Ever dreamed of stepping away from work for a while or even retiring multiple times throughout your life? On today’s Labor Day weekend episode, we are talking mini retirements with a woman who has actually lived it, Jillian Johnsrud. She is joined at the roundtable by Paula Pant, who knows a thing or two about negotiating time off with a boss, and our resident CFP® OG, who helps people build the money runway to pull it off.
But what happens when your grand plan to pause work goes off the rails? We will dig into the pitfalls that trip people up. Bosses who are not buying it, budgets that crumble under Netflix binges and late-night Amazon shopping, and retirees who realize too late they do not actually like this whole not-working thing. From practicing retirement before you quit for good to spreading out life’s disappointments instead of stacking them all at age sixty-five, today’s conversation is about making mini retirements stick without wrecking your future.
And of course, no Friday episode is complete without Doug’s trivia. Since it is Labor Day, he has cooked up a question about the ultimate labor of love, having a baby. How much does that really cost in the United States? Grab your guesses, and let’s see if Paula, OG, and Team Jesse can catch a break this week.
FULL SHOW NOTES: https://stackingbenjamins.com/when-early-retirement-goes-wrong-1728
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic: How Early Retirement Goes Off the Rails
During our conversation, you’ll hear us mention:
- Mini retirements
- Negotiating with bosses
- Retirement plans derailed
- Pitching time off
- Creative sabbatical stories
- Collaborative conversations
- Anticipating obstacles
- Financial runway
- Automating payments
- Emergency funds
- Planning timelines
- Practicing retirement
- Retirement as a skill
- Health expectancy
- Capability vs. cost
- Spending shocks
- Overspending in retirement
- Underspending in retirement
- Mission creep
- Core memories
- Nostalgia bias
- Choosing priorities
- Both work and leisure
- Saying “I choose not to”
- Many retirements vs. one big trip
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jillian Johnsrud
Another thanks to Jillian Johnsrud for joining our contributors this week! Hear more from Jillian on her show, Everyday Courage, at Everyday Courage | Jillian Johnsrud.
Check out her hit book Retire Often: How anyone can take multiple career breaks to unlock adventure, advance their career, and find financial freedom.
Paula Pant
Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on X: @AffordAnything
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- As of 2020, what was the total cost of having a baby, including labor and delivery in the USA?
Mentioned in today’s show
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Tune in on Monday when we welcome two pros with tips to help you get ahead.
Miss our last show? Check it out here: Dr. Danielle McGeough’s Guide to Avoiding Burnout (SB1727).
Written by: Kevin Bailey
Episode transcript
[00:00:00] bit: I, uh, I don’t like my job and, uh, I don’t think I’m gonna go anymore. [00:00:05] Jillian: So you’re gonna quit? [00:00:07] bit: Nuh, I’m just gonna stop going. [00:00:09] Jillian: So are you gonna get another job? [00:00:11] bit: I don’t think I’d like another job. [00:00:15] Paula: Well, so what do you wanna do? [00:00:17] bit: I want to take you out to dinner and then I want to go back to my apartment and watch Kung fu. [00:00:22] bit: Do you ever watch Kung Fu? I love Kung Fu. [00:00:31] Doug: Live from the basement of the YouTube headquarters. It’s the Stacking Benjamin Show. [00:00:47] Doug: Am Joe’s mom’s neighbor, Duggan. What happens when that early retirement or mid-career pit stop goes off the rails? Well, as mom says, she’ll stop and put it back on. Today we are diving into retiring often with the woman who’s lived that reality. Jillian John’s rude, or if we were in the old country, Yian Ys. [00:01:08] Doug: Rude plus a woman who’s negotiated with her boss for a 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 CFB OG Plus, of course, we’ll include a pit stop halfway through for our year long trivia contest. [00:01:31] Doug: 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 or leaving. It’s Joe Saw Sea. Hi. [00:01:54] 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, a Labor Day weekend episode. We’re so happy you’re here. Sit back and relax. And by the way, in the future, if you wanna join us live, we do these live on YouTube normally on Fridays. [00:02:14] Joe: So no, not 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 uh, we’ll start with a guy across the card table from me. Mr. OG is here. How are you my friend? [00:02:29] OG: Man, I’m just happy to be here. [00:02:31] Joe: Ready to celebrate Labor Day. [00:02:34] OG: I’m celebrating by not laboring. [00:02:36] Joe: Well, I think that’s the point, isn’t it? We stop and we rest and we don’t labor. My dad, he [00:02:41] OG: always told me in Labor Day, you’re supposed to labor. He’s like, we’re gonna pull weeds. We’re mowing the grass. We’re, we’re painting the fence. It’s Labor Day. You’re, you’re meant to labor today. [00:02:49] OG: And I was like, all right. [00:02:50] Joe: I love how dad pulled the con. [00:02:51] OG: I don’t, I don’t do that anymore. I do that to my kids. [00:02:53] Joe: Yeah. You teach, you teach the young kids. This is all about laboring in the yard. Yeah, it’s about [00:02:57] OG: labor. [00:02:58] Joe: And the woman who’s laboring high above Manhattan, Paula Pant, is here. [00:03:02] Paula: How are you? I am great. [00:03:03] Paula: 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 catchup day for all kinds of work. [00:03:16] Joe: So wait a minute. So you con yourself like OG con kids to get stuff done? [00:03:20] Joe: Do I, do we have to labor? I do, 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. [00:03:31] bit: Absolutely. [00:03:32] Joe: Uh, Jillian Johns Ru joins us. How are you? [00:03:35] Jillian: Thank you. Very good. Very good. You know, September is the busiest garden season, so all five children will be laboring in the yard because like it’s, it’s harvest time. [00:03:45] Jillian: We gotta get this stuff done. [00:03:47] Joe: But Jill, do you have to lie to them like OG