How To Tell Your Boss You Want to Retire Often (SB1728)

Summary

Podcast Summary: The Stacking Benjamins Show

Episode: How To Tell Your Boss You Want to Retire Often (SB1728)

Release Date: August 29, 2025
Hosts: Joe Saul-Sehy, OG, Doug
Guests: Jillian Johnsrud (author, "Retire Often"), Paula Pant (Afford Anything)

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Episode Overview

This lively Labor Day weekend episode explores the unconventional idea of taking "mini retirements" throughout your career, not just at the end. Joe, OG, Paula, and guest Jillian Johnsrud discuss how and why to step away from work periodically, how to pitch it to your boss (especially if you’re not self-employed), the financial and personal planning involved, and the broader benefits of practicing retirement before making it permanent. The conversation is peppered with personal anecdotes, strategies, and the show’s trademark humor.

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Key Discussion Points & Insights

1. What Is "Retiring Often"?

• Jillian Johnsrud has taken 12 mini-retirements over her life and recently authored a book on the topic.
• "It's something that feels a little impossible or a little crazy or weird. And then once it's explained, people are like, oh, I mean, I guess I could do that. And it's also life changing." (Jillian, 05:35)

Definition:

• A "mini retirement" is described as taking a break of a month or more from your job to focus on something meaningful outside of work.
• It can happen between jobs or as a negotiated leave with your employer.

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2. How to Pitch a Mini-Retirement to Your Boss

The Four Elements of a Successful Pitch (Jillian, 09:55)

• Be Positive: Focus on aspirations, not burnout.
• Make It Interesting & Specific: Tie it to a meaningful, concrete event or goal.
• Frame as a One-Time Event: Present it as unique to reduce pushback.
• Bring Solutions, Not Problems: Come prepared with how your absence will be managed.

“It all has to be true. But it can't be the whole truth because the whole truth is too big... keep it real simple, but use those four things.” (Jillian, 10:02)

Example Pitch:

"My parents always planned to take a bike trip through Croatia at 60. My dad passed away, and my mom is turning 60. I'd like to do this with her, but I need extra time off. Here’s a plan for how my work will be covered." (paraphrased, 10:49)

Paula’s Tactical Tips:

• Anticipate and address all your boss’s pain points; where possible, enact solutions in advance.
• If you're replaceable, try to arrange coverage with colleagues. If you’re not, propose ways to cross-train staff or document procedures. (12:09)

"You don't ever want to bring them a problem. You want to bring them solutions." (Paula, 12:09)

Acknowledging Obstacles:

Jillian recommends naming the tough issues up front to disarm objections and open collaborative dialogue. (13:18)

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3. Planning—Financial and Logistical Preparation

OG’s Advice:

• Don’t surprise yourself any more than your boss; prepare your finances and logistics months in advance.
• Consider automating bills, covering all responsibilities at home, and understanding how unpaid time will affect your budget. (14:33–16:58)
• “What are the things that might break if I don’t pay attention to them?” (OG, 16:23)

Runway Required:

• If a mini-retirement is just a month and you have a job to return to, your regular budget with some savings should suffice.
• Quitting for a year? Plan for at least a year’s expenses, plus 6–8 months’ runway to find another job. (Jillian, 17:04)

Timing Your Ask:

• Generally, ask your boss 3–4 months in advance; 12 months is too early in most office cultures. (18:02)

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4. Practicing Retirement—Why It Matters

The Flaw of Saving It All for Age 65

• Many people discover, too late, that they dislike the “retirement” they dreamed about.
• Jillian and Paula liken practicing retirement to dating before marrying; you need a test run to know if it suits you. (19:15–22:11)
• “Retirement is a skill, and like any skill, it requires practice.” (Paula, 20:39–20:42)

"Spread out the disappointments. Don’t feel all the disappointments at once at 65—pace them out throughout your life, every mini retirement." (Jillian, 22:11)

Flexibility & Course Correcting

• Plans change due to life events (health, markets, family needs).
• OG: “The action of actually planning is the thing. The conversations ...are the thing that’s most important.” (22:59)
• Embrace mini retirements as small experiments—test and adjust as you go.

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5. Is the Trend of Retiring Often Growing?

• Sabbaticals are twice as common as a few years ago (though statistics admitted to on-air improvising!) (25:42).
• Especially for workers in their 20s and 30s, job changes are more frequent, often leading to natural career pauses.
• The old model of one job and a late-life retirement no longer fits many people; mini retirements in between jobs are more attainable and can prevent the “big retirement” letdown. (Jillian, 26:02)

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6. Overcoming Limiting Beliefs

• Don’t fall for the false dichotomy that you can either work endlessly or retire forever—you can do both, in cycles.
• Paula: “Most of us as children, we are taught a very, very linear, specific way to live our lives... But ultimately, if there’s something ...you’re truly committed to doing, you can always find a way to make it happen.” (32:32–33:27)
• Reframe “I can’t” into “I choose not to,” which puts the control back in your hands. (Paula, 33:54)

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7. Navigating Trade-Offs and Memory-Making

• Jillian suggests that while big “epic” mini-retirements can be exhilarating, multiple smaller ones with loved ones build cherished memories over time. (51:38)

“The cool thing feels cooler initially and the little things with people you love gain more traction as you age in your memory.” (Jillian, 52:27)

• Paula references “nostalgia bias”—cherished memories grow rosier over the years, whether from many small trips or one big one (53:45).

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8. Health, Capability, and Timing Your Dreams

Jillian’s 4 Health Quadrants (45:03–46:24)

• Life is not just about money—physical capability, preferences, and priorities change over time.
• Don’t defer high-physicality goals (like hiking a long trail) to after age 65, since the average “healthy life expectancy” in the U.S. is just 66.

“If you feel regret about that, feel it now where you have the ability to change your mind..." (Jillian, 46:42)

Paula adds: Our lifelong interests and abilities shift. What you treasure at one age may not matter (or be possible) later. Look for themes in what’s always brought you joy. (49:03)

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Notable Quotes & Memorable Moments

• "Retirement is a skill, and like any skill, it requires practice."
  — Paula Pant (20:42)
• "It all has to be true, but it can't be the whole truth... If you try to tell the whole truth, you'll lose the plot."
  — Jillian Johnsrud (10:02)
• "Spread out the disappointment. Don’t feel all the disappointments at once at 65—pace them out…the same way with mini retirements."
  — Jillian Johnsrud (22:11)
• "The action of actually planning is the thing... because anybody who retires right now...in five years from now, they're gonna go, 'Well, that didn't happen.'"
  — OG (22:59)
• "Rephrase 'I can't' as 'I choose not to.' ...There's such a difference between saying I can't versus I choose not to."
  — Paula Pant (33:54)
• "You're going to show up to that retirement party whether you're dressed for it or not."
  — OG (30:12)

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Timestamps for Important Segments

• 05:35 — Jillian introduces the concept of "retiring often" and her book.
• 09:55 — How to pitch a mini-retirement to your boss (Jillian’s four elements).
• 12:09 — Paula’s tactical negotiation strategies.
• 14:33 — OG on the importance of planning and “runway.”
• 17:04 — How much financial buffer is enough? Jillian defines mini-retirement.
• 19:15 — Problems with waiting until age 65 and the importance of rehearsing retirement.
• 22:11 — The value of spreading out life’s disappointments and learning from mini-retirements.
• 25:42 — Mini-retirements: trend or wishful thinking?
• 32:32 — Overcoming limiting cultural beliefs and the false dichotomy.
• 45:03 — The four health quadrants: capability, costs, and aging.
• 51:38 — Should you save for one big dream or pursue multiple smaller ones?
• 55:16 — The anticipation of mini-retirements is itself rewarding.

