The 4 Greatest Money (And Life) Lessons I Have Ever Learned

0:00The richest people I know, in the sense of feeling rich, are not the wealthiest. They're the ones who have figured out their list. They spend deliberately on the things on it, they underspend mercilessly on the things that aren't on it, and they almost never compare their list to anyone else's because they understand that the list is the entire game and the size of the list is not the point. Hello friends, this is Tyler Gardner welcoming you to another episode of Your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing.

0:44So let's get started and get you one step closer to where you need to be.

0:52Quick note before we dive in, August's pre-order incentive for my book Real Wealth is now live, and this one is my favorite so far. Pre-order this month, Tell me you did at tylergardner.com book, and I will send you a draft chapter of a new book that I'm already working on. And no, not even my editor at Norton has seen this writing yet. This sneak peek is yours to keep, delivered to your inbox in early September. Pre-order today, and you're locked in for every monthly incentive through December 1st. tylergardner.com book. Now let's get into it. Good morning or good afternoon, and welcome back.

1:29Thank you, as always, for choosing to spend some time thinking about money with me. Today's episode is going to be, I would say, a little different, but also a little similar. I've been getting more notes than usual lately from listeners saying they like the episodes where I stop talking about expense ratios for 15 minutes and instead try to figure out what we're actually doing here. The Sedona episode was the most listened to thing I've put out this year, and the Cavafy episode was actually a close second. There seems to be an appetite among the people who listen to personal finance podcasts for the personal finance podcast to occasionally, and I'm using a technical term here, chill out about the technical material and instead grapple with the philosophy, the why behind the how.

2:19So today is one of those episodes. I want to explore four money lessons. These are the four greatest I've learned to date. I'm hesitant to say greatest because I'm 43 years old, which is exactly the age at which a man begins to think he's figured out more than he actually has. But these four are genuinely the ones I keep coming back to. They're the ones that, when I sit on the porch with the bloodhound at six in the morning and try to think about what I actually believe about life and money, are the ones that hold up time and again. A small caveat, since I'm trying to be honest about my voice today, I figured most of these out in the way one figures out anything important, which is slowly, badly, and against my will.

3:05I would like to claim I arrived at them through some elegant program of reading and reflection, but the truth is I learned them by getting things wrong for 20 plus years and then finally noticing the pattern. My credentials for offering these to you are not that I figured them out gracefully. My credentials are that I'm willing to admit how I figured them out, which I will do as we go. And familiar ask before we get into it, if the show has been useful to you in any way. If you've ever listened to an episode and thought about money or life in a different way, a review on Apple or Spotify would genuinely be the best thing you could do for the show.

3:43It's how new listeners find the show, and it's how I know that this entire endeavor, me walking around the woods of Vermont talking into a phone about money, my bloodhound looking at me with slight concern in their eyes, is actually reaching anyone besides the deer and the squirrels. All right, let's get into it. Lesson one. Time is not your greatest asset. Knowing what to do with it is. I want to start with a lesson that has, I think, gotten me the most pushback from listeners over the years, because it cuts directly against one of the most popular ideas in modern personal finance, which is the idea that time is the asset, and that the entire game is to free up as much of it as possible, and that freeing up the time, buying back the time, that is the end in and of itself.

4:39I do not fundamentally agree with that framing, or rather I agree with it about 10 % of the way. And then I think the framing leads people directly off a cliff of anxiety and staring into the great and endless ennui. Here's what I've observed both in myself and in many of the people I've worked with over the years. People work very hard for a long time. They sacrifice, they save, They invest. They delay. They spend years organizing their lives around the idea that the prize at the end is going to be free time. Time to themselves. Time without obligations. Time, finally, to do what they want. And then, and this is the part I want you to sit with for a minute, they get the time.

5:29And a real and uncomfortable percentage of them are not happier. Some of them are noticeably less happy because, you guessed it, they don't exactly know what to do with the time. They've spent so long pursuing the absence of structure that they forgot to ask themselves, what kind of structure do I actually want? Let me tell you something I've never quite said out loud on this show and which I'm going to say now because it is genuinely true and I think it illustrates this point. Saturday is my least favorite day of the week. I know. I know how that sounds. I work for myself. My family is wonderful.

