A few of my closest friends met up this past weekend to play some nerdy board games, giving me FOMO naturally (alas, they’re on the other coast). While I had to miss out on the satisfying brain burn I did get to hear about some of the banter.
One friend, a partner in a law firm, asked the other, a senior engineer in tech:
“How do I get people who work for me to do great work, because it sounds like there’s a motivation generational gap in the legal profession these days?”
(She’s relayed the same struggle to me in the past, so I like how she’s canvassing friends for answers!)
My engineer friend asked what makes people want to be lawyers. The answer was basically “money and status.”
He explained:
In engineering, there are goals above money and status – engineers actually like to build and solve hard problems. As a manager, I use those goals to motivate doing great work. Build better things and solve harder problems, and you’ll get the opportunity to build even better things and solve even harder problems. Not as easy to do if the only levers you have are money and status.
I’ve thought about this personally quite a bit. In 1999, when I was going through the on-campus recruiting tourney for my first job out of college I was focused on trading gigs. I had read Liar’s Poker many times (Lewis admits it was a cautionary tale that backfired). I was the head TA for a 200+ person 300-level investments course where I bullshitted my way through 2 15-minute lectures a week (while I felt like an imposter, the pure fear of trying to not be an idiot in front of an auditorium bootstrapped confidence).
I identified with trading because it struck me as a shortcut, a way to make good money only working market hours. It fit my self-image at the time — clever slacker. I looked with disdain at my peers sycophanting around the I-banking analysts at the career booths who were standing in the same building just a year ago in an ill-fitting suit to breathe the same air as someone “making 6-figures” (but no weekend to speak of). Guh-ross.
Of course, all of this was me being naive not to mention trying to position bad personal habits as somehow adaptive. Plus the hypocrisy — my goal was the exact same — make money. There was no thought of any kind of craft. I would have chosen anything that made loot efficiently.
[To be contrasted with my sister who wanted to be a veterinarian since she was little and has been one now for 20 years and genuinely loves her job.
In a cute aside, her husband is a successful businessman but their kids think she makes way more $$ than him because her job is so visibly important.]
As my trading career progressed, my attitude evolved. It is a mixed bag (what’s not?) but generally stimulating. It can be extremely fun occasionally while being boring and repetitive most of the time. It can be stressful, but it’s not life and death, and the acute stress is focusing.
Yet, there are 2 properties that stand out in the context of who trading will attract AND who it will keep.
The first is evergreen — it’s an honest living. It’s you heads-up vs the market. No clients, no sales, nobody to blame. Here’s a computer, make money come out of it. This is a bit less pure where firm politics can play a role but this is more relevant on the actual business/management side but less influential on a moneymaker in a seat and totally impertinent to sole props.
The second property is this business of “prestige”. In the late 90s, trading, especially floor trading, was still a misfit profession. The holdovers were either Marisa Tomeis or Vinnies with Bayonne accents, drug-dealer smart and scary OR aspy disagreeable chess or bridge prodigies who’d be unemployable in any org with performative norms. They were all hyper competitive. The Ivy Leaguers were starting to show up, but selected from a pool of those willing to be called “clerks” and earning $30k to start.
Well, it’s 2025. The jig is up. Asian high schoolers, future doctors in a prior era, are rockin’ Jane Street tees. Starting pay has compounded at 10% pa since 2000, far outpacing inflation. Market-maker is not just an accepted but coveted career choice. I benefited from entering a relatively null-prestige career whose underlying business boomed.
That boom re-shaped perceptions going forward. The trading world, flush with massive profits, formalized and consolidated. There used to be hundreds of different color jackets on those trading floors but the flywheel of technology, scale and leverage has centralized market share over the past generation.
[See A Former Market Maker’s Perception of PFOF]
One wonders.
- Does lure of prestige and the abundance of information that has blossomed around catering to its aspirants corrupt the signal?
- Are they still hiring the type of kid who is banned by Vegas casinos by age 22 (an example of someone in my cohort who later led one of the SIG-alum trading outfits that is well-known in the arb world)?
- Is that person even a desirable candidate today? Or is the selection process, the internships + high attrition rates, the best heat-seeking missile for long-term talent?
- How porous is this defense against the climbers easily identified by those robotic “is this gonna be on the test” eyes?
This matters to the authentics. The hackers. The ones who would do the job for less.
Remember Cate Hall’s line:
The most important thing to hire for is deeply giving a fuck, and no amount of money will get someone who doesn’t care to care. This means you should pay people enough that it’s easy for them to say yes, but not enough that it’s hard for them to say no.
Or Adam Mastroianni:
Eventually I realized, no, what I really want are the students who give a hoot… It’s not that hard to give people skills. It’s way harder to give them interests… trying to substitute external incentives for internal incentives is like trying to power your country with whale blubber when everybody is walking around with a hydrogen cell battery inside them.
Chasing a prestige job strikes me as a recipe for disappointment. They are overbid because they slough demand from other gate-kept high-prestige fields whose status afford them the sociopathic luxury of self-perpetuating hazing rituals, exactly the kind of thing a trained hoop-jumper will recognize as a legible and critically, safe, ladder. So even if you chase a prestige job for the right reasons, you are now surrounded by this low-imagination bore at best or socipath at worst (see Max Read’s amusing Toward A Theory of The Millenial Ambition Psycho).
This is all diagnosis. And fairly obvious but probably impolite to say because it captures so many people. Why wouldn’t it? We’re born to copy.