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Light-Hearted & Engaging Moments

• OG and Doug’s banter about retirement party dress codes and advanced ages.
• The playful trivia segment on the real cost of labor and delivery in the U.S. (winner: Jillian with her close guess, 43:32).
• Frequent audience interaction and jokes about running, camping, and old school vs. modern “sabbatical” culture.

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Resources & Next Steps

• Jillian Johnsrud’s Book: Retire Often – available everywhere books are sold.
• Podcast Connections:
  • Paula Pant’s Afford Anything podcast
  • Stacking Benjamins YouTube channel (catch the team live on Mondays)
• Financial Planning: OG offers personalized help via stackingbenjamins.com/often

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Takeaways

• Mini-retirements are possible for regular employees, not just entrepreneurs.
• Planning, pitching, and practicing retirement skills will make your future full retirement far more successful—and less risky.
• Embrace both small and large breaks; memories, flexibility, and health don’t last forever.
• Challenge linear life scripts—retire (even briefly) before you actually retire!

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"Make your life a science experiment! Retire often, learn as you go, and enjoy the journey—not just the destination." (paraphrased from Jillian, 27:45)

Transcript

[Joe]

Two hours ago, Kyle arrived at the bar.

[OG]

Hey, what's everyone drinking?

[Joe]

Thirty minutes ago, Kyle got his friends.

[OG]

Another round of drinks.

[Joe]

Cheers.

[OG]

Five minutes ago, Kyle decided to drive home drunk. A minute ago, a law enforcement officer.

[Joe]

Pulled up behind Kyle. Sir, have you been drinking tonight? A chain of events that began two hours ago is about to change Kyle's whole world. Drive sober or get pulled over. Paid for by nhtsa this episode is brought to you by Indeed. When your computer breaks, you don't wait.

[OG]

For it to magically start working again.

[Joe]

You fix the problem. So why wait to hire the people your company desperately needs? Use Indeed's sponsored jobs to hire top talent fast. And even better, you only pay for results. There's no need to wait. Speed up your hiring with a $75 sponsored job credit@ Indeed.com podcast. Terms and conditions apply. I don't like my job and I don't think I'm gonna go anymore.

[Jillian Johnsrud]

So you're gonna quit?

[Joe]

Nuh. I'm just gonna stop going.

[Jillian Johnsrud]

So are you gonna get another job?

[Joe]

I don't think I'd like another job.

[Paula Pant]

Well, so what do you wanna do?

[Joe]

I wanna take you out to dinner. And then I wanna go back to my apartment and watch Kung Fu. Do you ever watch Kung Fu?

[OG]

I love Kung Fu.

[Doug]

Live from the basement of the YouTube headquarters, it's the Stacking Benjamin show. I'm Joe's mom's neighbor, Doug. And what happens when that early retirement or mid career pit stop goes off the rails? Well, as mom says, you'll stop and put it back on. Today we're diving into retiring, often with the woman who's lived that reality, Gillian Johnsrud. Or if we were in the old country, Ilian Jonsrud. Plus a woman who's negotiated with her boss for time off before Paula Pant. And the guy who's designed the plans for people to create a stream of income to live on while they're gone, our resident seat, og plus of course, we'll include a pit stop halfway through for our year long trivia contest. Can Paula and team Jesse continue to reel OG back in? Let's find out. And now here comes a guy who pitched a month off to his boss and accidentally got elected employee of the month for leaving. It's Jo Sal Sehi.

[Joe]

Not a true story, but there were days where that could have been true back in the day. Hey everybody. Welcome to Friday on the Stacky Benjamin show on this special beginning of Labor Day weekend episode. We're so happy you're here. Sit back and relax and by the way, in the future, if you want to join us live, we do these live on YouTube normally on Fridays. So number on Fridays. What am I talking about? Normally on Mondays. So Monday afternoons, come join us on the YouTube channel. But let's meet the team, and we'll start with a guy across the card table from me. Mr. OG is here. How are you, my friend?

[OG]

Man, I'm just happy to be here.

[Joe]

Ready to celebrate Labor Day.

[OG]

I'm celebrating by not laboring.

[Joe]

Well, I think that's the point, isn't it? We stop and we rest.

[OG]

And we always told me in Labor Day, you're supposed to labor. He's like, we're going to pull weeds. We're mowing the grass.

[Joe]

We're.

[OG]

We're painting the fence. It's Labor Day.

[Joe]

You're.

[OG]

You're meant to labor today. And I was like, all right.

[Joe]

I love how dad pulled the con.

[OG]

I don't do that anymore. I do that to my kids.

[Joe]

Yeah, you teach, you teach the young kids. This is all about laboring in the yard, about labor. And the woman who's laboring high above Manhattan, Paula Pant is here. How are you?

[Paula Pant]

I am great. You know, I always labor on Labor Day because usually by the end of the summer, there are a lot of, like, projects that still need to be tied up, things that you're behind on. It's just, it's a great catch up day for all kinds of work.

[Joe]

So wait a minute. So you con yourself? Like OG cons his kids to get stuff done. I know we have to labor.

[Paula Pant]

I do.

[Joe]

I do. The boss says we have to. And the woman who is in the wilds of Montana, I believe, I think she is right now. Jillian John joins us. How are you?

[Jillian Johnsrud]

Thank you. Very good, Very good. You know, September is the biggest, busiest garden season. So all five children will be laboring in the yard because, like, it's. It's harvest time. We got to get this stuff done.

[Joe]

But, Jillian, do you have to lie to them? Like OG has to lie to his kids?

[Jillian Johnsrud]

No, it's like brute manipulation and like, forced. Sorry. We're just. Everyone else is relaxing and that is not your fate in life.

[Joe]

That's not the way it works. That sounds like my mom growing up. We had this gigantic garden. Well, she supposedly she had the garden, but I think my brother and I, Jillian, truly had the garden.

[Jillian Johnsrud]

Oh, yeah.

[Joe]

Was our responsibility. Now, some of our very money, geeky friends may have heard you talking about the topic that we have today. I, I wanted to do this a little different so that everybody gets something new and fun. But for people that aren't in that community, they may not know that you just wrote a book about retiring often. What made you decide to write a book on this topic we're going to dive into today.

[Jillian Johnsrud]

It's something that feels a little impossible or a little crazy or weird. And then once it's explained, people are like, oh, I mean, I guess I could do that. And it's also life changing. So it's like a good combo of very possible but also very life changing.

[Joe]

I thought something life changing here, Jillian, for all of us would be, what if we instead of do this in the positive way like any other podcast would do, let's do this in the negative way. Let's like, what happens when it goes off the rails. So Jillian and Paula and OG will lean on their expertise. You, Jillian, have retired often in your own life?

[Jillian Johnsrud]

Yeah, absolutely. I think I've done 12 of them now. A nice neat dozen.

[Joe]

And. And you're just starting, right? You got like 12 more in you for sure.

[Jillian Johnsrud]

For sure.

[Joe]

Absolutely. We're also going to talk about how to negotiate this with your boss, because I know what half of our audience says. They're always like, oh, that sounds good. You're self employed. Well, no, I think this is something you could sell your boss on. So we have a woman who knows a little bit about negotiation helping us with that, Paula.

[Paula Pant]

Oh, yes, yes. So I didn't realize you wanted me to say something that precise juncture.

[Joe]

Yeah, I need to do that better. I need to figure out, if only.

[Paula Pant]

What is my name?

[Jillian Johnsrud]

Wait a minute.

[Joe]

Yes, and I think you might have a financial plan. Need a financial plan to do that, which is, oh, gee, your contribution today. Sound good?

[OG]

I was on mute. Yes, sure, sounds great. I will contribute in the same high quality fashion that I have for the previous roughly 15 years.

