You build a plan around a goal, the goal changes, and the spreadsheet keeps marching toward the old one. Joe Saul-Sehy and a roundtable of regulars, joined by Financial Bliss Coach Kelley Long, CFP, ask what happens when the house, the career, or the family you saved for stops being the life you want. They play a game of keep it, kill it, or change it, then get practical about the real invoice for changing course: cash runways, taxes, selling while markets are down, and the stubborn pull of sunk costs. You’ll also hear why staying put has a price of its own.
What You’ll Walk Away With
- A three-card game (keep it, kill it, change it) applied to a house the kids have outgrown, a plan built around children that no longer applies, and a career plan with a countdown
- Why people regret never questioning a goal far more than missing it, and what a story from base camp has to do with it
- How to tell whether you want to stop working or just want out of a job you’ve outgrown, a lot like mistaking thirst for hunger
- The “invoice” for changing course, and the fixed expenses worth covering for a year while you figure it out
- A test-drive trick that lets you feel a change before you make it
- A way to compare a big decision by taking the money out first and asking what you’re really trading
- What to do when you need cash and your investments are down
- Why a big tax bill can be worth paying, and what happens when a rule of thumb swallows the reason behind it
- Sunk cost versus switching cost, and why only one of them is a feeling
- The “too small blanket” problem, and the flexibility you can build in from the start
Why This Matters Now
Most of us spend plenty of energy checking whether we’re on track, and very little asking whether we still want to go where the track leads. If you worry about a change you can’t undo, or you’ve outgrown a plan you built with good intentions, this conversation treats changing your mind as a cost you can plan for. Getting good with money was never about living yesterday’s life more efficiently. It was about having more choices tomorrow.
From the Basement
Joe reports that his new tendon came from an Olympian, at his request, and that standing up is now a major athletic event. Doug’s trivia is a cautionary tale about the worst side hustle ever pitched, and the Detroit Lions provide a live demonstration of a plan with an Achilles heel.
Resources Mentioned
Lynda Gratton: What If You Live to 100? Here’s How to Actually Plan For It: our conversation on the hundred-year life
Financial Bliss Coach: Kelley Long’s coaching practice, with links to her podcast and book
But Who Will Take Care of You When You’re Old? Financial Planning for People Without Kids by Kelley Long: her forthcoming book on planning without children
Our Topic: When life goals change: Should your financial plan change too?
Topic/Article Title Here (Publication Name Here)
During our conversation, you’ll hear us mention:
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Kelley Long
Another thanks to Kelley Long for joining our contributors this week! Hear more from Kelley on her show, Financial Bliss with Kelley Long at Financial Bliss with Kelley Long – Podcast – Apple Podcasts.
Work with Kelley by visiting Financial Bliss Coach
Preorder her upcoming book But Who Will Take Care of You When You’re Old?: Financial Planning for Life Without Kids.
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.
Doc G
Another thanks to Doc G for joining our contributors this week! Hear more from Doc G on his podcast, Earn & Invest, on Apple Podcasts.
Check out his latest book The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy.
Doug’s Game Show Trivia
- On October 23, 1992, authorities at an airport in Colombia detained a woman suspected of smuggling heroin that had been surgically implanted in her buttocks. How many ounces of heroin did authorities discover?
Mentioned in today’s show
Join Us on Monday!
Tune in on Monday, when we kick off Halloween week with Chuck Jaffe, who returns to Mom’s basement to show us how to turn trick-or-treating into a fun money lesson for kids and take the fangs out of finance!
Miss our last show? Check it out here: Wharton’s Corinne Low on How to Get More Life Out of Your Money, Time, and Career (SB1913) | Stacking Benjamins.
Written by: Kevin Bailey
Episode transcript
[00:00:00] opener: Ah, shake and bake, Cal. Woo! Shake and bake
[00:00:08] Doug: Live from the basement of the YouTube headquarters, it’s The Stacking Benjamins Show
[00:00:23] Doug: I’m Joe’s mom’s neighbor, Doug. And you ever make a decision and think, “Yeah, I’m good,” and then within a year the goals have completely changed? How do you adjust your money to fit your new best life? From deciding to have kids, not have kids, go to school, change jobs, take a sabbatical, and more, we’ll explore it all.
[00:00:43] Doug: But that’s not all we’re exploring. Our trivia contest is red hot, and today we’ll find out which of our contributors is going to make a big move. And now a guy who thinks a big move is from the sofa to the computer, it’s Joe Saul-Sehy.
[00:01:02] Joe: Hey there, Stackers. And that’s right, Doug, at this juncture after ankle surgery, that’s a huge move. I never knew until now, Doug, how, like how, how painful it would be just to try to stand up. Yeah. Just a good
[00:01:15] Doug: time. I can’t imagine why, uh, after somebody sliced into you, put some metal parts in and some, some tendons from Lord knows what animal, no, why would we expect pain?
[00:01:24] Joe: I’m the bionic man now, Doug. That’s the good news. I am now the bionic man, but I also found out it wasn’t from some animal. Like, my tendon is from a person. And so I requested- A former person … I requested an Olympian.
[00:01:39] Doug: Oh.
[00:01:39] Joe: Which, which is great, which I’m sure they- Nice … fulfilled that. How are you today, man?
[00:01:43] Doug: I…
[00:01:43] Doug: You know, I’m a lot like my putting, inconsistent but optimistic.
[00:01:47] Joe: Oh, well, that’s good. That’s good. Yeah. You know- Yeah.
[00:01:50] Doug: What things are
[00:01:50] Joe: looking
[00:01:50] Doug: up …
[00:01:51] Joe: every, every day can’t be a 10 out of 10.
[00:01:53] Doug: No, they’re not all gimme putts either.
[00:01:55] Joe: No, you gotta have some sixes and sevens to know what a 10 looks like. Y- do you wanna meet a six or seven?
[00:02:01] Joe: How about Jesse Cramer?
[00:02:03] Doug: Perfect segue. Fantastic word choice, Joe. I was
[00:02:06] Jesse: wondering who you’d segue to.
[00:02:07] Joe: I… If it was anybody else, Jesse, I would not have begun it that way. How are you, man?
[00:02:12] Jesse: How am I, Joe? I’m doing well. No, I’m doing well. Uh, current insults aside, um, got nothing to complain about. We’ve got gorgeous fall weather up here in upstate New York, and, uh, life is good.
[00:02:25] Jesse: Family’s good, work’s good, no complaints.
[00:02:27] Joe: We only kid because we love you, man.
[00:02:29] Jesse: I
[00:02:29] Joe: appreciate that. Your
[00:02:30] Jesse: goals.
[00:02:30] Joe: We’re gonna talk about how the goal has changed today. Your goals have changed over time.
[00:02:34] Jesse: Totally. Uh, yeah, we will talk about them, but, like, I, I can think of one that maybe the listeners can appreciate.
[00:02:39] Jesse: I mean, at one point I was pretty gung ho on the fire path, and if I could find a way to retire at 44 instead of 46, or 42 instead of 44, I was interested in learning more. And then I figured out that if you just find a way to enjoy work more, you aren’t necessarily looking for- Ah … such a quick escape. So, yes.
[00:02:58] Jesse: Yeah. Goals do indeed change.
[00:03:00] Joe: That topic may come up later again, Jesse. I’m glad you brought it up. And you also started off in engineering, and- Yeah … now you’re in financial planning.
[00:03:08] Jesse: Correct. And, and when I was an engineer for the first few years, and when I was in school for engineering, I mean, I would’ve told you I was all in on engineering.
[00:03:16] Jesse: I thought it was really cool, and I still do think it’s really cool. But it is just funny to think that sometimes life takes you in interesting new directions and introduces you to new ideas that will take hold of you, and that’s what happened to me.
[00:03:28] Joe: Well, OG is not here today. That’s the bad news. But the good news is- Hmm.
[00:03:33] Joe: It is bad news … is we kept the G. We kept the G, Jesse, with Doc G in Chicago, Illinois. Doc G, Jordan Grumet, is here. How are you, man?
[00:03:41] Dog G: I’m good. It ain’t nothing but a G thing. One G versus another G. I’m wondering if you and Doug shopped at the same discount shirt store, just complementary colors.
[00:03:51] Joe: We did. It’s, it’s the team uniform, you know, where it’s gotta look similar, but not exactly the same.
[00:03:56] Joe: I
[00:03:56] Doug: got a free bowl of soup with mine.
[00:04:00] Joe: Was super. Your goals have never changed, uh, Jordan.
[00:04:03] Dog G: I’m a man without goals. I have no goals. No, uh, my goals change periodically.
[00:04:08] Joe: But you did, you’ve told this story publicly in other places, a physician for a long time and realized that the burnout was real, and you wanted, you know, really a midlife change.
[00:04:19] Dog G: Yeah, you know, one of my goals, which quickly led to burnout, was to save every single person who needed help. And, uh, that’s one of the things about you go into something like medicine and you think you can cure and save the world, and I quickly found out that that goal was unrealistic, and it certainly did lead to some burnout, for sure.
[00:04:35] Joe: And that’s why you never have offered Doug help, is because you realize you can’t save everybody.
[00:04:39] Dog G: It’s… I was about to say, and some people are beyond help, so there you go. I can compliment on his shirt, though.
[00:04:44] Doug: I’m, I’m over here catching strays- … minding my business.
[00:04:48] Joe: Th- there is a reason why we bring this up today specifically.
[00:04:52] Joe: It’s a great follow-up on our conversation, Doug, the awesome conversation we had with Dr. Corinne Lowe on Wednesday, just this wonderful discussion about the goals, and are we doing the things that we really value, and what currency do we really value, and are we negotiating with the people in our life to make sure that we get the things that we truly want?
[00:05:13] Joe: She is a Wharton professor and economist, and if you didn’t listen to Wednesday’s show, I encourage you, after you hear this one, to definitely go back, ’cause this is a one-two punch. But the person who we also built it around has an upcoming book on this topic, and she is my longtime friend from, uh… W- we, we go way, way, way back.
[00:05:33] Joe: What, Kelly, like three weeks?
[00:05:34] Kelley: Approximately.
[00:05:37] Joe: Uh, we met at FinCon, and you have Financial Bliss Coaching. How are you?
