms which Jill, you and Jen helped us kick off 2025 by talking about this very topic. And what I love about what the three of us discussed to kick off 2025, which seems like yesterday, by the way, that we were just starting this year, was you guys talked about it isn't just about looking at your cash flow, which is kind of what we're talking about here, but examining the pieces of your cash flow and going, do I really care about this? Like, I love the mindfulness of digging into your budget and asking, is this meaningful?

[Jill Ceriani]

Yeah, we talk a lot about values based spending and I think that that's something that we've come to over the years. Certainly frugality is woven into that for us as the host of the Frugal Friends podcast, but recognizing that it's not this race to the bottom, but being able to manage our resources well in a way that we can feel really confident about. And I think just tangibly speaking of what do I feel really good about spending money on? What brings me joy? What's life giving? Where am I happy and not full of regret when I'm spending in this area? And where are there maybe some easy nos, right? We don't want to start with the most complicated area. We don't want to start with deprivation, which I think is where a lot of people begin in creating budgets. And it's just so ridiculous. It's kind of similar to all of the advice out there about minimizing or decluttering. Like start with the junk drawer. Don't start with the mementos and the pictures of grandma. Like, begin with the things that are going to be easiest to cut that don't mean hardly anything to you and then move on from there with where else can I be trimming if necessary and spending more if necessary? I think Especially with the audience that we talk to a lot. It's about how to spend. We can be really good at saving, but there's also this, this skill to knowing how to spend money well in a way that aligns with those values that we talked about in a way that's congruent with our cash flow and really sets us up to live a life that, that we actually want, not one that's just been marketed to us.

[Joe Saul Sehi]

I love your, you know, race to the bottom discussion. You can't shrink your way to greatness. Like, having a great life is not about having less life. Which brings up the last piece here. Regret number five, waiting too long to spend their money. I mean, let's go to not your current book, Jordan, speaking of books, but go back to taking stock. I mean, you kind of address this in that book.

[Jordan Grumman (Doc G)]

I mean, a lot of people who spend time listening to podcasts like this one will probably die with excess money. And this gets back to what Jill was talking about. How do we spend in a way that's congruent with who we are, our values, et cetera? I'm a little bit different in the sense that our. But I actually think we give too much credit to spending completely, right? So I think buying things gives us very short term happiness that disappears fast. I think spending on experiences is probably a little bit better, and there's some great data about how that has a little bit longer lasting effect on happiness than spending on things. Ultimately, I think the spending that really is great for us is when we spend on becoming a better version of ourselves, right? So it's. It frees us to do the things that really light us up. It frees us to connect with the people we want to connect with. Maybe it makes life a little easier. It is really hard to die with zero, right? The Bill Perkins die with zero. It's really, really hard to do that. And I don't think we should beat ourselves up for not getting there. But I also think we probably shouldn't die with 10 million either. I think we've got to find a happy medium in which we're not stressing about whether we're spending too much or too little, but we're using that money in ways to really try to make our lives as better as possible. Getting rid of things we don't like, spending consistent with our values, becoming a better version of ourselves, being generous and helping other people. Like these are all really good uses of our money that probably do move the needle when it comes to happiness.

[Joe Saul Sehi]

Jill. It also strikes Me, as Jordan's talking, you probably have two different types of people that listen to your show. People that feel like they need to be more frugal. Right.

[Jordan Grumman (Doc G)]

But.

[Joe Saul Sehi]

But you also have these people that, you know, frugality is the name of the game. Like, there have to be some hoarders in your audience. Like, I'm not spending a dime.

[Jill Ceriani]

This is the frugal person's problem for sure. And I can see it in myself, too, that I think this would be the way that I lean of waiting too long to spend the money. I'd rather keep it, you know, hoarded in my freezer than pull it out and use it. So we really need to take stock of what is enough. I think that that's an important conversation curiosity to have with ourselves. What do I want and what. What is going to be enough to get me there and how do I want to utilize, as Jordan's describing, this tool, this resource? How do I want to manage this in a way that is very intentional, that isn't full of deprivation? And I think it's going to require a bit of some reframing for those of us who might lean in this direction of, you know, it's not that I'm spending down my savings, but I'm using what I intentionally set aside. And again, that's going to be a total shift. When we talk about transition when we are retiring, that's a. That's a transition from working years to retiring years, to our expectations of self, our view of self, the way that we relate with the world and those around us. And so I don't think we can expect this to just shift overnight. But I do think that there can be some mindset changes that happen as we go to be able to make that transition as smoothly as possible and be as gracious with ourselves as possible while recognizing I saved up this money for a purpose.

