[Podcast Intro:] You’re listening to ChooseFI. The blueprint for financial independence lives here. If you’re looking to unlock the secrets to financial independence and early retirement, you’re in the right place. Stay tuned and join a community of like-minded people who are getting off the Instagram and taking control of their lives in the pursuit of financial independence. ChooseFI, your home for financial independence online.
00:00:00
Brad: All right everyone, we are back. Last week, we talked about incremental gains. Have you listened to that yet? You know, we’re allowed to say this. That’s now essential listening. Listen for us to point out essential listening. Last week was one of them. Today, we’re doubling down, but I’m not happy with part two. I just don’t like doing part twos. So today, the detour is the journey. Think about this. You are on the path to financial independence. In a period of months, you know 80% of everything you’re gonna know about this topic. Why would you stay with us? Why would you still be here? Why are we still wildly entertained by this conversation and this journey? Because the detour is the journey. That’s the fun part. And with that, welcome to ChooseFI.
00:00:53
Jonathan: Brad, how you doing, buddy?
00:00:55
Brad: Yeah, Jonathan, I am doing quite well. This is great. And it’s funny because I mentioned three weeks ago when you first came back that my least favorite thing was doing titles of episodes. And I kid you not, in our doc, I had incremental gains part one, incremental gains part two. So, thank goodness you’re here. Not acceptable. But then Brad below that said, make very bad titles and have Jonathan jump on title responsibilities and start doing intros again. Yes, and give him lots of positive feedback along the way. It doesn’t work so well, I’m such a sucker.
00:01:28
Jonathan: You really, really are. Right on the back.
00:01:31
Brad: All right, so it’s funny. Detour is the journey. So, Aaron and I are getting set to go down to Camp FI in Florida in a couple of days. This will be in the past by the time this episode airs. But we actually decided to take a little detour to Savannah, Georgia on the way down. It’s like a 10-hour drive to this random Hawthorne, Florida. So, figured we’d split it up a little bit so we didn’t have to do 10 hours in one day. And I’m actually using, we talk about travel rewards points all the time. I actually have a free night certificate from Hyatt that I fear is going to expire unused otherwise. So, there’s a couple of really nice category four Hyatts there in Savannah, Georgia. And you can use these free night certificates that you get from the Hyatt credit card, they are good for category one through four hotels. So, I’m like, well, this is perfect. There’s an Andaz Savannah, which is a really nice kind of swanky-ish brand, I guess, from Hyatt. So, I’m gonna use that free night certificate, which is great. And I might, might, might even be able to somehow swing an upgrade on the room if all goes well. So, I’ll keep you updated on that. But yeah, it’s neat. I’ve never been to Savannah, so I’m pretty excited. I think I’ve told you in the past that I’m a huge Premier League soccer fan. I’m an Arsenal fan going back almost 30 years at this point. And they have a big match against Liverpool. So, what’s neat is there are Arsenal supporters clubs in lots of cities around the country. And there is a Savannah Arsenal supporters club. So, we’re gonna go meet up with them at the local pub and watch the match. And yeah, it should be a nice little time.
00:03:09
Jonathan: Oh, that’s fabulous, man. Well, you know, I didn’t know you were gonna be so literal with my setup here. I mean, that’s great. I’m super thrilled by it, but I was absolutely staying in a metaphorical space. I had all sorts of life lessons planned, but cool. Great detour.
00:03:24
Brad: Yeah, quite literal detour. Little happy single, all of us get latched on to words. Brad might feel guilty of this. We used “unpack” about 45 times in a couple of the early episodes, but you get a phrase stuck in your mind. And every child has discovered the word literal at some time and had a week with “literally”, I couldn’t do another thing. Literally, I’m just absolutely, my daughter had a great time with her cousin on this family trip that we just got back from. And the cousin had discovered the word literally. And my daughter has now come back and everything is literally. I’m like, I don’t think that word means exactly what you think it means. I mean, maybe it’s, yeah, you’re burning through it. You’re burning through my patience. I can’t hear it. But in this case, I was going for a hardcore metaphorical lane for us with detour. And what I wanted to talk about was just how this conversation that we’re having, which is, you know, at its core, it feels like a nuts and bolts, mathematical equation. And there we are, ends up giving us the opportunity to explore all these other things. And so, you know, we’re gonna go into incremental gains here, part two, yes, yes, in a second. And there’s a lot of goodness there. But before we do that, I wanted to just take a second and just underpin why we’re going to be able to do so many episodes of the show, even when that list is done. Because when you reclaim your most precious non-renewable resource, your time, and you start moving towards designing a life that you actually don’t really need or want to retire from, there’s a lot of really cool things that happen along the way. And so I think our community, the word retirement doesn’t have the same connotation for us.
00:05:00
Jonathan: Ooh, okay, all right, I like it. I see the energy coming on the other side here. We’re landing the ship.
00:05:05
Brad: But that word retirement, you know, there’s nothing inherently wrong with it, except for the baggage that’s put on it. And in this perfect world, you’re loving life. You’re loving the journey. You’ve created the space to have your cake and eat it too, in a very calorie-conscious way.
00:05:24
Jonathan: Very calorie-conscious, indeed. And it’s funny because I sent you a post that I saw in the ChooseFI Denver group this morning from Brady. And he said, “Fire achieved. Now looking forward to meeting, learning, and adventuring with all of you.” And he’s standing there all excited in this picture. There’s a banner that says, “congratulations, quitter.” It was great. It’s just so funny. But it really speaks to FI. It’s not about the numbers. It’s about meeting, learning, adventuring, right? It is about the detours. If this was just the nuts and bolts of money, this show would have been over nine years ago. This is about life optimization in every possible way.
00:06:08
Brad: Jonathan, I was gonna ask you about what board games you’ve played recently. Last I heard, you are a board game aficionado, or at least you used to be. I’m not sure. Obviously you’ve been coding for the last 5,000 hours, but in a prior life you were.
00:06:16
Jonathan: I’m really, I’m getting back to roots, man. Looking at Minesweeper right now.
00:06:19
Brad: Anybody else? Windows 95?
00:06:26
Jonathan: I love Minesweeper. It’s so funny. Most people had no idea what Minesweeper was all about. That is one of the best logic games, logic puzzles that exist.
00:06:35
Brad: You found your tribe, people. You know you found your tribe when Jonathan brings up a random game from 30 years ago.
00:06:43
Jonathan: No, all jokes aside, I was phenomenal at Minesweeper. Literally. I loved that game.
00:06:48
Brad: Oh, that was amazing. We’re gonna build a whole episode about removing the mines from your life so you can truly see the path.
00:06:54
Jonathan: That’s probably weird.
00:06:56
Brad: He’s really stretching this metaphor thing, man. I don’t know.
00:06:58
Jonathan: Yeah, I do love board games. I have found myself taking a little bit of a step back. Not, not, not. All right, so here’s the thing. Being a board gamer requires being around other individuals that love the board game. I’m in the lane with young children. My oldest is eight. So you can work down from there, right? And time and attention span. I am finding ways to do board games, but I’m leaning into a lot of these, you know, kind of junior age games. So I’ll just tell you though, yes, we’re doing them. Here are our current family favorites. We love Uno Attack. Now I think this was one that we received as a birthday gift for my son. The base game is still just regular Uno, which probably everybody is familiar with, but it comes with a mechanical launcher. And so what happens is when you receive something like a draw two, or you go to play something, but you don’t have the right card, so you have to draw. Instead, you press this launcher activator trigger, and it has a jack-in-the-box style mechanism. So each time you press the button, it’s charging, and the sound goes with it. Da-na-na, na-na-na-na-na-na-na-na. And you know, you know, it’s kind of like hot potatoes, right? You know it’s about to shoot out all of these Uno cards, but it doesn’t actually give you a card until someone is unlucky enough to like win the lottery and get 15 or 16 Uno cards. So it just objects a massive amount. So this one has been, it’s kind of a nice mix-up on the Uno game. And my kids are really enjoying that.
00:09:20
Jonathan: And there’s two others that I’m gonna give an honorable mention to. Actually, no, one of them is the absolute best. Ticket to Ride Junior. Ticket to Ride Junior is the most fabulous game for kids under the age of 10. And it’s a plausible entry to adults for the genre as well. It takes all of the best elements of Ticket to Ride and makes it accessible. And if you’re a parent, you’ll appreciate this. It puts every game inside of a predictable 20 to 25 minute window. That’s the critical part.