[00:05:41] Kelley: I’m great. Thanks so much for having me, guys. And I gotta just say, everybody here is in over-seeding, so I haven’t golfed in, like, three weeks, so I’m dying.
[00:05:49] Joe: In three weeks. I don’t think I’ve golfed in, like, five years, so I think we’re- My game is
[00:05:54] Kelley: suffering.
[00:05:56] Joe: Uh, uh, Jesse, are you a golfer?
[00:05:58] Jesse: I dabble. I actually haven’t played at all this summer. Uh, life just got a little too busy, but I, I can swing a club a little bit.
[00:06:06] Joe: How about that, Jordan?
[00:06:08] Dog G: I went to a driving range once, and I accidentally hit the person on the side of me And I think they might have banned me for life.
[00:06:19] Dog G: In the
[00:06:19] Joe: state of Illinois, yeah. Kelly, I asked everybody else about their story. I haven’t asked you about yours, and I’m gonna wait on that, ’cause your story is pivotal to really this topic that we’re gonna talk about today. But tell us a little bit about Financial Bliss Coaching and, and what you do.
[00:06:34] Kelley: Sure.
[00:06:34] Kelley: I, as you can see through my-
[00:06:37] Joe: And I moved her backstage. Which I’m so good at. K- Kelly, we have these buttons, did I pick the wrong … Great story. Could you email the rest to us?
[00:06:47] Kelley: I feel like Miss Piggy just pulled me off stage. That’s right. Never mind. Um, so I, um… You know, I’ve had many, many different career lines, but for the last five years or so I have managed a part-time coaching business out of my home in Tucson, Arizona, helping individuals, mostly women and couples, who feel overwhelmed by their finances, and so people who are intimidated by everything when it comes to money, and helping them get organized and feel more confident.
[00:07:15] Kelley: So, um, but I have a podcast, and most excitingly, I have a book coming out on, on financial planning for people without kids in February.
[00:07:22] Joe: That is so, so awesome. And I know that, uh, writing a book is a labor of love. Did you love writing it?
[00:07:29] Kelley: You know, when I first signed the deal I thought, “Oh, the writing is gonna be the easy part.”
[00:07:33] Kelley: But I really had to change my entire lifestyle to create accountability and make sure it got done. And it wasn’t through until, like, the fifth time of reading the entire book through that I felt confident that I could put this into the world, and that was probably eight weeks after I had submitted it.
[00:07:48] Kelley: So- Wow. … it’s been a terrifying process.
[00:07:52] Dog G: Sounds about right.
[00:07:53] Joe: Sounds about right. Yeah. I was gonna say the long pause when I asked you the question said everything there- Yeah … ’cause it is not easy. But I’m so glad you’re bringing that into the world, ’cause you’re gonna help a lot of people, like you will today as we talk about what happens when the goals change, ’cause the goals for all of us change all the time.
[00:08:08] Joe: And yet, as a former financial planner, I’ll, I’ll be the first one to tell you often th- the money doesn’t change soon enough. So we’re gonna talk through that, but first, we have a couple sponsors who help us make sure we give all of this to you for the value price of nothing. We’re gonna hear from them, and then Kelly, Doc G, Jesse, Doug, and I, we’re gonna dive into how to make sure that the plan works to fit new goals.
[00:08:40] Joe: All right, we spend a lot of time around here talking about reaching your goals, and today I’ve got a different problem. What if you spent 10 years working toward the goal and you realize, “I don’t want that anymore”? Maybe you saved for the big house, and now you wanna live downtown. Maybe you built a career around, around maximizing income, and now you’d rather maximize Tuesday afternoon.
[00:08:59] Joe: Maybe you financially prepared for children, your life takes a different path. Maybe you saved for retirement in Florida, and then somebody actually took you to Florida and you decide, “Wait a minute, humidity’s not my thing.” Our goals change, but here’s the problem. Our money doesn’t automatically change with them.
[00:09:14] Joe: So Kelly, let’s start with you. You’ve actually lived this. When did you realize that you’ve been financially preparing for a future that wasn’t going to be your future?
[00:09:26] Kelley: Well, it was a bit of a process, but, uh, probably the first clue was about six years ago, I was pregnant and finally expecting my first child, and found out pretty early on, I was almost 40, so I knew, uh, not to tell the whole world yet that probably wasn’t going to happen.
[00:09:42] Kelley: And my first disappointing thought was, “I’m not gonna get a maternity leave.” And I thought, “Well, that’s not a good reason to become a parent.” No. So I, so I, uh, at that moment, started to think through, you know, what were the motivations for parenthood. And, you know, long story short, we did go through some scientific processes to fully ensure we explored the path of parenthood before saying, “Okay, let’s decide how much further we wanna go,” and deciding, you know what, at this point, the life I envisioned for myself as a parent is not the life that we would have.
[00:10:16] Kelley: At the time, my husband and I were living in the city of Chicago, right in the city, and we were thinking we would eventually move to the suburbs, and had decided that wasn’t gonna be for us. And I always pictured my life as a parent of being kind of chaotic with like dogs and lizards and lots of kids, and this like super crazy household.
[00:10:33] Kelley: And a- approaching 40, I was like, “I might only be able to and wanna have one kid,” and that would be a much calmer, different thing. And so we kinda put the brakes on trying, and then decided ultimately to not have kids a- and switch our status to child-free by choice, and it literally changed everything.
[00:10:54] Joe: I can’t wait to dive into that, and we are gonna dive into that a lot more.
[00:10:57] Joe: Doug G., you’ve looked at this from the other side of life. In your book, Taking Stock, you talked about people and regrets at their end of their life. How often did you encounter people who faithfully pursued these goals long after the goals stopped being important to them?
[00:11:14] Dog G: I think it actually is really easy to do that.
[00:11:17] Dog G: So we see this all the time, whether it’s financial goals or, you know, a big one which we get all the time is people say their goal is to be a great parent, and they spend all their time being a great parent, and then the kids grow up, move away, and build their own lives. And maybe they don’t have grandkids, or maybe they have grandkids, but are located somewhere where the parent can’t be involved.
[00:11:37] Dog G: And it becomes this real questioning of, do I move on and decide to build new goals, new hobbies, new things to do? Or do I still cling to this idea that I’m gonna be calling my child if, let’s say your kid’s in college, calling your kid every day in college, talking to their teachers, planning their curriculum, or are you going to kind of step away and let them manage some of those things on their own?
[00:12:01] Dog G: So that’s a common one I used to see a lot. Certainly same thing with career. You’d see people who entered these big careers and find that they started dreading going to work.
[00:12:08] Joe: Oh.
[00:12:09] Dog G: Uh, but it was the thing they were working on for their whole life. They have enough money, they have enough accolades, and yet the idea of leaving is something that they just can’t manage.
[00:12:19] Joe: Well, and that’s funny because that was my follow-up was were people more likely to regret failing to reach a goal if they didn’t reach their goal, or failing to ever question the goal?
[00:12:31] Dog G: 100% failing to ever question the goal. It’s amazing how many people I talk to who never reached actually their goals, but gave it a really great try, and how that actually felt important.
[00:12:46] Dog G: I tell the story in my book, Taking Stock, of a gentleman who took a sabbatical in his 20s to climb Mount Everest. Uh, and everyone thought he was crazy. He was in the middle of he was, uh, corporate America, and these were big earning years where he could really get promoted. He took a whole year off sabbatical, trained for six months, went to Everest.
[00:13:03] Dog G: They got to base camp. They didn’t get much further. The weather changed, uh, and he had to go back home. And he went back into corporate America, and I met him doing hospice, and he was dying of leukemia in his 40s, and he could not stop talking about that trip to Everest. It was never the fact that he didn’t succeed.
[00:13:20] Dog G: It was that he had the courage to go out there and go after it, and he told countless stories of the things that happened while he was there, and that was a, a memory that really was important to him. So I, I don’t think it’s whether you succeed or fail, it’s whether you have the courage to try.
[00:13:33] Joe: I had this early on.
[00:13:34] Joe: I had a, uh, my high school track coach was fantastic. He’s actually the main reason that I received a scholarship to run in college. I remember going to one of the state meets, and he and I had this long conversation. He regretted becoming a singer. He was a really good singer, and he regretted never going for it, but he had so many people tell him that, “You know what?
[00:13:53] Joe: You’re not gonna make any money doing that,” that he didn’t try. And he was only… I mean, I have no idea. I was a, I was, you know, 17. I had no idea how old he was, but I’ll bet he was in his late 40s and was already on this cycle of regret, you know, not questioning what he had done. Jesse, this shows up in financial plans, you know, goals changing.
[00:14:13] Joe: Are most financial plans actually built to notice when the, when the goals change?
[00:14:18] Jesse: Are most financial plans built to notice when the goals change? Good question. I’m in the middle on that, ’cause on the one hand, you, you could make the argument that the financial plan without the goals themselves- That there’s no real, like, purpose of the financial plan without the goals themselves.
[00:14:34] Jesse: Like, what are you striving for? ‘Cause I think ideally the financial plan is answering, is answering questions for the subject of the plan, for the family in question. Like, can you do this or can you not do this? If you really wanna do this thing, can you do it by this particular date or not? And, and so those questions I think are kind of built into the plan itself.
[00:14:55] Jesse: Then again, I mean, some people out there just look at a financial plan as just, like, a series of numbers, and updating the plan just means updating the numbers. And it’s probably pretty possible if that’s your mindset that you just keep on updating the numbers, updating the numbers, forgetting about the fact that there ought to be some goals on the other side, and next thing you know, you know- Yeah, that the numbers
[00:15:12] Joe: are going towards something.
[00:15:13] Jesse: Correct. Right. You know.
[00:15:14] Kelley: There’s also, like, the so many levers you can pull in financial planning that make the plan more flexible. Mm-hmm. So if the plan’s not gonna tell you the goals have changed, but if the goal’s changed… So for example, something I talk about a lot is 401, great, easy way to save money, and obviously if you have an em- a 401with employer match, you should be getting that money unless you’re at risk of being homeless.