has to lie to his kids? [00:03:50] Jillian: 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. [00:03:59] Joe: That’s not the way it works. That sounds like my mom growing up, we had this gigantic garden. [00:04:04] Joe: Well, she supposedly, she had the garden, but I think my brother and I, Jillian, truly had the garden. Oh yeah. It 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. [00:04:32] Joe: What made you decide to write a book on this topic we’re gonna dive into today? [00:04:36] Jillian: 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, a very possible, but also very life changing. [00:04:52] 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. Like, what happens when it goes off the rails? So Jillian and Paula and OG will lead on their expertise. You, you, Jillian, have retired often in your own life. [00:05:11] Joe: Yeah, absolutely. I think I’ve done 12 of ’em now. A nice, neat dozen. And, and you’re just starting, right? You got like 12 more in you? For sure. For sure. Absolutely. We’re also gonna talk about, uh, how to negotiate this with your boss, because I know what half of our audience says. They’re always like, oh, that sounds good. [00:05:31] Joe: 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. I’ll put us with that, [00:05:38] Paula: Paula. I’m, oh, yes, yes. So I didn’t realize you wanted me to say something at that, that, that precise juncture. [00:05:47] Joe: Yeah, I need to do that better. [00:05:48] Joe: I need to figure out if only I, that is [00:05:51] Paula: my name. Wait [00:05:52] Joe: a minute. Yes. And I think you might have a financial plan, uh, need a financial plan to do that, which is, uh, OG your contribution today. Sound good? [00:06:02] OG: I was on mute. Yes. Uh, sure. Sounds great. That’s great. I will contribute in the same high quality fashion that I have for the previous, roughly 15 years. [00:06:12] Joe: 15 years [00:06:13] OG: and some [00:06:13] Joe: change. All right. We’ve got Jillian here, Paula here, and OG here to dive into it with Doug and I. You know what though? We also have a couple sponsors to make sure we can keep on keeping on. So we’re gonna say hello to them and then sit back and relax and maybe grab a piece of paper and start lining up. [00:06:30] Joe: Grab a calendar. Let’s get retiring often on your agenda. So we’re gonna do that here in just a moment. [00:06:45] Joe: 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 gonna 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. [00:07:08] Joe: I think it might include just a little bit more than that. So we’re gonna go through four key scenarios about making sure this doesn’t go off the rails, but Julie, in 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 oh Gee’s office and saying, I’m gone for a month. [00:07:33] Joe: Peace out. Like, how’s, how’s that gonna work for you? [00:07:37] Doug: He’s asking me to do that. Usually it’s like, please make that happen. Doug, your vacation’s been pre-approved. I didn’t ask for one. Oh, I know [00:07:49] Joe: I already packed your desk. How do you actually though Jillian craft this story to your boss so that the boss is in in complete shock when you’re like, Hey, I got a great idea. [00:07:58] Jillian: First, I think it starts with, this can’t be entirely your boss’s problem. They have their plate full, 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. I’m burned out and I don’t wanna look at all y’all’s faces anymore, so I need you to figure this out ’cause I’m leaving. [00:08:14] Jillian: 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. [00:08:34] Jillian: And so I always tell people it’s, it’s kind of memoir rule rules in that it all has to be true, but it can’t be the whole truth. ’cause 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. [00:08:50] Jillian: If you went to your boss and you said, Hey, my parents, they always planned when they were, were gonna retire at 60, they were gonna 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 spike trip. [00:09:06] Jillian: 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? Uh, it would be really meaningful to like help her celebrate this new season of her life. 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 like those four elements, it’s gonna get you off to a good start. [00:09:29] Joe: Well then you’re not, it, it sounds like you’re, you’re asking them to help you with the stream come true. Yes. Like, let’s collaborate together on making this happen. [00:09:38] Jillian: Yeah. You want the conversation to be very creative and collaborative like, so you don’t have to have every detail worked out, but say, I have some ideas. [00:09:46] Jillian: I know there’ll be some challenges, but I put some thought into this. Here’s some of the things that I figured out of how this might work. [00:09:52] Joe: Paula, there’s gotta be some key tactical things that we can use, some tactical strategies we can use when we walk in with Jillian’s. Four things to try to negotiate this. [00:10:02] Joe: What if the boss isn’t still, isn’t that enlightened and, and is like, no, I think you should get back to your desk and leave the bike in for, for your mom or whoever, whoever’s gonna be in the story, [00:10:13] Paula: right? Well, there are a couple of things. First, um, to Jillian’s point, you don’t ever want to bring them a problem. [00:10:18] Paula: 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? [00:10:34] Paula: 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. [00:10:51] Paula: A piece of accounting or a nurse in the operating room. Yeah. Yeah, exactly. So when I say, uh, 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. [00:11:11] Joe: I like that Also, Jillian, because whether you end up getting Roblox or not, you’re already thinking through what potential obstacles the boss might bring up ahead of time. [00:11:22] Jillian: I think it’s really important, especially when you’re bringing something kind of maybe emotional important to you that you articulate. [00:11:30] Jillian: 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. [00:11:50] Jillian: So just say, say the negative things out loud to get the ball rolling. [00:11:54] Joe: I know that we pay a lot of attention lately, especially to the stoics. Mm-hmm. But I also