[Joe Saul Sehi]

Yeah.

[Jill Ceriani]

There was a reason I have defined my enough and I know what my plan is, and I'm educated on the numbers and there is permission for me to do with this. What I have decided to do, what.

[Doug (Joe's mom's neighbor)]

I took from all of that, Jill, was that you keep your money in the freezer.

[Jill Ceriani]

That's where my grandmother catches her money. She thought she would. I mean, this is not uncommon for those who live through the Great Depression, but yeah, cold hard cash.

[Joe Saul Sehi]

Cold hard cash. Jesse, geeking out kind of about what Jill's talking about also strikes me that if you are frugal and you do intentional spending like this, this feels to me like the type of Stuff that you write about consistently, you're going to, number one, have to save less money because of the fact that you're only spending intentionally. Number two is your tax issues are going to be much less because of the fact that you know you're not as worth like it just. And your asset allocation can be a little sloppier. Like, there's so many benefits to being frugal that, that work out in your financial plan.

[Jesse Kramer]

Oh, a hundred percent. It is funny. If you find joy in a very frugal lifestyle, then like, more power to you. Why complicate it from there? And to some extent I would also argue, like, if you're a person who is spending too much, I'm going to echo what both Doc G and Jill said here. Like, if you're a person who's spending too much, are you sure you're getting joy out of that extra spending? Because on average, the data might say otherwise.

[Joe Saul Sehi]

But if you had clients, though, where you had to say, loosen up, like, because I did, I had clients, right? To say, you know what? Like Jill said, you accumulate this money for a reason. Let's live. Let's live.

[Jesse Kramer]

It's a touchy topic though. And that's, I mean, one thing I'm learning firsthand is that there are so many really interesting topics that are also touchy topics. I mean, estate planning can be one of them. The idea of loosening the purse strings can be another one of them. When someone is sitting there fearful of what's going on in the market or fearful of what's going on in society, you don't want to just beat them over the head with statistics about, don't time the market. It's timing, it's time in the market. You know, it's the first step is to, I think, say, like, I hear you and I feel what you're feeling, and I totally get it. And so if someone is not spending enough money, there are some really good conversations to be had about why that is. And if they realize they could be spending more, if they feel some sort of like, insecurity or they feel some sort of what is it? It's not abundance. Mindset, scarcity. Mindset scarcity. So there's some really good conversations to have, like preliminary conversations before just saying, like, you know what, Joe? Like, this is kind of dumb. You should be spending more money. I know that's callous. It's more callous than any one of us would put it out there. But my point is, oh, you tell.

[Joe Saul Sehi]

To me that way you would say it that way.

[Jesse Kramer]

It's one of many very interesting but also sensitive subjects to bring up in financial planning, but an important one nonetheless.

[Jordan Grumman (Doc G)]

You know what I've also noticed too is I run a mastermind and we talk lots about money and enough. And one thing that I've actually learned is it's not that people aren't spending enough. It's they're accumulating too much. So I see a lot of people who are getting to the end of a career that they don't enjoy, and they're sticking around to accumulate more, not because they actually need them more, but because they're afraid and they don't have a good understanding of enough. And so what happens is they lose years of freedom, right? Instead of being home doing things they love to do, they're working at a job they don't like. So it's not even almost sometimes that they're not spending enough. It's that they're accumulating too much. And in the process of accumulating, they're keeping themselves from doing things they might enjoy.

[Joe Saul Sehi]

Which is sad because I think a lot of the time, especially Jill, very frugal people, like they, they over feel the expenses, but they under feel this other limited resource of time. You know, the fact that I don't have. I don't have time. Well, speaking of time, I think that's. This is a great time to end this chat. This survey of five things that a retirement planner says that they would regret in five years. And Jesse, I, I think I'm with you. I don't think people are phrasing these. I'm going to regret these five things. But still, I think overall, pretty good list.

[Jesse Kramer]

I agree. I mean, it is a good list. Like these are nothing here, reinventing the wheel, but like fundamentals that, that any.

[Joe Saul Sehi]

Retiree ought to be aware of, and hopefully stackers. You were able to take away one or two good things that you would have never heard on the how to Money podcast, not once. This is going to be the funnest month raising more money than Joel and Matt for our 501C. I mean, we're helping kids and we get to make fun of Joel and Matt, which is great. All right, let's find out what's going on, where all you guys are, because you know what? The next thing to do is stackers. We talked about listening to the podcast, reading the books, doing the stuff. Well, these people have been doing all that fine work. So, Jill, let's start off over at Frugal Friends what are you and Jen up to this crazy month of November?

