Most of the financial decisions keeping you up at night are two-way doors. You can change them. You can undo them. The real one-way doors — the decisions that actually lock you in — are rarer than you think, and the problem is we’re spending the same emotional energy on both. Joe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff’s uncertainty framework from Wednesday and run it straight through real financial life: career changes, portfolio risk, entrepreneurial pivots, and the moment you finally flip the kill switch on something that isn’t working.
What You’ll Walk Away With
- The one-way door versus two-way door framework applied to real decisions — and why automating your savings contributions is the most underrated version of this idea
- Jesse’s anchor: why life insurance changed everything about how he sleeps at night now that there are passengers in the car with him
- Paula’s anchor: why avoiding debt entirely is the entrepreneurial version of keeping your burn rate survivable when revenue gets unpredictable
- OG’s anchor: long-term belief in human ingenuity as a financial strategy — and why short-term geopolitical noise is actually an opportunity for investors who aren’t panicking
- Why selling assets in a taxable brokerage account to cover business payroll is a two-way door — until enough time passes and it quietly becomes a one-way door
- The kill criteria conversation: how Jesse built an 18-to-24-month runway into his career change before he ever made the leap
- Why the Everest turnaround time is the most important financial planning concept most people have never applied to their own goals
- OG’s client story: when the right risk tolerance isn’t the mathematically correct one — it’s the one that lets you sleep at night without calling your advisor
- Paula on the pivot strategy: keep iterating the broad direction until you find the product-market fit, because the version that works might look nothing like what you started with
- Why a career shift becomes more of a one-way door the longer you wait — and what Rocky Mark’s electrical engineer to content creator question reveals about timing
Why This Matters Now
The worst financial decisions happen when people treat reversible choices as permanent ones and freeze — or treat permanent choices as reversible and act too fast. This episode gives you a framework for telling the difference before the emotion hits, which is the only time it actually helps.
From the Basement
Joe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff’s Wednesday framework and apply it to the messy real world of careers, portfolios, entrepreneurship, and retirement identity. The trivia competition takes a dramatic turn when OG margin calls Jesse on a Mount Everest question — and the full margin call rule set gets read aloud for the first time in recorded history after Dottie in Wichita makes a call nobody wanted to receive. Jesse wins the point. OG loses one. The coalition closes the gap.
Resources Mentioned
Stacking Benjamins Community — stackingbenjamins.com/basement
Afford Anything podcast — Paula Pant; Joe joins most Tuesdays for listener Q&A; youtube.com/affordanything
Personal Finance for Long-Term Investors — Jesse Cramer’s podcast; current series: 14 biggest risks in retirement, Charlie Munger-inspired inversion framework
Stacking Benjamins Wednesday episode — “Why Uncertainty Is an Opportunity” with Simone Stolzoff; stackingbenjamins.com
Stacking Benjamins Vault — stackingbenjamins.com/vault
Stacking Benjamins Newsletter (The 201) — stackingbenjamins.com/201
OG financial planning calendar — stackingbenjamins.com/og
Our Topic: How to make smart money moves when everything feels uncertain
During our conversation, you’ll hear us mention:
- Financial uncertainty
- Market volatility
- Career instability
- Income swings
- Geopolitical risk
- Financial anchors
- Emergency funds
- Cash reserves
- Business burn rate
- Avoiding debt
- Mortgage anxiety
- Life insurance
- Family responsibility
- Payroll pressure
- Long-term optimism
- Investment policy
- Retirement identity
- Enough number
- FIRE planning
- Job identity
- One-way doors
- Two-way doors
- Reversible decisions
- Home downsizing
- Selling assets
- Career pivots
- Sabbatical risks
- Skill atrophy
- Entrepreneurial runway
- Portfolio risk
Our Contributors
Jesse Cramer
Another thanks to Jesse Cramer for joining our contributors this week! Hear more from Jesse on his show, Personal Finance for Long-Term Investors – The Best Interest, on Spotify.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Paula Pant
Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on Twitter: @AffordAnything
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- On this date in 1953, Edmund Hillary and Tenzing Norgay became the first confirmed climbers to reach the summit of Mount Everest. Since then, thousands have followed in their footsteps. Rounding to the nearest 100, approximately how many unique climbers have successfully summited Mount Everest?
Mentioned in today’s show
- Why Uncertainty Is an Opportunity (and some Wall Street players don’t want you to know that) SB1847
- Jeff Bezos’s 1-Way vs 2-Way Doors
- Grit or quit: the power to walk away
Join Us on Monday!
Tune in on Monday when we find ways to add money in your pocket without adding more risk.
Miss our last show? Check it out here: Why Uncertainty Is an Opportunity (and some Wall Street players don’t want you to know that).
Written by: Kevin Bailey
Episode transcript
[00:00:00] opener: You heard of this thing, the eight-minute abs? [00:00:03] OG: Yeah, sure. Eight-minute abs. Yeah, the, uh, exercise video. Uh-huh. [00:00:06] opener: Yeah. Well, this is gonna blow that right out of the water. Listen to this. Seven-minute abs [00:00:19] Doug: Live from the basement of the YouTube headquarters, it’s The Stacking Benjamins Show [00:00:34] Doug: Joe’s mom’s neighbor, Doug, and uncertainty is back. Markets feel shaky, careers feel shaky, and honestly, half of us refresh our brokerage accounts like the answer to life is heightened between the S&P and our blood pressure medication. So how do confident people make smart money moves when the future feels completely up for grabs? [00:00:55] Doug: We’re diving into the difference between one-way and two-way door decisions, why some risks are worth taking, and how to stop uncertainty from quietly ruining your financial life. Plus, halfway through the show, I’ll unleash my trivia challenge because nothing says emotional stability like watching grown adults panic over obscure facts. [00:01:18] Doug: And now, a guy who’s absolutely certain the microphone is on this time, it’s Joe Saul-Sehy. [00:01:29] Joe: Hey there, Stackers, and happy Friday to you. I am Joe Saul-Sehy, and I’m super happy you’re here with us because we’re gonna talk about uncertainty today. One thing we are certain of, it’s Friday, and you are here, and we are here, and we’re gonna have a great time, [00:01:43] Joe: aren’t [00:01:46] Joe: we, Doug? [00:01:47] Doug: Yes. Maybe. We may- I mean, you’re asking a lot of- Wow … you want a lot of commitment from me. [00:01:53] Joe: On a Friday, bring in the energy. Yes, absolutely. Let’s see if… Why am I turning to OG to see if he’ll bring the energy? Please, God. [00:02:00] OG: I, I just wanna know why we’re working on Fridays. It is summer, and I was told, uh, I- I mean, it’s in my contract, we do not have Friday work days. [00:02:09] OG: So who do I see about this? [00:02:12] Joe: Somebody who’s super happy we’re working this particular Friday. She’s like, “How quickly can we be done?” Paula Pant is here. [00:02:18] Paula: Hello. I’m always happy to spend Friday with you. There’s the energy. [00:02:22] Joe: Well, fan- fantastic. And the guy who rounds out the team here on Fridays, Jesse Cramer’s here. [00:02:29] Joe: How are you, man? [00:02:30] Jesse: It’s actually still Thursday here in Rochester. We have, uh- We’ve retrograded a few time zones. [00:02:36] Joe: You went backwards. What, what happened? [00:02:38] Jesse: We’re going back to the future. Doug was telling me all about it. It’s this movie that came out when Doug was, like, midlife crisis 40-ish, and it’s all about time travel. [00:02:48] Joe: On today’s show, here is, uh, what’s going on, Stackers. On Wednesday, we had Simone Stolzoff join us. Even if you didn’t listen to Wednesday’s episode, and, and by the way, I would go back and listen to it, but you can wait until we’re done with this conversation. But he talks about uncertainty and this idea that there’s so much uncertainty, not just now but all the time in the markets, and some people can deal with it. [00:03:13] Joe: Some people have a really hard time dealing with it. How do we get through it all? How do we get through the, the times of uncertainty? And he had so many great points, but what I thought we truly needed was the ability to go and look at our p- at our portfolios and our financial lives, and how do we put these into practice? [00:03:32] Joe: So I’m super happy because today Paula and, and OG and Jesse, we’re gonna go over exactly some of the biggest, uh, techniques and biggest ideas that Simone had from Wednesday. Don’t worry