really like some of the Chinese philosophers in a very much like sun sues the art of war. Mm-hmm. I love this phrase. Define the battlefield. You know, and, uh, the best battles the one that’s never fought. [00:12:09] Joe: Right? Yeah. If we think about the battles at a time and know these are the potential problems, then I don’t have to fight that battle. Speaking of that, OG. I wanna go back to before this, before this even happens because I think to Jillian’s point and to Paula’s point, you gotta articulate the audience, but I think you also gotta be financially ready to go. [00:12:29] Joe: I mean, there’s gotta be a little bit of runway. What, what are some of the potential obstacles we might need to clear before we take our mini retirement? [00:12:37] OG: The thing that I’d add to what both of them said earlier is I was watching a video on, um, conflict with, uh, Chris Voss, the hostage negotiator guy. And one of the things that he said was always start with the thing that they’re gonna think when you say the thing that’s coming out next, like, you’re probably gonna think I’m a big jerk, but I actually don’t want the salmon. [00:12:59] OG: And they go. Oh, because they can’t go. You’re a big jerk. ’cause 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. [00:13:14] OG: So as you are, 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, if one of my employees came and said this, I, I wanna take a month off to go bike riding in Europe. I go, you’re crazy. We don’t have the time. [00:13:29] OG: Like this is the busy time. And you start with, hey, you’re probably gonna 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 the 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. [00:13:50] OG: Just ’cause 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. You know, 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. [00:14:05] OG: You know? And honestly, if you’ve done a really good job of, you know, emergency funds and that sort of thing, maybe you can do it. But I think you gotta think through how am I going to, you know, uh, 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? [00:14:26] OG: Like, for example, do I have to automate all my credit card payments? You know, I’m gonna 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? [00:14:43] OG: You need to think through those things long in advance, not just the money aspect of it, which obviously you gotta 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 and what’s that look like? [00:15:01] Joe: What kind of a, a typical runway do you see people have, Jillian before they take a mini retirement? Is it six months? Is it two years? [00:15:08] Jillian: 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 nine to five to focus on something that matters to you. [00:15:21] Jillian: 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, if it’s unpaid time off, you have to cover that. And then you have to cover the cost of whatever adventure you have. [00:15:37] Jillian: 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 gonna be outta the workforce for a year, you might wanna plan on another six months, eight months of runway to find that next job. And so the runway is, is much bigger. [00:15:54] Jillian: Like you, you’d want a much bigger emergency fund in that case. [00:15:57] Joe: How early in this planning do I start talking to my boss? I mean, if I wanna take a month off. Do I start talking to them six months before the month off? [00:16:06] Jillian: 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. [00:16:15] Jillian: If it’s too early, if you know it like six to 12 months off in most corporate cultures, if it’s happening 12 months away, 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 you leaving. [00:16:36] Joe: Uh, 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. [00:16:44] OG: Right. Thesis paper. Don’t ask me how I know. [00:16:47] Joe: Let’s talk about the second, uh, scenario of retirement coming off the runway. And this is waiting until age 65 to figure out what retirement really looks like. [00:16:58] Joe: 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. [00:17:16] Joe: Would you wanna marry those people? [00:17:17] Paula: Nope. The thing is, so I come from an arranged marriage culture. Um, 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 supposed to be described. [00:17:32] Paula: Which one? [00:17:32] bit: Come on. Yeah. Number [00:17:34] Doug: three, I’ve seen this show. This is an awesome show. It’s called Married At First Sight. This what episode were they on? [00:17:42] Joe: Doug’s gotten to the bar some nights and had that thought. Which one of these people am I going home with? It’s funny. Yeah, they [00:17:48] Paula: took tonight they took the Nepalese arranged marriage culture and turned it into a TV show. [00:17:54] Paula: 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. [00:18:17] Paula: It’s, um, 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 know, whatever age that is. You are not gonna be good at anything the first time you do it. [00:18:35] Paula: 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. [00:18:45] Joe: Jillian, what Paul is saying is that why you really dive heavily into this, that practicing retirement is super important. [00:18:52] Jillian: 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 run like a 5K? And they’re like, no, no, no, no, no, I’m not. I don’t wanna waste any time on five Ks. I’m just gonna sit at my desk and work really hard 60 hours a week. [00:19:09] Jillian: And then one day I’m just gonna start running a marathon and I’m gonna be awesome at it. Actually, no, I’m gonna put down [00:19:14] Joe: the donut and run the marathon. [00:19:17] Jillian: And then the justification is, well, I’ve been listening to podcasts about marathons. I’ve read some books about marathons, so I’m pretty sure I’m gonna be awesome at it. [00:19:23] Jillian: 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. [00:19:41] Jillian: 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 ’cause 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 ’cause I have tasted the promised land. [00:20:04] Joe: But I think the other side is valuable too. Mm-hmm. 