Moontower #160

First, Happy Labor Day!

Sorry about Moontower being a day late. I was traveling much of last week then off-the-grid camping until yesterday. Today’s letter is a follow-up to last week’s Moontower. I wrote last week:

Since leaving my trading career nearly 18 months ago I’ve allowed myself a lot of space to explore. I’ve been wary of narrowing my focus prematurely. However, the last few months have started revealing opportunities that warrant deeper dives. I’ll discuss them when it makes sense to. In the meantime, I felt compelled to write about the meta-framework that has helped me filter opportunities.

I published the post this week.

The post will be especially useful to those who @khemaridh describes as having a “pebble in their shoe”. We are all compartmentalized to some degree. But integration is something that matters more to some than others. The cost/benefit varies by individual. Many are bribed by high salaries to work on things they don’t feel great about (ad tech and some finance stuff come to mind). No judgment from me.

No matter how you start out in your career, it’s inevitable that the cost/benefit changes. You can become more inspired or just get bored. Money may matter less or you find you want more of it.

These changes in attitude coincide with changes in your internal compass. I’m not talking about your morality. I’m talking about the sense of your own potential.

You realize that chasing your own potential naturally integrates you.

If you feel uneasy about how compartmentalized your life feels, I’d bet at least even money that you are not reaching for your own ceiling.

I can anticipate an objection already. Especially on Labor Day. “Bruh, I can’t be chasing my own potential, I gotta knock out this rent.”

You’re 100% right. I’m not suggesting you pull the cord, and chase a fantasy. If in this compartmentalized state (think a starving artist waiting tables or cubicle drone who fancies themselves the next Neal Stephenson), you aren’t taking any part-time steps towards your “passion”, it’s not your passion. It’s just a fantasy. I can tell you from my experience of being a horny 19-year-old once upon a time that there are no prereqs to having a fantasy.

But if you want to make your potential and dreams real you have to take actions. You will need to be intentional. Living deliberately, designing your own omakase life, is hard because society offers many pre-made dishes that satisfy your first need — literal hunger. If anything, menus are convenient.

The problem with menus is their designs are highly suggestive. From ads for Happy Hour to the order of the list, the nudges are everywhere. But no menu ever suggests that you check out the restaurant next door. If you walked into this particular restaurant, the management rightly acts as if this is where you intend to be.

That assumption itself is not as neutral as it appears.

The restaurants you see are the ones that can afford to attract you with shiny logos and prime real estate. Imagine it’s 1994. To go off the beaten path you’d to, what, call your friend on a landline for their epicurean input? I’ll just look for the golden arches thank you very much.

The internet changed all that. From Citysearch (I’m old) to Yelp, we could get fed and happy at the same time. And have a new experience. Choice can be overwhelming or life-affirming. (Your perspective has more to do with the quality of your own taste/filters, but that’s a topic for another day). From remote work to new careers to permissionless access to your own audience, the internet has also changed the menu of work.

Am I being cheeky when I compare what you do with your working life with what you choose to eat? I don’t think by much. Sustenance and delight are not the same. To say someone is surviving versus thriving is a softer way of saying that person is slowly dying. Language is a funny thing that way.

So going back to the objection…”bruh, I gotta knock out this rent”. Yes, you do, but don’t forget that’s just survival. Some people are so trapped that is enough. We grade on curves for good reasons. But for you, a person voluntarily reading this utterly whimsical letter where life and death definitely do not hang in the balance, you cannot make this objection convincingly.

The internet has made ordering off the metaphorical menu easier. Embrace it. You can exchange an existential problem (“what am I doing?”) for a technical problem (“how am I going to sustain what I actually want to do?”). You don’t make that trade because it’s easy.

You do it because it’s worth it.

Anyway, that’s a wordy-enough preamble to the longest post I’ve written. It’s part philosophy, part story, and part reference so feel free to skip around.

Design Your Own Engine (31 min read)

The post is the output of observing myself on a lag.

Practically speaking, I felt the need to write it because as I transition my activities from total free-form to even modest focus, it was useful to think about how to narrow attention and consider at least second-order effects of how you could do that in an integrated (more efficient) way.

I talk about sustainability which is a super-category of monetization. I have little experience there but have some meta-principles and hopefully encouraging and pragmatic thoughts for those who aren’t skilled at being commercial-minded (like myself).

Finally some rah-rah at the end that hopefully manages to not be too cliche. Even if it is, you get to see what cliches seem worth bearing mind from the sea of cliches I could have chosen from.