if you haven’t heard that interview yet. I’ll explain all the different concepts, but then, uh, you might wanna go back and listen to Wednesday. [00:03:55] Joe: Speaking of listen, we’re gonna listen to a couple of our sponsors because they help us keep on keeping on. We only have two sponsor breaks during our shows, now and in the middle of Doug’s trivia. So hang on for just a moment. We’re gonna make sure that we can keep making this free for you, and then Paula, OG, Jesse, Doug, and I, we’re going to dive into your ability to get through uncertain times, and hopefully make it a lot better. [00:04:29] Joe: All right, let’s dive into this idea of uncertainty, guys, because certainly we deal with it every day. And even though we’ve all put systems in place, and we’re gonna be talking about that as we dive into this topic, there are some areas that trip us up more than others. I know that, um, well, I do really well with, like, geopolitical conflicts, something that we’ve talked about here in the last several weeks, obviously f- for good reason. [00:04:54] Joe: I don’t go make changes to my portfolio because of that I do think a lot about my portfolio when I think about the possibility over the years of, of income instability, and the fact that there might be income instability. And I go mess with long-term money, or want to mess with long-term money because of short-term decisions. [00:05:13] Joe: That’s kind of my Achilles heel. Jesse, what would you say is yours when it comes to all this? [00:05:19] Jesse: I definitely feel more certain when I’m in control, and, and may- maybe by definition, not reinventing the wheel here. For example, when I think about, say, my family members, like, the way that their futures will unfold, that makes me feel uneasy. [00:05:35] Jesse: Like, if that makes sense. Like, I, I, I always know I’ll be okay. I can fend for myself. I’ll figure out a way. I’ll make sure I’m okay. But then when I think about, you know, providing for other people and, and making sure that they’re okay in their futures, that, that gives me a lot of unease. That’s the kind of thing that can put my kind of stomach in a little bit of a knot. [00:05:53] Jesse: And so- [00:05:54] Joe: Just the fact that there’s passengers on your journey. [00:05:57] Jesse: That’s exactly correct. [00:05:58] Joe: Yeah. [00:05:58] Jesse: That’s exactly correct. And so anyway, I’ve, I’ve noticed over the last couple years, I’ve made some changes to my kind of financial plan, my personal financial life because of that fact, and kind of to help me sleep better at night because there are now some passengers with me. [00:06:12] Joe: That’s a good one, an important one to recognize. Paula, how about for you? What’s yours? [00:06:18] Paula: I think for me the biggest thing is because business can be so volatile, and because business has so many expenses associated with it, including paying payroll, um, and paying everybody on the team, the times when it is not generating the revenue that we need it to generate, I stop paying myself entirely, and then I have to sell off assets in a taxable brokerage account. [00:06:43] Paula: And often that is totally unplanned, but you know, that’s what’s required in order to just pay rent and buy groceries. But [00:06:50] Joe: you worry about that possibly coming up, and that can be your stumbling block. [00:06:53] Paula: Yeah, yeah. Exactly. Exactly. [00:06:56] Joe: Yeah. OG, how about for you? I could see you, you know, worried about both of those. [00:07:02] OG: It’s funny listening to, uh, Jesse’s conversation about, like, being responsible for other people. Um, welcome to being a dad, brother. Like, that’s, that’s kind of part of that transition. I, I remember when we had our first kids, I was thinking to myself, like, sometimes when I would talk to my wife about our kids or, like, when she was pregnant, all the conversations were like, “I wonder what this kid’s gonna be like. [00:07:26] OG: You know, how are we gonna teach him or her, and what is that growth and development gonna look like?” And all that I thought about was like, “How am I gonna feed everybody?” [00:07:33] Joe: Oh. [00:07:34] OG: Like, I’m good. I can feed me. So far I’ve figured out how to feed two people. I’m just not entirely sure how we’re gonna feed three or four or five, you know? [00:07:41] OG: So I can appreciate your, you know, your sensation of that. It gets better, I promise, on the other side of it. Joe, when you were talking about uncertainty and some of the other stuff, you said, “Hey, I deal well with political stuff or just kinda news cycles,” and I’m with you on that one. That stuff doesn’t get my ire up at all. [00:07:58] OG: Sometimes I even think it’s comical, and, uh, it creates great opportunities, honestly. If you’re an investor and you see other people making mistakes, you know, you’re just like, like, “Oh, I get to get that on sale later,” you know? It feels a little bit, um, like you’re taking advantage of the system maybe. For me, it’s really around kind of the second-tier decisions, like the dominoes that fall because of the decision that you make, and spending more energy and more time on thinking about, “Okay, well, if I do this, then what are the other kinda next order effects that might be happening, and how can I gain the same certainty I have around the first decision with the other decisions as well?” [00:08:34] OG: ‘Cause I don’t like surprises of really any kind. I’m kinda convinced that most people don’t like surprises. So just a easy financial one, right? Paula was talking about selling something in her brokerage account. Like, okay, so you sell it because you ha- need the cash flow or this opportunity comes up, and then you find out you didn’t think through it, and you find out, “Oh, shoot, I sold the wrong thing, and now I have a $3,000 tax bill that’s due in April.” [00:08:55] OG: Mm. Like, un-fun surprise, you know? So I wanna gain some certainty, clarity around, like, those second- and third-tier decisions, or any decision that I think is irreversible. And I know we’re gonna talk a little bit about that at the end, so I’ll save that kind of for later, but that’s where I really wanna spend a lotta energy thinking time on what are the next dominoes that are gonna fall by do- by pushing this one button? [00:09:18] OG: I know what immediately happens, but what are the second-order effects and third-order effects? [00:09:22] Joe: Yeah, to your point, I really sometimes think the geopolitical panic is laughable. There was an absolutely horrible incident that happened way back in 2004, that you guys may or may not remember, but there was a tsunami in the Indian Ocean just… [00:09:39] Joe: And it was a horrible situation. It was a horrible loss of life. I didn’t wanna take advantage of that. Nobody ever, ever, ever wants to take advantage of that. But what I thought was completely stupid, OG, was people began selling all these assets in, in Singapore, which has a bunch of barrier islands around it. [00:09:58] Joe: Wasn’t affected at all, and the Singapore exchange goes right through the floor along with everything else. And I thought, “How dumb.” Like, like, just, just how dumb to sell that exchange. So I went to buy it up, not to take advantage of a loss of human life, to be clear, to take advantage of the stupid investors that thought that was a great time to sell. [00:10:18] Joe: Like, why are you selling this, this thing and obviously just selling everything from that part of the world? It was a, it was a horrible time, but it was also a time when I went, “How ridiculous.” A way to deal with it that Simone talked about that was he, he said was really important is to create these anchors. [00:10:36] Joe: You know, these financial anchors that can help you out with, “You know what? I do worry about geopolitical risks, so that’s why I have an investment policy statement so that I will not make moves except on these days.” So we set these financial anchors, and I’m wondering for you guys, what, what’s some of the anchors around the things that you do? [00:10:54] Joe: Paula, dealing with maybe even what you talked about. You can’t know when an income stream for you or for us at Stacking Benjamins, right, but we don’t know as an entrepreneur when that’s gonna hit. But how do you try to plan against that? What’s your anchor? [00:11:07] Paula: A couple of anchors. One is maintaining cash reserves, and that works until it doesn’t. [00:11:12] Paula: Like- [00:11:12] Joe: Right … [00:11:12] Paula: when times are good, you’re like, “Cool, I’m shoring up the cash reserves.” And then when times are bad, you’re like, “I’m dwindling, I’m dwindling, I’m dwindling, I’m dwindling. I’m done.” [00:11:21] Joe: Yeah. When it becomes a burn rate, that’s when [00:11:23] Paula: you start to- [00:11:23] Joe: Yeah … yeah. [00:11:24] Paula: It has a part… I guess, a partial success rate. [00:11:26] Paula: Like, it, it’s certainly better than not having done it. Sure. But it’s Plan A. I guess the other piece of it is, is avoiding debt. For me, that’s been a big one. As long as I’m operating all cash, then the worst thing that happens is I burn