00:09:48
Brad: Yeah, that’s nice. Cause it’s interesting. Again, I’m gonna say this probably every episode. I’m going back and listening to every single old episode of ChooseFI. And it’s a time capsule, which is fun for me. This has been like our journals, if you will, for almost a decade. And at that time, at the very beginning, my younger daughter, Molly, was only five years old. So we were actually talking about board games in one of those very early episodes. And I was saying that it’s so fascinating when you trust your kids and when you believe in them, what they can live into. And at that point, Molly was five, Anna was eight and change. And we were playing adult games. And I said, those two kids can play at any table with any adults anywhere in the world. And we were actually, in that case, talking about Monopoly Deal. And Molly, at the time, couldn’t read. But she memorized all the cards and everything that each of the cards did. And she was able to play at an adult level at five years old. She played Ticket to Ride and Catan at five or six because that’s what we played.
00:09:49
Brad: So I would say it would be interesting to see if Zachy, if you had him, instead of playing the jujube version, kind of mosey him into the adult versions. I think you’d be very pleasantly surprised at his ability, but I hear you about the 20-minute thing, so I can’t solve for that. He’s ready, he’s ready. I just, it’s just, if you’re keeping track of points for yourself and for a child and for maybe, you need to have at least one or two other really interested people for that one, so there’s a little bit of setup. Casual players and families that are kind of tiptoeing their kids into board games where the kids haven’t already decided they are going to learn this, like, no matter what, you know what I mean? Like, there’s a difference there. Molly decided. When the person makes a decision of their own, it’s one thing. If you’re trying to, you know, ease them, and I remember asking you there, like, you know, Brad, do you ever, like, you know, kind of throw the game a little bit, give them a little table? And you said, no, of course not. That would never, ever. I was like, all right.
00:10:43
Jonathan: I literally would never, ever do that because I want them to. People do that? That’s a thing? Never in my household would that be. But also, not for nothing, but I want them to know that when they beat me and beat us, beat adults, that they did it through their own skill and ingenuity and intelligence. And, right? Like, people know when things are thrown and given to them. So, here’s what I do, and this is my balance. I’ve always had your words in mind. I’m like, all right, I don’t, I agree with you. I do agree. I just, I feel like your kids are going to be there regardless, and they had that hunger, and I feel like if my kid gets crushed too soon, you know, it’s not, oh, I’m going to come back and take you on, but he checks out. So, it’s kind of recognizing the psychology of your kid a little bit in this context, but here’s what I will say. I ask him ahead of time, you know, especially after he has the wheels, is this a teaching game or are we playing to win? So, if it’s a teaching game, you can ask me, should I do this, dad? Should I? And I might give you a little hint about, ooh, I don’t know. But if it’s not, because you’re not going to tell everybody, oh, I beat dad. Oh, in the teaching game, you beat dad? Oh, that game that we played, is that what we’re talking about? Yeah. You know, so there, he knows. He knows.
00:12:43
Brad: So, this kind of is what I found to kind of be a way to navigate this. The other game, I’ll just say it real quick, is junior detective. And what they did here is they put in 30 packets with a scenario and it is like Clue or Cluedo is what it’s called in other countries, but it’s a much smaller, simpler mechanism. You’re going to visit eight or nine different locations. You’re going to learn a certain amount of information. And there’s one where it’s like an inverse situation, but you have to be smart enough to know that it’s the opposite of what it says. So, you get the reverse, you know, elimination logic. So, there’s a little bit of complexity, just the right amount. Also a time-constrained game, about 30 minutes. And it brings together Guess Who and Clue.
00:12:58
Jonathan: Wow.
00:12:59
Brad: And it’s entertaining. My kid loves it. It is 30 scenarios. So, every time some little kid has done some sort of prank or a crime and you’re solving them as the treehouse detective game. Yeah, my kid loves it. And a good birthday present. I think we got it as a gift. All three of those, fantastic gifts, fantastic entries to games in general.
00:13:13
Jonathan: Okay, I like it. Mine will be, I played Pandemic for the first time ever. I’m like a decade late to the party.
00:13:16
Brad: You already had COVID, man. I mean, everybody was trained. They were all ready to go prior to this.
00:13:20
Jonathan: This is blowing up 2016, 2020, but I’m glad in 2026 you deigned to explore it.
00:13:23
Brad: I did indeed. My kids got this for Christmas and yeah, it was cool. This was like a pupil has become the master kind of scenario where Molly and Anna were teaching this game to me. And I swear, it is a cooperative game, which is wonderful because my head was spinning. I mean, they had this advanced strategy and I’m just like furiously trying to keep up. It’s a wonderful game. And I can see how people absolutely love it. I need to play a couple more times, but yeah, it was really fun to play with them, A, and B, to have them teach me not only the basics of a game, but the real subtle strategy was very cool, very cool.
00:13:50
Brad: Yeah, that game’s a lot of fun. I think COVID kind of ruined it for me, but great game.
00:13:54
Jonathan: Anyways, now that we’ve had this pretty awesome sidebar, why don’t we get back to our show, which is actually about detours. What I wanted to communicate. As you get this space, right, you’re going to be able to finally have time to explore not just the priorities that have been put on you by maybe the job that you find yourself in or the school or the requirement, but truly maybe for the first time in five, 10, 15, or 20 years, what do I want to do with the next chapter? What, you know, you have one life and there’s an infinite number of things that you could learn, you could be good at, you could incrementally improve in, you could use to benefit your life in some way. And the normal paradigm just constrains you and locks you into something that says, hey, retirement, on the other side of retirement, that you get your gold watch and then you can go, you know, Florida, golf, love Florida, love golf, but we all get the shtick, right?
00:14:45
Brad: All right, so, well, I have actually a mixed relationship with golf, we’ll come back to that. All right, anyways, the point is, what does it look like? I was talking to this one fella and he was at his daughter’s graduation or something like that. And I was just talking about how I had learned, you know, a little bit of coding and here’s what I was doing. And he said, you know, I would have loved to have learned, he works for Apple actually now, middle management, works for Apple. He said, I would have loved to have learned Swift and I just don’t have any time, you know, I don’t know what I would do with it now. Why do you have to do something with it? Well, why does there have to be an outcome? Well, you know, why is it that you’re mandated to like, you picked a life when you were 16 or 17 and incrementally all of your time and options are sucked away, so you’re stripped in, and you’re like, you know, I would have loved to, but you know, that time’s passed and now I’m just like, really? Really?
00:15:55
Jonathan: Right, and so this is the thing, detours are the thing. So if anybody were to talk to me five or six years ago, they would be aware that, you know, I have certain skills in certain areas and incrementally I’ve been able to get better at this skill of podcasting and other things like this. But anybody that talks to me now would know that I’m very competent in development and that’s something that it’s interest led and using talent stacking, which we’ll talk about a little bit later, it’s something I’ve been able to pivot and use in various aspects of my life and my business. And I could go, Brad, that same pattern is observable in your own life, but you pick different detours.
00:16:32
Brad: Yeah, Jonathan, as you were talking about that with the guy from Apple, I was actually thinking about a friend of ours from the FI community who we met way back when at the original Camp Mustache that we went to in Florida in 2017. Her name was Emma and she actually, she was great and you probably remember her for this, where she was very dubious about us creating a podcast and she grilled us on it, grilled, to the point where we’re like, oh, I don’t know if this is such a good idea anymore, but quickly. I’m turning the question of my life decisions here, I clearly have made the wrong choice. But we did convince her and she’s like, oh, like that sounds like a really great idea, which was really wonderful.
00:17:24
Jonathan: And it’s interesting, I just saw a post of hers on Facebook from her local Barnes & Noble and Barnes & Noble named her novel, she came out with a novel last year, the Barnes & Noble pick of the month for the entire Barnes & Noble chain. I looked up her novel, it’s called Tilt and it has almost 2,500 reviews on Amazon. Usually get about one review per 100 sales, so that suggests she sold a quarter of a million books on Amazon, which puts her probably in the top one hundredth of a percent. Time Magazine named it one of the 100 must read books of 2025, she’s one of the most successful authors in America, like first time authors. And this is our friend Emma, who we met at a FI event nine years ago.
00:18:16
Brad: That’s what’s so cool is the people in the FI community have so many fascinating interests. And like you said, sometimes these are detours from a regular career, but you never know where it’s gonna lead you. Could you and I have ever imagined that we’d be podcasters on one of the biggest podcasts in the world for nine years? There’s no world where we could have imagined that. Emma put out a novel and it was one of the most successful books, period, end of story, for the entire year of 2025 in the world. That’s incredible.