6:09We have a beautiful life in Vermont. By every conventional metric, Saturday should be the day I love, the day everyone is working toward. I find it slightly disorienting, not in a tragic way, but in a what do I do with this kind of way. The day stretches out in front of me with no structure, no meetings, no deadlines, no podcast to record. And a part of me, by about 10 in the morning, you know, after I've occupied the first five hours of the day with a visit to the gym, a great breakfast, a cup of coffee, and a chapter of a book on the porch, after that, a part of me starts to feel a low-grade anxiety that I have not figured out what the rest of the day is for.

6:51And by two in the afternoon, if I haven't planted myself in some kind of project or activity, I'm usually mildly out of sorts. And by five, my wife has gently, lovingly, suggested that perhaps I should just start dinner, which is her diplomatic way of giving me something to do. This is, I should say, a relatively new diagnosis on my part. For most of my adult life, I assumed I was supposed to love Saturdays, the way everyone else seems to love Saturdays. It took me genuinely into my late 30s to admit, with some shame, that I don't. When I left teaching to become a financial advisor, my father said something to me that I have thought about probably once a week ever since.

7:36He said, the thing you're going to miss most about teaching is the structure of the academic year. I remember nodding politely at the time and not really hearing it, because at 33, you don't hear what your father says to you about anything until about 15 years later, when you suddenly hear it all at once. But what he meant, and what I have come to understand he was completely right about, is that a school year is one of the most beautifully structured calendars a human being can live inside. There's the start of the term. There are sports seasons that begin and end. There are parents' weekends, holiday breaks, the long countdown to spring, the seniors' last week, graduation, the summer, and then the whole thing begins again.

8:22There are end-of-term parties, there are semester finals, there are cycles. The year is marked. The passage of time is marked and celebrated. It comes to a natural close, and then it renews itself again. What my dad was saying, in a way I didn't have language for at the time, was that the structure was not a constraint on the meaningful life. The structure was the meaningful life. The cycles, the markers, the rhythms, these were not what got in the way of living. These were how the living happened. Take that structure away, and what you have, for all intents and purposes, is the same day repeating itself, which is, of course, the actual plot of the film Groundhog Day.

9:09And I will tell you that one of the more disorienting realizations of my early 30s was understanding that Bill Murray's character in that film is not in some kind of supernatural trap. He is, more or less, in retirement. He has unlimited time, no obligations, and the same day to Phil, again and again, until he eventually figures out that the only escape is to do something genuinely meaningful with each loop. The film, if you haven't watched it recently, is much more theological than it gets credit for. He doesn't escape by becoming powerful. He doesn't escape by becoming rich. He escapes by figuring out what the day is for.

9:53He escapes by deciding what to do with his time. I think about this constantly when people tell me their financial plan is to retire as early as possible. I always want to ask them, and sometimes, depending on how well I know them, I do. And then what? Not as a gotcha, as a real question. What does the calendar look like in the absence of whatever it is you're currently doing? What are the rhythms? What marks the passage of time? And the vast majority of the time, in my experience, the honest answer is something like, I don't know, but I'll figure it out when I get there. And I want to suggest, as gently as I can, that this is not a plan.

10:33This is a hypothesis about the future you that you are betting 15 years of work on. And the future you, when she or he arrives, is going to be the same person you currently are, just a little older. They're not going to magically know what to do with 12 ,000 free hours a year because you handed them the hours. Here's what I've come to believe, which is not what most personal finance people will tell you. Time, like money, is a raw material. That's it. It's iron ore. It's a blank canvas. It is enormously valuable in the abstract and almost worthless in practice unless you have, before you encounter it, figured out what you intend to do with it.