[Joe]

15 years and some change. All right, we've got Jillian here, Paula here, and OG here to dive into it with Doug and I. Before we get going on this great topic, I just want to be clear here. I've got a couple nice notes lately from people who go, you know, seems like you've had some business owners on. I didn't know that you talk so much to entrepreneurs. I'm never talking to entrepreneurs. I am always, always talking to people who work 9 to 5. So if it seems like the topic is entrepreneurial today, it's because I want our stackers to think like an intrapreneur. And every study shows that if you think like an Entrepreneur, meaning you're entrepreneurial, but you're working for somebody else. Your career is much more likely to go well. You're much more likely to enjoy your work. You're going to take control of as much as you possibly can. You're going to be the go to person, which I'll tell you, is a much more fun place to be. So this is not an entrepreneurial topic, may sound like it, but it's not. Today, we're going to help you help your boss understand that you retiring often. It's going to be great for everybody. You know what, though? We also have a couple sponsors to make sure we can keep on keeping on. So we're going to say hello to them and then sit back and relax and maybe grab a piece of paper and start lining up, grab a calendar. Let's get retiring often on your agenda. So we're going to do that here in just a moment. All right, here is a scenario I think that we've all seen from time to time. Somebody comes up with this big aha plan. They're going to do a thing like a mini retirement. And they didn't do enough planning. And then they realize far too late that they've either blown the budget, they shock the boss, they discover that there's only so much stuff on Netflix they can watch before they get too bored. I think it might include just a little bit more than that. So we're going to go through four key scenarios about making sure this doesn't go off the rails. But Jillian, a place where it goes off the rails initially for 98% of our stackers who are employed by somebody else, pitching it to their boss. Like, I'm, I'm just imagining Doug walking into OG's office and saying, I'm gone for a month. Peace out. How's, how's that going to work for you?

[Doug]

He's asking me to do that.

[Joe]

Usually it's like, please make that happen.

[Doug]

Doug, your vacation's been pre approved. I didn't ask for one. Oh, I know.

[Joe]

I already packed your desk. How do you actually, though, Jillian, craft this story to your boss so that the boss is in complete shock when you're like, hey, I got a great idea.

[Jillian Johnsrud]

First, I think it starts with, this can't be entirely your boss's problem. They have their plateful, they have a real job. They've got enough stuff going on. You can't just show up and be like, yeah, I'm like, I'm so tired and burned out and I don't want to look at all Yalls faces anymore. So I need you to figure this out because I'm leaving.

[OG]

So.

[Jillian Johnsrud]

So you have to set up the stage. And I encourage people to kind of focus on four things. It should be positive, like, not like, I can't stand to look at you people, like, let me leave. It should be something interesting, ideally something specific instead of like a really general thing. And then ideally, if it can be kind of a one time event. And so I always tell people it's kind of memoir rules in that it all has to be true. But it can't be the whole truth because the whole truth is too big. It's too complicated. If you try to tell the whole truth, you'll lose the plot. So keep it real simple, but use those four things. And that could sound like if you went into your boss and you said, hey, my parents, they always planned when they were going to retire at 60, they were going to do this bike trip through Croatia. For a month they've been dreaming about this. But you know, my dad passed away a few years ago. This year my mom's turning 60. She really still wants to do this bike trip. I have a week of pto, but I would need another three weeks off. Is there any way that I could take a month off and do this bike trip with my mom? It would be really meaningful to help her celebrate this new season of her life. And if you've done some of the logistical planning of what this would look like for your employer and you come up with a story that has those four elements, it's going to get you off to a good start.

[Joe]

Well, then you're not. It sounds like you're asking them to help you with this dream come true. Like, let's collaborate together on making this happen.

[Jillian Johnsrud]

Yeah. You want the conversation to be very creative and collaborative so you don't have to have every detail worked out. But say, I have some ideas. I know there'll be some challenges, but I put some thought into this. Here are some of the things that I figured out of how this might work.

[Joe]

Paula, there's got to be some key tactical things that we can use. Some tactical strategies we can use when we walk in with Jillian's 4 Things to Try to negotiate this. What if the boss still isn't that enlightened? And it's like, no, I think you should get back to your desk and leave the bike in for your mom or whoever, whoever's going to be in the story.

[Paula Pant]

Right. Well, there are a couple of things. First to Jillian's Point, you don't ever want to bring them a problem. You want to bring them solutions. So think through what would be all of the barriers for your boss. Do they have to train and onboard somebody else? Do other people in the company have to pick up little components of your job? And this is very much going to depend on the structure of the type of work you do. Right. If you are a shift worker and you can talk to some of your colleagues and have them pick up your shifts, that is going to be a very different scenario than if you are in a situation where you're the only person who's trained to do a very specific thing, and there's nobody else who has the training to do the type of thing that you do.

[Joe]

A piece of accounting or a nurse in the operating room.

[Paula Pant]

Yeah, yeah, exactly. So when I say start with the solution, it's how do you make sure that this in no way becomes your boss's problem? How do you go to them with a solution not just already thought of, but, like, to the extent that you are authorized to do so? Already enacted?

[Joe]

I like that also, Jillian, because whether you end up getting roadblocks or not, you're already thinking through what potential obstacles the boss might bring up ahead of time.

[Jillian Johnsrud]

I think it's really important, especially when you're bringing something kind of maybe emotional important to you, that you articulate the challenges that you think that they're thinking. Because sometimes if your boss likes you and you're kind of friends and you say, like, I have this big goal and this big dream, it's really hard for them to be like, yeah, there's a whole bunch of problems with that, though. So if you can articulate them first, it really speeds along this productive, creative, collaborative conversation. So just say, say the negative things out loud to get the ball rolling.

[Joe]

I know that we pay a lot of attention lately, especially to the Stoics, but I also really like some of the Chinese philosophers in a. Very much like Sun Tzu's the Art of War. I love this phrase, define the battlefield, you know, and the best battle is the one that's never fought. Right. If we think about the battles ahead of time and know these are the potential problems, then I don't have to fight that battle. Speaking of that og, I want to go back to before this, before this even happens, because I think to Jillian's point and Paula's point, you got to articulate the audience, but I think you also got to be financially ready to go. I mean, there's got to be a Little bit of Runway. What are some of the potential obstacles we might need to clear before we take our mini retirement?

[OG]

The thing that I'd add to what both of them said earlier is I was watching a video on conflict with Chris Voss, the hostage negotiator guy, and one of the things that he said was, always start with the thing that they're going to think. When you say the thing that's coming out next, you're probably going to think, I'm a big jerk, but I actually don't want the salmon. And they go, oh, because they can't go, you're a big jerk because you've already just said, like, you ordered the salmon. They bring it out, and you go, listen, you're gonna think I'm a complete jerk, but I actually don't want this. Can I have something different? And they're more likely to be like, oh, yeah. Okay, cool. So as you start framing these conversations, like Jillian said, putting yourself in the shoes of the person who you're talking to and going, well, what would I do if one of my employees came and said this? I want to take a month off to go bike riding in Europe? I go, you're crazy. We don't have the time. Like, this is the busy time. And you start with, hey, you're probably going to say, it's super busy. And it's, you know, it's crazy. But here I have this idea, and it totally disarms the situation. Anyways, you were talking about the money aspect of it, and really, the big thing when it comes to this is this can't be something that you just kind of spring on yourself, just like you're springing on everybody else. Just because it's the first time your boss is hearing about it. It's probably not a good idea to be the first time that your money plan is hearing about it. If you wake up on Monday and go, you know what I should do? I should probably take the next month off because I am tired of seeing all these people's faces. And honestly, if you've done a really good job of emergency funds and that sort of thing, maybe you can do it. But I think you got to think through, how am I going to not just afford it, because there's that aspect of it, but if I'm truly away, if I'm truly detached from something, what are the things that might break if I don't pay attention to it? Like, for example, do I have to automate all my credit card payments? You know, I'm going to Be in another country. Is it hard to use my phone to make my amex payment? You know, can I automate that? How am I going to make sure that if I leave my house that the AC doesn't break or I have pets or something like that? You need to think through those things long in advance, not just the money aspect of it, which obviously you got to cash flow that out and make sure that you're good. But then I'd say even the next step of it is what else is going on in your world that if you step away from, you are responsible for? What's that look like?