[00:15:34] Kelley: But Plowing extra money in there, basically you’re, you’re committing to seeing that money at 59 and a half or older. But for people who are thinking that they might not wanna stay in a job or a traditional career at least till that point, there are more flexible ways to save that leave that option open, so like the Roth IRA, for example.
[00:15:51] Kelley: So part of it is, like, when I’m working with people on their financial plan, like, how flexible do you need this goal to be?
[00:15:57] Joe: Yeah. That’s the frustrating thing, is that we get into things, Jesse, like tax optimization, you know, kind of what Kelly’s talking about. We, we look at tax optimization, we’re like, “Heck, I should be putting more money in the 401,” but we forget, to your point, that there’s something on the other end of this.
[00:16:11] Joe: There’s a time I’m gonna come asking for this money.
[00:16:14] Jesse: Yeah. And on that idea, the, the… you used tax optimization as the example there. It’s very tempting and very easy to get caught up in the weeds of financial planning an- and to literally, to, to be that person who, who, what is it? Misses the forest for the trees, is very tempting and very possible to become that person who misses the forest for the trees, who gets so caught up in the, the tax optimization here, and should I own VOO or SPY?
[00:16:40] Jesse: Which of these S&P 500 ETFs has a lower expense ratio? That next thing you know, you’ve forgotten about the fact that really the reason why you’re doing this is to go see the Himalayas, like Doc G’s example. And at the end of the day, so many of the small decisions just pale in comparison to the, to the big reasons why.
[00:16:58] Jesse: It’s like I, I don’t wanna be tone deaf and tell someone, “It doesn’t matter whether you own VOO or SPY. It really doesn’t matter.” But, but that’s probably the better message for the average person to hear, is that these minutia do not matter, or at least they just pale in comparison compared to the big, important goal-setting stuff.
[00:17:16] Joe: Do you know how much you just angered the over-optimizers in our audience? It, it totally matters. It 100% matters.
[00:17:24] Kelley: It’s fine if that’s your, you know, if that’s your hobby. Like I tell people all the time, if money is a hobby for you, like fiddling with your money, this is gonna be a lot easier for you to figure- Yeah
[00:17:32] Kelley: this stuff out. But it doesn’t have to be a hobby in order for you to be good at it.
[00:17:35] Joe: Totally.
[00:17:36] Dog G: I will tell you, I, um, never have heard on the deathbed regrets about VOO versus SPY. I mean, I’ve heard so many regrets, and I’ve just, I haven’t heard that one. Not even my Bogleheads dying patients.
[00:17:49] Joe: Apparently you were in the wrong room.
[00:17:51] Joe: “Oh my God, I should’ve been using VOO the whole time- … instead of SPY.” Kelly, back to you. Do we, do we sometimes keep funding these old goals? You know, uh, Doc G was talking about some of the regrets we have when we die. Do we keep funding them because it feels like admitting the old v- version of ourselves was wrong?
[00:18:09] Joe: Like, it, it sounds like going through the, “Well, we’re gonna be child-free” thing- decision-making even was, well, you know, if I wanna fit in with society, I should probably try to have kids like everybody else. Like, it’s a box we’re checking.
[00:18:23] Kelley: That’s part of it, and I’m still in the process of kind of figuring out how this looks for our finances because when we really settled on, like, this is not part of our life, we had been living very frugally, and still to this day live beneath our means in many ways.
[00:18:37] Kelley: I drive a 2016 Ford Escape and just can’t bring myself to upgrade my car, even though I easily could, and maybe I should if I’m gonna do more traveling. Even just the thought of, like… Well, let me take a step back and say when we got to that point, I ran the numbers and thought, “Well, okay, if my biggest disappointment was that I wasn’t gonna get some time off work, like, maybe I need to plan for that anyway.”
[00:18:57] Kelley: And I started crunching my own numbers and realized that I didn’t need to just take a sabbatical. I could actually retire-
[00:19:03] Jesse: Mm …
[00:19:03] Kelley: at Coast FI, at least, at the time. So I did. I resigned from my great job. I had, I had an amazing job. I was peaking, and I just was like, “I’m out of here.” And people were very suspicious, like, “Where is she going?
[00:19:13] Kelley: Is she gonna steal…” Like, I, I got shut off from my company files. I’m like, “I am really not going to work for a competitor. I genuinely wanna, like, meditate for a month.” And now, of course, that was six years ago, so they believed me, but even then, it was, like, five years later when we realized, oh, we’re not just Coast FI.
[00:19:31] Kelley: We’re actually technically financially independent, so we could either stop working and stop earning, or we need to start spending more money, or we’re gonna die with way more than is necessary for people that really have zero heirs. Like, I have one sibling. He has no kids. My husband has one sibling. She has no kids.
[00:19:48] Kelley: Like, we are the end of the line, so.
[00:19:50] Doug: Wow.
[00:19:51] Kelley: Uh, uh, we’re, like, still getting used to spending more money. For example, three months ago, we liquidated an insane amount of low basis, high growth stock to buy a condo for cash, which was, like, a huge growth edge. Obviously not at all tax optimized. I’ll have to report back in March what our tax bill is going to be.
[00:20:11] Kelley: But at the end of the day, owning a place in Traverse City was more important to us than having a low tax bill. Even talking about it, like, my stomach is kind of like, “Ooh, God, we’re gonna have to pay so much in taxes.” Ugh. But when I go back to that place and have, you know, my own room, and, uh, we were staying with relatives in, literally in a basement prior to that.
[00:20:30] Kelley: That going and having that own space is gonna exceed any pain I feel from paying taxes. Yeah. So everything you’re saying, it just fits right in.
[00:20:37] Joe: Don’t knock being in a basement, Kelly. It’s great. Oh. And by the way, being able to live
[00:20:41] Kelley: that close to Doug- I spent five summers in a basement.
[00:20:45] Joe: Living the dream is what you call it, right?
[00:20:48] Joe: All right, uh, what, uh, Stackers, you don’t know is before we hit record today, I asked our panelists to draw up three different little cards, and one of them says keep it, one of them says kill it, one of them says change it. We’ve talked a lot about people whose life’s changed but their financial plans haven’t, so we’re gonna put some of these old plans on trial and, uh, Kelly, Jordan, and Jesse are going to decide.
[00:21:15] Joe: First, and we’re gonna have you all at the same time, I’ll say one, two, three, and have you put them up. Do you stay the course? Do you admit this isn’t the life you want anymore and blow up the old plan? Or, and this is w- well, what I love about financial planning and the discussions that we have, is that sometimes it’s option three.
[00:21:31] Joe: Maybe it’s not this way or this way. Maybe there’s a middle ground. Maybe we just change it. Maybe we do something there. So I’d love to hear what you have, but cards up before you explain. Okay, case number one, it’s a couple in their early 50s. They bought the four bedroom forever house when their kids were young.
[00:21:48] Joe: Well, now the kids are gone. They love their neighborhood, but they use approximately 7% of the house now, right? So do they keep the house? Do they kill the house? Do they sell the house? Do they somehow change their thinking about the house? All right, everybody ready? You got yours? Three, two, one, show ’em. We got keep it, keep it, keep, everybody keeps the house.
[00:22:15] Joe: Doc G, why did you say keep it?
[00:22:18] Dog G: I’m all about quality of life. I think you live in a neighborhood, you like the neighbors, you get along, you have community. You could totally stress about being more efficient. You could stress about using less space. You could stress about having a less heat bill or electric bill.
[00:22:35] Dog G: But if you’re doing okay and you love where you are, your quality of life is going to be way outweigh all those efficiencies.
[00:22:43] Joe: Kelly, but only 7% of the house. I mean, you said keep it. But is, is it because of what Doc G said or anything to add?
[00:22:50] Kelley: Well, I started to say change it, thinking, “Well, maybe you could rent out some of the rooms if you needed to.”
[00:22:54] Kelley: And then I thought, “Well, I, we’re, I’m going to assume that this is not a financial sacrifice.” Sure. So keep it for the same reasons that Doc said.
[00:23:01] Joe: Jesse- Yeah … why did you say keep it? I thought that you’d be like, “Oh, get rid of the house.”
[00:23:05] Jesse: Can I ask, what… This is an odd question. What is the lawn like at this house?
[00:23:10] Jesse: Describe the lawn to me.
[00:23:11] Kelley: Are they in Arizona with rocks? Because that is a big consideration.
[00:23:15] Joe: Well, or, or Arizona, Kelly, I’ve seen the Arizona lawn too with the AstroTurf.
[00:23:19] Kelley: Mm-hmm.
[00:23:20] Jesse: Mm.
[00:23:20] Joe: Yeah, there’s a good one. It could be that. Uh, let’s say it’s, uh, Scott’s, uh, Turf Guard Plus- … phenomenal- Yeah … best.
[00:23:28] Jesse: Like, well, well taken care of?
[00:23:29] Jesse: It’s like a nice, it’s a nice lawn?
[00:23:31] Joe: It’s a
[00:23:32] Jesse: nice lawn. Because, I mean, let’s face fact, the grass is not greener-
[00:23:35] Joe: Oh …
[00:23:35] Jesse: for them to move.
[00:23:37] Joe: Man.
[00:23:38] Jesse: How’d you like that setup?
[00:23:40] Kelley: It- My dad’s lawn keeps him healthy- … ’cause he, he, it’s his activity. I also would say if you had told me they were in their early 70s, I would’ve said kill it.
[00:23:49] Joe: Why is that?
[00:23:51] Kelley: Because fi- early 50s there’s a lot that, you know, you got a lot of life left, and you might decide to, you know… There’s a question in the chat about, uh, are the grandkids nearby, if they have grandkids. Maybe you still have this dream of hosting lots of people, and only four times a year your house is full, but you still can have a full house.
[00:24:07] Joe: It’s interesting, because if somebody said kill it, I was gonna say, what if the mortgage rate was 2.8%? Mm-hmm. You know?
[00:24:13] Kelley: That was I just assumed that was not a factor.
[00:24:17] Joe: All right, case number two. Uh, for years you’ve assumed children were part of your future. Your financial plan reflects that, bigger home than you’d otherwise need, aggressive savings, life insurance, a career strategy designed around maximizing income, retirement estate plans built partly around supporting children and eventually leaving an inheritance.