[Jill Ceriani]

Yeah, we've got lots of episodes coming out on YouTube, so we've been really going heavy at video recording ourselves. So that's been really fun. People can follow us on YouTube. And we've still got our new book out. We released our book this year, buy what you love without going broke. So that's a good one as well. Just for kind of learning the skill of spending.

[Joe Saul Sehi]

Yeah.

[Jesse Kramer]

And I.

[Joe Saul Sehi]

Well, and I love the piece of it that we spoke about just a little bit today of thinking about what do I really value much more than trying to shrink your life? What do I actually value and spending that way? And that's at the Frugal Friends podcast where finer podcasts are found. Finer podcast, like Jesse's podcast, which has 15 different names, but we'll call it the Personal Finance for Long Term Investors podcast. How about that? I got it right this week.

[Jesse Kramer]

That was pretty good.

[Joe Saul Sehi]

That was pretty good. Thank you.

[Jesse Kramer]

One of many different names. You're right. One of many different names. It's like Gandalf in Lord of the Rings. Depending on where he is, he goes by name to White Gandalf. Graham Mithrandir. We're going deep there.

[Joe Saul Sehi]

Wow.

[Jesse Kramer]

What's going on on Personal Finance for Long Term Investors? We've got a cool episode coming up with a professor who specializes in the marketing of debt, really like financing and mortgages. And so that one's coming up next week. Then we'll have an AMA episode and then a deep dive episode the day before Thanksgiving coming out. And it's all about health around the holidays because, you know, health and wealth are two sides of the same coin. And so while you're eating your third piece of pecan pie, you're going to.

[Joe Saul Sehi]

Tell me to eat better over the holidays, are you, Scrooge?

[Jesse Kramer]

You'll have to listen and find out, man.

[Joe Saul Sehi]

And that is that the Personal Finance for Long Term Investors podcast, where finer shows like Frugal Friends are found and awesome shows like Earn and Invest. What's going on at Earn Invest in.

[Jordan Grumman (Doc G)]

November, Jordan, Just before this comes out on Thursday, I have Beth Pinsker on. She's a journalist at MarketWatch and she wrote a book called My Mother's Money, all about exactly what we talked about with estate planning. She helped her mother through a chronic illness and managed her finances before and after her death. And she goes deep on what you need to know about managing a parent's finances.

[Joe Saul Sehi]

Wow. And I would think, consequently, than your own.

[Jordan Grumman (Doc G)]

Very much so.

[Joe Saul Sehi]

Yeah. And that is it. The Earn and Invest podcast. Also where finer podcasts are found. Let's say a big thank you before we say goodbye to all of our friends hanging out with us on YouTube. Guys, you guys were amazing as usual. Nice job. Give yourself a big pat on the back. Let's though, turn it over to Doug. I don't know why I turned over to Doug and asked this question. Doug, what are what are our takeaways? What's on our to do list for today's show?

[Doug (Joe's mom's neighbor)]

Well, Joe and everybody else, buckle up. It's about to get a bit bumpy. First, take some advice that Jill shared at the beginning of the show. Your budget should be like an Olympic gymnast. What?

[Joe Saul Sehi]

Agile.

[Doug (Joe's mom's neighbor)]

Agile and flexible. Second, remember what Jesse said about estate plans. You could probably get away without having an estate plan if you don't have testes. But it doesn't mean you shouldn't have one. Especially if you want want to specify who gets your magic. The Gathering cards. But the big lesson. If you see a meteor hurtling through the sky like in today's trivia, don't bother telling Joe's mom. She'll remind you that the real Fireball is locked in the pantry. And no, you can't drink any of it until after Jeopardy. She wants to beat you while you're sober so she can brag to her friends down at the biker bar that she beat you fair and square. Thanks to Jill Sirianni for joining us today. You'll find Jill's Frugal Friends podcast wherever you're listening to us now. We'll also include links in our show [e-mail] thanks to DOC G for hanging out with us today. You'll find his insightful podcast Earn and Invest wherever you listen to Finer podcasts. And finally, we've got Jesse in the top of the mountain position. When you're the last credit, that means you are sitting in the catbird seat, man. Thanks to the Jesse Kramer for joining us today. You'll find Jesse's totally fly podcast Personal Finance for Long Term Investors wherever you listen to this show and Jill's show and even Jock G's show. All the shows, you get them all right there. This show is the property of SB Podcast LLC, Copyright 2025 and is created by Joe Saul Sehive. Joe gets help from a few of our neighborhood friends. 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 spots. Come say hello. Oh, yeah. And before I go, not only should you not take advice from these nerds, don't take of advantage 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.