00:18:43
Jonathan: I think the one thing that, the pattern there should be the result was not the issue, right? You can’t guarantee the result. There’s no one that’s going to guarantee 100% certainty that if you do this, it will be financially, economically, pat on the back, rewarded, guaranteed. If that is the case, you’re missing the forest for the trees. But what you start getting is one, you can have fun with the journey, right? You’re gonna hear that thing over and over again. And two, you can fail forward. The whole Thomas Edison thing, oh, I gotta, you know, I had a thousand failures. No, I know 1000 or 100 or whatever the number he used was, a hundred things that don’t work. And then we’re gonna nail it on the next one. You have way more information than the person that never tried. I’ve experienced that in a very real way over and over and over again, to the point that it just doesn’t phase me when something doesn’t work. Like, and imagine that, think about the difference. The person that says, you know, I tried to cook, but it was a disaster. I’m such a bad cook. Just, I’m just never gonna. Versus the person that’s like, all right, yeah. I wonder what the difference was between this.
00:09:49
Brad: So I would say it would be interesting to see if Zachy, if you had him, instead of playing the jujube version, kind of mosey him into the adult versions. I think you’d be very pleasantly surprised at his ability, but I hear you about the 20-minute thing, so I can’t solve for that. He’s ready, he’s ready. I just, it’s just, if you’re keeping track of points for yourself and for a child and for maybe, you need to have at least one or two other really interested people for that one, so there’s a little bit of setup. Casual players and families that are kind of tiptoeing their kids into board games where the kids haven’t already decided they are going to learn this, like, no matter what, you know what I mean? Like, there’s a difference there. Molly decided. When the person makes a decision of their own, it’s one thing. If you’re trying to ease them, and I remember asking you there, like, you know, Brad, do you ever, like, you know, kind of throw the game a little bit, give them a little table?
00:10:43
Jonathan: I literally would never, ever do that because I want them to. People do that? That’s a thing? Never in my household would that be. But also, not for nothing, but I want them to know that when they beat me and beat us, beat adults, that they did it through their own skill and ingenuity and intelligence. And, right? Like, people know when things are thrown and given to them. So, here’s what I do, and this is my balance. I’ve always had your words in mind. I’m like, all right, I don’t, I agree with you. I do agree. I just, I feel like your kids are going to be there regardless, and they had that hunger, and I feel like if my kid gets crushed too soon, you know, it’s not, oh, I’m going to come back and take you on, but he checks out. So, it’s kind of recognizing the psychology of your kid a little bit in this context, but here’s what I will say. I ask him ahead of time, you know, especially after he has the wheels, is this a teaching game or are we playing to win? So, if it’s a teaching game, you can ask me, should I do this, dad? Should I? And I might give you a little hint about, ooh, I don’t know. But if it’s not, because you’re not going to tell everybody, oh, I beat dad. Oh, in the teaching game, you beat dad? Oh, that game that we played, is that what we’re talking about? Yeah. You know, so there, he knows. He knows.
00:12:43
Brad: So, this kind of is what I found to kind of be a way to navigate this. The other game, I’ll just say it real quick, is junior detective. And what they did here is they put in 30 packets with a scenario and it is like Clue or Cluedo is what it’s called in other countries, but it’s a much smaller, simpler mechanism. You’re going to visit eight or nine different locations. You’re going to learn a certain amount of information. And there’s one where it’s like an inverse situation, but you have to be smart enough to know that it’s the opposite of what it says. So, you get the reverse, you know, elimination logic. So, there’s a little bit of complexity, just the right amount. Also a time-constrained game, about 30 minutes. And it brings together Guess Who and Clue.
00:12:59
Jonathan: Wow.
00:13:00
Brad: And it’s entertaining. My kid loves it. It is 30 scenarios. So, every time some little kid has done some sort of prank or a crime and you’re solving them as the treehouse detective game. Yeah, my kid loves it. And a good birthday present. I think we got it as a gift. All three of those, fantastic gifts, fantastic entries to games in general.
00:13:13
Jonathan: Okay, I like it. Mine will be, I played Pandemic for the first time ever. I’m like a decade late to the party.
00:13:16
Brad: You already had COVID, man. I mean, everybody was trained. They were all ready to go prior to this.
00:13:20
Jonathan: This is blowing up 2016, 2020, but I’m glad in 2026 you deigned to explore it.
00:13:23
Brad: I did indeed. My kids got this for Christmas and yeah, it was cool. This was like a pupil has become the master kind of scenario where Molly and Anna were teaching this game to me. And I swear, it is a cooperative game, which is wonderful because my head was spinning. I mean, they had this advanced strategy and I’m just like furiously trying to keep up. It’s a wonderful game. And I can see how people absolutely love it. I need to play a couple more times, but yeah, it was really fun to play with them, A, and B, to have them teach me not only the basics of a game, but the real subtle strategy was very cool, very cool.
00:13:50
Brad: Yeah, that game’s a lot of fun. I think COVID kind of ruined it for me, but great game.
00:13:54
Jonathan: Anyways, now that we’ve had this pretty awesome sidebar, why don’t we get back to our show, which is actually about detours. What I wanted to communicate. As you get this space, right, you’re going to be able to finally have time to explore not just the priorities that have been put on you by maybe the job that you find yourself in or the school or the requirement, but truly maybe for the first time in five, 10, 15, or 20 years, what do I want to do with the next chapter? What, you know, you have one life and there’s an infinite number of things that you could learn, you could be good at, you could incrementally improve in, you could use to benefit your life in some way. And the normal paradigm just constrains you and locks you into something that says, hey, retirement, on the other side of retirement, that you get your gold watch and then you can go, you know, Florida, golf, love Florida, love golf, but we all get the shtick, right?
00:14:45
Brad: All right, so, well, I have actually a mixed relationship with golf, we’ll come back to that. All right, anyways, the point is, what does it look like? I was talking to this one fella and he was at his daughter’s graduation or something like that. And I was just talking about how I had learned, you know, a little bit of coding and here’s what I was doing. And he said, you know, I would have loved to have learned, he works for Apple actually now, middle management, works for Apple. He said, I would have loved to have learned Swift and I just don’t have any time, you know, I don’t know what I would do with it now. Why do you have to do something with it? Well, why does there have to be an outcome? Well, you know, why is it that you’re mandated to like, you picked a life when you were 16 or 17 and incrementally all of your time and options are sucked away, so you’re stripped in, and you’re like, you know, I would have loved to, but you know, that time’s passed and now I’m just like, really? Really?
00:15:55
Jonathan: Right, and so this is the thing, detours are the thing. So if anybody were to talk to me five or six years ago, they would be aware that, you know, I have certain skills in certain areas and incrementally I’ve been able to get better at this skill of podcasting and other things like this. But anybody that talks to me now would know that I’m very competent in development and that’s something that it’s interest led and using talent stacking, which we’ll talk about a little bit later, it’s something I’ve been able to pivot and use in various aspects of my life and my business. And I could go, Brad, that same pattern is observable in your own life, but you pick different detours.
00:16:32
Brad: Yeah, Jonathan, as you were talking about that with the guy from Apple, I was actually thinking about a friend of ours from the FI community who we met way back when at the original Camp Mustache that we went to in Florida in 2017. Her name was Emma and she actually, she was great and you probably remember her for this, where she was very dubious about us creating a podcast and she grilled us on it, grilled, to the point where we’re like, oh, I don’t know if this is such a good idea anymore, but quickly. I’m turning the question of my life decisions here, I clearly have made the wrong choice. But we did convince her and she’s like, oh, like that sounds like a really great idea, which was really wonderful.
00:17:24
Jonathan: And it’s interesting, I just saw a post of hers on Facebook from her local Barnes & Noble and Barnes & Noble named her novel, she came out with a novel last year, the Barnes & Noble pick of the month for the entire Barnes & Noble chain. I looked up her novel, it’s called Tilt and it has almost 2,500 reviews on Amazon. Usually get about one review per 100 sales, so that suggests she sold a quarter of a million books on Amazon, which puts her probably in the top one hundredth of a percent. Time Magazine named it one of the 100 must read books of 2025, she’s one of the most successful authors in America, like first time authors. And this is our friend Emma, who we met at a FI event nine years ago.
00:18:16
Brad: That’s what’s so cool is the people in the FI community have so many fascinating interests. And like you said, sometimes these are detours from a regular career, but you never know where it’s gonna lead you. Could you and I have ever imagined that we’d be podcasters on one of the biggest podcasts in the world for nine years? There’s no world where we could have imagined that. Emma put out a novel and it was one of the most successful books, period, end of story, for the entire year of 2025 in the world. That’s incredible.