[00:24:36] Joe: Now, you know you’re gonna be child free. The family-oriented plan you’ve spent years building, keep it, kill it, change it? Three, two, one. We gotta kill it, and two, change it. Kelly, you changed it.
[00:24:52] Kelley: Yes. I still live in a four-bedroom house
[00:24:56] Joe: Yeah …
[00:24:56] Kelley: uh, that we bought, we bought after the fact because we could. But we have dropped our life insurance coverage to the most part.
[00:25:03] Kelley: We have minor, tiny plan… I do have a, a whole life policy that we keep paying into because it provides long-term care rider, and I don’t qualify for long-term care due to a pre-existing condition. So we’ve kept some of it, some of our plan in place because it works for us. I mentioned earlier that we are technically financially independent, but we’re continuing to work, which is why a- at the spending level that we’re at right now, we changed our spending.
[00:25:25] Kelley: So now we, we kind of elevated our, our lifestyle, which goes against everything any conservative financial planner and particularly CPAs would say, but it’s been a really fun development.
[00:25:38] Joe: Well, and, and here’s the interesting thing that I wondered knowing we were gonna talk about this today, you and I.
[00:25:44] Joe: Does removing this, what was gonna be a huge financial obligation, I remember Scott Galloway saying on our show that, uh, children will F your life up. He goes, “They’re great, but they will totally F up your financial picture.” But removing that, does that necessarily mean you need less money, or does it mean the money suddenly has a different job?
[00:26:02] Kelley: Yeah, I mean, it totally depends on your values and your priorities. Right now, instead of we could have said we don’t need it and downsized our life and, you know, gone to live on a boat somewhere, instead now we’re just, you know, making the improvements that we want. There’s literally somebody in my front yard right now installing Rockware, so that’s a college tuition payment, and that’s our joke.
[00:26:20] Kelley: Like, when we spend a big chunk of money it’s like, “Oh, there goes one more year of-” “… 529 contribution.” But, you know, I definitely don’t wanna be a child-free token person, like, that just happens to be one aspect of my identity and it’s not my primary- Sure … identifier. And so, uh, I don’t, like, get into the whole like, “Yeah, I took four naps on Saturday,” because a lot of people with kids do that, too.
[00:26:42] Kelley: But- Sure … we could have made different choice. I also wanna bring up the generational aspect of it because I’m in my late 40s, and the elder millennial, Gen X, we did kind of grow up with the assumption that we’d eventually be parents, and a lot of us did make a lot of choices. And it’s circumstantial versus choice when we get to later in life and kind of realize this and might make changes.
[00:27:00] Kelley: That’s one of the reasons that my financial options are greater going into my 50s than, say, some of my other clients who either have kids or didn’t have that assumption. But a younger generation that is, like, declaring early on that they’re not gonna have kids, they’re already making different choices.
[00:27:14] Kelley: Their plans already look different, and so it’s almost like a different conversation with those folks around their financial plans.
[00:27:20] Joe: Oh, that is interesting. Yeah, you make that decision very early on, then that, that changes everything. Jesse, it sounded like you’re the one that said kill it. That means blow up the plan, start over?
[00:27:31] Jesse: I think so. Yeah. Or at the very least- If there’s ever, if there’s ever a need to kill a plan… I, I could just see if someone f- spends years of their life, you know, really going in one direction and then finds out that to some extent that path they’re going down is completely closed off, or that they need to do a, I don’t know what the…
[00:27:52] Jesse: I- is it 180 degree turn, or is it a 90 degree turn? I guess I don’t know. But either way, you’re making, like, a sharp departure. It’s a
[00:27:57] Joe: 180.
[00:27:58] Jesse: Is it a 180?
[00:27:59] Joe: Mm.
[00:27:59] Jesse: You’re making a sharp departure from the direction you were going down. I, I think that’s an excuse to kill it. And in the context of financial planning, I mean, that doesn’t mean I’ve saved up all this money, now I should spend all this money.
[00:28:11] Jesse: Like, no. But I do think it means going back to the drawing board about what the big audacious goal is. ‘Cause I think in, in this example, it sounds like the big, the big, important, audacious goal is no more. Probably need to go back to the drawing board and, and start over.
[00:28:26] Joe: Yeah, that’s interesting. And Kelly, I love the way that you put it.
[00:28:29] Joe: I’m not defined by being child free. It’s like absence of children is not my, is, is not, not my define. But what does define you? I like what Jesse said. What does, you know? Because now your life has, has a whole different meaning attached to it. It’s y- there’s other things that, that are the most important things in your world.
[00:28:48] Kelley: Yeah, I mean, I love other people’s babies. I just don’t want them in my house full time.
[00:28:52] Joe: Yeah. Well, that’s why I’m excited about being older, and I’m seeing my friends’ children have kids, and I’m so happy to be the quote, “uncle,” you know? Uh, good times. All right, uh, let’s do one more before we break for our big trivia competition.
[00:29:05] Joe: You’re 45 years old. You make $220,000. You built your financial plan around grinding it out 10 more years, and then you’re gonna early retire. You’re gonna jettison at 55. One problem. Anybody wanna guess what the problem is?
[00:29:21] Kelley: You hate your job.
[00:29:22] Joe: You hate your job. Nice job, Kelly. The career plan that gets you to retirement at 55 is what’s on trial.
[00:29:29] Joe: Do you keep it, grind it out, bank the 220, retire at 55, find your fulfillment someplace else? Do you kill it, leave the career path, and rebuild the financial plan around something different? Or do you change it, maybe new employer, new role, consulting, fewer hours, sabbatical, preserve some of the economic engine, but just overhaul the experience?
[00:29:51] Joe: Everybody ready? Three, two, one. Change it, kill it, kill it. Let’s start with Jesse, who two times in a row now has been the dissenting opinion. Why change it?
[00:30:04] Jesse: I, uh, you guys don’t know I’m on a lag over here, so I get to see how Kelly and Jordan vote, and then I just flip up something different.
[00:30:12] Joe: Is this… Well, you’ve lived this.
[00:30:13] Joe: You’ve lived this before, the change it.
[00:30:15] Jesse: Yes. And, and so the reason why- Except
[00:30:17] Dog G: he killed it. But he didn’t change it. He killed it. Sorry, go ahead.
[00:30:20] Jesse: As you were describing the definitions in this particular case, the change it resonated with me. Because you’re at 45, you, you, you say you wanna retire at 55, and that’s grand.
[00:30:31] Jesse: But I, I really like this idea, you mentioned sabbatical as one of the options in the change it category. ‘Cause I like this idea of, of testing out if early retirement really is the thing that you want versus is it just stepping away from the job that you hate. I think, I mean, I can just attest to my personal circumstances, was I was conflating dislike for my job, and it was really only certain aspects of my job.
[00:30:55] Jesse: I was conflating that with a desire for early retirement. It’s like, the silly one is, um, when you’re really thirsty, sometimes your body mistakes it for hunger. And so sometimes when you overeat, you’re, you really just need water. Or maybe that’s just me. I don’t know. Uh, but I, I think there’s something similar here, where it’s, it’s not uncommon for someone to think they really want to retire at 40 when really you just need a little bit of a change of, of occupation.
[00:31:20] Joe: Maybe that’s why I can’t lose weight, is I think it’s ice cream. I just need… If I’m thirsty, I just have ice cream.
[00:31:25] Dog G: Yeah. Jesse, I was with you on that until we used the word hate I think life is too short to hate your job. And th- let’s put it in perspective. When you’re 22, and you have no resources, and all the time in the world, you can afford to hate your job for a while to make money.
[00:31:43] Dog G: When you’re 45 or 50 or 55, you are really losing the game if you’re spending most of your time doing things you hate. I mean, life is short, you could die at any minute, and you’ve already used up half your life, and you’re telling me you’re gonna still spend 40 to 50 hours a week doing something you hate?
[00:31:58] Dog G: If, at 45 or 50, you have not evolved enough, matured enough, and built enough to be able to subtract what you hate out of your life, at least for part of the time, you’re kinda not doing it right. You’re kinda wasting the precious time you have, and we all know you can’t buy or sell time, so the only thing you can do is change the activities you’re doing as time passes.
[00:32:21] Dog G: And life is too short at that age to hate your job.
[00:32:25] Kelley: It’s funny, I can tie these two together with a great story. Okay. When I was 29 years old, I was in a talk at the Cincinnati Chamber, and our speaker told a story about how his granddaughter w- had just been born, and he was in the hospital, and he’s like, “And I’m standing there, and someone’s passing me my brand-new granddaughter, and I flash back to what felt like yesterday, and someone was passing me a joint at Woodstock.”
[00:32:47] Kelley: Time flies, man. Life is too short to stay in a job you hate. It’s too short to stay in a marriage you hate, and at the time, I was in a marriage I hated, so I had practice at changing the goals. Because it took all the courage and identity I didn’t even know I had to say I made a huge mistake, very publicly, I was…
[00:33:06] Kelley: No one in my family had ever been divorced, and I left my marriage, and that was a huge lesson in changing the cultural script for me that did help me later on in life to make this change. I, I totally agree with Doc G. But then the other piece is, I talk about the health, wealth, time triangle in my book, where when you’re young, you have your health, and you have time, and when you’re old, you hopefully, you make it, you’ve got wealth and time, but you might not have your health.
[00:33:31] Kelley: In middle age, most of us have some wealth, and we still have our health, but a lot of us don’t have time because we’re too busy working jobs, raising kids. And so people without kids, we have that, like, trifecta. So that’s why I said kill it. Because now you have the trifecta. You can take time to regroup.
[00:33:45] Kelley: Life is short, but at 45, you might have 45 more years, and that’s a lot of time to make your wealth back and spread out your working years over more of your living years so that you can enjoy your healthy years.
[00:33:58] Joe: We recently had a interview with, uh, Linda Gratton. Linda was talking about living, Kelly, to your point, a hundred-year lifestyle, and about maybe what that means is more sabbaticals and more just finding work that you enjoy- Yes
[00:34:12] Joe: versus, you know, checking out early. Because, um, well, Jesse, you said it at the top of today’s show, right? That, you know, finding that work you love is how changed your feeling about the fire movement. You’re like, “I don’t wanna retire early. I wanna find something I could do forever.”
