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

Your Money Guide on the Side

Tyler Gardner shares four profound life and financial lessons learned through years of trial and error, emphasizing that wealth is not about time or numbers alone

Key takeaways

• Time is not your greatest asset; knowing what to do with it is.

Main topics

• Financial philosophy
• Purpose in life and money

Notable quotes

The richest people I know, in the sense of feeling rich, are not the wealthiest. They're the ones who have figured out their list.

Conclusion

True wealth isn't measured by savings or retirement age but by how intentionally

Transcript preview

Speaker 1 (0:00) The 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. Speaker 1 (0:27) 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. So let's get started and get you one step closer to where you need to be. Speaker 1 (0:52) Quick 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 slash book. Now let's get into it. Good morning or good afternoon and welcome back. Thank 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. So 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. I 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. It'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. I 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. And 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, we 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. And by 2 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. He 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. There 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. And 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 fill 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. He 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. This 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