This is Redfin’s chief economist, Daryl Fairweather on her decision to study econ at MIT instead of engineering and her family’s reaction:
I definitely needed buy in from my dad since he was, you know, helping pay for my education. So I called him up and told him that I loved the Freakonomics book so much I was going to major in economics. Uh, he tried to immediately talk me out of it or at least like interrogate me. why I was making this change.
He was especially concerned about economics because one of the things that allowed my grandmother to excel in her career was that with architecture, you know, you’re judging the building, you’re not judging the person. But I think in the humanities or the social sciences, you are, like the person who is delivering the message sometimes is the message.
And as a black woman, I might have, like, undue bias against me or people might perceive that my research is biased because of my identity. And the work won’t be able to speak for itself because it’s more subjective than mechanical engineering or architecture or something like that. So he had some grounds there.
And he, you know, he had a career as a prosecutor, so he knew firsthand that people will judge you. The judge will judge you. The jury will judge you. And sometimes for things that are outside of your control, that are just based on, you know, your signifiers. So he was concerned and he was so concerned that after he talked to me he called his mom, my grandma, to tell her what was going on and try to get her to talk me out of it.
And she like had this really weird response, or at least at the time I thought it was weird, where she told me that I should continue to pursue engineering because I would find a better husband in engineering. And she said that businessmen were only concerned with status. And I tried to correct her and say like, well I’m not majoring in business, it’s a separate major.
I’m majoring in economics. But I think what she was concerned about was, yeah, who would my spouse be? And I think from her experience, uh, engineers are just like more logical and less maybe egotistical than people who pursue money as their career. So she was concerned about that.
Daryl mentions something just ahead in the interview regarding what she saw when she got to campus.
When I got to college and I was around the other students and people were like identifying based on their majors, I I knew that what I wasn’t, like I was hanging around mechanical engineers and I just wasn’t like them. Like they had been working on cars and they had done engineering projects and they were like so much more passionate about it than I was.
And same with the people that were pursuing biology or or a career in medicine. They just had this passion that I didn’t have for those things. But then I found like this, I found like, I found, I found the thing that I could get passionate about once I started learning about economics and that’s when I got really dug in.
This takes me back to my engineering friend at the beginning of the post and his roommate in college, also a dear friend. They were the real deal. Tinkerers, hackers. Hardware obsessed. The roommate was MacGyver meets mad scientist — his room covered in tools and components. I still remember him wearing the dirty Cornell HEV shirt. always going to “work on the car”. He is an epic snowboarder, mountain-biker, high-diver, muay thai fighter and surfer — in fact he did his Phd in Honolulu.
Today, he’s building f’n Waymos (2 years ago he took a few of us on a 1-hr ride thru SF in it) and loves his job as much as my sister loves hers. As you might guess, he’s super smart but he’s also scary competitive (I’d literally skip class to be able try to knock him off the Crazy Taxi leaderboard on Dreamcast or foosball — no competition was beneath us). After graduating, I told him he should come to trading because his competitiveness, comfort with risk, and totally overclocked mentals would kill it. He could not understand the allure. I’ll paraphrase his puzzled reaction:
You’re doing it just for money, you’re not building anything. What’s the point? If you build something cool you’ll make money anyway.
This was obvious to him at 22.
The funny thing to me is over time I’ve come to feel that the way my sister and he see the world is child-like. Simplistic.
“We should heal animals.”
“Wouldn’t it be cool if cars drove themselves?”
These are the thoughts of a child.
There’s not a whole lot of thought to how much of the surplus they could extract from the usefulness. Just a faith that the surplus would be “enough” for them to not have to do things they see as pointless.
Meanwhile, the finance/lawyer brain is all about structuring. How do I roll this up to compress the entire future of activity into a price for today that can be exchanged? Transferring risk to its most efficient holder is a valuable service (see Finance Guilt) but do the thought patterns that make you good at this turn into an optimization virus crowding out any sense of play?
Does packaging the future gloss over the living of it? The finance brain lives in the future, when thriving demands we are present. If you are a craftsperson whose life’s work is rendered but a number on a page, have “they” assassinated the mystery of creation? It used to feel like you were outside and then you show up to work and there are walls and a ceiling. You can see the max upside, and it’s well below the rays of hope you used to stand in but didn’t look at directly.
There’s been an unusual number of “?”s in this essay. I don’t have a better answer to my friend about why a corporate lawyer should be motivated by anything other than status or prestige or money. Just like liquidity is a public good and worth cultivating, the messy process of ensuring our rules are justly conceived and upheld is an ideal. But I doubt that this sits at the base of most people’s decision to go into corporate law any more than one becomes a dentist because they were obsessed with teeth their whole life. The truth is a dumb 20-year old chooses our lives for us and it takes creativity and courage to make a graceful exit from an expensive choice.
The reason for a colleague whose work is uninspired but still arrives at their job each day starts with unflattering premises, either about them or you. It’s too late to fix the problem — it starts earlier in the pipeline. If you chose a job because it would give you a prestigious existence and discovered the prestige is empty calories congrats —you’re awake. Just imagine how much other crap you now need to unlearn?
If the prestige is satisfying, congrats as well, for you have a long, profitable career ahead of you. And as you rise, you’ll be surrounded by people just like you.
But please, for the rest of our sake, play amongst yourselves.
🔗Related reading
Moontower’s select sections from Paul Graham on Finding and doing your work