[00:34:29] Jesse: Yeah. It, it worked for me.
[00:34:31] Jesse: And, and granted, you know, I don’t know, is it easier said than done? I’m not sure. But I was mistaking… I wasn’t exactly sure what the, the problem was, right? It’s like you know something’s wrong, but it’s hard to put your finger on exactly what it wa- what it is. And I guess there are multiple solutions to any given problem.
[00:34:50] Jesse: Sometimes you feel this desire to run toward one particular solution when you’re not even aware of all the different solutions that might be out there, let alone have you actually analyzed all the different solutions that are out there. And so right, in my case, I thought, yeah, retiring early and just going to spend my time on all these passion projects sounds like the thing I want to do.
[00:35:09] Jesse: And I, I probably would enjoy it. I think any of us might enjoy this idea of, yeah, you know, leave stressful work behind and just go spend time doing things you love. That sounds great. But there happened to be a second solution for me, which was just find a more fulfilling way to spend my, my working hours.
[00:35:25] Jesse: And, and so far so good.
[00:35:27] Joe: Well, this gets to what Doug G. talks about a lot, which is purpose, right? Which is finding that, finding that thing. I was gonna say. I beat you to it, Kelly. I got that one.
[00:35:35] Dog G: I’ll, I’ll just have you know it’s been a whole, you know, 30 minutes and I have not used the P word yet- You have not
[00:35:39] Dog G: and Joe was the first one. So give Doug G. some credit here. He didn’t jump to his old standby. I was thinking
[00:35:45] Kelley: it, but I was gonna let you take it,
[00:35:46] Dog G: Doug. There’s room for everybody.
[00:35:47] Joe: Well, we are overdue for our trivia contest. People are wondering, “When the heck are we gonna do our trivia contest?” So let’s pivot to that right now.
[00:35:55] Joe: For those of you new to Stacking Benjamins, on Fridays our three contributors, Jesse and OG, who is away today on his sabbatical for a week, and Paula Pant, who also has the week off, the three of them are locked in this, well, year-long trivia competition that couldn’t be much closer. It was closer last week, but Doug, give us the score of this shindig so far as we’re almost a quarter of the way through Q4.
[00:36:25] Doug: Yeah, Joe. Last week was a thrilling week because we had a three-way tie going into that question, and coming out of that week OG gained a point. Mm. So it is now 10 points for Jesse and Paula, and 11 points for OG.
[00:36:39] Joe: Which means, uh, Doug G., you’ll play for OG, so that means unfortunately you’ve gotta guess first.
[00:36:45] Joe: And because of the fact that Paula almost every year, Kelly, finishes last, that means you’ll get to guess last, ’cause, well, you play for Paula. Sound good?
[00:36:54] Kelley: Sounds great.
[00:36:55] Joe: All right. And Jesse can, can play for himself.
[00:36:59] Doug: Works for me.
[00:37:01] Kelley: May the odds be ever in your favor.
[00:37:04] Joe: All right. One person has a question. You guys gotta answer.
[00:37:07] Joe: Doug, what’s today’s trivia question?
[00:37:12] Doug: Hey there, Stackers. I’m serial entrepreneur and guy whose lemonade stand is currently seeking Series B funding, Joe’s mom’s neighbor, Doug. Around here, we’re always looking for ways to make a few extra bucks. Maybe you freelance, sell something online, you pick up a weekend gig. But just remember, some side hustles are better than others.
[00:37:32] Doug: Because on this date in 1992, authorities at an airport in Colombia detained a woman after becoming suspicious of what was described as her, and I’m quoting here, “Unusually large buttocks.” And apparently this wasn’t the result of squats. Authorities discovered that she was allegedly attempting to smuggle…
[00:37:53] Doug: I love a legend. Allegedly attempting to smuggle heroin that had been surgically implanted in her buttocks. Now, I’m all for multiple streams of income, but once your business plan requires general anesthesia, maybe you just drive for Uber. So contributors, here’s your question. How many ounces of heroin did authorities discover in her buttocks?
[00:38:16] Doug: I’ll be back with the answer right after I update my LinkedIn profile to remove willing to explore unconventional revenue opportunities
[00:38:25] Joe: Oh, I love this question, and I love looking at the, Kelly’s face, for those of you not on YouTube with us, as she reexamines her life choices to even come on this show, like, what-
[00:38:35] Joe: what, what am I doing here?
[00:38:37] Kelley: Well, there’s a reason it’s not a Colombian butt lift, I guess.
[00:38:42] Joe: Uh, Doc G, you have the pleasure of going first. All right.
[00:38:48] Dog G: Doc G wants to keep it. Sorry. Sorry, go ahead. Oh, you want me to say something.
[00:38:52] Joe: Yeah, how many ounces? Um- Ounces, right, Doug? Ounces of cocaine. Yes, that’s
[00:38:57] Doug: correct.
[00:38:57] Dog G: Ounces- Yeah, the, the question is- … in the butt … how big is that kadunkadunk gonna be? I’m thinking you could comfortably, without being too oversized… And we’re talking about both buttocks, right? So we’re talking a g- about a combined- Combined … buttock range here. Combined
[00:39:14] Joe: range. Combined.
[00:39:15] Dog G: Um, I’m gonna guess that you could do 15 to 20 ounces fairly easily on, on each buttock.
[00:39:23] Dog G: I’m thinking about liquid ounces, but yeah, so let’s, let’s say, I’m gonna say, um, 20 ounces each side. That’s gonna give us a grand total of 40 ounces- 40- … of heroin …
[00:39:33] Joe: ounces-
[00:39:34] Dog G: 4-0 …
[00:39:34] Joe: of heroin. Jesse, what do you think of that number?
[00:39:37] Jesse: I think that’s a… Yeah. I, I was wondering if, if Doc G with me- you know, his medical experience, obviously might have an unfair advantage here.
[00:39:46] Jesse: Seems like a reasonable guess. I was thinking, you know, this woman, it’s a brave choice. Not all heroines wear capes, mainly because the cape might- … not actually fit over your inflated buttocks, as it were.
[00:39:59] Joe: Over your heroine?
[00:40:00] Jesse: Correct. Correct. Exactly. I’m gonna say that she was really going for, you know, mucho dinero, and, uh, let’s go with 60.
[00:40:12] Jesse: 60 ounces.
[00:40:13] Dog G: Yeah. S- That’s more the Brazilian m- butt lift, I think. Yeah.
[00:40:17] Joe: It could’ve … Could’ve been. All right, Kelly, we got 40 and we got 60.
[00:40:22] Kelley: Well, I was… I’m wishing I knew more about how heroin was priced, because what would be, like, the, the financial tipping point where I would go, “You know what? Yeah, I’m gonna put that in my butt.”
[00:40:31] Kelley: Don’t we
[00:40:32] Doug: all wish we
[00:40:33] Kelley: knew more about that? No. My my best friend is Colombian, and Colombian women are known for their buxom behinds. So I’m gonna say in order for it to catch the attention, it would probably be closer to 100 ounces.
[00:40:48] Joe: Oh, yeah. Hm. To actually have somebody flag it. Hm. All right.
[00:40:53] Kelley: If she, assuming she was Colombian.
[00:40:55] Joe: We’ve got 40 ounces from Doc G, 60 ounces from Jesse, 100 ounces from Kelly. Who’s closest? We’re about to find out. We’ll be right back. All right, Doc G, you opened this at 40 ounces. I thought, “My goodness, that those are big buttocks,” and yet Kelly and Jesse said, “Nay, nay, they can be bigger than that.” What are you thinking?
[00:41:17] Dog G: This is always the point where I get insecure. Where I start thinking, you know, all I get is the downside and they get the upside, and yeah, maybe 20 ounces isn’t that much. So I don’t know. I don’t know. I’m, I’m within a factor of 10, I think.
[00:41:34] Kelley: I think this is 40 ounces, so.
[00:41:36] Joe: Jesse’s-
[00:41:36] Dog G: Yeah … I-
[00:41:37] Joe: Jesse’s-
[00:41:37] Dog G: I think I’m within a factor of 10.
[00:41:39] Joe: Okay. Uh, Sir Mix-a-Lot said, “Baby Got Back,” said 60 ounces, baby got a lot of back. Heck, w- Kelly’s answer, 100, baby got a lot, a lot, a lot of back.
[00:41:47] Jesse: Yeah. I liked, as, as Kelly was giving her rationale, I’m just thinking of these two TSA agents and one of them being like, “Do, do you think they have, like, four pounds of heroin in their ass?”
[00:42:01] Jesse: You gotta get closer to look at that. And the other agent being like, “No, I, I don’t think so. I think, I think she’s just Colombian.”
[00:42:05] Joe: Oh, my god.
[00:42:06] Jesse: You know, I, I could picture this conversation.
[00:42:08] Joe: How awkward would that be to approach somebody if they’re like, “Hey, we think you have heroin in your buttocks,” and she goes, “Oh, thank you.
[00:42:14] Joe: Thank you very much.”
[00:42:15] Dog G: I wanna bring up that Ron2027 guessed 30, so I’m feeling a little better now.
[00:42:19] Joe: All right. Well, Kelly, you were at 100. You feeling good?
[00:42:23] Kelley: Yeah, I mean, this was the ’90s, so this is before BBLs were a thing.
[00:42:26] Joe: Yeah, who knows? You know what? One person knows. Scary to say, but it’s Doug. Doug, who’s taking home the grand prize today?
[00:42:37] Doug: Well, hey there, Stackers. I’m internationally recognized businessman and guy who once made $11 selling stuff I found in Joe’s mom’s garage, Joe’s mom’s neighbor, Doug. She still calls it stealing. I call it monetizing underperforming assets, and that’s why I’m the businessman. Anyway, I’ve been thinking about this whole side hustle thing, and I think we’ve gotten away from the basics.