[Joe]

What kind of a typical Runway do you see people have, Jillian, before they take a mini retirement, Is it six months? Is it two years?

[Jillian Johnsrud]

Well, it depends how long your mini retirement is and if you are negotiating it off or if you're doing it in between jobs. I kind of define a mini retirement is a month or longer. Stepping away from your 9 to 5 to focus on something that matters to you. So if you're only taking a month off and you're negotiating that with your employer, so you know you have a job to come back to, I think your normal financial plan probably works. You would need to cover, if it's unpaid time off, you have to cover that. And then you have to cover the cost of whatever adventure you have. But it's not super significant. Now, if you're planning to quit your job and leave and take a year off, yeah, you've got a year of expenses. And if you're going to be out of the workforce for a year, you might want to plan on another six months, eight months of Runway to find that next job. And so the Runway is. Is much bigger. Like, you'd want a much bigger emergency fund in that case.

[Joe]

And how early in this planning do I start talking to my boss? I mean, if I want to take a month off, do I start talking to them six months before the month off?

[Jillian Johnsrud]

It's a little bit job specific. You know, some people are. No, in my industry, like, I would need to have this much Runway, but in general, I say about three to four months. If it's too early, if you do it like six to 12 months off. In most corporate cultures, if it's happening 12 months away, it's just basically not happening. Like, there's no thought process, there's no bandwidth. Zero action will be taken. So three to four months is about the sweet spot where it gives you enough time to prepare, but not so much that everyone procrastinates.

[Joe]

You leaving and then two days before. It's like that third grade science homework. Oh, I had the last six weeks to work on it, and I did nothing. Right.

[OG]

Thesis paper. Don't ask me how I know.

[Joe]

Let's talk about the second scenario of retirement coming off the Runway. And this is waiting until age 65 to figure out what retirement really looks like. And I feel like, Jillian, this is part of what you're trying to avoid is, you know, let's not get to this quote later that a lot of people wait for, and then we end up disliking it. Paul, I feel like this would be a little bit like marrying somebody without ever dating. And I know you and I talking a little bit. You've had some great dates lately. Would you want to marry those people? Nope.

[Paula Pant]

The thing is. So I come from an arranged marriage culture. My parents got married. They did not meet each other prior to their wedding. My dad actually told me that when he arrived at his own wedding, he was, like, looking at all of the women there, wondering which one was which one is. Yeah.

[Doug]

This is an awesome show. It's called Married at First Sight. This. What episode were they on?

[Joe]

Doug's gone to the bar some nights and had that thought. Which one of these people am I going home with?

[Paula Pant]

They took. They took the Nepalese arranged marriage culture and turned it into a TV show. So that does happen. It's happened for millions of people. I mean, you can make that work. But I think that at least in the United States in 2025, for most people. People want to know, in the context of retirement, it's better if you can practice retiring before you actually retire. Right. Because the construct that we currently have is this binary. It's you're working or you're not. It's very much a cliff, like, working, working, working, working. And then there's this cliff. And like, now you're not. So you're really thrown into the deep end. At the age of 65 or 67, or when you. Whatever age that is, you're not going to be good at anything. The first time you do it, the first time you swim, the first time you ride a bike, the first time you rollerblade. Like, why would you be good at retirement? Retirement is a skill, and like any skill, it requires practice.

[Joe]

Jillian, what Paul is saying is that why you really dive heavily into this, that practicing retirement is super important.

[Jillian Johnsrud]

Absolutely. I kind of compare it to running a marathon. Some people are obsessed about the idea of running a marathon. And you're like, oh, yeah, that's so cool. And you go, well, have you. Have you, like, ran like a 5K? And they're like, no, no, no, no, no, I'm not. I don't want to waste any time on 5Ks. I'm just going to sit at my desk and work really hard, 60 hours a week. And then one day I'm just going to start running a marathon and I'm going to be awesome at it. Actually, no, I'm going to put down.

[Joe]

The donut and run the marathon.

[Jillian Johnsrud]

And then the justification is, well, I've been listening to podcasts about marathons. I've read some books about marathon, so I'm pretty sure I'm going to be awesome at it. And it's like, well, why don't we just try it out a little bit? Why don't we give it a little test run? What's the harm in taking a month or taking three months? Work out some of the kinks and get your bearings. And if nothing else, like, let's say you take a month off and it is amazing. It is absolutely magical. And you're like, this is the best month of my entire life. Then when the time comes to retire, you might be confident moving into that new season of life. You might not get stuck in one more year syndrome, because you're like, I've done it. I've lived it. It was great. And now, like, I'm ready to go all in. I'm not scared about looking down the barrel of these next 40 years because I have tasted the promised land, but.

[Joe]

I think the other side is valuable, too. I mean, at the time, it might suck, but learning that it's not everything or it's not what you truly wanted. I think, Jillian, that's also great data.

[Jillian Johnsrud]

It's really helpful. And I sometimes I have a dark sense of humor. I kind of view it as, like, there will be some disappointments. Some things will not work out as you anticipate they will. I'm of the mindset of, like, spread out the disappointment. Don't feel all the disappointments at once. At 65, pace them out throughout your life, every mini retirement. Deal with your three little disappointments. Get them out of the way.

[Joe]

Johnny Dreams spreading disappointments wherever you go. Yeah, that is deeply dark, my friend. Oh, gee. How many times have you and I talked about on the show about the important thing about your retirement plan is that it's sticky? And I feel like what Gillian's talking about here makes it stickier, which means it's easier for your plan to stay in place and you're not going to blow up your plan.

[OG]

I think the biggest thing here is recognizing that no matter what you think you're going to do or how you think you're going to spend money, or what you hope the market's going to do when you retire, or any of these things, the reality is that all of it's going to change. And maybe that's the scariest part about it, is it's like you have this plan. It's all I's are dotted and T's are crossed. And I know exactly when I'm going to do my Roth conversions. And I know the exact day I'm going to file for Social Security. And I know all these things are going to happen. I'm going to spend this money on this day to do this trip with these people. And then you have a medical event or the market takes a crap, or a family member needs assistance, and that kind of pulls you away for a period of time or the trip that you wanted to do you thought was 20,000 and it's really 40,000. And so, you know, there's all these different things that are going to happen. I think that the biggest thing around retirement planning is pointing the boat in the right direction and rowing in the direction that you want to go and recognizing that every so often you have to get out the map and go, am I still pointed in the right direction? Because you're never going to be on course. You're never going to be exactly right. And the action of actually planning is the thing. The conversations that you have about planning is the thing that's the most important. Because I can guarantee that anybody who retires right now and they have all their stuff laid out perfectly in five years from now, they're gonna go, well, that didn't happen. That happened in a different order. That's different. Think about the person that retired five years ago. You know, they retired on January 1, 2020. Life is good. Retirement. Woo. By the end of March, they're like, well, a third of my money's gone. So that sucks. Also, a lot of my friends are dying. That sucks worse. I can't go anywhere that sucks. Think about all the stuff that happened. And five years later, yeah, we can't get back the people that we lost. But your money has exploded. If you stayed the course, you have 5x the money that you thought you did, or 3x the money that. What if you're still spending like it's 2020 now, what are you giving up? It's the other side of that, right? You could be doing all this other stuff, but you just said, well, My plan was 2020. My plan was five years ago. You have to do this exercise on a regular basis. And having those experiences like you guys are talking about here throughout your career is really helpful. My question with all of this is, how likely is it to happen to the average person? Is this the wave of the future? Because I don't hear a lot of this stuff. I don't hear a lot of these one month, three month, six month times off. And, Jillian, it sounds like it's more common, or at least that's the direction maybe the world is headed.

