As a divorced man of a certain age, I have gotten seriously into bikes. It's a little embarrassing. As a younger man I laughed at the movie This is 40, when all the dads walked into a coffeeshop wearing their bib shorts and clip-in shoes. But here I am, a grown adult, fawning over two-wheeled contraptions that cost more than my first car. Much more.

About two months ago, my friend died. She was a little past 50. She was diagnosed with cancer in December and gone by September. She was a beloved professor, a damn fine poet, and a mother to four children. I've been trying to figure out how to talk about her, in public and in private, because while I adored her, I struggle to understand how she lived her life.

For most of the last 18 months, I have been deathly afraid of the stock market. In the precipitous drop from the heights of January of 2022 to August of that year, I lost a ton of money. I didn't expect it to happen, I couldn't understand why it was happening, and I didn't know what to do about it. Every day I watched the Nasdaq plunge, then rise just a little, then plunge again. I felt like I was in a bunker taking heavy fire, and I had to make a plan to fight my way out.

Many years ago, I made a decision that I would value my time over money. That felt like a noble and empowering decision to a 25-year old, but in the years since I've kicked myself more than once, such as when my friends tell me about their recent trip to Barbados or how evenly their new Green Egg roasts pork butts.

That's all to say that sometimes my funds run a little lower than I'd like and, since summer is quiet in academia, I'll pick up a side gig for what my grandfather used to call "walking-around money." This year I decided to write study guides at a company called GoodGuides[1] for around $800 a pop. Writing thirty pages or so on various pieces of fiction would be, I figured, easy money.

About a week ago, my four-year-old came into the kitchen and announced that mommies and daddies should live in the same house. I told him that sometimes they did, and sometimes they didn't, and I reminded him that his friend Jordan's mommy and daddy lived in different houses, just like we did. My son nodded, seemingly satisfied. Then he walked back out into the den to watch Bluey, and I poured myself a big glass of whiskey.

I'm losing my grip on technology. When my kids ask me for a new video game I have to google it to see how it works, and I still don't understand it. Does this game let my six-year-old talk to random people online? Does it have its own currency? Is that somehow convertible to actual money or will it eventually turn into crypto? I'm becoming knowledgeable about things that I don't care about, and that new knowledge is crowding out the other stuff I'm currently struggling to hold onto.

I was recently in Charleston, South Carolina with a friend of mine, walking the beautiful streets and stopping into restaurants for a dozen oysters and she-crab soup. We did all the sights and at some point found ourselves in a museum looking at a small exhibit of cowrie shells. You'd recognize a cowrie shell if you saw one--a smooth dome about the size of your thumb, curling up on the underside with what looks like tiny little teeth.50. I could also say that I understand the silly price target she's put on Tesla ($4,600 by 2026), and I understand how much her ARKK fund has fallen in the last year (50%). In short, I don't take Ms. Wood's hot takes very seriously., I decided. But since I had given up on “good” bacon, why not see how far I could ratchet this whole thing down?

Hedge fund manager du jour, Cathie Wood, recently suggested that artificial intelligence is not only a lot closer than everyone thinks, but that it is capable of spurring unheard of growth. "Within 6-12 years," Wood tweeted, "breakthroughs in AGI could accelerate growth in GDP from 3-5% per year to 30-50% per year. New DNA will win!"

I'm not a big numbers guy, but even I understand the difference between 3-5 and 30-50. I could also say that I understand the silly price target she's put on Tesla ($4,600 by 2026), and I understand how much her ARKK fund has fallen in the last year (50%). In short, I don't take Ms. Wood's hot takes very seriously., I decided. But since I had given up on “good” bacon, why not see how far I could ratchet this whole thing down?

Back when WallStreetBets was hot news, a friend of mine who had no money in the market asked me about the meme stock phenomenon. She wanted to know what I thought about the "little guys" trying to take down hedge funds for the sake of sticking it to the man. And I told my friend that I was horrified. "Why?" she asked me. "Because," I blurted, "it goes against everything that investing is supposed to be!"

There’s nothing sexy about being responsible.

I do not feel sexy when I go to the store to buy bread. And while I am decidedly not sexy when I go to the store anyway, I do feel a little sexy when I go to the store to buy wine. I can pay precisely as much for a bottle of wine as I want, and the more money I pay, the more I scratch the itch.

It takes real discipline to be responsible, especially with money, because money has the potential to let us do whatever we want. Maybe the biggest reason people struggle to balance their finances is their inability to separate what they should do from what they want to do.

Imagine that the human mind is like a ski slope. When you're young it's all fresh powder with nary a track to be found. As you get older you find yourself taking the same routes down to the bottom, and by the time you get into middle age those routes are so deep that it's impossible to ski any other way. You start each day at the top by seeing the same problems, you solve them with the same processes, and you continue to arrive at the bottom with the same conclusions you've always had. This is the way Michael Pollan, in his book How to Change Your Mind, describes the decision-making process, and while it may (or may not) be effective, it is, at the very least, limiting, predictable, and ditch-dull boring.

We all keep making the same dumb moves: sell into a route, buy at the top, constantly reallocate, chase the market. So many of us keep messing with investments that, if allowed to just sit for a while, would slowly and consistently grow.

This is basic stuff. Everybody’s heard it. We've seen what happens before, so why do we keep making stupid mistakes? Why doesn’t the stuff we learn have a significant impact on our behavior?

I’m a lit nerd, so lately I’ve been reading a few books by V.S. Naipaul, who died a couple of years ago. Naipaul was a British writer who won the Nobel Prize back in 2001. He was, by many accounts, an abhorrent human being, but a masterful writer. He’s dead now, so his personality matters a little less. But I think that his death marked the end of a certain type of public figure.

I got into an argument the other night about climate change. I was out with my wife and some of our friends and, for reasons I find difficult to explain, when I get a tall PBR and a shot of Evan Williams in front of me, I feel free to say whatever comes to my mind. This really isn’t a mature way to behave, but a PBR isn’t a mature thing to drink, at least not after the Willamette pinots that came with our dinner and so anyway, I said some dumb stuff.

I used to live in what was affectionately known as the "Tendernob" section of San Francisco, a little strip with Nob Hill style and Tenderloin prices. It was a sweet spot, a Goldilocks area, a perfect place for the new kid in town. And every afternoon as the fog would roll in from the west, the hedge fund managers would roar past my apartment in their Audi S5s trying to beat the traffic over the Golden Gate Bridge.