[00:42:58] Doug: Mow some lawns, walk some dogs, sell some plasma. Maybe don’t let somebody perform elective surgery so you can sneak narcotics through airport security. If your onboarding paperwork at this new job includes the phrase, “Now this is gonna pinch a little,” keep looking. Before the break, I told you about the woman detained at an airport in Colombia, who may or may not have been Kelly’s friend, in 1992-
[00:43:20] Doug: after authorities became suspicious of her unusually large cheeks. We- we’ll go with cheeks. Turns out authorities discovered heroin that had allegedly been surgically implanted in her posterior. So how many ounces did they find? Well, the correct answer was 76 ounces fewer than Kelly’s guess, 36 ounces- Ugh
[00:43:44] Doug: fewer than Jesse’s guess- Ugh … just 16 ounces less than Doc G. Oh, my goodness. Miraculously, Doc G has won the day because it was 24 ounces of heroin. Mm.
[00:43:55] Dog G: That’s pretty good. I wasn’t that far.
[00:43:56] Joe: 24 ounces- … of heroin.
[00:43:59] Dog G: The one time I didn’t wanna win-
[00:44:01] Joe: I know …
[00:44:02] Dog G: it goes to OG. ‘Cause- The one time I would’ve been satisfied- OG now-
[00:44:06] Dog G: to lose …
[00:44:07] Joe: goes ahead by two, as we’ve got maybe four trivias left, maybe five trivias left this year.
[00:44:14] Kelley: Sorry, Paula.
[00:44:16] Joe: Paula already is very used to-
[00:44:19] Kelley: She knows the feeling …
[00:44:20] Joe: Kelly being on the other side, yeah. Speaking of the other side, let’s talk about the other side of this. We talked about goal setting and how important it is to really to keep up with the goals, but let’s talk about money because you don’t, Kelly, change your goals for free.
[00:44:34] Joe: Depending on where your money’s at, where it’s sitting, what’s going on, I’m gonna ask this general question of all three of you, but we’ll start with you. What’s the invoice? You know? So y- you change goals midstream, what are some of the money things we have to consider that, uh, might not be what we want it to be and we’re gonna have to change it?
[00:44:56] Kelley: Yeah, so my story happens to be, like, on, the positive side, like, “Oh, we can spend more money,” but most people who are looking to… or thinking about changing a goal, they first crunch the numbers and really have to find out if it’s even feasible or what kind of sacrifices and trade-offs they need to make to change the goal if they are going to go that route.
[00:45:13] Kelley: Particularly I see this with career changers or people looking to start a business. I mean, you need to know what your non-negotiable monthly… It’s all about cashflow to me to start. What’s your non-negotiable monthly outflow amount that you have to have either saved in a savings account that you can easily tap for, I would say, at least a year to make a big change to your goals or your life?
[00:45:33] Kelley: And what areas are negotiable? Like, you know, you could pause Peloton, but are you willing to sell your house?
[00:45:39] opener: Mm.
[00:45:39] Kelley: Downgrade your car? Are you… You know, how, how important is this to you and what does that look like? For a lot of people, there’s a sudden change, and that often is a not a great thing, uh, or it starts with not a great thing.
[00:45:52] Kelley: Either a large windfall from an inheritance, so first you have to grieve the loss of a loved one. Um, deciding or figuring out you’re not gonna have kids. That often, for me even, came with a grieving process. Sure. So there’s a time to kind of adapt, but then there’s the sudden change, the diagnosis, the, um, the accident that oftentimes we think of, of negative things, but there’s also that, “Oh my gosh, I am pregnant.
[00:46:11] Kelley: Ah.”
[00:46:11] Dog G: Yeah.
[00:46:12] Kelley: And so you might have to more quickly make some decisions, and so that’s where you come into more change it versus kill it. I always first am like, “What are your fixed expenses, and how important are all of those to keep going? And can you at least bankroll a year of those while you figure out if this is the right goal change for you?”
[00:46:30] Joe: So your budget might get pinched. You may have to build your emergency fund, were two of the big expense changes that might change. Selling your… I mean, it might be as big as selling your house, you mentioned. Mm-hmm. Jesse, what are some other things on that invoice of, “Well, we might take a hit here”?
[00:46:49] Jesse: My mind immediately jumped to maybe some of the softer invoices, Joe, of just like I think of the conversations that we’ve had as a family that, that led us to our goals in the first place, or d- like the agreed upon goals.
[00:47:02] Jesse: And then, you know, that kind of feeling of like unwinding those conversations or figuring out, like almost doing like a postmortem of like, oh, where did we go wrong, or why didn’t we think about this beforehand, or, or just what conversations do we need to have now to set the new goals going forward? I was almost thinking of some of those invoices as being, you know, equally as challenging, if not more challenging, than figuring out the numbers themselves.
[00:47:26] Joe: Jordan, you’re nodding your head.
[00:47:27] Dog G: Yeah, I mean, sometimes I think we have to remember that money actually isn’t the goal, and what we’re talking about is really what that money buys us. And so when we think of just money, I think we get, like, the sunk cost fallacy. Like, I, I worked this hard to make all this money, and to…
[00:47:44] Dog G: so to pivot and change is really hard. But if you start saying, “Well, I’m in my job, and it’s really stressful, and I’m having two panic attacks a day, and I could change jobs, but then I’m gonna make less money, and I might have to do a week less of vacation.” And so let’s take the money out of it and say, “Well, what is the cost benefit ratio?
[00:48:06] Dog G: So if I change jobs, I get less vacation, but also less panic attacks. And if I stay in the job, I get more vacation, but more panic attacks.” And then you can actually look at your value system and look how you feel and say, “Well, what’s more important to me?” And some people are gonna say, “You know what?
[00:48:20] Dog G: Those panic attacks are horrible. I never wanna feel that again, and it’s worth giving up a week of vacation for.” And other people say, “You know what? I’ve kinda had panic attacks all my life, and it doesn’t feel good, but I can manage it, but I really live for that two weeks- Right, right … of vacation in the middle of winter.”
[00:48:34] Joe: I gotta b-
[00:48:35] Dog G: And so- I gotta
[00:48:35] Joe: panic about something. Why not the job?
[00:48:37] Dog G: Yeah, yeah, exactly. So I mean, all being said and done, I think the best way to figure out the financial trade-offs is actually to take the finances out of it for a moment and look at what you’re really trading because we mistake it as I’m trading investments or I’m trading money or I’m trading compounding in the future, which is really scary, right?
[00:48:55] Dog G: Because it’s the idea of, oh, I’m gonna take less money, and so I’m not gonna invest it, and it’s gonna compound to be 10 times as much in however many years by the time I retire. I mean, that can get really dizzying. Let’s look at what’s the life we wanna live, and what are those true costs and benefits, and how do we, how do they really match up with- without worrying so much about the exact dollar amount?
[00:49:14] Kelley: I love that, ’cause I talk to people all the time who think they wanna cut back on work, particularly busy parents. And I’m like, “You know what? You need to take a month off or a week off and see how you spend your time,” because it’s so easy for us to take time off thinking we’re gonna have, like, this new personality.
[00:49:30] Kelley: “Oh, I’m gonna start working in the garden, and I’m gonna take daily walks, and I’ll do yoga every day.” And then all you… you spend all your time cleaning. Knowing yourself and how you fill your time before y- particularly when it, your change is about freeing up more time and trading less time for money, is be honest with yourself about would you actually exploit this for what it, what you want it to be?
[00:49:50] Kelley: And first maybe work on those changes to your personality and your preferences and your default behaviors before you give up the paycheck.
[00:49:56] Joe: Yeah, I like this test driving idea. I don’t think we do that nearly enough. Test drive what it’s gonna be like. You know, when people are going to have kids, as an example, figure out how much more money that’s gonna cost, and start putting that money into savings so that you can feel the tight budget, you know?
[00:50:10] Joe: Or Kelly, you mentioned your car. You know, if you decided that you were gonna take on a car payment later on, then pay it to yourself into a car fund to see what that new payment feels like. Jesse, let’s say I decided I made the move. I’m making the move. I need 100,000 bucks. So we figure out what this costs.
[00:50:29] Joe: One problem is I haven’t done the things Kelly talked about. I don’t have the money sitting in cash. I have to sell investments. Let’s say those investments are down right now. We’re gonna deal with a couple different things, but let’s say those investments are down right now. Do I wait, wait for the investments to come up before I make this change?
[00:50:48] Joe: Do I bite the bullet? Walk me through that. Walk me through the thinking process.
[00:50:54] Jesse: That’s a hard one. I think a good rule of thumb in financial planning is that, i- is, is essentially to not necessarily time the market. Like, if you need cash now, like if, if your cashflow suggests that you, you need liquid money in your hands right now, that probably means that your portfolio ought to be able to support that in some way.
[00:51:13] Jesse: And that means that, you know, if you don’t have the, the literal cash or the short-term bonds or whatever you wanna think of to supply that $100,000 today or over the next few months, you need to make a change now in order to support that. And, and from that point of view, that means selling your investments while they’re down, which is something that, you know, the way you framed the question, Joe, is obviously something, it’s, it’s something we don’t wanna do, is have to sell an investment when it’s down.
[00:51:38] Jesse: And, and that’s where the conversation might go to level two, a little more nuanced, which is to say, you know, is this $100,000 need so incredibly urgent that you must pursue it right now? You know, can you afford to give yourself three or six or 12 months to, to let maybe whatever investment market you’re in recover so that your, your asset, you know, has more value?
[00:52:00] Jesse: Uh, it’s hard. I mean, w- when you hear a story of someone who says like, “Well, we decided to move across the country, so I just had to liquidate my whole 401and, and pay the 10% penalty and pay all those income taxes,” it, it’s like, well, listen, if, if you had to move across the country, on the one hand, we, you, you empathize with someone who feels boxed into a corner and that’s their only option.
[00:52:20] Jesse: But it does beg the question of like, was it really your only option? Because it, it, it can be such a painful financial move to sell an investment when it’s down or to raid your retirement accounts, that you, you probably wanna try to find an alternate path if it’s available to you.
[00:52:37] Joe: Yeah. I think maybe we talked about play testing just a moment ago.
[00:52:40] Joe: Play test before you do it. That buys you a little bit of time maybe to raise some cash to figure out what you need cash for and when you need it. Maybe it’s not all at once. Kelly, let’s do the opposite. It’s up 500%, and now you’re gonna have this gigantic tax bill.
[00:52:55] Kelley: Well, I think people forget, and I think Dokty’s gonna like this answer, that it’s not all about the money.