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. [00:20:15] Jillian: 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. [00:20:24] Jillian: 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 the way. Dreams, Johnny, [00:20:39] Joe: spreading disappointments wherever you go. [00:20:44] Joe: That is deeply dark by Fred. 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 Jillian’s talking about here makes it stickier, which means it’s easier for your plan to stay in place and you’re not gonna blow up your plan. [00:21:02] OG: I think the biggest thing here is recognizing that. No matter what you think you’re gonna do or how you think you’re gonna spend money or what you hope the market’s gonna do when you retire or any of these things, the reality is that all of it’s gonna 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. [00:21:23] OG: And I know exactly what I’m gonna do, my Roth convergence, and I know the exact day I’m gonna file for social security. And I know all these things are gonna happen. I’m gonna 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 you know, a family member needs assistance and that kind of pulls you away for a period of time. [00:21:45] OG: 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 gonna 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. [00:22:00] OG: 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 gonna be on course. You’re never gonna 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. [00:22:18] OG: 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 1st, 2020, life is good retirement. [00:22:37] OG: Woo. By the end of March they’re like, well, 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. [00:22:56] OG: If you stayed the course, you have five x the money that you thought you did, or three x 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. [00:23:11] OG: You have to do this exercise on a regular basis. And um, and having those experiences like you guys are talking about here throughout your, 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. [00:23:32] OG: I don’t hear a lot of these one month, three month, six month times off. And um, Jillian, it sounds like it’s more common, or at least that’s the direction maybe the world is headed. [00:23:42] Joe: Is it where we’re headed, Jillian, or is it just where you think we should have it head [00:23:46] Jillian: both. [00:23:47] Joe: I [00:23:47] Jillian: don’t know if I’m remember the exact statistic, but sabbaticals are about double of what they used to be just a couple years ago. [00:23:53] Jillian: Oh, wow. [00:23:53] Doug: Yeah. Yeah. We make them up all the time, Jillian. Don’t worry about it. Perfect. [00:23:57] Jillian: It’s exactly double than what it was 36 months [00:24:00] Doug: ago. Statistically speaking, stay with confidence. That’s right. They’ll all buy it, [00:24:06] Jillian: but for a lot of people, especially workers, twenties, thirties, for them, their largest increase of like a raise or promotion is probably gonna come in between jobs. [00:24:17] Jillian: 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 gonna happen. So if they’re gonna switch jobs every four or five years and they’re facing the reality of, well, I might end up having to work longer. [00:24:36] Jillian: 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, [00:24:55] Joe: well, and I like the idea, Jillian, of what OGs talking about, because if you’re spreading these out, I like turning it into your darkest appoints through your life. [00:25:04] Joe: 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 retirement with all of these big dreams. Mm-hmm. And when it’s not what they thought. This is why the average person in retirement spends 18 months in total bliss. [00:25:22] Joe: And then they have the biggest darkest depression of their life. This is research according to longevity expert Ken Dyal, retirement expert, Ken Dyal. 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? [00:25:41] Joe: 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. [00:25:48] Jillian: Absolutely. [00:25:49] Joe: Yeah. I also think though, oh gee, 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. [00:26:01] Joe: Right? I just see some of these things that are problematic with early retirees. All of a sudden you’ve got stuff that, that, uh, you know, late night shop, Amazon. You ever done that OG where you got a little bit of, uh, you mean by late night? You mean like [00:26:14] OG: 8 0 5? [00:26:16] Joe: That’s eight night. That’s late night. No G time. [00:26:19] Joe: I know that’s late night [00:26:20] OG: 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. [00:26:36] OG: If, 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. Like I, you know, I think it’d be really great to pay for my grandkids college. It’s like, cool. A hundred dollars a month, their babies, let’s just kind of drip that in to the plan and just see how it works out. [00:26:57] OG: No, no, no, no. Let’s take 70 grand and like fund it all today. It’s like, oh, okay. I mean, you’re taking a little wind outta the sails here. There’s some other changes and you know, sometimes it’s not a 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. [00:27:15] OG: Turns into a week and a half on the islands, which, you know, we were gonna drive to. Now we’re flying, we were gonna 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. [00:27:38] OG: 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 gonna do the same stuff when you’re 97 that you’re doing when you’re 67. I’m not sure that that’s the case. Not likely. Yeah. I mean, it’s not, not the case, but statistically I’d say that 97 year olds are a little slower in their spending than 67 year olds. [00:28:00] OG: 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. [00:28:17] Joe: Which, and then you get there and all of a sudden you’re doing, I mean, you’re gonna show up no matter what planning you did or didn’t do. [00:28:24] OG: Yeah. I think show up at the party regardless whether you’re dressed for it or not. Right. Oh, that’s good. Love. Hold on. Tm. Tm. I got trademark. That one got got trade quick. [00:28:32] OG: You’re showing up to the retirement party whether you’re dressed for it or not. Dang it. It’s a good one. [00:28:37] Joe: I’ve got, I’ve, uh, I also love, uh, the contributions of the people