through all of my savings and all of my liquid investments. [00:11:44] Joe: And that is interesting, because that makes your burn rate smaller, right? [00:11:48] Joe: I mean, when you think about being a company, if you keep your… I remember when I was an early entrepreneur, one of the best piece of advice I got from somebody was keep your overhead low. I was talking to this one guy about how as a young entrepreneur, I was gonna do all these things, that I was gonna have all this brick-and-mortar stuff. [00:12:03] Joe: He goes, “Avoid brick and mortar at all cost.” Mm. “Keep your overhead low.” You’re talking, Paula, about keeping your overhead low so the burn rate’s smaller. [00:12:10] Paula: Well, not… I mean, kind of, sort of. Like, I keep my overhead low by not hiring more people, but I don’t wanna let go of the team that I have, and just maintaining the team that I have has very high costs associated with that. [00:12:23] Joe: Absolutely. And the other thing that strikes me is if you maintain your credit rating, you’ve the ability if you need to, to take on debt later as a last resort still in your pocket. Right. [00:12:33] Paula: Yeah. [00:12:35] Joe: Jesse, what’s your anchor? [00:12:38] Jesse: My anchor, first I like to have my microphone on. That’s kind of my baseline anchor, you know? [00:12:42] Jesse: That way people can hear me when I’m actually speaking. Uh, well, it is, it is funny, ’cause again, going back to my first answer, which just had to like do with having these other passengers in the car with me, the unique and new feeling I’ve had over the recent years is having life insurance makes me feel a lot better. [00:12:59] Jesse: Like, that’s this anchor that makes me say, “Okay, if I get hit by a bus, at the very least there’s gonna be enough liquid cash on hand that everyone’s gonna be okay.” And then for a few years, right? It’s, it’s gonna last for a while. And then also part of that life insurance leads me to maybe my next thing that makes me nervous, which is Paul was just talking about debt. [00:13:16] Jesse: I think of my mortgage. Having a mortgage never used to bother me, and it still more or less doesn’t. Like, you know, you, you make your monthly mortgage payment. It’s kind of like the equivalent of paying rent. Either way you’re making some sort of monthly payment. But when I see that number next to our house of like how much debt is still on the house in the form of a mortgage, that is something that I, I, I wish… [00:13:36] Jesse: It’s a shackle that I wish I could break, that I wish I could get rid of. And I’m trying to be prudent about it. I’m not, you know, liquidating my 401just to pay down the mortgage. But all of a sudden, paying down the mortgage is a much higher priority to me today than it was, you know, a few years ago, than it was before I had children. [00:13:54] Jesse: So it’s just kind of funny how, yeah, sometimes these, these uncertainties or certainties can kind of ebb and flow in life as, as things change. [00:14:01] Joe: It is wild that we’re now two for two with debt being, or the avoidance of debt being an anchor, but from two totally different perspectives. One from the entrepreneurial side, the other from the fact that you’ve got passengers in the car. [00:14:12] Joe: Well, really, Paula, and, you know, when you talk about being an entrepreneur, it is passengers in the car still. [00:14:17] Paula: Yeah, you know, because it’s, I’m res- responsible for payroll. [00:14:20] Joe: Yeah. [00:14:20] Paula: And that payroll goes to support the livelihood of the people on the team, particularly the people who are full-time. They’re depending on it. [00:14:28] Paula: They, and they’ve got families. They’ve got kids. They’ve got mortgages. They’ve got, uh, they’re relying on it to pay all of their bills. [00:14:36] Joe: So we’ve got emergency funds, OG, and we’ve got, uh, staying away from debt. What’s another anchor? [00:14:41] OG: Yeah, I was gonna say, I’m very pro-debt. So I would not… That would be, it’s a different kind of anchor, I suppose. [00:14:47] Doug: OPM, baby. OPM. Yeah, [00:14:49] OG: that’s right. I say that a little tongue in cheek for those who are not picking up on the sarcasm. Although I’m, to be fair, I’m not as petrified by it as maybe Jesse is, ’cause I, I, I think the other side of that for me- is just belief in the long-term time horizon, just as a big, broad brushstroke of, like, ingenuity and everything gets better over time, and by being a part of this, you know, whatever you wanna call it, this time in the history of mankind, right? [00:15:24] OG: Like, it’s never been as good as it could be than it is right now. And I also believe that history tells us that everything in the future will also be better. Now, I say that with, like, a big, broad brushstroke, ’cause that’s not entirely true of, like, every specific little, teeny, tiny thing. But in the expanse of, like, investing and that sort of stuff, I look at it and I say, “My goodness, like, access to capital hasn’t been easier. [00:15:51] OG: Entrepreneurship is on the rise, and we innovate and create new stuff as a, as a species faster than we ever have, and that’s gonna continue to make radical changes in our lives,” which I think will be good. So I believe long-term in the future. So the short-term stuff doesn’t really bother me. I’ll, I’ll… [00:16:11] OG: So I don’t have as much of a strong opinion about, like, “Oh my gosh, I must get rid of my house mortgage.” Although, to be fair, if somebody handed me a check for the payoff amount, I’d probably pay off my house. [00:16:21] Joe: Well, and you’ve also talked about for you, the nature of having a 15-year loan versus a 30. We’ve debated that on the show, and you’re like, “You know what?” [00:16:27] Joe: Yeah. Although you can do it my way, that I’ve talked about, take the 30 and invest the difference. You’re like, “Nope, give me the 15.” [00:16:33] Doug: I’m just picturing- Yeah, I mean … OG looking at a check for the exact amount of the payoff thinking, “Hmm, what should I… Why would they… That’s a funny amount.” Ferrari. “Why would they have written it for that amount?” [00:16:42] Doug: House. “What should I do with this?” [00:16:44] OG: House payoff, super car. House payoff. Like, Grant Cardone would tell me to buy assets. Like, a super car is an asset, right? He does. So YOLO. So I think just, like, history, I think I can sum up all my comments with history, both reflecting on the past to see where we’ve come from as a country, society, whatever you wanna say. [00:17:05] OG: Also, the market stuff that’s happened over my investing career and my lifetime, but then also, like, a belief in the future and, you know, just unrelenting optimism about that stuff, which I know you guys are gonna giggle about ’cause you’re like, “When I think of unrelenting optimism, I think of OG.” Those are probably- Synonymous. [00:17:27] OG: exactly, exactly like when you look it up in the dictionary, it’s, like, got a picture of me. [00:17:30] Doug: That’s [00:17:31] Joe: dumb. [00:17:31] OG: Positive [00:17:31] Joe: self-optimism. [00:17:32] OG: But as it relates to investing and time horizon, I do have it. [00:17:37] Joe: What do you think that Doug’s anchors are? [00:17:40] Doug: Oh, this ought to be good [00:17:42] OG: What do I think? I mean, Doug is an anchor, so can you have an anchor and be one at the same time? [00:17:48] Joe: I don’t know. Doug’s anchor’s probably that gut feeling. You talk about unrelenting optimism. His probably, “I just have a gut feeling it’s gonna go well. It’s fine.” Yeah. [00:17:55] Doug: What’s wrong with that? [00:17:56] OG: Bourbon’s probably an anchor. [00:17:58] Joe: TikTok financial influencers named Chad Money Alpha. Like would that, would that be a good anchor? [00:18:04] Joe: No? [00:18:04] Jesse: Doug’s got a lot of equity built up in, uh, flannel wallpaper- … and I feel like that’s gotta make him sleep well at night. [00:18:11] Joe: Tarton Cozy. It’s so cozy in here. I wanna ask about a couple other anchors that I had thought about. Paula, what about the anchor of maybe knowing what your enough number is? You know, knowing that you’re gonna be okay. [00:18:24] Paula: Well, I think that depends on are you working as a means to an end, or are you working because you enjoy the game? If you’re working as a means to an end, if you’re literally just in it for the paycheck, then absolutely know what your enough number is, know what your FI number is or your FIRE number, and then have a path to be able to walk away. [00:18:41] Paula: Because if it’s a means to an end, then necessarily it’s not your true calling, and you need freedom in order to be able to, to discover what your true calling is and move in that direction. But by contrast, if it is your true calling, if you’re doing it because you love the game, you love the process, you love to build, that’s different. [00:19:01] Joe: Jesse, you brought up earlier with your life insurance anchor, which I really liked. Uh, you know, this idea of anchors around these life events that happen to us that we can’t predict. One that we can predict, though, is retirement. You see how, what a bumpy road that