[00:52:59] Kelley: Uh, w- that what it’s in service of, and, and we tend to, as financial folks, we give a lot of best practices and rules of thumb, and those are great ways to live and those are great ways to make sure that we’re making the most of the way money works. But- Or always have a choice to generate a big tax bill and blow the whole thing up.
[00:53:18] Kelley: And people often forget that. Like, that’s an option, and it’s not the worst thing ever. Yeah, it sucks, but so does not living your life because you don’t wanna pay capital gains taxes. I recently talked to somebody who had all of her money wrapped up in real estate. She had no heirs. She was approaching r- what she wanted to be her retirement age, but definitely, like, third-of-life-type decades.
[00:53:42] Kelley: And she was refusing to sell a rental property because of the capital gains taxes and, and she couldn’t find a proper Section 1031 exchange. I’m like, “Just sell the property and retire and pay the taxes.” But she had bought into that rule so heavily that she completely forgot the point.
[00:53:57] Dog G: Isn’t that ironic?
[00:53:58] Dog G: It’s like, “I’m not gonna sell this thing ’cause I’m gonna have to pay taxes, so I’m gonna wait till it’s lower so that when I sell it, it’s worth less.”
[00:54:07] Kelley: I’m gonna keep working at, at a job I don’t want.
[00:54:09] Dog G: I mean, if you’re rich enough to be worried about your tax brackets, then you just borrow, honestly. I mean, if you’re really in that position, if you’re that rich, then fine.
[00:54:18] Dog G: Just, just buy, borrow, die, whatever. You know? That’s right. Take care of it some other way.
[00:54:22] Joe: That’s a point. There was a guy on the radio in Detroit earlier in my career who always said, he’s like, “My goal, remember our goal is to have Bill Gates’ tax bill. That’s our goal.”
[00:54:29] Dog G: Yeah.
[00:54:29] Joe: Like, truly.
[00:54:31] Dog G: Well, uh, see, unfortunately in the American system, the poor people don’t pay taxes, the middle pay tons of taxes, and the really wealthy don’t pay taxes or not much.
[00:54:40] Dog G: So, you know, what you’re really… The problem is you’re really screwed ’cause if you’re in the middle, that’s when you’re gonna pay tons and tons of taxes. Yeah. Rich people pay a lot less.
[00:54:47] Kelley: As a percentage of income.
[00:54:49] Dog G: Correct. And, and well, the really rich do buy, borrow, and die and pay almost nothing.
[00:54:54] Kelley: Right.
[00:54:54] Kelley: Right.
[00:54:54] Dog G: So there’s lots of… You know, we, we don’t need to get into this here. Yeah. But there’s lots of ways around paying taxes in the US that don’t exist anywhere but in the United States.
[00:55:01] Joe: That’s
[00:55:02] Kelley: true.
[00:55:02] Joe: I think, Kelly, you know, one thing I’ve heard all the way through this is that we, uh, that our goals will change.
[00:55:08] Joe: I mean, for each of you, your goals have changed in ways that you wouldn’t have expected when you were 22 years old. And yet we have some 22-year-old stackers listening to us. How do they set up their plans so that they’re not facing this, “Do I pull money out of my 401like Jesse was talking about?” You know?
[00:55:25] Joe: Or, “I don’t have the emergency fund when I need it. How do I build a financial plan from the beginning that builds in the fact that my goals are probably gonna change between now and the time I die?”
[00:55:37] Kelley: The number one tip I have for somebody who is young and healthy is the HSA. Opt for the highest deductible plan, and of course, very ableist comment here, if you don’t…
[00:55:47] Kelley: If you ha- are healthy, buy the lowest, lowest premium, highest deductible plan, sock as much money as you’re allowed to into your HSA, invest that money, don’t spend it. That will free you from job lock. So when you get to be 45, 50, even if you need health insurance at that point, it’s… But your body… Like, I feel like the day after my 40th birthday, my body was like, “Oh, here goes the gallbladder, and there goes the tendon,” you know?
[00:56:12] Kelley: Uh, but I had a well-funded HSA that allowed me to leave a job with the only real thing that I needed from that job was group health insurance, and take on the financial risk of an adverse health event. That is the number one financial freedom tip I have for a young person.
[00:56:27] Joe: What’s interesting, Jesse, is Kelly k- kind of talks about the HSA as a change my mind fund, right?
[00:56:32] Joe: I changed my mind about this job, I changed my mind about this thing. But should, should I think about, say I don’t have an HSA available, should I have a change my mind fund?
[00:56:40] Jesse: The place my mind went to, Joe, was, you know, at, at 22 or 25, at that young age, that building flexibility into the plan i- is vital, and there are different ways you can do it.
[00:56:51] Jesse: And I think my, my tip almost has to do with this mindset shift of when I think of financial planning, I call it, it’s a too small blanket problem. It’s like you’re going to bed, and you just don’t have a big enough blanket. We’ve all been there sleeping on our friend’s couch. And you pull it up over your chest, and now your toes are getting cold, so you pull it down over your toes, and now your shoulders are cold.
[00:57:09] Jesse: And, and in financial planning, there just aren’t enough resources to make everything perfect, so you have to make some concessions. And in order to build in the flexibility that we’re talking about here, you’re gonna have to make some concessions in other parts of your financial plan. And, and one example might be, well, I’m gonna build up a bigger than typical taxable brokerage account.
[00:57:30] Jesse: Like, that’s awesome. It just means that you might not be get- taking advantage of all the tax advantage accounts, just ’cause you don’t have enough money to, to max everything out. Or, or maybe you say, “I just, I’m gonna carry a larger than typical emergency fund. I’m gonna carry 18 months of cash at all times so that I have that flexibility to pursue some dream or some interest when it strikes me.”
[00:57:49] Jesse: Well, that cash is gonna feel like quote, unquote, you know, dead money most of the time. Um, so anyway, the point is that, uh- You have to make a sacrifice in some way and accept the fact that maybe you aren’t maximizing all the avenues of your financial plan, of your investment options, because you’re choosing to build this flexibility into your plan.
[00:58:07] Joe: I love it. Every plan has an Achilles heel, and if you think you have the perfect plan, I don’t think you’ve looked at it hard enough. And I love the fact, Jesse, that you build the Achilles heel. And you d- like, listen, this extra money in my cash is gonna be dead weight until it’s not, and then I, then I deploy it.
[00:58:26] Joe: And you know the Achilles heel. Uh, I absolutely love that. People are like, “No, this plan can’t fail.” I’m like, “Oh yeah, I’ve seen plans fail in so many phenomenal ways.” I’ve been a Detroit Lions fan for a long time. Oh. Every- Same … plan fails, Kelly, as you know. Oh my goodness, this team. Ugh. Ah. I wanna ask one more question before we say goodbye, ’cause I can hear somebody, one of our Stackers listening, going, “You know, this discussion you guys are having is fantastic justification for every flaky decision I’ve ever wanted to make.
[00:58:57] Joe: Hate my job? Quit,” right? “Tired of my house? Move. Don’t like my plan? Eh, forget the plan. We’re, we’re, we’re being flexible here.” How do I know my goals actually change versus I’m just having a little bit of discomfort, Doug?
[00:59:13] Dog G: I think it’s the other way around. I think if you don’t wanna do smart things with your money, you’re gonna find every reason not to do it, and this conversation is not gonna be what sets you over.
[00:59:21] Dog G: You’re not gonna be a totally good at- You’re already screwing things up … finances and being r- yet. Like, so h- here’s what I think I think that again, we have to look at a mix of what we want out of life, both short-term, long, and long-term, and try to make decisions that are gonna support both of those set of goals.
[00:59:44] Dog G: And so I think it takes, uh, this is the problem, most people wanna lead with money, and this is where you always go wrong in my opinion. You have to lead with what you want in life and then build your financial plan around it. And I think if you can be honest with your goals short-term and long-term, know what a good life looks like to you, then you can back into a financial plan, and then you have a very clear question set every time you decide what to do or not do with your money.
[01:00:13] Dog G: Will this support my short-term goals and will this support my long-term goals? Now granted, we’re talking about what happens when your goals change. Well, guess what? Everybody’s goals change. And so good financial plans tend to be 50 to 75% the same, and it’s really that last 25%, which I think pushes us into one particular direction or another.
[01:00:33] Dog G: And so what you do is you get rid of what doesn’t work anymore now that your goal has changed, and you build in new stuff, and you wash, rinse and repeat as time changes and new things happen, and you, your value system and your identity evolves, as everyone’s does. And so I think that’s the easiest answer, is understand what your long-term and short-term goals are, and then you’re gonna be constantly evaluating and reevaluating your financial framework and seeing if it works for you, and if not, you’re gonna slowly pivot.
[01:01:02] Joe: Kelly, I’m so glad you brought this topic to our attention. It’s perfect at the end of this week. I feel like, you know, children, one of those check boxes, I called them when I was a financial planner by the way, the Puritan ethic goals. You know, where, okay, I gotta retire early or I gotta retire, so I gotta put money there.
[01:01:20] Joe: I have to have the house, so I have to own a house. I have to have the good job, I have to have the, I have to have the, have to have the… How much does identity trap us in the wrong financial plan?
[01:01:32] Kelley: I was just gonna say that it really depends on, I, I’m assuming that most of the listeners are people who have a relatively, uh, responsible type of identity.
[01:01:42] Kelley: They think of themselves as financially responsible people, or they want to be financially responsible. And so really the reminder is more, it’s never too late to change your mind, and our identity is just- who we think we are. And we can change who we think we are. Um, so I, I use the example all the time that when I moved to Arizona, I really wanted to make friends, and being someone in my mid-40s moving into the suburbs where everybody lived here either because they were retired or because they had kids in school, how in the hell was I gonna make friends?
[01:02:13] Kelley: I was, had no kids, I w- I’m not retired, and I had to believe that I was somebody that people wanted to know, that I was a likable person. Now, people told me I was likable, but I had to believe that, and so there was an, a repetition aspect where I really had to, like, it sounds super unconventional and dorky, but I had to, like, every day be like, you know, “People like me.
