5 Money Milestones and the Lie Each One Tells

Tyler Gardner (0:00)

The six figures is just the receipt. It is evidence that the becoming happened. But the becoming is the actual asset. And the becoming is what carries you to the next milestone, and the next, and the one after that. So if you didn't feel anything when the salary number ticked over that threshold, that's not a failure of the milestone. That's the milestone working exactly as designed.

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.

Quick note before we dive in. July's pre-order incentive for my book Real Wealth is live, and this one is for the investors who are ready to go beyond the basics. Pre-order this month, tell me you did at tylergardner.com/book, and I'll send you Investing 2 Beyond the Foundation, a full hour video presentation on the five things every investor needs to know after they've mastered the fundamentals, yours to keep, delivered to your inbox digitally in early August. And if you pre-order now, you're locked in for every monthly incentive through December 1st. tylergardner.com/book. Now let's get into it. I wanna do something a little different again today, because a few months back, I published the Sedona, Arizona episode about the five things my wife and I learned about money and life from becoming snowbirds for the first time this year. And that episode was, against all of my expectations, the most listened to episode that I've put out this year. And a lot of you wrote in to say it was nice to hear an episode that wasn't about the difference between a Roth and a traditional IRA, or telling you to invest in low-cost index funds for the 400th time. So, we're gonna try another one of those today. What do I mean by that? Well, this episode's gonna be a little more personal, a little more philosophical, and, if I'm being honest, the closest thing to a homecoming I've done on this show.

Before I was a finance guy, I taught English. For most of my adult life, I have kept the literature and the money in separate rooms. The novels happen at night, the reels talking about money while I walk through the trails of Vermont happen in the morning. The two halves have largely tried not to make eye contact. Today, they're going to make eye contact.

We're going to be working over the course of this episode with a Greek poet writing in Alexandria in 1911, an 18th century English moralist who wrote what may be the most devastating philosophical novel ever published to pay for his mother's funeral, a contemporary British novelist whose work will, if you let it, sit on your chest for a week, and an American writer many people consider the defining novelist of his generation, who reached his own literary capstone and did not, by his own account, find what he had been looking for at the top of it. Each of them is going to teach us something specific about a financial milestone we are taught to chase. If I do this right, the literature and the money are going to turn out to be the same conversation, which is the suspicion I've been carrying with me for a long time, and I'm finally, on this episode, willing to test out loud.

So, here's the question I want to start with.

Have you ever passed a financial milestone that you had been waiting on, sometimes for years, and then felt absolutely nothing?

Not bad? Not good? Not transformed? Just nothing? Same cup of morning coffee? Same dog? Same vague, low-grade sense that something was supposed to happen and it didn't?

Well, I have. Multiple times. And I think most of you have too, even if you haven't quite admitted it to yourselves yet, because we exist in a financial culture that sells milestones the way the mattress industry sells mattresses, as the one thing that once acquired will fix your sleep, your back, your marriage, and quite possibly your sense of existential dread. We are told, again and again, that there is a number or a status or a structural change to our finances that will make us feel different, solved, done.

And then you arrive, and you just don't feel any of it.

I have a book coming out on December 1st of this year. As regular listeners know, this is the dominant fact of my professional life right now, and it has been for about two years. There's a real possibility that the book does well. There's also a real possibility that it doesn't, and that I will need to retreat to a yurt and become a cheese maker, which honestly sounds wonderful, and I'm not ruling it out. But somewhere in the back of my head, even as I'm doing the work, every interview, every newsletter, every cringey reel of me walking through the woods asking you to pre-order the book, I am already running a pre-mortem on what December 2nd is going to feel like. What happens that day? The most likely outcome is that it feels like any other Wednesday. Maybe a slightly more nervous Wednesday, but still largely a Wednesday. So today's episode, we'll explore four financial milestones that we are taught to chase. Four honest looks at what each of them actually delivers, and four works of literature that taken together build the argument I want to make, which is this, you need destinations. You absolutely need destinations. Without them, you don't set out. Without them, nothing happens. Compounding doesn't compound, discipline doesn't form, you stay in bed. But you cannot ever, and I mean ever, let yourself believe that any one destination is the one that's going to solve it. The wise person has multiple Ithacas. Always plural, the trap is believing in the singular.