can be for some people. What about the anchor around, you know, trying not to build your identity around your job? [00:19:23] Jesse: Yeah, I mean, right. I mean, there are so many different retirement topics that we could probably talk about here when it just comes to uncertainty and, and the different anchors in life. But, uh, yeah, there’s just at this point so much good research and copious research about kind of the personality or, like, the identity shift in retirement. [00:19:40] Jesse: And yeah, th- I’d say, you know, the average retiree probably underestimates how much of their social circle is tied to work, how much of their identity is tied to, “I wake up every day, and for 45 or 50 hours a week or 40 hours a week, I am a X,” right? It’s my job. It’s who I am, and it’s who I have been for 40 years. [00:20:00] Jesse: And to detach, I mean, really to like… It’s funny talking about anchors and boating terms. The term that you’ll sometimes hear people say is, like, they’ve been unmoored. [00:20:08] Joe: Oh, [00:20:08] Jesse: yeah. Right. Like, there’s another enabled term for you. Yeah. Like, retirement has made me feel unmoored. I don’t exactly know who I am or how to move through this world anymore. [00:20:16] Jesse: So right, it’s not just, like, the financial anchor of having six months of an emergency fund and having 25 times your expenses. Sometimes it’s also, like, those, those personality, identity, social relationship type anchors of who are you gonna be when you’re no longer a pediatrician. Not, not every retiree thinks about that. [00:20:35] Joe: It’s funny that you say that because as you’re talking about being, about unmoored, I’m like, “I’ve heard that before someplace.” And I realized halfway through you talking about it, Jesse, it’s in my keynote topic on the same happy retirement. I have a video of a guy talking about i- it’s being unmooring. He says it’s unmooring. [00:20:53] Joe: So it’s funny. I’m like, where have I wa- that, I’m hearing that somewhere. Oh, it’s in your own talk, damn it. [00:20:58] Jesse: I was gonna say some really smart person put it in a speech, Joe. Some, [00:21:01] Joe: some brilliant guy. I don’t know where that came from. As OG said earlier, we’ve got an idea that Simone talked about on Wednesday called one-door and two-door. [00:21:13] Joe: One door and two door decisions. One-way door and two-way door, that’s better, decisions, and also a Mount Everest analogy. We’re gonna get to those in the second half, but we always pause halfway through a Stacking Benjamins Friday show to see how our three frequent contributors are going to get on with this, uh, year-long trivia challenge we have. [00:21:34] Joe: Now, we’ve got an interesting thing happening. We’re not even halfway through the year, Doug, and OG is well ahead of record-setting pace. Our record is, uh, 18- 18 … points in a year, and, uh, what’s our score so far? [00:21:48] Doug: Well, right now we have OG at nine, so you’re right, not halfway through the year and he’s already halfway to the, uh, record. [00:21:57] Doug: So we’ve got a chance to break through that ceiling again. We have Jesse at four, he just picked up a point last week. And Paula, uh, sitting comfortably in her normal location and last with three points. I wanna point out, it’s important to note, competitors, we’ve got the gang back together again this week. [00:22:19] Doug: We only have four, maybe five more episo- Friday episodes left for you to use- Well, hold [00:22:25] OG: on a second … this [00:22:26] Doug: quarter’s [00:22:26] OG: margin call. There is never, there is not a game in America where halfway through the game the ref comes out and goes, “Hey, just so you guys know, each team’s got two timeouts. We’re getting late in the quarter. [00:22:37] OG: You might wanna think- No … about using them.” Just saying. You’re right, [00:22:40] Jesse: they put [00:22:41] OG: it on the television. Like that doesn’t… Don’t coach the game, man. Stay in your lane, bro. [00:22:45] Jesse: OG is a sore winner. [00:22:48] Joe: He [00:22:48] Jesse: is [00:22:48] Joe: hot. We just gotta remind the listeners who might be new to the show that we do have this instrument that hasn’t been in the show before called- Well, [00:22:56] OG: they were fixing to learn about it, but I guess not anymore, so- [00:22:59] OG: way to ruin the surprise, Doug. Appreciate [00:23:02] Joe: you. Called, called, called a margin call. Doug, Doug, how does a margin call work? [00:23:08] Doug: God, I don’t wanna s- Stay in your f-ing lane, man … I don’t wanna say anymore. I’m scared. I [00:23:13] Joe: think you gotta tell us how it works just for the audience, not for… Uh, Paula and Jesse can use earmuffs. [00:23:20] Doug: Any m- any player can call a margin call on any other player at any point during- I margin [00:23:28] OG: call Doug … [00:23:29] Doug: while the question is being asked. I’m gonna [00:23:31] OG: use all of my margin calls for the rest of the year on Doug not doing this ever again. [00:23:36] Doug: So as an example, if OG called margin call on me and I got the, the question wrong, I would lose a point. [00:23:47] Doug: Normally you get it wrong you just don’t get anything and the winner gets the point, but in this case the person getting margin called, if they get it wrong, they actually lose a point. And if the person- Yeah, that’s it. That [00:24:03] Jesse: is it. [00:24:03] Doug: That’s all I wanna say right now. [00:24:06] Joe: That is 100% it. Yes. All right. Uh, we have to have a question, though, to get this thing rolling. [00:24:12] Joe: Doug, uh, you’ve got the question. Is it okay, OG, if he asks the question? [00:24:17] OG: I serve at your pleasure. [00:24:19] Joe: All right, Doug. You’re, you’re ready [00:24:21] Doug: to go. Not even close to that. 3, 2… 3, 2, 1. Hey there, Stackers. Margin call. Uh, who are you margin calling, OG? [00:24:31] OG: Obviously Jesse. [00:24:33] Doug: Calling Jesse. Oh, boy. All right. [00:24:36] Jesse: Bring it. [00:24:37] Doug: Oh, boy. [00:24:38] Doug: Here we [00:24:38] Jesse: go. I knew that was just a charade. I knew there was no way- I was gonna [00:24:41] OG: do it anyway, but he just kind of, you know- [00:24:43] Jesse: Did you know that OG was born in the same town as the guy who invented charades? This is true. He’s gonna b- he’s gonna tell you about it in this trivia answer. [00:24:52] Doug: Hit it. [00:24:53] OG: Hey [00:24:53] Doug: there, Stackers. [00:24:55] Doug: I’m Joe’s mom’s neighbor, Doug, and on today’s date back in 1953, Edmund Hillary and Tenzing Norgay became the first confirmed people… Look at Paula’s excitement. Nepal trivia. [00:25:08] Paula: This is a Nepal question. This is- This is a Nepal question. You guys gave me a question that takes place- [00:25:14] Doug: Oddly enough, the town where OG was born. [00:25:19] Doug: Okay, I will continue. Edmund Hillary and Tenzing Norgay became the first confirmed people to summit Mount Everest, which means they were also the first people to look around and say, “You know what this mountain needs? More tourists and fleece vests and hiking sticks.” Speaking of uncertainty, Simone Stolzoff talked this week about Everest climbers using strict turnaround times so they don’t die chasing the summit. [00:25:46] Doug: So today’s trivia question is inspired by the world’s tallest bad decision. Rounding to the nearest 100, approximately how many unique climbers have scaled the mountain? I’ll be back- … with the answer right after I go scale the stairs to see whether Joe’s mom finally changed the lock on the cookie jar. [00:26:06] Doug: Apparently OG’s emergency snack reserve has gotten a little out of hand. [00:26:12] Joe: Oh, man. I only started laughing ’cause I saw Paula say a bad word with the mute on. [00:26:17] Paula: If the question had been how tall is Mount Everest, in feet it is 29,028 feet- Oh, oh … and in meters it is 8,848 meters. [00:26:27] Doug: Oh. Au contraire. You [00:26:28] Paula: coulda made that the question. [00:26:29] Paula: Au [00:26:30] Doug: contraire, my Nepalese descendant- … because the height of Mount Everest was not long ago revised with s- better laser, uh, altitude detection. It is now 29,035 feet. [00:26:45] Joe: Ooh. [00:26:45] Doug: It got taller, so that part’s good for you guys. [00:26:48] Paula: Nice. [00:26:49] Joe: But I like the fact that, uh, uh, that OG’s not the only one mad at Doug now, ’cause we had… [00:26:53] Joe: Doug, you asked the wrong question. So now all we got, Jesse just needs w- some excuse here. [00:26:58] OG: I wanted to see Paula go unhinged with the wrong answer of the- … of the, of the, the how many feet, ’cause that would’ve just been, like, under review. There would’ve been a protest. [00:27:08] Joe: It’d have been great. All right, we start off with you, OG. [00:27:12] Joe: Uh, unique climbers, not the number of climbers, [00:27:15] OG: but- I don’t have to go first. I was not margin-called. [00:27:17] Doug: But you’re in the lead. [00:27:18] Joe: You’re in the lead. You still go first. He just has to get it right- Yeah … or he loses a point. [00:27:22] Doug: That’s correct. [00:27:23] OG: That’s not fair. He has to go