hanging out with us live on YouTube. Our friend Paul, uh, from the Firelight podcast, uh, says, OG Speaks the truth. Been six years, retired and COVID was year one. [00:28:52] Joe: Things were never the same as expected. As long as we’re pointed north, we continued to course correct. Kay Sand 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. Uh, and then, uh, it shows up as da, but it is, uh, the great divide. [00:29:12] Joe: Boys says, uh, I just did this for four years, 20 hours for four years, and the substitute teacher for a year now back at 40 hours, which is cool, Jill. And 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. [00:29:29] Joe: Go. There’s nothing wrong with you. You just decided it’s another season and I’m going back to work. [00:29:33] Jillian: I think to Paula’s point, there is this like I’m doing one thing or I’m doing another and I’m gonna do one thing for a really, really long time, and then I’m gonna do this retirement thing for a really, really, really long time. [00:29:43] Jillian: And you can just do 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 gonna do cool work and I’m gonna live a cool life and I’m just gonna 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. [00:30:19] Joe: I feel like Paula, there’s been a fair number of questions, OG and I answer some questions here. We have full episodes. Paula, you and I can 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? [00:30:36] Paula: 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, uh, for many people go to college, get a job, work there for 40 years, retire in your sixties, because the structure seems to be set up with that dominant paradigm in mind. [00:30:59] Paula: 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 gonna put up barriers and, and maybe your current workplace isn’t that amenable to it, and you might have to switch jobs. [00:31:18] Paula: 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 gonna require some, some tough trade-offs or some sacrifice. [00:31:31] Joe: I’ve had too many emails from people over the years that have said maybe. [00:31:36] Joe: Two or three 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 ’cause 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. [00:31:57] Paula: Right. And, 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. Well, you’ve got so much more [00:32:17] Joe: power [00:32:18] Paula: Yeah. In [00:32:18] Joe: it where I can’t takes the power from you but going, Nope. [00:32:21] Joe: I, I choose not to. You’re retaining. [00:32:24] Paula: Right. Exactly. Orano, 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. Do [00:32:32] Joe: you know what you say it often about Paula every week here. What’s that? You say? I choose not to be good at trivia. [00:32:39] bit: That’s exactly what you say. [00:32:41] Joe: Let’s test that again right now, shall we? Because let’s try it. We pause halfway through every sating 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. [00:33:05] Joe: Would you like the good news first or the bad news? Let’s do the bad news. Well, the bad news is you’re not winning, which actually is good news. ’cause 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. [00:33:25] Joe: And while Paula choosing not to pay attention to the trivia for like the 18th year in a row. Uh, and 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, the good news is I think if you win every week of the year that’s left, you could still finish second. [00:33:42] Joe: So, no, I’m kidding. Can tie [00:33:44] bit: I for second? [00:33:47] Joe: You could, you could run the table and you could be winning by the first week of October, Paula. Whoa. Yes. All you gotta 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, it all starts right here, [00:34:02] Doug: Joe. [00:34:02] Doug: Hey, there’s stackers. I’m Joe’s mom’s neighbor, Doug. It’s the start of Labor Day weekend. And while we are 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. [00:34:22] Doug: 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. [00:34:40] Joe: Yes, she does. That woman, the teamwork makes the dream work right, and everybody is a big fan. [00:34:47] Joe: 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. Uh, oh, gee, you’re going first as of 2020. Total cost of having a baby. [00:35:00] OG: I think it’s a little silly to be using data from five years ago, so I’d like to report that to the fact department. [00:35:06] OG: There has to be some recent, um, more recent, uh, uh, data 2020 for god’s sake. There. Actually, [00:35:13] Joe: well hold on a second because I actually have the answer to that because, uh, Dr. Jordan Grumet from Earner and Invest helped us with this question. And actually Jordan said that they actually look at this every five years. [00:35:25] Joe: 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. [00:35:33] OG: Well, so says the person not answering trivia questions, but, okay. So says the person, so says the person in the field. He’s [00:35:39] Doug: a doctor and that also makes him a statistician. That’s [00:35:44] OG: alright. [00:35:45] OG: Well, based on backing out inflation five years ago in my brain, um, I’m gonna say that the answer, so this is, um, are we concluding all nine months of prenatal care here? Oh my god, that’s a fair question. Every week. [00:35:58] Doug: Every week, OG you gotta bring us this kind crap. Labor and [00:36:00] Joe: delivery. Cost of labor [00:36:02] OG: and delivery. [00:36:03] OG: Just l and d. Just blue. 19. When the, when the quarterback’s under center and just gets to snap. Orange 21. Orange 21. Okay. That’s what it was like for my middle kid. Alright. Uh, I’m gonna say that the answer is approximately, uh, 29,000. $847 and 11 cents. [00:36:33] Doug: You’re such a pain in the ass. You are such a pain in the ass. [00:36:36] OG: Oh gee. What do you think about that? 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. [00:36:47] Joe: Half the fun to 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 uh oh. [00:36:57] Joe: Gee’s gonna make the math difficult. All right. He says 29,847 change. Jillian, what are you thinking? [00:37:06] Jillian: 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. [00:37:18] Jillian: Yeah. Average. Yeah. I would say 17 is the average, unless you want like snacks and a blanket. And then it’s 50,000 [00:37:31] Joe: spoken like somebody’s been to a hospital before. Yeah. Alright, Paula, you’ve got, uh, 29, 8, 47 and 17,000. [00:37:42] Paula: Yeah. Well, well, OGs guest was 29, 8 47 and 11 cents. 