11:17The people I know who have retired well, and there are many of them, did not retire into time. They retired into projects, communities, hobbies, schedules, rhythms, things to mark the passage of weeks and months and years. They built calendars before they needed them. They knew what Saturday was before they had nothing but Saturdays. The people I know who retired badly did the opposite. They retired into the absence of structure and assumed, incorrectly, that the absence of structure was what they had been chasing. Within a year, many of them were, and should come as no surprise, working again in some form, because the alternative was to sit in the kitchen at 10 a.m.

12:03on a random weekday with a coffee and a phone and a slowly developing existential crisis. So here's the practical takeaway for lesson one. Before you organize your financial life around the goal of do everything I can to buy back my time, do me a favor, well, do yourself a favor, and write down, actually write down, what you intend to do with that time. Not in the abstract, specifically. What does Thursday look like? What does October look like? What does the next year of your life look like with no job in it? If you can't answer those questions in concrete terms, your financial plan, and in turn, your life plan, is incomplete.

12:48You might have a number. You don't have a life. And those are different things. The number is in service of the life, not the other way around. And the life, the actual texture of your weeks, your seasons, your rhythms, is the thing you have to design first before you design the financial plan that's supposed to enable it. Time is not your greatest asset. Knowing what to do with it is. This episode is brought to you by Factor. I've been traveling way more this year to conferences, media things, with rooms full of people who want to talk about money. And I do enjoy it, in the way a raging introvert enjoys anything, which is enormously at first, and then plotting an earlier flight home.

13:32The problem is the transition days. I get home, the fridge contains half a lemon and something I'm afraid of, and I have no energy to go to a grocery store. I've tried delivered meals before, and the meat was always the tell. It arrived with the texture of something that had been through a difficult experience. Factor solved all of this. Chef-crafted, dietician-designed, ready-to-eat meals with over 175 banned ingredients. So it's built around what supports a healthier lifestyle and nothing that doesn't. The short rib is outstanding, the shrimp and grits I could eat daily for lunch, and some weeks I do, and the vegetable sides are seasoned like somebody cares.

14:09Two minutes, no prep, no cleanup. I use Factor daily, and bluntly, you should too. So let's eat real. Head to factormeals.com slash tylerg50off and use code tylerg50off to get 50 % off and one free breakfast item per box for one year while supplies last until 10-31-26. That's code tylerg50off at factormeals.com, tylerg50off at factormeals.com. See website for more details. Lesson two. Work is not the enemy. Working on things you didn't choose with people you don't respect is the enemy. This is the lesson that took me the longest to understand and that has, in some ways, organized the entire second half of my professional life.

14:58We live in a culture that is genuinely confused about work. The dominant message in personal finance content, financial independence content and broader self-help content is that work is something to be escaped. The goal is to retire early. The goal is to engineer your life so that you can stop doing the thing you're currently doing as quickly as possible. Above all else, this is my primary gripe with the FIRE community's original messaging, as it always seems to be running from something, but never quite articulating what it's running towards. And I want to push back on this messaging hard, because I think it is one of the most damaging frames in modern financial thinking, and I think it leads people to organize their lives around the wrong question.

15:46The right question is not, how can I do less work? The right question is, what work do I actually want to be doing, and with whom? There's a substantial body of research on what makes work satisfying. And the consistent finding across decades of studies is that autonomy is the single biggest driver of work satisfaction. More than salary, more than benefits, more than prestige, the control over what you do, when you do it, and who you do it with is by a wide margin, the variable that most determines whether your work and in turn your life is fulfilling. I've known this in my bones since I was approximately 12 years old.

16:34Let me tell you about myself in sixth grade, briefly, because I think it explains a lot. I was the kid who hated group work. Genuinely, viscerally, philosophically hated it. Not because I was antisocial. I had friends. I was fine. But because the structure of group work as imposed by teachers was, even to my little 12 year old self, manifestly absurd. You were assigned to a group you did not choose. You were given a project you did not pick. You were told to collaborate with people whose work ethic you could not vet on a topic you may or may not have cared about on a deadline that had nothing to do with your own pace.