00:18:43
Jonathan: I think the one thing that, the pattern there should be the result was not the issue, right? You can’t guarantee the result. There’s no one that’s going to guarantee 100% certainty that if you do this, it will be financially, economically, pat on the back, rewarded, guaranteed. If that is the case, you’re missing the forest for the trees. But what you start getting is one, you can have fun with the journey, right? You’re gonna hear that thing over and over again. And two, you can fail forward. The whole Thomas Edison thing, oh, I gotta, you know, I had a thousand failures. No, I know 1000 or 100 or whatever the number he used was, a hundred things that don’t work. And then we’re gonna nail it on the next one. You have way more information than the person that never tried. I’ve experienced that in a very real way over and over and over again, to the point that it just doesn’t phase me when something doesn’t work. Like, and imagine that, think about the difference. The person that says, you know, I tried to cook, but it was a disaster. I’m such a bad cook. Just, I’m just never gonna. Versus the person that’s like, all right, yeah. I wonder what the difference was between this and what the target was.
00:19:03
Jonathan: I wonder why I missed. I wonder how I could tweak that and move it forward. Are you collecting data for what you’re going to do next? Or are you making identity statements about why you could’ve, woulda, shoulda not done it?
00:19:13
Jonathan: Yeah, I mean, that is the epitome of fixed mindset versus growth mindset, right? If fixed mindset is I am X, it could even be a theoretically positive thing. I am intelligent. But what that actually does when people have that fixed mindset is they usually don’t challenge themselves because they don’t want anything to dispel the myth of this fixed mindset. So I am intelligent for a 15 year old means, hey, maybe I, and they’re not saying this overtly, but maybe I shouldn’t go in that AP statistics class or AP calculus class because I might find out and I might prove to everybody that I’m not intelligent. But whereas if you have a growth mindset, you just want to learn, you wanna iterate, you wanna test, you wanna fail, frankly, because you know that it’s gonna move you forward.
00:20:06
Brad: I can’t think of any success in my life that didn’t come with just a whole host and litany of failures, but you fail forward. You don’t just give up at the first sign of distress. You learn something. And Jonathan, how many things have we tried together and many things work, many, many, many things don’t, but you don’t sit there and cry about it. You move forward and you iterate and you try something else. And there’s a third category. Some things don’t work yet, right? Some things you make that first attempt and it’s still flatlining and it doesn’t have a pulse, but you take the pivot, you move where the opportunity is, and then something you did over here ends up circling around and you end up using it over there. And that’s actually what I’ve personally experienced in particular, if you think about, you know, with ChooseFI and my own arc to development and various other things, I have gone and tried something and failed in fabulous fashion, taken that and moved to another area and learned a new skill based on the window that opened up to me.
00:21:01
Brad: And then with the benefit now of a couple of years in the space, going back with fresh eyes to take a look back at, you know, things that we missed in the first pass. How can we have a crowdsource show? I mean, look at where we are now and what the goal is with what we’re trying to achieve now. I would say there has never been a podcast or radio show even that has the possibilities of achieving what we said was our mandate early on, crowdsourcing personal finance. There’s never been anything like this that there is right now. And that we had the idea for it, that wouldn’t it be cool if back in 2019, 2020, we couldn’t pull it off. Were we failures? Or were we just a little bit ahead of ourselves? And now we’re catching up.
00:21:44
Jonathan: And this idea that’s still with us, it still keeps us up at night, that this show needs to exist, that it needs to be here. You know, we’re fortunate enough to still have the opportunity to deliver on that nine years later. And you’re here for it. You’re a part of it, you know. And in upcoming episodes, you’re truly going to be contributing to it, crowdsourcing personal finance.
00:22:01
Brad: So Jonathan, I’m thinking about our timeline here. I think if I have this right, next week we will be releasing our goals for 2026 episode, which is gonna be really our first stab at this new interactive approach. We’ve been collecting feedback up to this point. We’ve been pouring through them. We started working on putting it together. Next week we get to share it with everybody.
00:22:24
Jonathan: Yeah, I’m super excited about that. So yeah, we launched this on January 5th when we came out with our first episode with you back on the podcast. And if you want to be part of the show, you just always log into your account. Obviously a free account, choosefi.com/login. And right at the top, there’s gonna be, be part of the show, calls to action, get involved. And we’re gonna have our recurring comment segments like frugal wins of the week and travel rewards and all sorts of things like that, life hacks, et cetera. But then there are gonna be very timely ones like this big goals for 2026.
00:23:02
Brad: This is a really fun one. We’ve had dozens of these come back to us. Jonathan, you and I are gonna talk about our goals, which I’m very excited about. And it’s gonna be a great episode. And that’s what’s cool about crowdsourcing this is we can just keep having these different calls to action. You can always, always, always be part of the show. Just log into your account and send us feedback. Send us feedback on the episode. Jonathan has in the feed there when you log in each episode. And we have, you can give feedback on the episode. We wanna touch on these things. If there are things you agree with, don’t agree with, you have questions, you want further clarification, we can do that. We can get our friends and colleagues to give us voicemails and additional info. This is all doable. You are part of this community. You’re the lifeblood of the community. And we need you to make it happen.
00:24:02
Jonathan: I think this is a really important point because we’re going so hard on the crowdsourcing this year. This is going to be a weekly recurring thing where we’ll be in this loop of asking for feedback or sharing your feedback. And we’ll literally be doing some of them in the same time where we’re sharing the feedback we have on a prior mention and then at the same point, letting you know about the next thing. But here’s the big one. The where are they now? Or how can I follow up with this person? Or I have so many more questions. We wanna make that very easy. But there’s different types of feedback. Some, the person leaving the feedback wants other people to reach out. They want other people to connect. And some for various reasons, privacy, et cetera, sensitive information, they don’t want that connection. We’re using this platform for both, but we’re giving you the choice how you wanna give us the feedback.
00:25:00
Brad: Do you want people to follow up with you if they have more questions or they have answers? Do you want that directly? Or would you like for that connection not to be made? Do you wanna preserve the anonymity? We are okay with you interacting with this platform to show either way. We wanna respect your privacy, but still give the community the benefit from that ability to share with you. So when you leave your feedback, you’ll have the option there. If you don’t want it to be linked to your account, or you would rather preserve your anonymity when you’re sharing it, maybe because you’re sharing raw numbers and you’re whatever, or maybe because there’s something sensitive in there, et cetera, you will have the option just to request anonymity. But conversely, if you want accountability and you want people to connect with you and reach out and give you more information and just cheer you on the way on this detour maybe that you’re on, don’t request anonymity. Let us connect them with you so that we can cheer each other on and we can help you see the goals that you’ve set for yourself.
00:25:51
Jonathan: I think it’s gonna be a really good mirroring and it’s a balancing act. We’re trying to be very respectful of the privacy that maybe they might want, while at the same time, really encouraging this thing where the community encourages the community. And we just get a chance to facilitate this conversation, which is so much fun. It really is.
00:25:55
Brad: All right, Jonathan, incremental gains. We’re gonna get back to our list.
00:25:57
Jonathan: Just part two, really part two, Brad.
00:25:58
Brad: You’re welcome, you’re welcome.
00:25:40
Jonathan: I wrote this down. I’m just kidding, I’m just kidding. Last time we covered 14 incremental gains, little things that you didn’t know that you didn’t know. And we’re gonna see if we can do slightly better. We’re already 30 minutes in. We’ll see, I don’t think so. We can do a little bit better than 14 this time around. We have over a hundred on our list. So we’ll see how far we get and we’ll just have fun with this today. Brad, you kick things off.
00:26:08
Brad: Okay, real quick, at the top, what’s your FI number? Your FI number is your annual expenses multiplied by 25. This works for any amount of annual expenses. We’re not prescriptive on you have to spend X number of dollars per year. Just whatever your life costs, multiply by 25. So if your life costs $60,000 a year, your FI number is 1.5 million, okay?
00:26:30
Jonathan: Now, another really important aspect of this is knowing your net worth, okay? When you get started with FI and every step along the way, I do this every single quarter, is I calculate my net worth. So I add up all of my assets. I just log into every account, jot them down. I take the market value of my home. That’s on my asset side, my liabilities. You have to include your liabilities if you’re gonna include your assets, right? So my mortgage, any kind of loans or debts that I have, and you just take all your assets, you subtract your liabilities, that comes out to your net worth, okay?