11. That’s right. And 11 cents. So I’m going to take the over, and I’m gonna go with 29,847 and 12 cents. [00:37:59] Joe: It turns out the answer is 29,000 847, 11 and half cents. [00:38:03] Doug: I used to like you, Paula, [00:38:06] Joe: so you think it’s more expensive than 30,000? [00:38:09] Paula: Uh, you know, 30,000 was actually the number that was in my head. [00:38:12] Joe: Yeah. [00:38:13] Paula: When I first heard the question, my thought was probably it’s gonna be around. $8,000 out of pocket, depending on the, the size of somebody’s deductible and co-insurance. [00:38:24] Paula: I thought you say baby, [00:38:26] OG: the size of [00:38:27] Paula: somebody’s baby. [00:38:29] Jillian: By the pound [00:38:30] Paula: per pound, [00:38:31] Jillian: by the, [00:38:32] Joe: like the deli. [00:38:35] Paula: Like a scale. [00:38:38] Joe: That’s where they weigh ’em when they’re born. Yeah, that’s where they get you. That’s where the hospital gets you. [00:38:46] Paula: So yeah, my thinking is basically, depending on the terms of your deductible, your co-insurance, your copay, it’s probably gonna be like eight grand or so for the average family. [00:38:55] Paula: But I think that the total cost, total cost is probably about 30,000. [00:38:59] 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. Og you kicked this thing off at 29 8 4 7 11. You had to have known since the beginning of the year when you took the big lead that somebody’s gonna go after. [00:39:25] Joe: You and Paul, Paul had decided to make sure that you’ve only got a 50% chance of getting part of it. You feeling good still, though? [00:39:34] OG: Uh, I feel like it’s close. Having only had three children and writing checks for each one of them, I, I just distinctly remember how much each one of those checks were for. [00:39:45] OG: Although, you know, we never skated outta there without complications, so maybe my data is skewed by having small issues along the way. [00:39:52] Joe: Jillian, your number includes complications sometimes. [00:39:55] Jillian: Yeah, you gotta balance out the budget. Babies with the expensive ones. [00:40:00] Joe: And then Paula, the sky’s the limit. 29,847 and 12. [00:40:05] Paula: It’s just, it seems hard to get outta the hospital for anything less than 30 grand. [00:40:10] Joe: Will you take a check? Right. Alright, Doug, the answers are locked and loaded. Who’s taken this week’s winnings home? [00:40:23] Doug: Hey, 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 hardworking stackers out there. [00:40:44] Doug: Thank you. Today we are talking about, that’s as sincere as I get. I mean, come on, just take so sincere. That’s, that’s all I got there. Almost tear up. There’s nothing patronizing about that at all, 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? [00:41:10] Doug: Well, I’ll tell you this, it was $10,982 and 2 cents. Less than what Paul guessed. 10,000 9 82 and 11 cents less than what OG guessed, and just 1,865 more than what Gillian guessed. Whoa. Because the correct answer is 18,865, making Gillian our winner. [00:41:36] Joe: Does it feel like being back in the home country, yli? It does. It does. Y route. [00:41:43] Jillian: Congratulations. Nice work. Thank you. I’m so invested now, [00:41:49] Joe: but OG it sounds like your experience, uh, wa was a little off that number. [00:41:53] OG: Yeah. I think the most recent one for which we have data is a 2016 data, and I, I believe it was in the high thirties. [00:42:01] OG: Holy. So. Wow. Wow. Holy cow. That one was the cow. Easiest one. So I guess we got too many blankets or [00:42:09] Jillian: free coffees. It stay two of snacks. That really gets you like the first pudding is good. The second pudding, they’re about a thousand bucks a pop. [00:42:19] Joe: Well, in a pudding pop. That’s even more, yeah, that’s outrageous. [00:42:22] Joe: Don’t even, don’t even ask about that. All right. Congratulations, Jillian. And, and you know what that means? Oh, G has 11 and Jesse has 10 and a half. [00:42:34] Joe: Hey, coming into, [00:42:36] OG: it’s all for the gram guys. It’s all for the gram. [00:42:39] Jillian: Whoa. He can send me a thank you card later. Yeah. I, I think [00:42:42] Joe: he needs to Jillian, I think he clearly needs to. Are you gonna be at FinCon? I am. I am. Well, he needs to buy you beer or something. Whatever beverage of choice that you have, I’ll let him know. [00:42:52] Joe: 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? [00:43:06] Jillian: 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. [00:43:21] Jillian: And so there’s a little bit of a, I think a mistake of saying, you know, I really want to like, I wanna hike the Pacific Crest trail ’cause I’m 32, but I’ll just wait till I’m 65. That’ll be cool. I’ll probably still totally wanna do that or be able to do 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. [00:43:49] Jillian: Super fun. But maybe when I’m 75, like it won’t be my jam anymore. 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 citizens. [00:44:08] Jillian: So I have a feeling that cruising is still possible into your seventies, 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 frontloading the affordable stuff that could also maybe require a high degree of capability. [00:44:28] Joe: I saw in the Wealthy Accountant blog this idea last fall that the average healthy life expectancy, Jillian, not life expectancy. [00:44:35] Joe: Mm-hmm. But healthy life expectancy United States is only 66. [00:44:39] bit: Mm-hmm. [00:44:39] Joe: So if we wait till after 66, to your point, to do some of these high capability things, we we’re not gonna get ’em. [00:44:46] Jillian: Yeah. You, to Paul’s point, sometimes you just have to admit that. I’m just not gonna do that. I’m choosing not to do it, and I’m gonna let that experience pass me by if you feel regret about that. [00:44:56] Jillian: 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, I did a cross country road trip in my twenties and it was