first, otherwise he [00:27:27] Doug: can- Don’t tell me about the rules, Doug. [00:27:31] Joe: We’ve never put that in the rules. [00:27:32] Doug: Read the rule book, OG. Come on. Fair’s where pigs win blue ribbons, OG. [00:27:38] OG: You guys figure out new things every single week to make this thing crazy. [00:27:41] Joe: This is a new thing we didn’t figure out apparently, Doug. We didn’t do anything. [00:27:46] OG: I suppose. I mean, we can just check the tape from last time this happened, but that’s okay. [00:27:51] OG: Um, so, uh, number of unique climbers in the history of all mankind, recorded climbers, unique climbers. Uh, the answer is very simply… And I actually happen to know this, because the most recent guy is fr- I know you guys are laughing, but from my hometown. I know him very well. But the answer is 3,300 is the… [00:28:12] OG: Uh, you said nearest hundred, Doug? Is that what you wanted? I did. I [00:28:16] Doug: did. [00:28:17] OG: So 3,300 is the closest hundred to the number of unique. Summiter. Do, do… Oh, uh, just out of clarity, you said summiters or climbers? [00:28:26] Doug: To have summited. [00:28:27] Joe: Summiters. [00:28:27] Doug: Summiters. [00:28:28] OG: Who have summited. Yeah. Okay, just to make sure. Okay. Yes. It’s, uh, 3,300. [00:28:32] OG: All [00:28:32] Joe: right, Jesse, you’ve gotta beat that or you’re going backwards, my friend. [00:28:38] Jesse: I, I know I can beat that. I know I can beat that. It’s just a matter of if I can beat Paula. I have to do head games now with Paula ’cause she knows. She [00:28:45] Doug: can’t even get that, at the height correct, so I think you’re [00:28:50] Jesse: safe. All right. [00:28:51] Jesse: Well, Edmund Hillary was 1950-ish, so it’s been 75 years, and for a while probably nobody at all was climbing it, but recently I think a lot of people have tried to- been climbing it. I’m gonna say 50 people a year for the first 50 years, and a lot more people a year recently. So what does that get me to? [00:29:13] Jesse: 7,000 people. Nice and easy. [00:29:16] Joe: 7,000 people. It’s almost roughly double OG’s answer. Paula. Paula, I gotta say this is a very tall question for somebody who may be slightly, uh- See [00:29:29] Doug: what he did there? … [00:29:30] Joe: not tall. I mean, you look up to a lot of people, but I, I would guess if you’ve ever stood under Everest, like, you look way up. [00:29:37] Paula: Y- yeah. I mean, there, there is some power in standing at 14,000 feet looking up another 14,000 feet to the summit. [00:29:45] Doug: Have you done that? Have you been up there? [00:29:47] Paula: Uh, I’ve been up not on Everest, but on Annapurna at- Right … 14,000. [00:29:50] Doug: But in that spot where you then can then look up. [00:29:53] Paula: Yeah. Yeah. It’s crazy. Wow. That is, that is a crazy, crazy- Wow [00:29:57] Paula: sight to be at 14,000 looking up another 14. Like, being like, “Oh, that’s the altitude where, like, commercial airplanes fly.” Yeah. [00:30:08] Joe: When you told us to take that trip, Paula, it was the same. We got up to the top of our hike at 14,000 feet, and my buddy Todd said exactly what you said. He’s like, “I’ve been up to the top of the Rockies several times, but I’ve never- Yeah [00:30:20] Joe: been looking straight up at these- Yeah … at these mountains. Still crazy. At [00:30:24] Paula: another 14 vertical, you [00:30:26] Joe: know? [00:30:26] Paula: Yeah. Yeah. [00:30:27] Joe: Beautiful hike going up to Annapurna. Great suggestion, Paula. Jesse, you had something? [00:30:32] Jesse: I was just wondering, like, when you guys were there and looking up, if you had to round to the nearest hundred, how many- [00:30:37] Jesse: people did you see above you? [00:30:39] Joe: Asking for a friend, Paula. [00:30:42] Paula: I’m gonna take the under, so, uh, thr- I’m gonna go 3,299 as my guess- [00:30:48] Joe: Well, [00:30:49] Paula: you gotta round to a hundred, so … if I’m rounding to the nearest hundred, that would be 3,200. [00:30:52] Joe: 3,200. So we got 3,200, 3,300, and 7,000. So you think Jesse’s way off. [00:31:00] Paula: Yeah, I do. Yeah. [00:31:02] Paula: Yeah. I think, I think a lot of people climb to base camp. I think very few summit. Maybe 10 a year, 15, 20 a year. But also not for the first handful of years, you know. So if Tenzing Norgay and Edmund Hillary were 1958, uh, I would guess 53. Uh, I would guess commercial didn’t really develop in earnest until maybe the ’70s. [00:31:28] Paula: Yeah. So yeah, I’m, I’m just gonna take the under. [00:31:32] Joe: Well, we’ll see if Paula’s line of reasoning finally works out for her. We will be- You, you [00:31:37] Paula: could’ve asked the height. That one, that one I got. We- In feet or meters, I got them both. [00:31:45] Joe: If only. If only. All right, OG, we started with you, and we’ll start with you here on, uh, the second half of today’s show. [00:31:55] Joe: 3,300. Uh, you got a lot of room on the upside, not much on the downside. [00:32:01] OG: Yeah. I mean, I’m filing all of this under protest, uh, because you guys are rigging everything against me, so, um- [00:32:07] Joe: I, I, I don’t know. How did we do that, Doug? How did we do that? [00:32:10] OG: It’s okay. No, no, it’s fine. [00:32:11] Joe: We didn’t change a single thing. [00:32:14] Joe: Jesse Cramer, y- your number’s like double everybody else’s. Does that worry you? [00:32:18] Jesse: Uh, I protest because just like OG forced you to margin call me, you guys forced me to guess a really, really high number. So similarly to OG, I’m gonna protest [00:32:30] Joe: Good. Now all the protests are in, Doug. Now everybody’s angry. Paula, you angry? [00:32:35] Paula: No, no, I’m, I’m the one, uh… But you know, the Nepalese are known as peaceful people. [00:32:41] Joe: Except Doug asked the wrong question. Except for that, yes. All right. Uh, he [00:32:45] Paula: had, he had to make it a fair competition. [00:32:48] Joe: Doug, you’ve got the answer. Is Jesse losing a point? Is OG gaining a point? If OG gains a point and Jesse loses a point, that means Paul is back to tied for second. [00:32:59] Joe: Is that what’s gonna happen, Doug? [00:33:00] Doug: Well, Joe, let’s find out. Hey there, stackers. I’m altitude adjuster and combination cracker, Joe’s mom’s neighbor, Doug. Turns out climbing Everest is a lot like investing. Everybody’s excited on the way up, but the people who survive are the ones who know when to turn around. [00:33:16] Doug: In fact, most Everest deaths happen during the descent because climbers are exhausted, low on oxygen, and too committed to the goal to quit, which honestly sounds a lot like somebody holding onto a meme stock six months too long. So how many unique climbers, rounding to the nearest hundred, have scaled Everest? [00:33:34] Doug: Well, I will tell you that it was 3,901 more than what Paula guessed, 3,900 more than what OG guessed, and just 200 more than what Jesse guessed. Ooh. The correct answer is 7,200- Ooh … making Jesse our winner- … and avoiding the margin call. Oh. [00:33:54] Jesse: Wow. How do I go double or nothing on OG? [00:33:58] Joe: Congratulations, you survived the margin call, Jesse. [00:34:01] Jesse: So I get one and OG loses one, correct? [00:34:04] Joe: Nope. [00:34:05] Doug: He doesn’t. That was the mistake we had in the rules for a couple of weeks in there- Yes … where I think I thought that the person margin calling would lose one if it failed, but that is not the case. [00:34:16] Jesse: So it’s just that I get one, and then that’s the end of the score changes. [00:34:19] Joe: You just get one. He can’t margin call you again for the rest of the quarter. [00:34:23] Jesse: Got it. So there’s no downside to losing a margin call? Are you guys sure about [00:34:27] Joe: that? There’s a downside to you. [00:34:29] Jesse: Right, but there’s no downside to calling margin call and then not following up with, uh, by winning? [00:34:35] Paula: Yeah, that doesn’t sound right. [00:34:36] Jesse: As it stands in- It does not sound right … in [00:34:38] Paula: the 2026 rule book- Yeah, that doesn’t sound right at all. I think- Yes. Send [00:34:40] Jesse: it to Wichita … [00:34:41] Paula: margin call poses a risk to the person- But- … taking out margin. [00:34:45] Joe: We’re gonna have to do it next year because in the original writing of the rules, we did not have it. Then we tried to institute it partway through the year, and, uh, it was Stacker Annette who called us out on that and said you could not margin call without… [00:34:58] Joe: Yeah. [00:34:58] Jesse: Yeah, it was… It got ugly there for a bit. [00:35:01] Paula: Wait, so does Jesse get two points? [00:35:03] Joe: Jesse gets one point- What the- … and avoids losing a point. No, [00:35:05] Jesse: Paula. What? Uh, they’re saying I was put at risk, but I had nothing to gain by it. [00:35:10] Paula: This is… What? N- none of this makes sense. Absolutely none of it. [00:35:15] Joe: Wait, wait a minute. [00:35:16] Joe: Are you saying… Wait a minute. Hold on a second. Are you saying there’s nothing about the Stacking Benjamins trivia competition that makes sense? Are you actually postulating that? [00:35:26] Paula: It just… The more I