Perfectionism, Portfolios, and Schmitts Gay Beer

In a recent New Yorker article,¹ Leslie Jamison writes about people who are perfectionists to the point of near madness, many of them unable to function at all because of their feelings of inadequacy. There is now in fact a branch of psychology devoted to the study and treatment of self-destructive perfectionists.

Jamison, and the psychologists she profiles, distinguish this condition from people who merely pursue excellence, because unlike them, perfectionists can never be satisfied. Even if they reach their goals, Jamison writes, they don’t “touch that fundamental sense of being unacceptable.” Perfectionism in this view is a symptom of a psychological disorder that often stems from childhood trauma, sibling rivalry, or other sources.

The unremittingly dark picture that Jamison paints is not consistent with my experience. I know creative, highly successful people whom I would call perfectionists, in that they’re rarely fully satisfied with their work product, yet who lead normal, well-adjusted lives.

The Serious Investor’s Burden

Sometimes when people meet me who know a lot about investing, they say flattering things about my career; the word “legend” was used about me yesterday on X (not a brag, it’s relevant). I usually grin weakly and thank them, while I’m internally rejecting the praise as my brain runs through a random selection of my fuckups over three decades of managing money.

As I’ve written before, it’s impossible for a serious investor to be fully satisfied with his results. If his stocks went down, he’s sad; if his stocks went up, he didn’t buy enough of them and is sad; if his stocks went up and he bought enough, but other ones he considered buying and didn’t went up more, he’s also sad. You see the problem.

I’m having a good year, yet I don’t like to watch CNBC because there are stocks I sold that have gone up ten times since then, and I can’t stand it when their names scroll by. As I walk around my neighborhood, even the license plates on parked cars pain me, if they have the ticker symbols of stocks I’ve lost money on. I can’t forget any big investment mistake I’ve ever made, but I don’t consider myself psychologically unwell.

I lost a lot on Kazkommertsbank (KKB)

I once heard an anecdote about an extremely successful London-based hedge fund manager — he returned 39% annualized for an eight-year stretch in the 90s and is now a multibillionaire — whose children thought they’d soon be poor because every night at dinner he moaned that he was “going broke.”

Then there’s the GOAT, Warren Buffett, who says in public that there are no called strikes in investing, yet in private is known to spend a lot of time lamenting the opportunities he missed, like Walmart and Amazon. If you read his annual letters, they can sound as if he’s trying to convince himself that he’s done a good job running Berkshire Hathaway. To me, he seems reasonably content with his results, but not truly happy.

The Creative Arts

Van Gogh considered “The Starry Night” a failure, and Monet cut, burned, and kicked 500 of his paintings. These are extreme examples, and in both cases did indicate psychological disorders: Monet attempted suicide and Van Gogh succeeded.

But there are also artist perfectionists who are emotionally healthy, just determined to get as close to their vision as possible. Stanley Kubrick was known for shooting dozens of takes, including a world record for one shot in The Shining. Steely Dan’s Walter Becker and Donald Fagen often demanded many takes from different session players before settling, and remixed “Babylon Sisters” 274 times. Were they difficult to work with? Sure, but look at the incredible results.

Meanwhile, much of the art we see has a “good enough” quality, which has always been true but seems especially so now in the era of streamers and their hunger for content. When an eight-episode miniseries has only enough plot for two, someone mediocre has deemed the scripts good enough and delivered them to another mediocrity. You only need to compare the first five seasons of Game of Thrones, sourced from George R.R. Martin’s painstakingly written books, to the last three seasons, which went past the books and were full of shorthand Hollywood cliches.²

In their drive for perfection, Kubrick and Becker/Fagen likely saw and heard flaws in every finished work, even their most acclaimed. John Lennon called “Across the Universe” “A lousy track of a great song.”³ Woody Allen says he never watches his own movies: “I just cringe when I see them, I don’t like them.”⁴ In all cases, at some point they had no choice but to release the product to the world, with its perceived defects.

My oldest friend is a comedy genius named Robert Smigel, aka Triumph the Insult Comic Dog. I recently texted him that I had rewatched an SNL parody commercial he’d written, “Schmitts Gay Beer,” starring Adam Sandler and Chris Farley. The first thing he said about this beloved parody, with 3.2 million YouTube views and 2,000+ comments, was, “The music ruined it,” referring to the version currently streaming.

The original video was set to Van Halen’s “Beautiful Girls,” and when the rights expired, SNL substituted a generic guitar riff that lacked the humor and precise editing of the VH song. You and I wouldn’t notice the problem, but Robert does. He always treated his sketches as works of art — not even knowing, in the 1980s and 90s when they first aired, that they’d live forever on the internet — and he was determined to extract every laugh, all with only a few days from the concept until going live.⁵

Kubrick, Allen, Becker/Fagen, Smigel: all perfectionists, rarely fully satisfied with the art, but all prolific and none fitting Jamison’s psychological profile.⁶

Steve Jobs

I have to end with one of the legendary perfectionists, who exasperated his team with endless revisions and would scream and cry when the product didn’t meet his standards. Still, Steve Jobs knew that it had to be released, deficiencies and all, famously saying in connection with the launch of the first Macintosh (which had a toolbar he didn’t like), “Real artists ship.”

Conclusion

Those who seek something beyond mere excellence must spend their careers in a penumbral space far past “good enough” but short of “perfect,” accepting that the latter state is unattainable. Often they must overcome the resistance of mediocrats (my word) even to approach their original visions. While they can experience triumphant moments, they’re rarely completely happy. They are the ones whose contributions last.

With original Van Halen song:

triumphicdhq

A post shared by @triumphicdhq

1. “Enemy of the Good” (August 4, 2025)

2. I predict that when Martin finishes the book he’s writing, HBO will remake the final seasons with new actors in most of the roles. I don’t know if anyone reading this will live to see it. Besides Martin, I pray for the health of 89-year-old Robert Caro, who has been researching and writing the fifth volume of his LBJ bio for many years and has said he won’t let anyone else finish it, presumably fearing it would come out below his standards.

3. As noted by Andrew Hickey in his essential podcast “A History of Rock Music in 500 Songs,” among The Beatles Paul McCartney was relentless with the musicians until he got his tracks exactly as he wanted, while Lennon probably lacked the attention span and drive to do the same thing.

4. I also cringed on rewatching Manhattan, but that was for other reasons.

5. I cited to Robert two of his other works that I knew he loved: the Steve Martin SNL show opener “I’m Not Gonna Phone it in Tonight” and the cartoon “Christmastime for the Jews.” He agreed they were close to perfect, but within seconds found a flaw in each one.

6. Robert is fully normal, except for his deranged conviction that the New York Mets will win another World Series in our lifetimes.