[Joe]

Is it where we're headed, Jillian, or is it just where you think we should have it head?

[Jillian Johnsrud]

Both. I don't know if I remember the exact statistic, but sabbaticals are about double of what they used to be just a couple years ago.

[Doug]

Yeah, we make them up all the time, Jillian. Don't worry about it.

[Jillian Johnsrud]

Perfect. It's exactly double than what it was 36 months ago.

[Doug]

Statistically speaking, with confidence.

[Joe]

That's right.

[Doug]

They'll all buy it.

[Jillian Johnsrud]

But for a lot of people, especially workers, 20s, 30s, for them, their largest increase of like, a raise or promotion is probably going to come in between jobs. And so this idea of, I'll work in one career, in one profession, one company for 40 years, and I'll get a pension and I'll retire at 65, most people are like, yeah, that's not going to happen. So if they're going to switch jobs every four or five years, and they're facing the reality of, well, I might end up having to work longer, what if I just take a month? What if I take three months in between jobs? What if I enjoy a little taste of what I'm hoping to do with my life instead of trying to stockpile all of these hopes and dreams until maybe I can retire at 67, maybe it'll be 70, who knows? They might not be buying a house till they're 40. So.

[Joe]

Well, and I like the idea, Jillian, of what OG's talking about, because if you're spreading these out, I like turning it into your dark disappointments through your life. And instead, you're getting a little playful and you're like, you know what? That wasn't what I thought it was. So now I get to move on. And instead of, you know, you see, so often these people approach, quote, retirement with all of these big dreams, and when it's not what they thought. This is why the average person in retirement, spends 18 months in total bliss and then they have the biggest, darkest depression of their life. This is research according to longevity expert Ken Dykewald. Retirement expert Ken Dykewald. And it's funny, whenever I've talked to audiences about that depression, the head nods I get in every room are huge of people that have been like, yep, 18 months in. I'm like, what is this? It is this, is this all but Jillian, what you're talking about is really making your life a science experiment. Which sounds way more fun.

[Jillian Johnsrud]

Absolutely.

[Joe]

Yeah. I also think though, OG there's this idea of in retirement, if you haven't play tested the idea of spending shocks or spending because you're bored because you have no idea. Right. I just see some of these things that are problematic with early retirees. All of a sudden you've got stuff that, that, you know, late night shop, Amazon. You ever done that, OG where you got a little bit of.

[OG]

I mean, by late night, you mean like 8:05?

[Joe]

That's eight night. That's late night OG time.

[OG]

I know that's late night in my house. I guess there's a little bit of a theory here that if you're a really good saver through your whole life, you don't really turn into a really good spender all of a sudden. But if you're a really good spender your whole life and now all of a sudden you're on a budget, you probably need to pay really close attention to that. If I see a problem in spending, it's more around wanting to pull forward a lot of the. Maybe some days into like right away today. I think it'd be really great to pay for my grandkids college. It's like cool. $100 a month, their babies. Let's just kind of drip that in to the plan and just see how it works out. No, no, no, no. Let's take 70 grand, like fund it all today. It's like, okay. I mean, you're taking a little wind out of the sales here. There's some other changes. And you know, sometimes not that it's like the big family trip that was, hey, we're gonna go hang out for, you know, a couple of days at the lake. Turns into a week and a half on the islands, which, you know, we were going to drive to. Now we're flying. We were going to fly. Now we're flying first class. You know what I mean? Like, it's kind of that creep, that maybe mission creep. I guess that's where I see the spending issues. Although I'd say for people who get to retirement with adequate resources, an equal crime is not spending enough early on. You think about that, that Runway of spending, and go, okay, well, I can spend this amount every single year. It's like, well, that presupposes that you're going to do the same stuff when you're 97 that you're doing when you're 67. And I'm not sure that.

[Joe]

Not likely.

[OG]

Yeah, I mean, it's not the case. But statistically I'd say that 97 year olds are a little slower in their spending than 67 year olds. So maybe some of that you can pull forward. So it's a balancing act for sure. But that all goes back to that planning piece, which is you can't just get to retirement, whether it's about your activities or it's about your money, and go, oh, thank God I made it. Whew, that's over. Now I get to retire. Never think about this ever again.

[Joe]

In which. And then you get there and all of a sudden you're doing. I mean, you're going to show up no matter what planning you did or didn't do. Yeah, I think show up at the.

[OG]

Party regardless whether you're dressed right or not. Hold on. Tm tm. I got trademark that one. Showing up to the retirement party whether you're dressed for it or not.

[Joe]

Dang.

[OG]

It's a good one.

[Joe]

I've got. I've. I also love the contributions of the people hanging out with us live on YouTube. Our friend Paul from the Five Lighter podcast says OG speaks the truth. Been six years retired and Covid was year one. Things were never the same as expected. As long as we're pointed north, we continue to course correct. K San says, I'm aiming for a month at a time, Jillian. Per year in the south of France. She wants to retire often once a year. Many retirements and then it shows up as da. But it is the great divide. Boys says, I just did this for four years, 20 hours for four years and substitute teacher for a year. Now back at 40 hours, which is cool. Jillian. People think I go into retirement and I have to stay retired. And if you don't stay retired, it's like, what's wrong with you? And you're taking that off the table. Go, there's nothing wrong with you. You just decided, it's another season and I'm going back to work.

[Jillian Johnsrud]

I think to Paula's point, there is this like, I'm doing one thing or I'm doing another. And I'm going to do one thing for a really, really long time, and then I'm going to do this retirement thing for a really, really, really long time. And you can just do PA both, like you can work really hard in your career for three or four years and then you can take six months and you can go enjoy yourself and have some fun and you can come back and you can do something else really interesting and meaningful. And I think if people get into this rhythm of I'm going to do cool work and I'm going to live a cool life and I'm just going to go back and forth between these, that transition into full retirement isn't as dramatic or as traumatic because you've been floating back and forth between these and living in kind of that gray area of I do both and both add value to my life.

[Joe]

I feel like, Paula, there's been a fair number of questions, oh, gee, and I answer some questions here. We have full episodes. Paula, you and I afford anything where we answer questions. I love what Jillian's saying because how often have you and I had the false dichotomy, I can do this or I can do this. And you and I answer with, well, why wouldn't we do both?

[Paula Pant]

Right? The issue is that most of us as children, we are taught a very, very linear, specific way to live our lives. You go to high school, then you, for many people, go to college, get a job, work there for 40 years, retire in your 60s. Because the structure seems to be set up with that dominant paradigm in mind. There can often be a lot of resistance to the idea of doing anything a little bit unconventionally, and it's not easy. And sometimes there are bosses that are going to put up barriers, sometimes there are entire companies that are going to put up barriers. And, and maybe your current workplace isn't that amenable to it and you might have to switch jobs. But ultimately, if, if there's something that you're committed to doing that you're truly committed to doing, you can always find a way to make it happen, right? Even if that's going to require some, some tough trade offs or some sacrifice.

[Joe]

I've had too many emails from people over the years that have said maybe two or three a year from people going, I like that topic, but I can't do that. I can't, I can't do that. And the answer is maybe because I don't live where you live, but most of the time what I've seen is that you're just not willing to make that choice. And that's okay. But. But the word can't, I think we use to your point, Paula, more frequently than maybe we should.

[Paula Pant]

Right. And I'd like to invite everyone to just see the power of rephrasing that as I choose not to because it's a totally valid choice to choose not to. But there is such a difference between saying I can't versus I choose not to.

[Joe]

Well, you've got so much more power in it where I can't takes the power from you, but going, nope, I choose not to. You're retaining.

[Paula Pant]

Right? Exactly. Or another way that I like to say it is. That's not a priority for me at this time. I say that about a lot of things.