awesome. [00:45:17] Jillian: 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, it’s gone. [00:45:32] Joe: Yeah, the whole camping thing I think is beyond OG as well. [00:45:36] Joe: Og you and your government sponsored camping trips, I think you’ve said. Yeah. [00:45:39] OG: I mean, we got to do lots of fun outdoor activities, uh, all courtesy of the US Treasury Department, US government, so I’m good. I don’t need to be outside ever again. It’s especially, especially overnight and especially sleeping. [00:45:51] OG: I’m just more concerned about the, um, 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, oh my, my gosh. There’s only like nine years to go. You just got that way, man. So like a little countdown clock that you guys have, like, this is my healthy life left. [00:46:06] OG: I got it [00:46:06] Doug: on the wall over [00:46:06] Joe: here. [00:46:07] Doug: This is, this is peak maleness right here. I, it, 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. [00:46:18] OG: Okay. All right. I like that attitude. Your, I though your pharmacy in your bathroom, the pill packs say otherwise, but, but definitely peak maleness for sure. [00:46:28] OG: Long as there’s Advil, everything’s peak, right? Advil in Burman. Yeah. You can do everything twice. This is [00:46:32] Joe: why I need to retire often, Jillian, is to just get away from this harassment in the workplace. It’s absolutely horrible. [00:46:39] OG: It is. Ageism, I’m sorry. Report me to hr. Whatcha gonna do [00:46:44] Joe: Paul. I am thinking as I’m listening to Jillian talk though about a different spreadsheet. [00:46:48] Joe: 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 one. Like I could do that when I’m 75, hiking Acadia National Park to go to the same area. I probably wanna do that now. [00:47:06] Paula: Yeah, absolutely. [00:47:08] Paula: 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. [00:47:25] Paula: What are the things that you loved as a kid that you still love now? Like for me, reading books, I love 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. [00:47:45] Paula: Whereas when I looked at other interests that kind of popped up like, like hiking and camping when I was in my early twenties, 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. [00:48:04] Paula: The rant Paula has had with me [00:48:05] Joe: about how bad any running at all sucks. [00:48:08] Paula: Oh, I’ve never liked running, have been epic. That has been a through line in my entire life. I have never liked running. I have a high degree of certainty that I never will, like running [00:48:19] Joe: just epic rants about how stupid running is. [00:48:21] Paula: Yes, that has also been a consistent through line throughout my life. [00:48:24] Paula: Books, yes. Running, no. Have you noticed that you’re, do [00:48:28] Joe: your books have more pictures now, or fewer pictures now than when you were young? [00:48:31] Paula: I’d say maybe the same amount. You know what? I actually just started, uh, rereading a whole bunch of the Goosebumps books by RL Stein. Oh, cool. Seriously, I go to the library and I get RL Stein Goosebumps and you can get like the versions that were printed in the nineties, like the old school ones. [00:48:47] Paula: 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. [00:48:55] Joe: I think some of those middle grade fiction books and just the choices kids have like really good writing for that age group. Yeah. 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. [00:49:06] Joe: 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 wanna do, or I can take a few. Not as expensive. Many retirements, but they won’t feel as fulfilling. But I’ll get more time to maybe make them fulfilling during that time. [00:49:30] Joe: 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 [00:49:41] Jillian: in the moment. The big epic thing is gonna 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 move 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. [00:50:11] Jillian: I. 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 as you age [00:50:31] Joe: in in your memory. [00:50:33] Jillian: Yeah, yeah, [00:50:34] Joe: yeah. Do you guys agree with that or do you agree with that? [00:50:36] OG: Well, we did a, um, 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 two and a half years ago and it’s still in the weekly parlance. So I don’t know that we’ll ever do that again. [00:50:54] OG: That was like kind of the big blowout thing. Not to say we won’t have like the one month things either. Uh, 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, uh, as the years go on. Even my daughter, who was at the time six. [00:51:12] OG: 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 a hundred percent core memory using the phrase from inside out for the Disney movie. That’s like core memory for our family for sure. [00:51:29] Doug: Wow. And that was like a third of her life ago. [00:51:31] Doug: I can’t believe she still remembers it. [00:51:33] 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. [00:51:47] Joe: Paul, are you on board with that as well? [00:51:48] Paula: Yeah, there’s research around what they call, um, 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. [00:52:12] Paula: There’s a bunch of research that was done by a professor named Leif Von Bin. Boen from the University of Colorado. It sounds like you, speaking of making up statistics, it sounds like you just made up that [00:52:22] Joe: name. [00:52:23] Paula: No, no. This is totally a [00:52:24] Joe: Doug moment. Uh, there’s research from Leaf, uh, Von Boen, [00:52:29] Paula: LEIF, LEF, who’s a professor [00:52:32] Joe: Hogwarts [00:52:35] Paula: at the University of Colorado. [00:52:38] Paula: I remember this ’cause I wrote an article about it and the memory of writing that article has gotten rosier. In hindsight, it’s kind better and better every time you think about it. It’s, [00:52:46] Joe: it was the best article you ever wrote. Yeah, [00:52:52] Joe: I remember. Um, when we spoke with, uh, former Wall Street Journal personal finance columnist, uh, 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 buildup 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. [00:53:20] Jillian: For a lot of people, especially if you’re