[01:02:31] Kelley: Like, truly, people want connection. People wanna be friends with me, or people wanna be friends with other people.” So that’s just one piece of it. I had to do some of that work around going out on my own and trusting that I would know when to pivot if I needed to. A lot of people wanna make sure they know for sure that they’re not gonna screw it up before they even take a step, and oftentimes it’s that first step that starts all the process of change in our lives, and that’s really, really scary.
[01:02:56] Kelley: So just believing that you can trust yourself to know when something needs to change is another part. So identity is, like, the key to it really.
[01:03:03] Joe: Yeah, that drives me crazy when somebody’s like, “I’m not gonna take the first step till it’s perfect,” ’cause that ain’t never gonna be perfect. It just is never gonna be.
[01:03:11] Joe: And, and Jesse, we spent a fair amount of time today talking about, you know, sunk cost, right? I sunk all this into my identity up until now versus switching costs. Can we talk about, like, financial terms the difference between the two of those? ‘Cause I think this is, like, an important financial planning concept.
[01:03:27] Jesse: Yeah. I was just still caught up, ’cause I too… I mean, like Kelly Long, I, I, I feel like Stuart Smalley. Isn’t it Stuart Smalley, Kelly?
[01:03:35] Kelley: Yes, yes.
[01:03:36] Jesse: You know- Gosh darn it. Gosh darn it. Good enough. People like me. It’s true. It’s not easy to put yourself out there, so good on you. Sunk costs versus switching costs versus all the other costs.
[01:03:47] Jesse: Well, I think the way I think of the difference, so sunk cost is this feeling of regret. It’s a behavioral bias or a kind of one of these economic irrational biases that we feel regret when we put a lot of time and effort and resources in a particular direction, and then once we decide to change direction, the regret overwhelms us and makes us feel like we can’t, because, oh, if I’ve already put in all this effort in moving this way.
[01:04:12] Jesse: And, and, you know, ultimately w- the, the, the rationalist would tell you sometimes the best thing to do is cut bait, and it sucks that you have the sunk cost, but you just have to deal with it and move on. Switching costs are more of like a, a economic reality, which is that it does take an additional amount of time, resources, energy to, to switch directions, to move, whether it’s, you know, uh, may- maybe a very simple, easy one could be moving from Chicago to Tucson.
[01:04:39] Jesse: Like, that is a, a switching cost. You know, you’ve got everything from the closing costs themselves to the time that it takes you to move to the, the mental hassle of packing everything up. But anyway.
[01:04:50] Joe: To finding new people in Tucson to like you.
[01:04:52] Jesse: Correct. Correct.
[01:04:53] Joe: Yeah.
[01:04:53] Jesse: I’ve been quite successful, for
[01:04:54] Kelley: the
[01:04:55] Jesse: record.
[01:04:57] Jesse: The switching cost is much less… It’s not about regret. It’s just more of a matter of fact.
[01:05:03] Dog G: Mm-hmm.
[01:05:04] Joe: You know, I think we spend an incredible amount of energy asking whether we’re on track, especially financial planning people that are interested in stacking benjamins. We’re on track for retirement, on track for the house, on track for college, on track for whatever that number is.
[01:05:19] Joe: Maybe every once in a while we should ask a different question. Do I still wanna go where this track is actually taking me? And I think we have to remember, Jesse, the way we ended it there, that maybe changing your mind isn’t free. You know? There might be taxes. You might have s- to sell something. You might make less money.
[01:05:40] Joe: You might work longer. You might have to admit something you spent 10 years pursuing isn’t important, which I think is, you know, something that a lot of us do. I think we gotta know that price, and we should plan for it, but the existence of a price doesn’t mean we shouldn’t pay for it, and here’s the thing, staying has a price, too.
[01:05:58] Joe: Mm-hmm. And I think often we think, “Oh, I’m not gonna make that move because the price is too high.” Well, you’re still gonna pay a price. Getting good with money was never to become really efficient at living yesterday’s life, it was to give ourself more choices about tomorrow. So, I, I think that was a fantastic discussion, and Kelly, I’m so glad we met at FinCon, and you actually brought this to my attention.
[01:06:23] Joe: So we can pre-order your new book, right?
[01:06:25] Kelley: Yes, it is available for pre-order. It doesn’t come out ’til February 2nd, but it is available on all platforms.
[01:06:30] Joe: You know what they tell people that if you buy stuff way ahead of time, that the deliciousness of thinking about it coming is a great experience itself.
[01:06:40] Joe: We talk about that on our travel show. If you book travel well in advance, like thinking about it, but reading your book, we can think about ahead of time. What’s it called? And let’s dive in for just a second.
[01:06:49] Kelley: First I wanna say that I have a quote right here next to me that says, “Never give up on a dream just because of the time it will take to accomplish it.
[01:06:55] Kelley: The time will pass anyway.” And I feel like that kind of sums up what we’re all saying. I
[01:06:59] Joe: should’ve just thrown it to you instead of that long soliloquy. Why didn’t you stop me?
[01:07:04] Kelley: My book is called But Who Will Take Care of You When You’re Old? Financial Planning for People Without Kids.
[01:07:09] Joe: Awesome. And, uh, can they pre-order it on your channel at Financial Coaching Bliss, I believe, Financial Bliss Coaching.
[01:07:16] Kelley: My website is financialblisscoach.com/book is where you can find all the pre-order links. I encourage people to use bookshop.org and send that money through a local bookshop, but of course you can get it from our friend Mr. Bezos or Barnes & Noble or Books A Million as well.
[01:07:31] Joe: I was so close. Financial Bliss Coach, not Coaching.
[01:07:34] Kelley: Mm-hmm.
[01:07:35] Joe: Yes.
[01:07:35] Kelley: Yeah, my YouTube channel is Financial Bliss Kelly Long.
[01:07:38] Joe: Awesome. We’ll link to both of them on our show notes at stackingbenjamins.com. Thanks for partying with us today. Doc G, what’s going on at the Earn and Invest podcast, my friend?
[01:07:48] Dog G: Well, believe it or not, our mastermind based on- I don’t believe
[01:07:51] Joe: it.
[01:07:52] Dog G: Believe it or not. Don’t believe it. Our mastermind based on earn and invest called The Wealth of Purpose Mastermind, has about 30 members, and we just did our annual in-person meetup in Chicago. Oh, cool. It was a lot of fun. It is amazing what it feels like to get together with a group of people that you’ve been meeting virtually for…
[01:08:09] Dog G: The, the mastermind’s been going almost four whole years, which is crazy, ’cause Joe and I can remember when we started talking about me doing this years and years ago. It’s been about four years, and, um, it’s just fantastic after knowing these people for years to actually be in the same place for a weekend.
[01:08:24] Dog G: We did a little bit of learning, a little bit of presenting, lots of sightseeing. Had, uh, deep dish pizza as well as apple pancakes and did some Chicago stuff.
[01:08:34] Joe: That’s fabulous. Fantastic. I remember you kinda fighting me on this. This is why masterminding is good.
[01:08:40] Dog G: I fight Joe on everything. If he brings it up, I fight him.
[01:08:44] Dog G: Pretty much. I
[01:08:44] Kelley: will fight you.
[01:08:45] Dog G: Joe’s like, “How about I give you a million dollars?” And I’m like- No … “No, Joe, I don’t want your million dollars.” Yeah.
[01:08:50] Joe: Yes. I need two. This… See, and I knew, Kelly, that he would say that, so now he’s giving me a million dollars just to prove. But, uh, yeah. Jesse Cramer, what’s going on at, uh, Personal Finance for Long-Term Investors?
[01:09:04] Jesse: I lose track of time, Joe. I don’t even know what weekend this is, I’ll be honest with you. But, uh-
[01:09:09] Joe: Th- th- this is October 20… 23rd.
[01:09:12] Jesse: 23rd. Man, flies by. It flies by I think I just released an episode, I might have just released a Charlie Munger episode, but either way, some recent episodes we talked about the three demons of overconfidence, we talked about some great Charlie Munger quotes, and I answered a listener question who, she, you know, she kind of said, “Hey, uh, I know financial planning looks unique for each person, but surely it follows some unified framework?”
[01:09:39] Jesse: Which is a really good question. And so we kind of talked about what that unified framework of, of retirement planning tends to look like.
[01:09:46] Joe: Awesome. Fantastic. Guys, we just filled your next couple days with good stuff. Between Jesse’s podcast, Doc G’s podcast, Kelly has a podcast, and pre-ordering Kelly’s book.
[01:09:59] Joe: I think you’ve got a lot of, uh, stuff on your plate to do. And think through those goals, because it’s important to think, “Is my money going really the way that it should be?” All right, that’s gonna do for today. Doug, you’ve got it from here, man. What should we have learned on today’s show?
[01:10:12] Doug: Well, Joe, first, even though she’s still driving a 10-year-old Ford, take some advice from Kelly Long.
[01:10:18] Doug: Sometimes changes to your goals are circumstantial rather than choice, but those circumstances can lead to some pretty great upsides if you have the right perspective. Second, don’t forget what Jesse said about your financial plan. It’s not just a bunch of numbers in a spreadsheet. It’s a numerical representation of your personal goals.
[01:10:35] Doug: If your goals change, there’s a good chance the spreadsheet needs to change as well. But the big lesson, diversifying your income is smart. A side hustle can help you pay down debt, build your emergency fund, or save for retirement. But if someone describes the compensation package in ounces, politely decline.
[01:10:57] Doug: Thanks to Kelly Bliss for joining us today. Learn more- Kelly Long for joining us … Kelly Bliss? Could be Kelly Long. We’re not really sure. Uh, to learn more about Kelly, her coaching, her book, But Who Will Take Care of You When You’re Old?, head to financialblisscoach.com. I got it right on the first try, Joe.
[01:11:13] Doug: We’ll also include links in our show notes at stackingbenjamins.com. Thanks to Doc G for hanging out with us today. You’ll find his significantly above average podcast, Earn and Invest, wherever podcasts are sold. And finally, thanks to Jesse Cramer for joining us today. Are you a long-term investor? Are you into personal finance?
[01:11:32] Doug: Well, does this guy have a podcast for you. Check out Personal Finance for Long-Term Investors today. This show is the property of SP 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.
[01:11:57] 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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