[Joe]

Do you know what you say often about Paula every week here?

[Paula Pant]

What's that?

[Joe]

You say, I choose not to be good at trivia. That's exactly what you say. Let's test that again right now, shall we?

[Paula Pant]

Because try it.

[Joe]

We pause halfway through every scintillating discussion we have here on Fridays on the Stacking Benjamin show to take a moment and have our Friday trivia challenge between our three frequent contributors, OG Paula and Jesse Kramer. And Jillian, you are on Team Jesse today, which means good news and bad news. Would you like the good news first or the bad news?

[Jillian Johnsrud]

Let's do the bad news.

[Joe]

Well, the bad news is you're not winning, which actually is good news because that means you don't have to go first. You get to guess second because you are in second place. OG is leading with 11. Team Jesse, including you now, have been reeling him in, though you're at nine and a half. And while Paula choosing not to pay attention to the trivia for, like, the 18th year in a row. We've only been doing the podcast for 15 years, so who. Who could do that math? Paula is at six and a half. So six and a half for Paula. But Paula, good news is, I think if you win every week of the year that's left, you could still finish second. So you could. You could run the table and you could be winning by the first week of October. Paula.

[Paula Pant]

Whoa.

[Joe]

Yes. All you got to do is win the next five. But to know who's what's what, we have to have a trivia question. So, Doug, what's on tap this week, man?

[Doug]

It all starts right here, Joe. Hey there, Stackers. I'm Joe's mom's neighbor, Doug. It's the start of Labor Day weekend, and while we're chatting here about how not to labor, some people are going to experience the ultimate labor of love this weekend. That's right. Someone listening to us right now, and I'm not at liberty to say who, is having a baby. So let's ask a money question about that. As of 2020, what was the total cost of having a baby, including labor and delivery in the usa? I'll be back right after I deliver Joe's mom's latest batch of muffins to the neighbors. She knows how to keep the whole street on her side.

[Joe]

Yes, she does, that woman. The teamwork makes the dream work. Right? And everybody is a big fan of the muffins. All right, let's talk about the muffins being born this weekend. Is that. Is that a good transition? I don't know. Oh, gee, you're going first. As of 2020, total cost of having a baby.

[OG]

I think it's a little silly to using data from five years ago, so I'd like to report that to the fact department. There has to be some recent. More recent data.

[Joe]

Well, hold on a second, because I actually have the answer to that because Dr. Jordan Grubbit from Earn Vest helped us with this question. And actually, Jordan said that they actually look at this every five years. So there will be new data in 2025, but the efficacy of doing it closer than every five years, it. It's. It's a waste of time.

[OG]

Well, so says the person not answering trivia questions, but okay, so says the person.

[Joe]

So says the person in the field.

[Doug]

He's a doctor, and so that also makes him a statistician.

[OG]

Yes. All right, well, based on backing out inflation five years ago in my brain, I'm going to say that the an or so this is. Are we including all nine months of prenatal care here? Oh, my God.

[Jillian Johnsrud]

That's a fair question.

[Doug]

Every week. OG you got to bring us this.

[Joe]

Labor and delivery. Cost of labor and delivery.

[OG]

L and D. Just. Blue 19. When the. When the quarterback's under center and just gets the snap. Orange 21. Orange 21. Okay, that's what it was like for my middle kid. All right, I'm going to say that the answer is approximately $29,847.11.

[Doug]

You're such a pain in the ass. You are such a pain in the ass.

[OG]

OG what do you think about them apples? Doug, I found your bugaboo just like you have mine. So I don't even remember what I said, but it's somewhere in the 29,000 range.

[Joe]

Change. Half the fun of making the show, Jillian, is watching these guys Just try to annoy the out of each other. That is it. Doug likes to do the math, and. Oh, gee's gonna make the math difficult. All right. He says 29, 847 change. Jillian, what are you thinking?

[Jillian Johnsrud]

I would say, like, there's a budget. A budget delivery if nothing goes wrong. And I'd probably put our budget number at six. But if you have to add in complications and stuff happening, I would probably go with 17,000. Yeah, I would say 17 is the average. Unless you want, like, snacks and a blanket and then it's 50,000.

[Joe]

Spoke like somebody who's been to a hospital before. All right, Paula, you've got 29, 847 and 17,000.

[Paula Pant]

Yeah. Well, OG's guess was 29, 847 and 11 cents.

[Joe]

That's right.

[Paula Pant]

And 11 cents. So I'm going to take the over and I'm going to go with 29,847 12 cents.

[Joe]

It turns out the answer is 29,847 11.5 cents.

[Doug]

I used to like you, Paula.

[Joe]

So you think it's more expensive than 30,000?

[Paula Pant]

You know, 30,000 was actually the number that was in my head.

[Joe]

Yeah.

[Paula Pant]

When I first heard the question, my thought was probably it's going to be around $8,000 out of pocket, depending on the size of somebody's deductible and coinsurance.

[Joe]

I thought you say baby, the size.

[Jillian Johnsrud]

Of somebody's baby by the pound.

[OG]

It's per pound.

[Paula Pant]

It's by the ounce.

[Joe]

It's like the deli.

[Paula Pant]

They've got like a scale.

[Jillian Johnsrud]

That's why they weigh them when they're bo.

[Joe]

Yeah, that's where they get you. That's where the hospital gets you.

[Paula Pant]

So, yeah, my thinking is basically depending on the terms of your deductible, your coinsurance, your CO pay, it's probably going to be like eight grand or so for the average family. But I think that the total cost. Total cost is probably about 30,000.

[Joe]

All right, 29,847, 11 for OG. 29,847 12 for Paula, Jillian, and Team Jesse. 17,000. Who's right? We're gonna find out. Just a second. We'll be right back. Oh, gee. You kicked this thing off at 29, 8, 47, 11. You had to have known since the beginning of the year when you took the big lead that somebody's gonna go after you. And Paul. Paul decided to make sure that you've only got a 50 chance of getting part of it. You feeling good still, though?

[OG]

I feel like, it's close. Having only had three children and writing checks for each one of them, I distinctly remember how much each one of those checks were for. Although we never skated out of there without complications. So maybe my data is skewed by having small issues along the way.

[Joe]

Jillian, your number includes complications?

[Jillian Johnsrud]

Sometimes, yeah, you got to balance out the budget babies with the expensive ones.

[Joe]

And then, Paula, the sky is the limit. 29,847 and 12.

[Paula Pant]

It's just. It seems hard to get out of the hospital for anything less than 30 grand.

[Joe]

Will you take a check?

[Jillian Johnsrud]

Right.

[Joe]

All right, Doug, the answers are locked and loaded. Who's taking this week's winnings home?

[Doug]

Hey there, stackers. I'm muffin taster and guy who sports a little muffin top at the beach. I'll let you decide which one's grosser. Joe's mom's neighbor, Doug. Ah, Labor Day. The weekend where you celebrate all the work that went into making your community what it was and the people who helped build it. And to all of you hard working stackers out there, thank you. Today we're talking about. That's as sincere as I get. I mean, come on.

[Joe]

So sincere.

[Doug]

Like, that's all I got.

[Joe]

There's nothing patronizing about that at all.

[Doug]

Doug, today we're talking about the ultimate labor of love, having a baby. According to 2020 numbers, what was the total cost of having a baby, including labor and delivery in the USA? Well, I'll tell you this. It was $10,982.12 less than what Paula gets. 10,982 and 11 cents less than what OG guessed. And just 1,865 more than what Yillian guessed. The correct answer is 18,865, making Yillian our winner.

[Joe]

Does it feel like being back in the home country? Y.

[Jillian Johnsrud]

It does. It does.

[Joe]

Congratulations. Nice work.

[Jillian Johnsrud]

Thank you. I'm so invested now.

[Joe]

But, Og, it sounds like your experience was a little off that number.

