Going Out on Top

How many Wall Street folks do you know that went out on top? None, right? They overstayed their welcome, get fired at age 47, then tumbled down a few rungs of bucket shops before they get spit out the bottom of the industry and end up teaching social studies. You see it over and over again, a pattern that is repeatable and familiar to all of us.

You know who went out on top? Bill Watterson, the creator of the comic strip Calvin & Hobbes. From Perplexity:

Bill Watterson stopped writing Calvin and Hobbes in 1995 for several interconnected reasons:

• Creative Exhaustion and Fulfillment: After a decade of producing the strip, Watterson felt he had expressed everything he wanted to say with the characters. He believed it was better to end the comic while it was still fresh and beloved, rather than risk it becoming repetitive or stale. As he stated, "By the end of 10 years, I'd said pretty much everything I had come there to say. It's always better to leave the party early.”

• Desire to Maintain Quality: Watterson was concerned that continuing the strip without the same level of inspiration and commitment would inevitably lead to a decline in quality. He wanted to avoid the fate of other long-running comics that outlived their creative vitality, preferring to preserve the legacy of Calvin and Hobbes at its peak.

• Opposition to Commercialization: Watterson was deeply opposed to the commercialization and merchandising of his work, which led to ongoing disputes with his syndicate. He resisted efforts to license Calvin and Hobbes for merchandise, adaptations, or other commercial ventures, believing it would undermine the integrity of the strip. This philosophical stance contributed significantly to his decision to walk away.

• Personal Burnout: Years of intense creative work and battles with publishers over issues such as merchandising and comic strip sizing left Watterson exhausted. He described having "virtually no life beyond the drawing board" during the strip's run, and ultimately lost the conviction to continue cartooning as a career.

In summary, Watterson ended Calvin and Hobbes to protect its artistic integrity, avoid creative stagnation, and remain true to his principles, even as the strip reached the height of its popularity.

A few other points about Bill Watterson. As you know, he fiercely resisted commercialization and licensing, which led to him missing out on about a billion dollars and bootleg Calvin-peeing-on-a-Chevy-logo stickers popping up all over the country. Nonetheless, he has a net worth estimated at $100 million, and he has retired from public life since 1995, hanging out in Ohio. He did give the commencement address one time at Kenyon College, if I recall.

I think about this a lot. I have been writing The Daily Dirtnap for 17 years—Watterson wrote Calvin and Hobbes for only ten. There are certainly days when I feel creatively spent, and those days have been piling up lately. Also, my revenue peaked in 2021, and has been gliding lower since then. Let’s just say that I am spending most of my time these days diversifying my revenue streams, preparing for the day when I am ready to walk away. 17 years is a long time to be doing anything. I still enjoy it, and oh my freaking God have the calls been insanely good lately, and I will never stop writing, but I am coming around to Nassim’s point of view that finance is depraved, and writing about finance is also depraved. I would rather write about other stuff, though I have been procrastinating on my novel lately.

I think it’s important to know when to quit, unlike an aging baseball player, playing far past his prime, not getting invited to spring training, and eventually getting bounced out of the Mexican League. You want to jump, not get pushed. Maybe you have some more baseball left in you, but is it good baseball, or are you embarrassing yourself?

Part of it is the money—it is hard to walk away from the money, on Wall Street, in sports, in entertainment, or anywhere else. I will say that I left Wall Street on top. Was I making gross amounts of money? Not really, but my reputation as a legendary ETF trader had been cemented, and if I had stayed longer, I probably would have gotten fired for sniffing some intern’s chair or something like that. I knew when to quit. Also, if you’ve been saving the money, then quitting is not so big of a deal—you have a pile of cash to fall back on. The sad stories are when guys keep working because they have to keep working, because they have that $30,000-a-month Hamptons rental and the wine cellar. Also, nobody wants to retire at age 47. We all have things we want to do. The happy stories are when Wall Street folks retire from the institutional business and become financial advisors at the big brokerages, working well into their 80s because they love it. The institutional business is a young man’s game. 22 to 47—that’s all the time you get, a lot like professional sports. After that, you had better have a plan for what you are going to do afterwards. Remember Kevin Maas, the upstart Yankees first baseman with matinee-idol good looks and a prodigious bat? He is a financial consultant for Charles Schwab now. You love to see when people have a productive second act.

But if you haven’t reached the top yet, then keep going! Tom Cruise, for example. I saw the latest Mission Impossible in the theater recently—the guy just has an insatiable love for filmmaking. Good for him. Matt Damon is still going, too. George Clooney doesn’t depend on a paycheck these days. Most women in Hollywood reach their expiration date in their late 30s, with few exceptions, and the trick is to go from hot to interesting, Meryl Streep probably being the best example. I told my wife that she has successfully gone from hot to interesting, and she almost threw me out of the car at 60 miles per hour. But yes, eventually Tom Cruise will be doing action movies in his 70s, and he will be embarrassing himself. But not yet. So keep going.

Some athletes that went out on top: Michael Jordan, of course. Rocky Marciano, who went 49-0, and retired at age 31. Barry Sanders—quit before he broke the rushing record. Mark Spitz, Floyd Mayweather, and Usain Bolt. As for entertainers, Cameron Diaz! She says her time away from acting has been the best years of her life. Grace Kelly became a princess. Daniel-Day Lewis, the weirdo. Bridget Fonda. You could say Jack Nicholson went out on top. Robert De Niro, not so much. When was the last time you saw a good De Niro movie? My point exactly. But like I said, Bill Watterson is the king of going out on top. He could have milked that comic strip for decades, but he said, I’m creatively spent, and enough is enough, and that was the end of that.

I guess writing is one endeavor where you never really wear out your welcome. J.K. Rowling is still writing books. They’re not selling 120 million copies like the first Harry Potter book, but they’re good books! Updike wrote into his eighties, and was still cranking out incredible stuff. Suzanne Collins might do well to quit while she is ahead, writing scads of Hunger Games sequels and prequels, and yes, it can be hard to get off that gravy train. It’s really something to follow an author over the course of his career, going from the early days of fluid intelligence to the later days of crystallized intelligence. For what it’s worth, I much prefer later Updike to early Updike, but I prefer early Barry Hannah to later Barry Hannah.

One last thing about newsletters. Richard Russell wrote his for 57 years, until he was 91 years old. His letter was beloved by many, but he did not go out on top—his circulation was much lower at the end than earlier in his career. Still, a stunning achievement, and if I wrote The Daily Dirtnap for 57 years, I would also be 91 at the end. Think I’ll pass. One of the things about going out on top is versatility—what else can you do? What else are you good at? Who knows, maybe the fat gray-haired guy will have a career in music. By the way, on a scale of 1 to Lizzo, I am about a four.