think through it, the less sense it makes. [00:35:33] Joe: It took her how many years- … of this show to have that happen? [00:35:37] Joe: Well, let’s go into the part that does make sense, which is, uh, our discussion about Simoni Stolzoff and this idea of uncertainty, which we know is gonna be there for our whole life, right? I mean, in investing and in everything that happens with- there’s always this fog around us, and dealing with it is really a struggle. [00:35:55] Joe: So let’s open up the second half of this discussion with this idea of one-way door versus two-way door decisions. And to tell you what this is all about, Simoni brought up a Jeff Bezos framework that some decisions are one-way doors, meaning you walk through it, you can’t walk it back. This is an irrevocable decision. [00:36:14] Joe: And others are two-way doors, and yet we treat tiny decisions often like they’re life or death events, right? You see us, Paula, putting off moves to our budget because, man, I don’t wanna… W- like, I don’t wanna get rid of the Netflix today because if I get rid of the Netflix and I decide two weeks later the new show comes out, what would I do? [00:36:35] Joe: So I j- I, I guess I’ll just keep it just in case. We do this all the time. [00:36:39] Paula: Yeah, we do. But with the Netflix thing, it’s low stakes. I think the bigger thing is when we have, like, big dollar high-stakes decisions but we put off making changes because, you know, we know that our home is too big and we could downsize, but there’s so much friction involved in that that it feels daunting, so we just never start the process. [00:37:04] Paula: Right? Or the car is too new. We could get something cheaper. But again, that’s a heavy workload, so we put off the process, and then three years go by, and then it’s not that new anymore. Not as new anymore, you know? [00:37:16] Joe: Yeah, 100%. And oh, gee, it seems like a lot of financial decisions like buying the investment, right? [00:37:22] Joe: I think this might be half of the reason why we automate, isn’t it? Is because left to our own devices, where we go, “Oh, no, no, I’ll send in a check every month,” or, “I’ll, I’ll go deposit money in my Vanguard account.” Like, yeah, that’s gonna happen. [00:37:34] OG: Well, but those are decisions that are changeable, you know, and that’s the whole idea. [00:37:39] OG: Like, is this a decision that you can fix, you can redo, you can edit, or is this something you’re locked in on? I think that decisions that you have that you can redo without much consequence, you should just do them. Like, pay almost no attention to the thinking process. And I also think this is a great opportunity, especially when it comes to, like, saving and investing, to radically, like, swing the, the, the pendulum in one direction because you can say, “I don’t know if I can max out. [00:38:08] OG: I don’t know if I’ve got enough cash flow to pull that off or if my lifestyle will be able to shrink down to be able to max out my 401. But to heck with it, I’ll just try it and see what happens because I can change it a paycheck later.” You know, to go from 1,000 bucks a paycheck back down to 500 or to 650 or something like that, and, and I’m off by one paycheck. [00:38:25] OG: You know, it’s not the end of the world to try that out. The harder things are which of these two jobs do I take? Not that you can’t change jobs, but, you know, when you’ve got an, you’ve got an outcome like that. Or something less and less frequent, but which pension option do I pick? Which Social Security option do I have? [00:38:42] OG: Although technically there’s a little bit of changes that you could do there, it’s a lot harder to unwind. So you get to make this once. Spend a lot of time. If you can make this decision tomorrow and change your mind the next day, don’t spend any time on it. Just get after it. [00:38:56] Joe: It is funny, though, because different investments are treated different ways. [00:38:59] Joe: I mean, uh, Jesse, let’s take this. OG, you know, talking about switching index funds, okay, two-way door, right? Calm down. Buying a house, though, maybe a little bit of a different idea. [00:39:10] Jesse: Yeah, I mean, I think, uh, ’cause another kind of conceptual term along with the doors and directionality is like the friction involved with some of these decisions, right? [00:39:19] Jesse: And so when you’re talking about, like, that home buying purchase, there are all these frictional costs, and then there’s just, like, the, the time that you’ve committed to making this choice and the, the hassle of moving all your stuff in and unpacking it. And so, right, so sometimes it’s, it’s not that you can’t undo the home purchase, ’cause, ’cause you can. [00:39:35] Jesse: You throw it back on the market. But there are all these frictional costs involved that kind of make it hard or make it feel like a sunk cost, and now you’re not gonna wanna undo it. So right. So I guess sometimes it’s, it’s not that, like, strictly speaking, it’s impossible to undo a particular decision. [00:39:49] Jesse: It’s just that some decisions are so much easier or so much less consequential to undo. I think that’s part of what Paula was talking about, too, is just like, well, sometimes it’s like, okay, it might be technically a one-way door, but if it’s not that big of a deal to undo it, then whatever. Pay the $5 penalty and undo the, undo the decision. [00:40:06] Jesse: But yeah, s- some are just, there’s, there’s so much friction involved in the decision and, and that really ought to make you pause and think first before you follow through and kind of walk through that door. [00:40:16] Joe: Is the difference here, Paula, I mean, I agree with all of what Jesse said, but also the fact that this is a huge amount of money. [00:40:22] Joe: We talk about a house versus maybe… I mean, don’t get me wrong, you put every- could put everything into an index fund. But is the magnitude of the purchase around a house the thing that changes it? [00:40:32] Paula: It’s all of the above. It’s the magnitude, it’s the friction, and then y- when it comes to a house specifically, the true one-way door is selling a house. [00:40:42] Paula: Because once you’ve unloaded that asset, you can never buy that asset back. Like, that seller is un- unless in a very, very rare circumstance, that seller might be willing to sell it back to you. But in 90, 999 times out of 1,000, that’s not gonna happen. That’s truly a one-way door. [00:41:00] Joe: OG, is changing jobs, let’s say, at age 40, is that a one-way door or a two-way door? [00:41:08] OG: I mean, I guess technically two. I mean, ’cause you can change jobs as many times as you want, I suppose, right? Or at least you could try to. I, I’m not sure. You know, depends on your skill set, maybe, is a better way to think about it, but it’s- [00:41:22] Joe: Well, and actually to your point, yeah, I mean, if I’m going from mechanical engineer to mechanical engineer, I’m not talking about that. [00:41:27] Joe: Yeah. I’m talking about changing careers at 40 [00:41:30] OG: I still don’t think it is. I mean, my– I don’t remember the research on this, but was- wasn’t it– Isn’t it something like, you know, the average person will have like three or four careers in their lifetime, not just jobs? You know, I mean, so I think you need to, you need to fish where the fish are sometimes, right? [00:41:47] OG: And, and you go to school, you do whatever, and you find out, like, “This is not the lane I wanna be in,” you know? And then now there’s a cost to doing that. Maybe education is one of these cost structure concepts where it’s like, you know, I go down the path of, “I’m gonna be an accountant,” and I realize I really hate accounting, but I w- I realize it too late. [00:42:06] OG: And I mean, into my senior year of college, and I think that’s too late. In reality, of course, it’s not. But now I’ve got all this cost like you guys were talking about in terms of sunk cost. It’s like, but I really wanna be an engineer, or maybe you’re an engineer, and you really wanna be a financial planner. [00:42:21] OG: There’s a, uh, or there’s some f- Did somebody say friction already? Is that why that’s in my brain? [00:42:26] Jesse: Yeah, [00:42:27] OG: Jesse did. Sorry. I’m trying to think of a new word than- [00:42:29] Jesse: What podcast were you on? [00:42:31] OG: Yeah, I know. Yes. But, uh- Abrasions. You know, there- [00:42:34] Jesse: Chapping … [00:42:35] OG: there’s, there’s gonna be some cost to unwinding something always, and whether or not you view that as a one-way street or a two-way street, I think is relative to your current situation. [00:42:47] OG: But, um, yeah, I just go back to decision-making, you know, kind of top of the funnel stuff for me, which is, can I undo this tomorrow? If the answer is yes, very little effort put into it In terms of thinking through the choice [00:43:00] Joe: It is interesting, r- uh, Rocky Mark hanging out with us live here on YouTube. We record these on Monday. [00:43:06] Joe: It’s always fun to pretend it’s Friday on a Monday. Rocky Mark said, “I’m trying to go from electrical engineer to content creator as