[OG]

Yeah, I think the most recent one for which we have Data is a 2016 data, and I believe it was in the high 30s. That one was the easiest one. I guess we got too many blankets or free coffees.

[Jillian Johnsrud]

Stacey, two of snacks. That really gets you. Like, the first pudding is good. The second pudding, they're about a thousand bucks a pop.

[Joe]

Well, in a pudding pop, that's even more. Yeah, don't even. Don't even ask about that. All right. Congratulations, Jillian. And you know what that means. Oh, gee. Has 11. And Jesse has 10 and a half coming into.

[OG]

All for the gram, guys. It's all for the gram. Whoa.

[Jillian Johnsrud]

He can send me a thank you card later.

[Joe]

I think he needs. Jillian, I think he clearly needs to. Are you going to be at fincon?

[Jillian Johnsrud]

I am, I am.

[Joe]

Well, he needs to buy you beer or something. Whatever beverage of choice that you have. I'll let him know. I've got two more big questions on tap and one, one thing you talk about in your book, Jillian, is about health. And you have these health quadrants in cost. Can you walk through your four health quadrants?

[Jillian Johnsrud]

Yeah, it's this idea that ideally over time our financial freedom will increase, but the reality that maybe our health, our capability or even our preferences will change over time. And so there's a little bit of a, I think a mistake of saying, you know, I really want to like I want to hike the Pacific Crest trail because I'm 32, but I'll just wait till I'm 65. That'll be cool. I'll probably still totally want to do that or be able to do that. That. So I think about what are things that require a high capability like those long through hikes or I did a 10 week trip with my kids in a pop up camper to 10 national parks. Super fun. But maybe when I'm 75, like it won't be my jam anymore. And balancing that out with the quadrants of what are things that are more expensive. So maybe they don't require as much capability, but they're really pricey, like an around the world cruise. I've been on some cruises, it was all senior citizen. So I have a feeling that cruising is still possible into your 70s, but maybe saving the things that don't take a lot of capability but are expensive for later decades in your life and kind of front loading the affordable stuff that could also maybe require a high degree of capability.

[Joe]

I saw in the wealthy accountant blog this idea last fall that the average healthy life expectancy, Jillian, not life expectancy, but healthy life expectancy, United states is only 66. So if we wait till after 66 to your point to do some of these high capability things, we. We're not going to get them.

[Jillian Johnsrud]

Yeah, to Paula's point, sometimes you just have to admit that I'm just not going to do that. I'm choosing not to do it and I'm going to let that experience pass me by. If you feel regret about that, feel it now where you have the ability to change your mind. If you just so decide versus getting to you know, 60 or 70, and then feeling that deep regret of, oh, actually I never did those things that I wanted to do. And now either I'm not capable of doing it, or I just don't want to anymore. You know, I did a cross country road trip in my 20s, and it was awesome. Like, we slept on people's couches and we camped and I slept on the frozen ground. I almost got trampled by bison, and it was, like, so much fun. And I am never doing it again. Like, I'm really, really glad I did it. And the season of life has passed me by. It's.

[Joe]

It's gone. Yeah. The whole camping thing, I think, is beyond OG as well. OG you and your government sponsored camping trips, I think you've said.

[OG]

Yeah, I mean, we got to do lots of fun outdoor activities, all courtesy of the U.S. treasury Department. U.S. government. So I'm good. I don't need to be outside ever again, especially overnight and especially sleeping. I'm just more concerned about the. You know. You hear that 66 number for both Joe and Doug? Do you guys. You guys get a little sense of dread? Like, oh, my gosh, there's only like nine years to go.

[Doug]

You just got away, man.

[OG]

So, like a little countdown clock that you guys have, like, this is my healthy life.

[Joe]

I got it on the wall over here.

[Doug]

This is. This is peak maleness right here. It doesn't get any better than this. And there's no way that I'm falling and crashing at 67. So I'm. I think I'm bringing the average up, if anything.

[OG]

Okay, all right. I like that attitude. Your pharmacy in your bathroom. The pill packs say otherwise, but definitely peak maleness for sure. As long as there's Advil. Everything's peak, right? Advil and bourbon. Yeah, you can do anything.

[Joe]

That's why I need to retire often, Jillian, is to just get away from this harassment in the workplace. It's absolutely horrible.

[OG]

It is ageism. I'm sorry. Report me to hr.

[Joe]

What are you going to do, Paul? I am thinking as I'm listening to Jillian talk, though, about a different spreadsheet. I mean, if we're putting this into action, I do like the idea of saying, you know what? I like this thing, like seeing the fall colors in Maine where I'm driving up Highway 1. Like, I could do that when I'm 75, hiking Acadia national park to go to the same area. I probably want to do that now.

[Paula Pant]

Yeah, absolutely. And. And I think it makes a lot of sense to think about not Just capabilities. But you know, as Jillian said, also just priorities. Desires, like the things that are important to you when you are a certain age are not necessarily going to be the things that are important to you at a different age. And I think a really good litmus test for that. What are the things that you loved as a kid that you still love now? Like for me, reading books. I loved reading books as a kid. I still love reading books now. I have a high degree of certainty that throughout my entire life, I will likely always love reading books because that has been a consistent through line. Whereas when I look at other interests that kind of popped up like, like hiking and camping when I was in my early 20s, I was really into that and it was kind of a phase and it passed. And now, I mean, if somebody invited me to go hiking and camping, I would say yes, but I'm less likely to initiate it.

[Joe]

The rants Paula has had with me about how bad any running at all suc.

[Paula Pant]

Oh, I've never liked running.

[Joe]

Have been epic.

[Paula Pant]

That has been a through line my entire life. I have never liked running. I have a high degree of certainty that I never will like running.

[Joe]

Just epic rants about how stupid running is.

[Paula Pant]

Yes. That has also been a consistent through line throughout my life. Books, yes. Running, no.

[Joe]

Have you noticed that your. Do your books have more pictures now or fewer pictures now than when you were young?

[Paula Pant]

I'd say maybe the same amount. You know what? I actually just started rereading a whole bunch of the Goosebumps Books by R.L. stalls.

[OG]

Seriously.

[Paula Pant]

I go to the library and I get R.L. stein goosebumps. And you can get like the versions that were printed in the 90s, like the old school ones. So I've been rereading some of those. But then there are the newer ones where the kids have cell phones. And that's kind of weird, but. But I read them all.

[Joe]

I think some of those middle grade fiction books and just the choices kids have, like, really good writing for that age group. I have a question that I hadn't thought about until we really got on this, guys. And I'd love to just get your takes. Like, let's say that I've got these two paths I can go down. I could take one big mini retirement, but it's this expensive grail kind of thing that I really want to do. Or I can take a few not as expensive mini retirements, but they won't feel as fulfilling, but I'll get more time to maybe make them fulfilling during that time. So do I, Jillian, do you save up for the big thing and take fewer or do you go, you know what? My money situation is my money situation and I hit the road as soon as I can.

[Jillian Johnsrud]

In the moment, the big epic thing is going to feel cooler. I think when you're 70 and you look back and you've done maybe six one month ones with people that you love that you could never recreate those experiences and you look back and like you did one of when your kids were really little and you did a road trip and you did one with your parents when they were still alive and you did one like as your kids went off to college and you did this really cool experience with them and you know, with your spouse before they passed away. They might be cool in the moment, but I think those memories in different seasons of life that you can't recreate, they exponentially become more important. So I don't think there's a wrong choice, but I think the cool thing feels cooler initially and the little things with people you love gain more traction.

[Joe]

As you age in your memory.

[Jillian Johnsrud]

Yeah, yeah, yeah.

[Joe]

Do you guys agree with that? Oh, do you agree with that?