00:27:01
Brad: And then finally, in this little triad here, being rich and being wealthy is not about your income. It’s about your net worth, okay? So we know plenty of people who make 300,000, $500,000 a year, something like that, but they spend every dollar. That person is not wealthy. Whereas contrast that with, we think this is the replicable path for middle-class people to get wealthy, FI, and if you’re making 50, 60, $70,000 a year, but you’re saving 30%, 40%, 50% over a five, 10, 15-year period, you are gonna be exceptionally wealthy and you’re going to reach financial independence. Which person would you rather be? I think it’s a no-brainer.
00:27:46
Jonathan: Yeah, and as you listen to this, there’s gonna be reasons that one setup or scenario that we present is invalidated for you. Well, that’d be great if I started when I was four years old or something along those lines. There’s a path for you. No matter where you find yourself, there is a path. You have your own path to financial independence. And there are people that, you just gotta remind yourself of this because sometimes it doesn’t feel that way. Someone has had it worse than you have it with more obstacles objectively than you have and has achieved financial independence. Like, okay, great, if I could find that. Well, you’re in the right place. This is why you’re a part of this community.
00:28:22
Brad: So we can start through the benefit of crowdsourcing this show. We can start to highlight, and I think ChooseFI has done a pretty admirable job over the years, really trying to facilitate that to the degree that we can. We’re gonna try to do even more. So if you’re thinking that every case study that you run has to do with a dual income family, married filing jointly in XYZ, and yep, I hear you. I hear you, but you know, at some level, you know it, but I’ll just remind you of it, that absolutely there are individuals that are not married, not filing joint, that are single income, that are making less than you make that have achieved financial independence. And so where you are now is a snapshot, but this is a moving picture, right? This is a snapshot of where you are in time. You have options.
00:29:10
Brad: The equation is very simple. It’s income and it’s expenses. You have a difference and you have choices around what you can do with the difference, but you have a lot of control over the various sides of that equation. We can spend time talking about, okay, you’re making 40K, you’re making 60K. We have had an incredible number of people report back to us that they used a single tactic mentioned on this show and got a 25K raise, a 10% raise, a 20K raise. Let me just point out to you that if you could get to the point where you had a couple of years of expenses just saved up, we’re not talking about 25 times your annual expenses, we’re saying you could cover your cost of living for the next couple of years, you could plausibly completely reset your life and pick a different path. Very plausibly, absolutely.
00:29:53
Brad: And I think part of the journey to FI clearly is not about deprivation mindset, it’s not about being a miser, but on some level being frugal, there is a power to it because like we’ve talked about repeatedly, small things add up to big things. So we are not prescriptive over what you can spend on. We are valuous. In fact, spend on what you value. And I think you should cut ruthlessly where you don’t. But I think part of this is most of us don’t even know what we’re spending money on. I think you need a periodic expense audit. I think you need to go through what you’re spending on a three-month basis and really look at it.
00:30:29
Brad: I think a lot of us just see our credit card bill at the end of the month and don’t pore into every line. And I’m not saying you need to do this every day of your life, but one time a year, do an expense audit and just have a sense of, Hey, are there things that I’m not utilizing anymore? Are there recurring subscriptions? Are there other things that may be in this season of life I just don’t need? Or maybe I don’t ever need. I think it’s really, really critical to get a handle on what does my life and it starts very granularly with taking that action and doing it.
00:31:01
Jonathan: I’m always very impressed by people that can say granularly, granularly, innocently, loving it.
00:31:09
Brad: Well done, sir. Well done. There was a little fumble there. I was like, will he get all the syllables?
00:31:16
Jonathan: Do you want to know what, did I ever tell you what my, the one word that I avoid is particularly? I can’t, I cannot, I had to say it. So I cannot, I’m incapable of saying that word.
00:31:28
Brad: You will human is particularly.
00:31:31
Jonathan: Yeah, it’s very hard.
00:31:32
Brad: So you’ll never hear me actually say it.
00:31:35
Jonathan: Well, you went with granular though.
00:31:36
Brad: So yeah, the expense audit is brilliant. And I think one of the things I’d like to do—we’re not there yet, but we’re going to get into the habit of this—is I think as a community, I’d like to see us start to do some version of our expense audits together. That way we could kind of benefit from understanding various costs, livings in various parts of the country and not every line item, but there’s particular things that I think are really useful. Like what’s the average amount spent for, you know, a family of four in California versus Virginia on food?
00:32:02
Jonathan: These are the types of questions that if you could kind of get to the heart of that, you could really start to know, do I have an expense problem or should I be putting my energy into income? I heard this line recently, I was talking with Justin Edwards, who’s the host of the SAS, that app podcast. He interviewed me and we recorded an episode that came out just at the end of 2025 called, I think they ended up naming it “Cockroach Mode,” but, and it’s a great title, had a lot of fun with that.
00:32:24
Brad: That’s awesome.
00:32:27
Jonathan: But basically the idea for it was we were talking to a development community, but I was definitely pulling in the life lessons that have stuck with me from, you know, being around this financial independence community for as long as I have now. And as we were going through my story, he reminded me of, I believe it’s the Jim Collins quote that says you can’t shrink your way to greatness. Now we were talking about it through the lens of cutting expenses and that was, uh, you know, it is a great phrase, but it’s kind of halfway true.
00:33:02
Brad: Right.
00:33:02
Jonathan: And all of us know this. Yes, you can’t shrink your way to greatness, but you also can’t grow if you’re bleeding, you should probably look.
00:33:10
Brad: Yeah, I totally agree. I think really drilling down on expense audit. Three other things I had here on the list were about very specific expenses. So for instance, the library, Jonathan, we’ve always said ChooseFI friends of the library, right? This is a way I love reading. It’s one of my absolute passions. My kids love reading. We would spend many, many, many hundreds of dollars a year at Barnes and Noble or Amazon, but instead we go to the public library. This is a nice frugal analog for instead of buying and then accumulating, go to the library and you’d be shocked at what your public library might even have. You might get state park passes, or you might get other things that you just had no clue. Just ask the librarians. They want to help. They love it when you go in there and ask.
00:34:04
Jonathan: And this harkens back way back to Liz from Frugal Woods when she was on the podcast way back in episode 12, right? She talked about free entertainment options being everywhere. This is especially true in cities. People always asked her, “Oh, Liz, you and Nate live in Boston. That must be so hard to pursue the path to FI.” And she’s like, “Well, actually we don’t need cars.”
00:34:20
Brad: Yeah.
00:34:20
Jonathan: We spend more on rent than we would, but we don’t need cars. We can get free activities and entertainment, especially with all the dozens of universities in Boston. But this translates everywhere for free every single night of the week. It’s only limited by our imagination and our actual ability to get out and do this. I think that’s just, I love when things are rethinks and yeah, many of us who are listening to this don’t live in cities, but the same holds true. There are free things happening in your local area every single night. Why not just explore and do something different?
00:35:01
Brad: And finally, Liz had on that same episode, the 72-hour rule, she called it, which is basically, it’s just, it’s like the Viktor Frankl quote, putting space between stimulus and response where, okay, I’m going to go and buy something. And it’s so easy. Jonathan, you know, that’s gone Amazon. It’s one click in most cases, maybe two or three at the absolute most. You could do that in seconds and not even think about it. What if you put a little bit of space between that stimulus and the response?
00:35:25
Jonathan: Exactly.
00:35:26
Brad: She talked about this holding period, this waiting period, put it in your cart, put a timer on your phone or do I put a little reminder in your calendar, come back in 72 hours and see if you still want it. That’s a nice way to decide. And then you will know for darn sure if you actually want it 72 hours later. If you do buy it gleefully, this is not the deprivation show by any means.
00:36:01
Brad: Alright, so I talked to Jonathan just before we got on this call and I said, you know, anytime we reference an older episode now, potentially up to six or seven years later, we need to just pause and just point out that that has factored into essential listening, right? There’s context there that will serve you now. And actually with this particular episode, Brad went out of his way to suggest to me that we actually need to extract multiple clips from that episode because in his words, “It’s literally the best thing that’s ever been created on this topic.”
00:36:31
Jonathan: And I’ll just say in this particular context, it’s not because Brad and I had any of the words; they were all Liz, but she was a phenomenal spokesperson for frugality and through the lens of what we’re all talking about in this conversation.
