Indulging Your Dormant Generative Urges

Indulge me as I weave through a reflection I’ve been lingering on for a few weeks.

I was listening to software entrepreneur Travis Kimmel on the Mutiny Podcast (link). The whole conversation is fascinating and honestly quite dense when it gets into finance. There is a section where Travis, who studied philosophy, discusses the role of liberal arts in business.

He used a word that keeps unfolding itself in my head — “generative”.

He approaches the word came from its anti-thesis — skepticism. Travis is a fan. “Skepticism enforces discipline”. That’s a tight phrase describing a critical function for investors and traders — scrutinizing claims. Naive optimism can easily domino into over-extrapolation which is a fancy word for what hindsight simply calls “stupidity”.

Skepticism plays a key role in sound decision-making. The Big Five personality test has a dimension called agreeable/disagreeable. In Being A Disagreeable Investor, I point to the advantages of being disagreeable. [FWIW, I have median scores on 3 of the Big Five traits but score higher than the 90th percentile on “conscientiousness” and “agreeableness”. I interpret conscientiousness as the ability to jump through hoops. Combined with a standardized test, getting through a selective college signals high self-control + satisfactory IQ. As far as me being “highly agreeable”, I’ll just be happy that firms I worked for didn’t give people that test and screen me out.]

Back to Travis. Despite, celebrating skepticism he argues that skepticism cannot exist on its own. It must be part of a team because it is fundamentally “non-generative”. It is a razor that reduces. It does not build.

Seeing it phrased this way was a personal revelation. It unlocked a reinterpretation of my work history. It goes like this:

• The first 12 years of my career I was on the trading floor. I was in the mix of hundreds of people. It was social and often raucous. I got to see what my competitors were doing because they stood next to me all day. When a smart competitor did something others did not it was like watching an “alien move” in chess. Why did they do that? What were they seeing? By observing what happened before and after, you could use pattern-matching to reverse engineer decisions and strategies. This allowed you to learn more from a given sample of trades than you could in fully electronic markets where you can’t easily tie the tape back to its actors. High learning rates are addictive. The job was fun.
• When I moved upstairs to the hedge fund my early impression was it appeared quiet and academic. Without the roar of a pit to direct my attention, I had to re-train my senses and build new tools to “see” markets. Since I was hired to build the commodity volatility business I also had to guide decisions about infrastructure. My first few years at the fund were long hours and lots of collaboration with dev teams. I loved it. For new reasons. I was building. It was highly generative.
• Once the cockpits and engines were built, it was time to pilot the plane. Like the trading pits, I was back to the daily dogfight. Trading is a constant parade of mid-air decisions for 7 hours. Except this was a lot less fun than the pits. On the floor, there was a Ralph Wolf and Sam Sheepdog camaraderie that came with being shoulder-to-shoulder with your adversary. Everyone is both an opponent but also a possible future employer/employee. My first backer was a guy in my pit who worked for another firm. The people who have my old job are friends from my pit days. Upstairs, you have your team to talk to which is great, but it’s one outlet. Otherwise, you’re always chatting with brokers. Voice brokers can be friends but they are always balancing a fiduciary conflict. There’s no escaping the poker dynamic of those interactions.

With the lower learning rate off the floor, only occasional forays into building after the initial heavy lift, and a dip in social stimulation (I’m no life-of-the-party but self-identify squarely with extraversion) the job became tedious.

This arc combined with writing as a larger part of my life and the urge to self-align with projects where “agreeableness” holds more value to make leaving the gig inevitable. When I think about work, I realize that the right fit for me will need to tilt more towards being “generative” and I never saw it in those terms so clearly. So thanks for the language Mr. Travis Kimmel.

If interested, here’s how I personally apply this to myself.

I’m not much of a consumer. I rarely buy stuff and I don’t collect anything. Every piece of matter that seems to accumulate in my life feels like a liability I have to service. Things own me, I don’t own things. I feel bad when I don’t maintain things, but I also have zero desire to maintain them. So minimalism is less of a design aesthetic and more of a gate-protector of my time (ironically, I’m not much a fan of minimalist, cold modern spaces. I like rich environments that feel tied to the past with taste in ways I don’t possess but love to admire).

I feel like I was supposed to be some kind of bizarro librarian. Bizarro because I don’t read that much. But I collect ideas. I collect them for synthesis. Ultimately, I want ideas to be combined so they are useful.

Collection and synthesis are generative functions. A team needs both with skepticism sprinkled in to “enforce discipline”. The functions are then passed to a do-while loop known as practice.

The requirements of practice act as a filter on the vastness of ideas one could choose to collect and index.

Applying this logic personally, I’m increasingly of the mindset that my constraint is “how do I teach” effectively. “Effectively” means arming others with the ability to improve their outcomes from learning. I’m not interested in teaching trivia. I want to enable agency in service of growth.

Finding smoother ways to both represent and communicate lessons is a generative task. If I shed restraint for a moment, I admit it’s actually compulsive. It stirs me in ways that the video game of trading does not.

I’m more interested in being obsessed than the actual output of a job (in the case of trading, the output is cash baby). But I’d rather be obsessed than rich.

Some are obsessed with being rich. Some have obsessions that lend themselves to getting rich (the best athletes, programmers, portfolio managers). I think my best chance of being happy with how I spend my time is being obsessed. And who knows, maybe that will lead to getting rich.

(I was born in America and have gotten lucky enough to consider myself rich by any broad objective standard. I purposefully live in a place that makes me feel like a small fish in a big pond so I don’t think of myself as rich but I’d be an ass to bring that attitude to a global perspective. Words have scale dependence.)