I’m knocking at 40. Not as easy as you all make it look.” Oh, content creation, th- that we make it look. I thought you were talking about the shift, Rocky Mark, and I was, s- I was thinking, “Wait a minute. [00:43:22] Joe: I don’t think we were talking about it being an easy shift.” I think it’s a tough shift. Whenever you change, whenever you change, and maybe even though it can be a two-way door, Paula, I think maybe you should treat it like it’s a one-way door to… W- what’s that, uh, phrase from the either The Iliad or The Odyssey where Achilles burns his ships? [00:43:38] Paula: Ah, yes. Okay, when you talk about the specificity of making that change, right? Once you leave a particular job, leaving that job is definitely a one-way door. Like, you are unlikely to get rehired at that same company. [00:43:52] Joe: Same organization, yeah. [00:43:53] Paula: Yeah, exactly. So that is, that quitting is very much a one-way door. [00:43:57] Paula: And then in terms of the career shift overall, like shifting from electrical engineer to content creator or, or any other career shift, the more time that passes, the more it becomes a one-way door. Because if you’ve not been an electrical engineer for three months, you can probably get an e- uh, an electrical engineering job again. [00:44:18] Paula: Your skills are still current enough. But if you’ve not been an electrical engineer for five years, it’s gonna be very difficult to get rehired. I mean, and maybe you can work for yourself or start a consulting business or something, but the more time that passes and your skill set atrophies- [00:44:35] Joe: The more it is a one-way door [00:44:36] Paula: the more it does become a one-way door, yeah. [00:44:37] OG: Yeah. Well, and this is one of those things, I think also w- when it comes to, like, the sabbatical idea Not that you can’t do it, but I think you have to be aware of what you’re talking about, where it’s like, especially if you’re in a technical field that every year has some reasonable advancement in terms of like new thinking, new tools, new whatever, and you go, “Oh, I’m gonna work really hard from 25 to 40, then I can take a 10-year sabbatical, and once the kids are done, then I’ll go back to work.” [00:45:01] OG: It’s like, maybe. A lot happens over f- five years or, I mean, sometimes even a year or two is, is hard to catch up in terms of what is going on if it’s a very specialized field. So not saying you shouldn’t do that. I’m just saying like that’s a, that’s a, that’s something to think about, right? [00:45:18] Joe: Let’s go on to the last construct that Simoni talks about, because at some point you’re chasing something and it just doesn’t become viable, right? [00:45:27] Joe: You’re going after something, and the uncertainty becomes just unbearable, and it’s time to go, “You know what? This is an uncertainty as much as it’s a, it’s an errand I shouldn’t be chasing.” To Doug’s point earlier around the Everest climbers, you know, Simoni talks about the Everest climbers having these turnaround times. [00:45:43] Joe: At some point they stop climbing, even if the summit’s close, ’cause you know that it’s going off the rails. What financial kinda kill criteria should we have around our goals, Jesse? Is there a framework you have where we go, “You know what? This just isn’t worth it”? [00:46:00] Jesse: My gut instinct, Joe, is to say that probably every situation’s gonna call for its own unique kill criteria. [00:46:06] Jesse: But, but at the same time, when we’re talking about this i- th- these, these ideas we’ve been talking about for the last 10 minutes of like the one-way and two-way door and all that stuff, absolutely. I think you need to understand what that, for lack of a better term, kill criteria looks like for you. I mean, I, I don’t know if OG was kinda smiling at me as I was talking about my kind of career change, right, from engineering to financial planning. [00:46:27] Jesse: ‘Cause like I had it in my mind that, “Hey, okay, what’s the worst case? A couple years I get into it, and, uh, I’m just not earning enough money to make it worthwhile. And at what point do I say, I have to look myself in the mirror and decide to go back to engineering?” For me, that was like 18 to 24 months. And I knew that going in, and that was kinda my runway. [00:46:45] Jesse: And I think maybe whether it’s kill criteria or maybe runway is a, is a, is a softer way of saying it. Like, whenever you make one of those big decisions, understanding what kind of runway you have to figure out if it’s worthwhile, I think that’s really smart. Uh, a really smart thing to do on day one. [00:47:01] Jesse: Hopefully ’cause on day one you’re not quite as emotionally invested, and, you know, you’re a little bit of clearer mind and able to say in that clear mind, “Here’s when I need to, to call it,” if it comes to that. I don’t know, again, going back to what you asked Joe, I don’t know if there’s like a hard and fast rule to follow, but I guess e- every situation I might have to react uniquely. [00:47:20] Joe: I do like the fact that you brought up coming up with it ahead of time though, because I do think it also makes you more focused when you know this is my shot. If it’s not over by then, then I’ve g- you know, I, I think every day becomes… You, you can feel the timer running. You know, Paula, you brought up entrepreneurship at the top of the show today. [00:47:38] Joe: This is the hardest with entrepreneurs, right? Because you’ll struggle with something for… You give yourself two-year runway. I’ve worked with entrepreneurs here. They give themself two years, the product still isn’t taking off, and they’re like, “But it’s just around the corner. It’s almost there. It’s so close.” [00:47:53] Joe: Like, that’s, that’s a painful place to be. [00:47:56] Paula: Yeah. To the extent that it’s possible, and of course every business is unique and different, so take this with a grain of salt and make it specific to your own. You know, your results may vary. But if there is any way to maintain the broad line of what you’re doing, but iterate, pivot, just, just keep pivoting until you find that right product market fit, like, until it… [00:48:20] Paula: Keep pivoting until it works, essentially. I think for many endeavors it can work, but it might not look anything like what it looks like right now. [00:48:30] Joe: I saw this with our friend Andy Hill. Andy went off and was working for himself, but really needed to supplement the income. So Paula, he kind of went full bore working for himself to working for himself part-time, just to make sure that he could keep the dream alive to the point where- Mm [00:48:46] Joe: he is today, where he largely just works for himself, does his own thing. Not, uh- Nice … not farming it out to other people. Yeah. [00:48:53] Paula: Yeah. So in that case, it was a stepping stone. [00:48:55] Joe: Yeah. The [00:48:55] Paula: part-time thing was a stepping stone. [00:48:56] Joe: Pivot- Yeah … pivot, pivot until you find it. I like that. Oh, gee, when it comes to the portfolio, it reminds me of a client that I had back in the day. [00:49:04] Joe: We set up her risk tolerance as X, and every time the market went, there was a, some geopolitical event or some problem, she would call afraid. And I finally flipped the kill switch and said, “You know what? We gotta back down your risk.” And she goes, “No, we can’t do that. No. Why? Why? Why?” I said, “Because you can’t sleep at night.” [00:49:21] Joe: “That’s why.” ‘Cause I’m tired [00:49:22] OG: of answering your phone calls. [00:49:24] Joe: Well, she admitted she was having trouble sleeping at night, which is why she was calling me. I’m like, this is disturbing… When your risk tolerance disturbs your mental health, who cares if 100% equities is, quote, “the right thing to do”? It’s not the right thing for you [00:49:38] OG: Well, I think this is just focused on the wrong thing. [00:49:41] OG: I mean, my second grade teacher used to say, “You’re focusing on the wrong syllable,” when we were practicing those two-syllable words that Doug struggles with all the time. So it’s like, you know, look at the eye roll. That was an epic eye roll. Just came up out of- [00:49:56] Joe: It’s hilarious [00:49:57] OG: you say that … out of, out of his nap, right to an eye roll. [00:49:59] OG: But the absent understanding the impacts, and this is what I was talking about earlier about, like, those second decisions. It’s like if, or second order decisions, like that’s perfectly fine. You know, if you wanna say like, “Well, I only wanna make 5% of my money because that makes me sleep better at night.” [00:50:16] OG: It’s like, all right, let’s make sure that you can sleep better until you’re 77, ’cause that’s how long you have to work till, you know? And so now you start evaluating the real impact of the decision, not just in the like I’m scared phase, which frankly happens to everybody. I know it happens, it’s happened to me many times. [00:50:34] OG: I distinctly remember during COVID, when markets down a whole bunch, going for a walk with my wife and going like, that was, at the time, kind of the third one of those, like, like