00:36:44
Brad: So that is episode 12 of our podcast. I went ahead and looked it up. Brad normally does this, so I took it away from him, but I’ll give you a little life hack here. We have a few patterns that have served us well since we started, there’s a lot of things that have just kind of been, you know, not discarded, but we just haven’t maintained them. And this one is a very good pattern. Anytime we reference an episode, there’s a shortcode to go to that episode. Now, obviously you’re in a, many of you are listening in a player of choice and that’s completely fine. Just go look at it in your podcast player, but choosefi.com/012. It will always be three digits at minimum. So if we get to episode a thousand at some point in the future, you know, and then you’re at four, obviously, but for episode 12, I was like, I think we’re going to make it to a hundred episodes, Brad, let’s just go ahead and proactively put the zero in there.
00:37:12
Jonathan: Exactly.
00:37:13
Brad: And we said a lot more words, right? So it’s like a Y2K scenario.
00:37:17
Jonathan: That’s right.
00:37:18
Brad: I don’t want to break the computers.
00:37:19
Jonathan: Can’t break the computers.
00:37:20
Brad: So episode 12, and it was on frugality, and she just did an amazing job on that episode.
00:37:29
Jonathan: So Brad, we kind of got smarter about this as we realized we were going to lean in and actually do as many of these as possible. And so we’ve grouped a bunch of the other ones, and we just want to talk about the 401k for a second. Now I know we’re speaking to potentially an audience that’s with us around the world. And increasingly as the audience has grown, we try to be mindful of that. And we try not just to have 40 episodes in a row talking about Roth and you’re in Canada and you’re like, come on guys, just can we move on please? But you know, bear with us here for a second.
00:38:03
Brad: The 401k, the 401k is the retirement vehicle that most of us are familiar with. It’s not by any means your only payroll deferral option. We’ll talk about some others, but the 401k is the one that if you are an employee, W2 wages, you’re likely familiar with this. And what we want to say, first of all, is if you are offered a match, maybe in contrast to fixed contributions, et cetera, but a match, so you have…
00:38:23
Brad: The option to contribute or not. Whether you max out your 401k or not is a different conversation, but you always, always… I’m trying to think of an asterisk with some case, but you always contribute enough to get the match.
00:38:40
Jonathan: Yeah, I think this is important. The obligatory caveat is we don’t give financial advice, but when talking to anybody in our own lives, I cannot imagine a scenario where I don’t say you have to get the match. It is in no uncertain terms part of your salary. Your employer has said, if you put X percent… you have to find out for your company what that means, but it might look something like, “We’ll match 50 cents on the dollar.” Really, 50% of your first 6% of your contributions, which basically means, okay, let’s say you make a hundred thousand dollars, so you put in 6% of your salary to your 401k, $6,000. They’re going to match that at 50%. So they’re going to give you $3,000 to go into your 401k.
00:39:25
Brad: No, I’m good. Could you imagine telling your employer? “Hey, part of my salary, you’re going to give me this $3,000, but I’m going to say no.”
00:39:32
Jonathan: But Brad, wouldn’t that lower what I’m bringing home by $3,000 though?
00:39:36
Brad: No, this is totally free money. This has nothing to do with anything. Obviously, your contributions that you put in the $6,000 come out of what’s going to end up in your checking account, but that is also a pre-tax contribution. So it’s going to lower your income that goes on your tax return every year.
00:39:54
Jonathan: So this is a very important thing. We believe very strongly here in maximizing as much as you possibly can your pre-tax retirement vehicles, like a traditional IRA, a 401k, or a 457b. These types of accounts give you a tax deduction in the current year. I think there’s a very high probability that, through the powers and the wonders of FI, you’re going to be able to pull most of this money out either tax-free or pretty darn close when the time comes.
00:40:27
Brad: Because there are massive standard deductions on our tax returns and lots of really interesting ways to do this. For me, I am not a big fan of the Roth accounts. I know that’s kind of the general personal finance wisdom, but I think for people pursuing FI, we’re a little bit different. We’re a little bit smarter. For most of us, traditional retirement accounts are going to be a massive benefit. Long story short, your 401k match is absolutely free money.
00:41:05
Jonathan: So anybody listening to this is probably thinking, “Didn’t you talk very favorably about the Roth earlier?” I think you need to think about it through the context of what we’re saying here. In earlier discussions about emergency funds, we pointed out a misconception that if you put money in a retirement account, you can’t access it till 59 and a half. In the case of a Roth, you can get contributions out, not gains, but contributions out tax and penalty-free. That’s yours. You can take it back if you want. There’s an undo button if you want to.
00:41:31
Brad: Right, but what we’re talking about here is tax optimization. If you think about the phases of financial independence that we’ve discussed, you discover financial independence and learn how to calculate an FI number. You then become aware of your number, control it by putting a plan in place, and rapidly move into this concept of tax optimization. This leads us to understanding the difference between marginal tax rates and effective tax rates.
00:42:27
Brad: In our graduated income tax system here in the U.S., we have tax brackets. Most people think that being in a certain tax bracket means all dollars are taxed at that rate, but that’s incorrect. If you just Google “2026 income tax brackets,” you will see the different dollars are taxed at varying percentages. So the first segment might be taxed at 10%, then 12%, and finally 22% for the remaining dollars.
00:43:19
Jonathan: Exactly. And how you determine your effective tax rate is by dividing your tax liability by your total gross income. So if your federal tax liability is $8,000 on a $100,000 income, your effective tax rate is 8%.
00:44:01
Brad: This gives you a much more accurate representation of your tax burden than just looking at your marginal rate. It’s crucial for understanding how various investment accounts, like the 401k and Roth IRAs, play into your taxes.
00:45:23
Jonathan: This is a great opportunity to mention another essential episode—the one about free money with Millionaire Educator. He talks about the 457 account, which helps understand those early marginal tax brackets.
00:46:01
Brad: Episode 13. That episode is essential listening, especially for public employees, as they often have access to both 401k and 457 accounts, which provide options for reducing taxable income.
00:47:15
Jonathan: And remember, when you separate from service, you can access the 457 money before 59 and a half without penalty. That’s a huge contrast to the 401k.
00:48:03
Brad: Exactly, and it’s the beauty of FI. We look at everything differently and understand the rules of the game to our advantage. There are plenty of ways to access your money before 59 and a half, as we’ve discussed in previous episodes.
00:49:02
Jonathan: We’re not claiming that Roth IRAs are bad; rather, we’re highlighting how valuable it is to access contributions tax and penalty-free. For many in the FI community, a traditional IRA or 401k can often be more advantageous.
00:49:50
Brad: The tax deduction today. So yeah, as I showed in my newsletter a couple of years ago, Jonathan, you and I will go through a case study, so I’m not going to try to prove the math now, but it’s really fast. It’s fascinating because what I showed is that it actually, assuming the tax rate is the same on the front end and the backend, let’s say that marginal bracket is the same 22%. It actually is the same amount. The answer is the exact same, whether you pick Roth or traditional, and there is a difference in what you actually are going to contribute because the difference between pre-tax and post-tax that’s outside the scope of our zipping through this thing now, but we are definitely going to do a case study on this.
00:50:32
Brad: Yeah, man. I don’t know, you know, at this point, I’ll be honest. I think all of us, you shouldn’t necessarily try to agree or understand based on what you’ve heard so far. But, but Brad’s really good at these numbers and he notices these patterns. And so it sounds like we have our work cut out for us to make sure that we can turn this into a story and we’ll be doing that in the next few weeks. And we’ll make sure that we have our numbers lined up, but I can see it. He’s got the bid on this one and there’s something here.
00:51:02
So the main thing I think for you to just take this away is really the difference between effective and marginal because ultimately level one confidence is not realizing that there’s a difference, right? So then level two is realizing and optimizing the point. And this is, this is helpful. I don’t really care so much about marginal tax bracket. What I care about at the end of the year is how do I lower my effective tax rate? Like which one of those, what’s going to lower my effective tax rates? You want to make moves that lower the percentage of that a hundred dollars that went towards taxes.
00:51:39
Brad: And you want to look at the tools you have available to do that. But then you go farther, you go Sean Mulaney, FI tax guy style. And this is where all of us need to end up really because we’re long-term thinkers. We don’t actually even care about the effective tax rate at the end of the year, what the FI tax guy would tell you. It’s an obvious point. As soon as you hear it, is that you care about the lifelong tax burden. What move should you make today?
00:52:01
In light of the fact that forget this year, let’s say you paid a higher tax rate this year on XYZ income, but you were going to be paying taxes over your entire working career. We care about when you look back, how did you optimize that income to help you achieve your goals? And so that is like graduate level stuff. And that’s comprehensive tax planning. And it’s kind of like, here are the different when we say, when we say, hey, pay attention to this right for you, but not for you, there’s nuance here because you need to think about what detours are you going to take and when are you going to say, Ooh, this now fits into my plan.