17:19And at the end of it, your grade was determined in part by the contributions of strangers. Now, when I would push back on this politely, well, I would like to think, but probably not as politely as I now remember, teachers would tell me that this was preparing me for the real world. That in the real world, you don't get to choose your colleagues. You don't get to choose your projects. You have to learn to work with what you're given. And I would think, and sometimes say out loud at the dinner table to my parents who must have been exhausted, no, that's not how the real world has to work. That's how one version of the real world works.

17:58There's another version where you get to do work, you actually choose, with people you actually respect, on problems you actually care about solving. And I'm going to be very interested in finding that version. It took me about 25 years to find it, but I did find it. And the lesson in retrospect was spot on. Here's what I've come to believe about work after more than 20 years of it in various forms. Work, when it is freely chosen and pursued with people you respect, is one of the most meaningful experiences available to a human being. It's not a thing to be escaped. It is one of the actual sources of joy and identity and structure and community in adult life.

18:42To organize your finances around the goal of no work is to organize your finances around the goal of no source of meaning, identity, structure, or community, which when you say it that way sounds insane because it kind of is. All you need to do is change the word work to projects or puzzles. What project do you want to solve with your time? What puzzle do you want to work on today? When I worked at the Hotchkiss School in Connecticut, I had what I now realize was one of the most professionally happy stretches of my life. The English department had an open office concept, a big room with desks for all of us, where we would grade together, plan together, complain together, laugh together, and occasionally argue about whether we were giving Thomas Hardy too much time on the syllabus.

19:33I would arrive in the morning genuinely excited to walk into that room. The colleagues I had there are still some of the best people I've ever met, and the projects we worked on were, by and large, things we had freely chosen. Courses we wanted to teach, books we wanted to read with students, debates we wanted to have. The work was hard and consuming, and there was a lot of it. And I loved every minute of it. Well, I didn't love every minute of it, especially when we were told what to do and who to work with, but the rest holds. This is what I keep meaning when I say work is not the enemy. The work I did at Hotchkiss was not the enemy.

20:11It was the substance. Now, I know I'm about to commit a kind of heresy here, but I'll say it anyway. I think remote work in many cases is one of the worst things we've done to ourselves over the last decade. I know that's not the popular position. I know there are wonderful arguments for the flexibility, for the time saved on commuting, and for people being able to work in their pajamas. I've run my own remote business for years. I am not unaware of the upside But here's what I think, having lived through both versions, when you are working with the right people on the right projects, being in a room with them is one of the most underrated joys of adult life.

20:55The accidental conversations, the shared laughter, the touch points, the did you see what just happened looks, the quick hallway debate that becomes a half hour debate that becomes the breakthrough on the project. None of that happens on Slack. Slack is a transcription of the conversation you're not even having. So no, work is not the enemy. The wrong work with the wrong people in the wrong structure, that is the enemy. And the answer is not to do less work. The answer is to do better work with better people in a better structure. Which finally brings me to retirement, which I think we have culturally confused with the absence of work.

21:41The way most people frame retirement is as an escape. You're running away from something, away from the job, away from the boss, away from the alarm clock. The retirement is the absence, the negation of the working life. I don't think that's right. I think the retirement model that actually works for the people I have seen do it well is the opposite framing entirely. Don't run away from work. Run toward the work you actually want to be doing. And then keep doing that work until you die. I had the privilege a few months ago, as many of you know, of having an hour-long conversation with Burton Malkiel that you never heard because I forgot to press record.

22:20Burton is 93 years old. He is by any measure one of the most influential financial thinkers of the last half century. He could have retired in the traditional sense 40 to 50 years ago. He has not because he gets exactly what I'm saying. When we spoke, he was as engaged, sharp, curious, and alive as anyone I have ever spoken to about anything. He's still writing. He's still thinking. He is still in the deepest sense working because the work for him is not separate from the life. The work is the life. And that's not his being a workaholic. That's his understanding that we're put here to find meaning, and meaning is found through good work with good people.

23:02I left that conversation knowing that Burton had just taught me something truly valuable, just by existing, what I had been getting wrong about retirement. The goal is not to stop. The goal is to figure out what you cannot stop doing, and then arrange your life so you don't have to. If you cannot articulate what you would do if money were not the question, what work you would still want to do freely with no boss and no deadline, then you don't have a retirement plan. You have a financial plan that's missing the most important variable. Work freely chosen and pursued with people you respect is not the enemy.