literally going, “I don’t know that I wanna do this for the third time.” Like, this is so stressful, and it’s so hard to have the weight of all of this for everybody, you know? [00:50:54] OG: And so we feel the same way. We’re not immune to it. But I think like in the context of what other choice is there, to me it becomes a real easy decision when it’s something like investment volatility. You know, it’s like, well, my volatility is scaring me. Okay. Well, what’s gonna scare you more? Being broke or running out of money? [00:51:14] OG: ‘Cause here’s what happens if we don’t get that. And, and maybe the answer is it’s a combo, you know? And I, I think having an understanding of what those other dominoes that fall are make, make those things a little easier to work through. [00:51:28] Joe: I think that’s a great way to leave it. The idea of building anchors, creating some rules before the emotions hit- The thinking about the kill switch and one-way doors versus two-way doors, some great constructs, I think, to work through to deal with uncertainty. [00:51:45] Joe: We are certain of a few things, and that’s what you guys are creating this weekend. Before we get there, OG, this, uh, last weekend in May, how you celebrating? [00:51:54] OG: Oh, I’m getting ready to go to Disney, obviously. Duh … ’cause- [00:51:56] Joe: It’s the end of May … it’s a [00:51:57] OG: shock. I’m [00:51:57] Joe: going to Disney. [00:51:58] OG: As if. Yeah. [00:51:59] Joe: Right. [00:52:00] OG: Um, nope, finishing my, uh, got a bi- big weekend of cycling this weekend, and then I’m gonna take a week off, a little recovery week while I get, like, you know, 30,000 steps walking around Disney parks. [00:52:11] OG: So you know, nice recovery- … on the legs week. [00:52:13] Joe: Duh. Paula Pant, what’s going on in the amazing show, Afford Anything? [00:52:19] Paula: Well, you know, on most of our Tuesday shows, Joe, you join us. You and I answer questions that come from the audience, and so we- we’ve had a couple of, of fairly entertaining ones with Joe, where your face was, like, the third guest on the show. [00:52:34] Joe: Like, wait, what? [00:52:35] Paula: We, we had this one recording. Uh, I think that episode probably just came out. I would say something, and Joe- Joe’s, like, verbally would say one thing, but his face would say something totally different. So if you wanna watch our YouTube channel, uh, youtube.com/affordanything, you see Joe’s, like, stated take, and then Joe’s, like, facial expression take. [00:52:55] Joe: Trying to hold it together for the audio people. [00:52:57] Paula: Yeah. And then- Exactly. [00:52:59] Joe: And then Paula calls it out, which- [00:53:01] Paula: Yeah. … [00:53:02] Joe: damn video. Drives you crazy every time. Video [00:53:04] Paula: killed the radio star, Joe. [00:53:05] Joe: Yes. So check out the Afford Anything audio feed, but don’t go near- Don’t go near that YouTube page, that amazing Afford Anything YouTube page, available where finer YouTube videos are found. [00:53:18] Joe: I guess it makes sense that the finest YouTube videos would be found on YouTube, wouldn’t it? [00:53:21] Paula: How, how did you guess? [00:53:23] Joe: So weird. Jesse Cramer, Personal Finance for Long-Term Investors, the show that’s, uh, rocketing up the greatest hits chart. What’s going on, man? [00:53:33] Jesse: Hey, uh, we might break into the, I don’t know, top 100 here soon. [00:53:37] Jesse: I think if you look at upstate New York personal finance podcasts produced by people 33 to 37 years old- You are number one … we’ve broken into the top, we’ve broken into the top 100. Uh, no, uh, I’m excited. So this past Wednesday, part one released. Next Wednesday, part two will release of a Charlie Munger inspired, uh, series of episodes, the 14 biggest risks in retirement, where we kind of use Munger’s version, uh, or Munger’s method of inversion, you know, invert the problem, look at it inside out. [00:54:07] Jesse: And we look at the, uh, the 14 biggest risks in retirement, and therefore, we kind of back out different things we can do to, to mitigate those risks. [00:54:15] Joe: It’s fabulous. I love that. That, that’s a good way to set anchors, too, you know? [00:54:19] Jesse: It is. It is. Charlie Munger was a, was a very much an anchor guy. [00:54:23] Joe: Right there. Uh, and that is that, the Personal Finance for Long-Term Investors podcast. [00:54:28] Joe: Before we say goodbye, we have had a chat in the back between Doug and I, uh, quite a chat since the halfway point. And, uh, so Doug, you did a little digging. [00:54:39] Doug: Yeah. Well, what’s worse than even the chat we had, Joe, was, uh, y- y- you never like to get a call from Dottie in Wichita. That’s a bad day. When, when you get the call from her instead of us having to reach out and ask for advice, then you know you’ve really messed things up. [00:54:55] Doug: And I was so intimidated and scared by OG, ’cause he was so angry, angrier even than normal, that I did not read the full rules. I will now, in their entirety, unabridged, read the rules of trivia. Each contestant gets one margin call per quarter. If a contestant has zero points, they can’t use a margin call. [00:55:21] Doug: They specify the opponent that they want a margin call. That’s rule number one. Rule number two, if the person margin called gets the correct answer, they gain a point as usual, and the margin callee loses a point Rule number three, if the person margin called gets the answer wrong, they lose a point, obviously. [00:55:42] Doug: Number four, if the margin called gets the wrong answer and the margin callee gets the correct answer, it’s essentially a two-point swing, which is what happened today. And lastly, if there is a tie, whether a margin call has been called or not, that point gets divided among those with the correct answer. [00:56:00] Doug: Those are the rules in their entirety. I mean, [00:56:02] OG: everybody knew this, right? We did [00:56:03] Doug: eliminate one controversial rule. [00:56:06] Paula: But this means you lose a point, OG. [00:56:08] OG: I’m aware of it. I know. [00:56:09] Paula: We, we had earlier established that there was no risk to the margin caller. [00:56:13] OG: No, you guys said that. Eroneously. [00:56:15] Jesse: OG tuned out. Yeah. Tuned out. [00:56:16] Jesse: OG just didn’t wanna speak up in the earlier conversation. He was [00:56:20] OG: hoping we could skirt by it. I freaking knew it. I was just waiting for you guys to catch up. Mr. Rules Guy that seems to know everything- Okay … but has to, like, have it… I, I’ve already got it on my card, bro. See? There it is. I already scribbled it out. [00:56:32] OG: See? [00:56:33] Joe: He’s just waiting for Dottie to catch up with Doug. Well, there we go. Just [00:56:36] OG: waiting for y’all to get with the program. [00:56:38] Joe: There we go. [00:56:40] Doug: So now, going into next Friday’s trivia, Jesse will have five points, OG will have eight points, and Paula, as happy as she is, at this moment will still have just three points. [00:56:51] Paula: That means The Coalition is tied with OG. Yes. The [00:56:58] OG: great news is I’m abstaining from all trivia questions from here on out. So I will, I will not answer. [00:57:05] Jesse: Now through Memorial Day- … no more questions for OG. [00:57:09] OG: Nope. I’m gonna… My answer is zero from here on out. I’ll see how many I win with zero as an answer. [00:57:13] Joe: Then he can’t get the record. He, he’s, he’s missing out on the record. All right, that’s gonna do it. Uh, we’ll keep fighting about this afterwards in the green room. Uh, Doug, you’ve got it from here, man. What should we have learned on today’s show? [00:57:25] Doug: Well, Joe, first, take some advice from Paula. Maintaining cash reserves can definitely help you deal with uncertainty. [00:57:33] Doug: Second, don’t forget what OG said. When the world seems scary, every decision feels major, but that’s just not reality. Even in uncertain times, many decisions you make are undoable. But the big lesson, never confuse a two-way door decision with a one-way door decision. For example, trying a new restaurant, two-way door. [00:57:54] Doug: Easy. Telling Joe’s mom you improved her cookie recipe, very much a one-way door. That’s a one-way door. It hurts when it hits you on the backside. Thanks to Jesse Cramer for joining us today. Wanna hear more from him? Check out his podcast called FILTI. And if you’re uninitiated, that means Personal Finance for Long-Term Investors. [00:58:19] Doug: It’s obvious. FILTI. We’ll also include links in our show notes at stackingbenjamins.com. 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 to OG for joining us today. Looking for good financial planning help? [00:58:36] Doug: Head to stackingbenjamins.com/og for his calendar. This show is the property of SB Podcast LLC copyright 2026 and is created by Joe Saul-Sehy. You’ll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots. [00:58:59] Doug: Come say hello. And oh yeah, before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time back here at the Stacking Benjamins show
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