00:52:43
Jonathan: And Brad, what I’m thinking about in particular is when we say, you know, 401k versus Roth, there is a point where we’re like, man, they’re actually at a pretty good tax rate right now. You really think you’re going to beat this down the road. And so, you know, you might look at the longer strategy of, you know, 10 or 12%, but I’m thinking about your daughter and, Hey, we had money and she put it in a Roth IRA, what do we think about, you know, the marginal tax brackets for 2026? They go up a little bit each year, but 2026, the 10% marginal tax bracket is the first zero to 12,400 for single filers, and it’s up to 24,800 for married filers. That’s a 10% tax rate. And then the 12%, which is this random tiny little addendum right before we go to 22, it goes up to 50,000 for the single filers and it goes up to a hundred thousand for the joint filers.
00:53:29
Brad: So that’s a lot of numbers and I get it, but is there a marginal tax rate that I’ve just mentioned 10 or 12% that would sway you back the other way?
00:53:38
Jonathan: Yeah, it’s a good question and it certainly does differ on your circumstances, but yeah, I mean, if you can lock in 10% or 12%, I think there’s a reasonable case to be made that you just pay the tax. But that said, Jonathan, honestly, so here’s the thing. We never know the future, right? Like that ultimately at the heart of this is we don’t know the future. So you’re just betting on the future.
00:54:01
Brad: Anybody who’s picking a Roth based on, again, the thing that we’ll show in the future is they are picking that income tax rates are going to be higher when they pull that money out because they are locking in a current rate. That is literally what you’re doing, whether you realize it or not. And frankly, you probably don’t; you’re making a bet on the income tax rates. Very simply now under the current confines of our graduated income tax system, I think, and especially the massive standard deductions that we get. I think there’s going to be a lot of quote unquote, free money.
00:54:45
Brad: I think for people in the FI community who have their expenses under control, when they reach FI, they’ve paid off a mortgage, their life doesn’t cost that much, I think they’re going to be able to pull almost all of their life expenses out tax-free from traditional 401ks. And also frankly, and this is another thing is tax gain harvesting. I’ll talk about this in a minute, but I think between those two, being able to pull out maybe Roth contributions or 457b contributions, I think there’s a very high likelihood you’re going to pay $0 in federal tax ever.
00:55:07
Jonathan: So that’s why it’s even not a slam dunk for me at 10 or 12%. I think for most people, it would be a slam dunk.
00:55:12
Brad: No, but this is great. So first of all, nobody’s saying you’re making a financial mistake by contributing to your Roth when you’re at a 10 or 12% marginal tax bracket. Like that’s just, beyond that, I think probably some of you are really surprised that Brad didn’t just jump on. Yes. And that should give you pause and slow you down and say, huh. Cause it’s easy just to say, oh, it’s simple. And I don’t have to worry about taxes on this money again, but do you decrease your option, your optionality down the road? There’s a lot here.
00:55:36
Jonathan: I mean, we’re basically at this point, we’re showing you the table of contents for what we’re going to get into over the next year. You know, every single one of these topics deserves its own episode. We haven’t given it justice. We haven’t broken out the spreadsheets yet. We’re still in this back of the envelope, this dog-eared back of the envelope and using the same one for seven years, you love my back of the envelope.
00:56:01
Brad: I did do an episode with Cody Garrett, episode 517 on understanding capital gains strategies. You and I are going to do a follow-up to that for sure, because this is a really important one: there is a 0% federal capital gains tax rate. And this is on your traditional brokerage account.
00:56:12
Jonathan: Okay. So let’s say you have stocks, ETFs, mutual funds, et cetera, in your regular brokerage account. And you sell them that incurs a capital gains tax. Okay. If they’re held for more than a year, it’s a long-term capital gains. And normally they’re really preferential rates on these. So we, as investors get showered upon just benefits showered on us generally. So we only pay for most people, 15%. But, but, but those in the FI community, most of us are going to pay 0% tax on our capital gains rate.
00:56:48
Brad: Because as Cody showed in that episode, if you’re married filing joint, your income for 2026 can be up to your taxable income. This is after your standard deduction and other items. So the standard deduction, I think for 2026 for married filing joint is 32,200 or something like that. So we’re talking, the taxable income is 98,900.
00:57:11
Jonathan: Okay. So let’s say you had no other income. You had $130,000 of long-term capital gains. That’s just the game. That’s not the sale price. That’s not the fair market value. That’s not what’s deposited in your bank account. That’s just the difference between what you bought it for and what it’s currently worth. 130,000. You say, “Hey, government, please tax me.” And they say, “Yeah, okay, we’ll tax you.” That’s $0, please.
00:57:35
Brad: Okay. So the FI community wins. If we let ourselves win, if we don’t listen to the bozos who don’t know anything about the FI community who think Roths and taxes are going to be so expensive and, oh, it’s horrible. We win at life. This is what we do. And we have so many ways to win, Jonathan. And I just, for people that are going to get mixed up in there, but you might have heard tax gain harvesting. This is money that is outside of your retirement accounts, right? So just for clarity and making sure we’re all on the same page.
00:58:05
Jonathan: But the point is the table of contents of this book of financial independence is awesome. The detours are incredible. It’s compelling. You do not know what you don’t know, but what you have discovered, what you have walked into is the stealth wealth community. And what you need to realize is when you’re living an entry-level, middle-class lifestyle that slots in with everyone else, but then on top of that, you have paid off cars. You have a paid off mortgage. You’re not financed up to the eyeballs on everything. Suddenly your life can look like everyone else’s at a tiny, tiny fraction of what everyone else is spending.
00:58:57
Brad: And that gives you opportunities because the tax code incorporates a pretty massive safety net because it recognizes that everyone’s in debt up to their eyeballs. So just think about that. If you can decrease, if you can crush how much it costs for your core expenses, right? Crush it ruthlessly, that gives you optionality with all the other things that you want to add back in. And it gives you the luxury, the privilege of kind of floating around the tax code, making choices based on where you are and what it is that you want to do. You want to preserve options.
00:59:27
Jonathan: Brad’s just highlighting via this table of contents entry, just a few of those that you need to be aware of. So today our title was detours and Brad, I’m telling you, man, this table of contents is looking attractive. I could do more of these, but I can’t do a part three, so it’s going to have to have a real title, but I want to keep the dialogue going.
00:59:38
Brad: So next week we’ll be breaking from this. We’re going to be doing the goals episode that we’ve been collecting feedback on, but we do want feedback on this episode. We want you to lean in. What were your aha moments? What would you like to see us talk about? In addition to this, what would you like to see some highlighter on? Where would you appreciate seeing the nuance? What would you like to bring to this conversation?
01:00:02
Jonathan: And the place to do that is to be a part of the community. You’re just gonna go to choosefi.com/login. You’re saying, “Oh, I don’t have an account.” Okay, create one. Go to choosefi.com/login, create an account. We do have an app now. I failed to mention this before, but this was a big push. And I had a lot of help from people in the community. There is now a ChooseFI app that you can find.
00:49:50
Brad: The tax deduction today. So yeah, as I showed in my newsletter a couple of years ago, Jonathan, you and I will go through a case study, so I’m not going to try to prove the math now, but it’s really fascinating because what I showed is that it actually, assuming the tax rate is the same on the front end and the backend, let’s say that marginal bracket is the same 22%. It actually is the same amount. The answer is the exact same, whether you pick Roth or traditional, and there is a difference in what you actually are going to contribute because the difference between pre-tax and post-tax that’s outside the scope of our zipping through this thing now, but we are definitely going to do a case study on this.
00:50:32
Brad: Yeah, man. I don’t know, you know, at this point, I’ll be honest. I think all of us, you shouldn’t necessarily try to agree or understand based on what you’ve heard so far. But, but Brad’s really good at these numbers and he notices these patterns. And so it sounds like we have our work cut out for us to make sure that we can turn this into a story and we’ll be doing that in the next few weeks. And we’ll make sure that we have our numbers lined up, but I can see it. He’s got the bid on this one and there’s something here.
00:51:02
Brad: So the main thing I think for you to just take this away is really the difference between effective and marginal because ultimately level one confidence is not realizing that there’s a difference, right? So then level two is realizing and optimizing the point. And this is, this is helpful. I don’t really care so much about marginal tax bracket. What I care about at the end of the year is how do I lower my effective tax rate? Like which one of those, what’s going to lower my effective tax rates? You want to make moves that lower the percentage of that a hundred dollars that went towards taxes.