really burned out or stressed about your job, just knowing that this is gonna happen, even if it’s happening in six months, creates a little bit more lightness and it makes that time more enjoyable and like more tolerable because you have like the light at the end of the tunnel. [00:53:37] Jillian: Even if the tunnel, you know, the light’s only gonna last for a month or two. [00:53:42] Joe: I thought you were gonna go dark and say, you know, even if it’s a train in the tunnel. Yeah. Glad we ended though on a high note, Jill. Nice job. That was good. Uh, absolutely love this topic and I love the idea of many retirements. [00:53:56] Joe: We’re gonna have Doug mention this again in a few minutes, but we gotta spend just a moment on this. Apparently Jillian, one of us may have written an entire book on this topic. [00:54:07] Jillian: That’s so weird. Isn’t that so? Who would do [00:54:09] Joe: that? How handy, how handy and convenient it’d be so great. Like you could have it as a handbook, as a manual. [00:54:15] Joe: 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 [00:54:21] Jillian: think you could probably order it right now and it would show up at your house in a few days. [00:54:26] Joe: Oh, that’s great. Yeah, it’s so convenient [00:54:30] Jillian: and we can get it at Amazon or everywhere. [00:54:33] Jillian: You can get it everywhere, wherever you want, 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 all over the internet [00:54:42] Joe: and the book is called Retire Often. I love this idea of retiring often. Alright, let’s find out what else is going on where all of you are, Jillian on. [00:54:52] Joe: Let’s stick with you for just a second longer. What are you doing this holiday weekend? [00:54:55] Jillian: Making those minions work in the gardens. We [00:54:58] Joe: gotta practice season up og what’s going on at the OG household on Labor Day weekend? Oh, [00:55:06] OG: it’s such a great week. We are, uh, uh, middle kid has varsity game number one on Friday out of town, so we’ve got a, uh, an away game to go to. [00:55:15] OG: And then from the there, the good news is [00:55:16] Joe: Labor Day weekend, it’s only 107 degrees in Texas, so [00:55:20] 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, uh, Texas a and m, which is where my oldest is gonna go. And, uh, we move him in, I guess is you’re listening to this, we have already moved him in, but then, uh, that’ll be kind of a right around day 10 ish or 12 ish of him being on his own. [00:55:40] OG: So it’ll be perfect time for us to come drop in for a little visit, go to a football game, and then, uh, with the long weekend, no worries on staying a little late. Staying staying up a little late on Saturday night. So. [00:55:51] Joe: Fantastic. Which means what, eight 15 then? [00:55:55] OG: Yeah. I’ll probably have to leave the game early to go sit in the car, take a nap, but I’ll catch the rest of it on, uh, sports Center the next morning. [00:56:02] Joe: And he teases us about being old Doug. He teases us about being old, and yet if it’s eight 15, [00:56:07] OG: he’s done. It’s a Saturday. It’ll be like 8 45. [00:56:11] Joe: Paula, [00:56:11] Paula: what’s going on in Afford Anything on the Afford Anything podcast? Well, you and I Joe, once a week. Typically on Tuesdays, we answer questions really that come we do, we do, we do. [00:56:23] Paula: We answer all of these questions. We are tackling a whole bunch of questions, listener submitted about inflation, about jobs, investments, about all of the various topics that we tackle. So if you wanna hear Joe’s wisdom on how to live your life. Come to the Afford Anything Podcast [00:56:40] Joe: with all that wisdom, OJI, all those years, I am ahead of you. [00:56:43] Joe: See, I mean, people can get a piece of that. There’s [00:56:45] OG: some benefit to that, that’s for sure. [00:56:48] Joe: Alright, Jillian, thanks Aton for joining us. Og. Paula, thanks for bringing it. Doug’s gonna bring it here at the end, by the way. Thanks 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 ’em on the screen, so we had a great time. [00:57:06] Joe: 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? Well, Joe first take some advice [00:57:15] Doug: from Yian Y Root, that’s not even Norwegian. I, I mean, I just totally processed it. It was pretty good [00:57:20] Jillian: actually. Uh, that’s pretty solid. [00:57:22] Doug: When you approach your boss about a sabbatical, be sure you make up some complete BS sob story about your goldfish being in hospice, and then butter ’em up by telling ’em how good their breath is today. [00:57:33] Doug: They’ll practically open the door for you on your way out. I don’t think you were even listening. I’m fairly certain. 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. [00:57:54] Doug: 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. I’m so weird when you say it that way for joining us today. [00:58:18] Doug: You can, she said it wrong her whole life. You can preorder her new book, retire Often on Amazon or wherever you buy books. We’ll also include links in our show notes at Stacking Benjamins dot com. Thanks to Paula Pam for hanging out with us today. You’ll find her fabulous podcast, afford anything wherever you listen to Finer podcast. [00:58:36] Doug: And finally, thanks also to OG for joining us, often today looking for good finance. He hates it when you say the T in often. Thanks. So I just had to slip that in there. Looking for good financial planning, help head to Stacking Benjamins dot com slash often for his slash OG for his calendar. This show is the property of SP podcast LLC, copyright 2025 and is created by Joe Saul-Sehy. [00:59:05] Doug: Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome team at Stacking Benjamins dot com, 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. [00:59:27] Doug: 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. [00:59:45] Joe: Doug, you ready to start this thing? [00:59:46] Doug: Let’s do it. [00:59:49] Joe: That sounded just like tone Looch. [00:59:50] Doug: Come on. It sounded You had to have heard it. Exactly. Yeah. Like tone lo, I swear. We need the, we need the drums to come in right after that. All right, here we go.
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