23:42Work that is imposed on you by people you don't trust, on projects you didn't pick, especially in your sixth grade math class, that is the enemy. The financial goal is to get from one to the other. The financial goal is autonomy over what you do, who you do it with, and why. This episode is brought to you by Element. We're at the tail end of a genuinely brutal summer up here in Vermont, and the thing that has been in my fridge since June is Element's version of an Arnold Palmer lemonade iced tea. A little caffeine alongside the salt and electrolytes is exactly what I want after a long walk with Dixie or in the late afternoon when I'd otherwise be reaching for a second cup of coffee that I don't actually need.

24:27Here's what makes it different. Most energy drinks use synthetic isolated caffeine. Element uses full-spectrum organic black tea extract from Caricho, Kenya. 7 ,000 feet of elevation, so the caffeine comes with its naturally occurring L-theanine and polyphenols. The result is a steadier energy, less spike, less crash, and only 50 milligrams of caffeine per serving. Enough to matter, not enough to regret. I also just got back from a weekend with college friends where I brought a box of Element, and by the end of the weekend it was doing three separate jobs. Getting everyone upright in the morning, putting us back together after disc golf and swimming, and standing in for coffee at four in the afternoon.

25:05I came home with an empty box and 11 new text threads asking where they can get it. Head to drinkelement.com slash Tyler, become an Element Insider, and you'll get four boxes for the price of three. That's drinkelement.com slash Tyler. And for the record, even though I love the iced tea, it does nothing to diminish my feelings about mango chili and watermelon salt. Lesson three. There is no heroic week, but there are a thousand unheroic weekdays. This is the lesson I most wish I had understood at 25 and I'm still learning in some form at 43. Most people I know, and I include myself in this for most of my adult life, are waiting at any given moment for what I have come to call the heroic week.

25:54The heroic week is the week when everything finally comes together. It's the week when you get serious about your finances, the week when you finally launch the business, the week when you start the gym routine and stick with it, the week when you fix the mortgage, the diet, the writing project, the mess in the basement, the relationship with your aging parents. The heroic week is always coming. It just never arrives. It is always a week or two from now when things calm down a little, when the project at work finishes, when the holidays are over, when the kids are out of the playoff season, when the renovation is done.

26:29Then, then will be the week. The heroic week is a fiction. It is one of the most reliable fictions of the modern adult mind. It does not exist, and it will not arrive. The reason it will not arrive is structural. By the time the current set of obligations clears, the next set will have replaced them. The conditions for the heroic week, The calm, the empty calendar, the perfect alignment of energy and time and will, those conditions are never going to be there. They're not coming. They are a mirage that recedes at the same speed with which you walk toward it. What is real and what nobody tells you is the alternative.

27:16The alternative is a thousand unheroic weekdays. The alternative is small flights of effort, repeated daily, mostly invisibly, mostly without applause. It is sitting down at the desk on a regular weekday in March and doing 400 mediocre words on the book chapter that has to be due in six weeks. It is going to the gym on Wednesday because it's Wednesday and Wednesday is a gym day, even though you don't feel like it, and it's raining outside, and the workout is not going to be very impressive anyway because you're exhausted. It is on a perfectly ordinary Thursday afternoon, calling your financial advisor or your accountant or your insurance person about the thing you've been meaning to call them about for nine months.

28:00It is unheroic. It is undocumented. Nobody's watching. Nobody's applauding. You don't get a montage. You get a Thursday afternoon. But, and this is the key, you are ever so slightly improved. I want to tell you briefly about how I started the social media business, because I think it illustrates the point, and because I am at this point contractually obligated to make at least one self-deprecating reference to my early TikTok videos per episode. When I started making content, I made four videos a day, sometimes more. Most of them were complete garbage. I'm not being modest. I've come back and looked, and I've actually kept them all up to prove this point exactly.