[OG]

Well, we did a pretty big thing a couple years ago with the kids and then with our my in laws with their grandparents. I mean, this was now 2 1/2 years ago and it's still in the weekly parlance. So I don't know that we'll ever do that again. That was like kind of the big blowout thing. Not to say we won't have like the one month things either. We're blessed to be able to do lots of stuff. But yeah, I think, I don't know, It'll be interesting to see the staying power of the big blowout thing as the years go on. Even my daughter, who was at the time six and she's nine now, is like, oh, that was so awesome. I remember everything about it. It was like that week and 10 day kind of period of time is definitely 100 core memory. Using the phrase from inside out for the Disney movie, that's like core memory for our family for sure. Wow.

[Doug]

And that was like a third of her life ago. I can't believe she still remembers it.

[OG]

She remembers vivid details about it now. It helps that we have an insane amount of pictures and videos that we sometimes watch. So whether she remembers it in the third person or first person is different, but there's different bits of it that we talk about.

[Joe]

Paul, are you on board with that as well?

[Paula Pant]

Yeah. There's research around what they call Nostalgia bias. Memories often tend to get rosier in hindsight. So I think that regardless of whether it's one big blowout thing or many multiple things, either way, so long as it's a cherished experience, the memories of those cherished experiences tend to get rosier as time goes on. There's a bunch of research that was done by a professor named Leif Von Boven from the University of Colorado.

[Joe]

It sounds like you. Speaking of making up statistics, it sounds like you just made up that name. No, totally a Doug moment. There's research from Leif Von Boven.

[Paula Pant]

L E I F Leif, who's a professor.

[Joe]

At Hogwarts.

[Paula Pant]

At the University of Colorado. I remember this because I wrote an article about it. And the memory of writing that article has gotten rosier in hindsight, better and better every time you think about was.

[Joe]

The best article you ever wrote.

[Paula Pant]

Yeah.

[Joe]

I remember when we spoke with former Wall Street Journal personal finance columnist Jonathan Clements about this too. He also said, jillian, you know, to plan this stuff ahead of time as far as possible because also the build up to it, the thinking about it, really makes it worth more too. Like, not just the memories, but the planning is so exciting that that can even change your trajectory and kind of breathe some life into your life as well.

[Jillian Johnsrud]

For a lot of people, especially if you're really burned out or stressed about your job, just knowing that this is going to happen, even if it's happening in six months, creates a little bit more lightness and it makes that time more enjoyable and more tolerable because you have the light at the end of the tunnel. Even if the tunnel, the light's only going to last for a month or.

[Joe]

Two, I think you're going to go dark and say, even if it's a train in the tunnel. Yeah.

[Jillian Johnsrud]

Yeah.

[Joe]

Glad we ended, though, on a high note, Jillian. Nice job. That was good. Absolutely love this topic. And I love the idea of mini retirements. We're going to have Doug mention this again in a few minutes, but we got to spend just a moment on this. Apparently, Jillian, one of us may have written an entire book on this topic.

[Jillian Johnsrud]

That's so weird.

[OG]

How handy and convenient it'd be so great.

[Joe]

Like you could have it as a handbook, as a manual. Where would somebody get such a thing and when could they get it? Let's say, hypothetically, if somebody had written a book about this topic, I think.

[Jillian Johnsrud]

You could probably order it right now and it would show up at your house in a few days.

[Joe]

Oh, that's great.

[Jillian Johnsrud]

It's so convenient.

[Joe]

If we can get it to Amazon or everywhere.

[Jillian Johnsrud]

You can get it everywhere. Unless you're in a foreign country, then I'm sorry, it is actually a little difficult. But if you are in the US Or Canada, it's, it's all over the Internets.

[Joe]

And the book is called Retire Often. I love this idea of retiring often. All right, let's find out what else is going on where all of you are. Jillian, let's stick with you for just a second longer. What are you doing this holiday weekend?

[Jillian Johnsrud]

Making those minions work in the garden. We gotta wrap this season up.

[Joe]

OG what's going on at the OG household on Labor Day weekend?

[OG]

Such a great week. We are. Middle kid has varsity game number one on Friday out of town. So we've got a, an away game to go to.

[Joe]

And then from there, Labor Day weekend, it's only 107 degrees in Texas, so.

[OG]

Oh, yeah, yeah. I mean, kickoff, it'll be seven, it's fine. Then the next day we are going to the home opener for Texas A and M, which is where my oldest is going to go, and we move him in. I guess as you're listening to this, we have already moved him in. But then that'll be kind of a right around day 10 ish or 12 ish of him being on his own. So it'll be perfect time for us to come drop in for a little visit, go to a football game. And then with the long weekend, no reason staying a little late, staying up a little late on Saturday night.

[Joe]

So fantastic. Which means what, 8:15 then?

[OG]

Yeah, I'll probably have to leave the game early to go sit in the car and take a nap.

[Joe]

Yeah.

[OG]

But I'll catch the rest of it on SportsCenter the next morning.

[Joe]

And he teases us about being old, Doug. He teases us about being old. And yet if it's 8:15, he's done.

[OG]

It's a Saturday. It'll be like 8:45.

[Joe]

Paula, what's going on at Afford Anything.

[Paula Pant]

On the Afford Anything podcast? Well, you and I, Joe, once a week, typically on Tuesdays, we answer questions. We do, we do. We answer all of these questions. We are tackling a whole bunch of questions listeners submitted about inflation, about jobs, investments, about all of the various topics that we tackle. So if you want to hear Joe's wisdom on how to live your life, come to the Afford Anything podcast with all that wisdom.

[Joe]

OG all those years, I am ahead of you. See, people can get a piece of that.

[OG]

There's some benefits of that. That's for sure.

[Joe]

All right, Jillian, thanks a ton for joining us OG Paula, thanks for bringing it. Doug's gonna bring it here at the end. By the way, thanks to everybody for hanging out with us on YouTube. You guys are I love the comments. I couldn't get to nearly enough of your comments, although we did show a bunch of them on the screen, so we had a great time. Thank you so much, Doug. You're gonna bring it home for us, man. What should be on our to do list at the end of this week?

[Doug]

Well, Joe, first, take some advice from Jillian Jansrut. That's not even Norwegian. I mean, I just totally Pretty good, actually.

[Jillian Johnsrud]

That's pretty solid.

[Doug]

When you approach your boss about a sabatical, be sure you make up some complete BS sob story about your goldfish being in hospice and then butter them up by telling them how good their breath is today. They'll practically open the door for you on your way out.

[Joe]

I don't think you were even listening. I'm fairly certain.

[Doug]

Is that a requirement? Second, don't forget what OG said about when you're old and wrinkly, you're showing up to the retirement party whether you're dressed for it or not. So maybe treat yourself and buy that new leisure suit now while you still look sexy in it. But the big lesson many retirements are supposed to refresh you here in the basement. It just means hiding from Joe's mom until she finishes yelling about who left the laundry in the dryer. It wasn't me this time, Ma. Thanks to Jillian, John's rude sounds so weird when you say it that way. For joining us today, you can she said it wrong her whole life. You can pre order her new book Retire often on Amazon or wherever you buy books. We'll also include links in our show [e-mail] thanks to Paula Pant for hanging out with us today. You'll find her fabulous podcast Afford Anything wherever you listen to Finer Podcasts. And finally, thanks also to OG for joining us all often today. Looking for good financial he hates it when you say the T in often. Just had to slip that in there. Looking for good financial planning help? Head to stackingbenjamins.com often for his flash OG for his calendar. This show is the property of SB Podcasts, LLC, Copyright 2025 and is created by Josal Siha. 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 advice from people you don't know. This show is for entertainment purposes only. Before making anything 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.

[Joe]

Doug, you ready to start this thing?

[Doug]

Let's do it. That sounded just like Tone Loke. Come on.

[Joe]

It's exactly like Tone Lo.

[Doug]

I swear that we need the drums to come in right after that. All right, here we go.