00:51:39
Brad: And you want to look at the tools you have available to do that. But then you go farther, you go Sean Mulaney, FI tax guy style. And this is where all of us need to end up really because we’re long-term thinkers. We don’t actually even care about the effective tax rate at the end of the year, what the FI tax guy would tell you. It’s an obvious point. As soon as you hear it, is that you care about the lifelong tax burden. What move should you make today?
00:52:01
Brad: In light of the fact that forget this year, let’s say you paid a higher tax rate this year on XYZ income, but you were going to be paying taxes over your entire working career. We care about when you look back, how did you optimize that income to help you achieve your goals? And so that is like graduate level stuff. And that’s comprehensive tax planning. And it’s kind of like, here are the different when we say, when we say, hey, pay attention to this right for you, but not for you, there’s nuance here because you need to think about what detours are you going to take and when are you going to say, Ooh, this now fits into my plan.
00:52:43
Jonathan: And Brad, what I’m thinking about in particular is when we say, you know, 401k versus Roth, there is a point where we’re like, man, they’re actually at a pretty good tax rate right now. You really think you’re going to beat this down the road. And so, you know, you might look at the longer strategy of, you know, 10 or 12%, but I’m thinking about your daughter and, Hey, we had money and she put it in a Roth IRA, what do we think about, you know, the marginal tax brackets for 2026? They go up a little bit each year, but 2026, the 10% marginal tax bracket is the first zero to 12,400 for single filers, and it’s up to 24,800 for married filers. That’s a 10% tax rate. And then the 12%, which is this random tiny little addendum right before we go to 22, it goes up to 50,000 for the single filers and it goes up to 100,000 for the joint filers.
00:53:29
Brad: So that’s a lot of numbers and I get it, but is there a marginal tax rate that I’ve just mentioned 10 or 12% that would sway you back the other way?
00:53:38
Jonathan: Yeah, it’s a good question and it certainly does differ on your circumstances, but yeah, I mean, if you can lock in 10% or 12%, I think there’s a reasonable case to be made that you just pay the tax. But that said, honestly, so here’s the thing. We never know the future, right? Like that ultimately at the heart of this is we don’t know the future. So you’re just betting on the future.
00:54:01
Brad: Anybody who’s picking a Roth based on, again, the thing that we’ll show in the future is they are picking that income tax rates are going to be higher when they pull that money out because they are locking in a current rate. That is literally what you’re doing, whether you realize it or not. And frankly, you probably don’t; you’re making a bet on the income tax rates. Very simply now under the current confines of our graduated income tax system, I think, and especially the massive standard deductions that we get. I think there’s going to be a lot of quote unquote, free money.
00:54:45
Brad: I think for people in the FI community who have their expenses under control, when they reach FI, they’ve paid off a mortgage, their life doesn’t cost that much. I think they’re going to be able to pull almost all of their life expenses out tax-free from traditional 401ks. And also frankly, and this is another thing is tax gain harvesting. I’ll talk about this in a minute, but I think between those two, being able to pull out maybe Roth contributions or 457b contributions, I think there’s a very high likelihood you’re going to pay $0 in federal tax ever.
00:55:07
Jonathan: So that’s why it’s even not a slam dunk for me at 10 or 12%. I think for most people, it would be a slam dunk.
00:55:12
Brad: No, but this is great. So first of all, nobody’s saying you’re making a financial mistake by contributing to your Roth when you’re at a 10 or 12% marginal tax bracket. Like that’s just, beyond that, I think probably some of you are really surprised that I didn’t just jump on. Yes. And that should give you pause and slow you down and say, huh. Cause it’s easy just to say, oh, it’s simple. And I don’t have to worry about taxes on this money again, but do you decrease your option, your optionality down the road? There’s a lot here.
00:55:36
Jonathan: I mean, we’re basically at this point, we’re showing you the table of contents for what we’re going to get into over the next year. You know, every single one of these topics deserves its own episode. We haven’t given it justice. We haven’t broken out the spreadsheets yet. We’re still in this back of the envelope, this dog-eared back of the envelope and using the same one for seven years, you love my back of the envelope.
00:56:01
Brad: I did do an episode with Cody Garrett, episode 517 on understanding capital gains strategies. You and I are going to do a follow-up to that for sure because this is a really important one: there is a 0% federal capital gains tax rate. And this is on your traditional brokerage account.
00:56:12
Jonathan: Okay. So let’s say you have stocks, ETFs, mutual funds, et cetera, in your regular brokerage account. And you sell them that incurs a capital gains tax. Okay. If they’re held for more than a year, it’s a long-term capital gains. And normally they’re really preferential rates on these. So we, as investors get showered upon just benefits showered on us generally. So we only pay for most people, 15%. But, but, but those in the FI community, most of us are going to pay 0% tax on our capital gains rate.
00:56:48
Brad: Because as Cody showed in that episode, if you’re married filing joint, your income for 2026 can be up to your taxable income. This is after your standard deduction and other items. So the standard deduction, I think for 2026 for married filing joint is 32,200 or something like that. So we’re talking, the taxable income is 98,900.
00:57:11
Jonathan: Okay. So let’s say you had no other income. You had $130,000 of long-term capital gains. That’s just the game. That’s not the sale price. That’s not the fair market value. That’s not what’s deposited in your bank account. That’s just the difference between what you bought it for and what it’s currently worth. 130,000. You say, “Hey, government, please tax me.” And they say, “Yeah, okay, we’ll tax you.” That’s $0, please.
00:57:35
Brad: Okay. So the FI community wins. If we let ourselves win, if we don’t listen to the bozos who don’t know anything about the FI community who think Roths and taxes are going to be so expensive and, oh, it’s horrible. We win at life. This is what we do. And we have so many ways to win, Jonathan. And I just, for people that are going to get mixed up in there, but you might have heard tax gain harvesting. This is money that is outside of your retirement accounts, right? So just for clarity and making sure we’re all on the same page.
00:58:05
Jonathan: But the point is the table of contents of this book of financial independence is awesome. The detours are incredible. It’s compelling. You do not know what you don’t know, but what you have discovered, what you have walked into is the stealth wealth community. And what you need to realize is when you’re living an entry-level, middle-class lifestyle that slots in with everyone else, but then on top of that, you have paid off cars. You have a paid-off mortgage. You’re not financed up to the eyeballs on everything. Suddenly your life can look like everyone else’s at a tiny, tiny fraction of what everyone else is spending.
00:58:57
Brad: And that gives you opportunities because the tax code incorporates a pretty massive safety net because it recognizes that everyone’s in debt up to their eyeballs. So just think about that. If you can decrease, if you can crush how much it costs for your core expenses, right? Crush it ruthlessly, that gives you optionality with all the other things that you want to add back in. And it gives you the luxury, the privilege of kind of floating around the tax code, making choices based on where you are and what it is that you want to do. You want to preserve options.
00:59:27
Jonathan: Brad’s just highlighting via this table of contents entry, just a few of those that you need to be aware of. So today our title was detours and Brad, I’m telling you, man, this table of contents is looking attractive. I could do more of these, but I can’t do a part three, so it’s going to have to have a real title, but I want to keep the dialogue going.
00:59:38
Brad: So next week we’ll be breaking from this. We’re going to be doing the goals episode that we’ve been collecting feedback on, but we do want feedback on this episode. We want you to lean in. What were your aha moments? What would you like to see us talk about? In addition to this, what would you like to see some highlighter on? Where would you appreciate seeing the nuance? What would you like to bring to this conversation?
01:00:02
Jonathan: And the place to do that is to be a part of the community. You’re just gonna go to choosefi.com/login. You’re saying, “Oh, I don’t have an account.” Okay, create one. Go to choosefi.com/login, create an account. We do have an app now. I failed to mention this before, but this was a big push. And I had a lot of help from people in the community. There is now a ChooseFI app that you can find in Android and iOS.
01:00:20
Jonathan: And it is a one-to-one replica of what we’re talking about here when we say to go to the website and log in, that you have access to this community inside your app store. Once you’re in there, you’re going to be able to connect with the community. You’re gonna be able to interact with this episode and leave us your feedback. And there are so many other ways to take action. It’d be pretty cool if one of your actions this week resembled or reflected something that was in this episode.
01:00:48
Jonathan: All right, my friends, the fire is spreading. We’ll see you next time. As we continue to go down the road less traveled.
[FINAL TIMESTAMP] Podcast Extro: You’ve been listening to ChooseFI Podcast, where we help middle-class America build wealth one life hack at a time.