Random bonuses:

  • You’ll learn the very basics of how a gas-powered engine works. (If this is the extent of your interest then do yourself the biggest favor in the world and check out this benevolence by @BCiechanowski.
  • When you see “:[hypertext]” that’s me experimenting with @ncasenmare new Nutshell technology on my blog.

Money Angle

I’m going to stick with a somewhat irreverent tack for Labor Day with this share.

On Meaningless Careers (7 min read)
by Jack Raines

Jack’s Young Money finance blog is consistently fun to read. A few excerpts from this post:

The abstract:

People love work.

The problem isn’t that the youngest generation hates work; the problem is that many of the jobs offered to the youngest generation aren’t work at all. The spreadsheet-heavy, mid-level-manager-dominated, buzzword-filled roles offered to us are jobs, but they are hardly “work.”

For any gamers out there, one of the oldest tricks in the book is giving your younger sibling an unplugged/disconnected controller, so they feel like they are “playing”, while you are in control the whole time.

Many “jobs” today are simply unplugged controllers. The work would get done, whether or not we take part in the process. We are simply moving numbers, smashing buttons, and staying busy, with no regard for actual productivity.

We never stop to ask “is this job necessary?” Because we are paid increasingly higher and higher salaries for our participation in this ever-growing proliferation of pointless jobs.

Sebastian Junger once said, “Humans don’t mind hardship, in fact they thrive on it; what they mind is not feeling necessary. Modern society has perfected the art of making people not feel necessary.”

The concrete:

Football was overbearing, painful, and straight-up frustrating at times, but from day one on the football team, I felt like my contributions mattered.

Contrast that with my experience working in corporate finance.

The people I worked with and worked for in corporate finance were great. My supervisors were certainly nicer than my coaches (which wasn’t a difficult hurdle to surpass, considering some of my football coaches called me things that cannot be repeated over text). And the work wasn’t hard. It was easy, simple. And anything that I didn’t already know how to do could be learned in a few days.

And the best part? I was paid a living wage for my efforts in this corporate finance job. And yet, I hated it. Actually, hate is much too strong of a word.

The opposite of love isn’t hate, it’s indifference. And I was aggressively indifferent to my work.

If pandemic-induced remote work showed me anything, it showed me how little “work” was necessary to do my job. I legitimately “worked” 5-10 hours per week at times, but I was always pretending to “work”, by either moving my mouse to look active or tinkering with files, models, and decks that didn’t really need tinkering to pass the time.

It was pretty obvious that if I didn’t show up for a day, week, or month, the show would go on. I was playing with an unplugged remote.

I was trading my time for a paycheck, with no regard for the actual work being done.

And I wasn’t alone.

The “prestige lie”:

The paradox of modern work is that the most prestigious jobs often involve the least actual work. If you can grind on tedious tasks longer than anyone else, you can get paid a lot of money. You gain material riches at the loss of your individualistic drive.

To quote David Graeber’s Bullshit Jobs:

Shit jobs tend to be blue collar and pay by the hour, whereas bullshit jobs tend to be white collar and salaried. Those who work shit jobs tend to be the object of indignities; they not only work hard but also are held in low esteem for that very reason. But at least they know they’re doing something useful.

Those who work bullshit jobs are often surrounded by honor and prestige; they are respected as professionals, well paid, and treated as high achievers – as the sort of people who can be justly proud of what they do.

Yet secretly they are aware that they have achieved nothing; they feel they have done nothing to earn the consumer toys with which they fill their lives; they feel it’s all based on a lie – as, indeed, it is.

Of course, this whole thing makes sense. Prestige is the lie we tell ourselves to justify our “bullshit jobs.”

We don’t like the work, and in the back of our heads, it feels like we are selling our souls and our time for a paycheck. If we dwelled on that realization too long, we would probably hop off this treadmill entirely. But prestige is that North Star that continues to pull us forward.

The thing about prestige is that it isn’t real. It’s a vanity metric. Don’t believe me? Then why are half of all middle-management jobs now called “vice president?”


Prestige has mollified our collective work restlessness, our existential angst. Prestige keeps those uncomfortable self-realizations imprisoned in the backs of our minds.

Prestige allows the show to go on.

But if you adjust your values, and if prestige loses its luster, the nothingness of these jobs becomes impossible to ignore.

This all ties back cleanly to my post. The prestige “North Star” is one of many compass headings that can leave you with that “pebble in the shoe” feeling.

I’d imagine Labor Day would be an important day for Graeber. A day to celebrate those shit jobs that pay by the hour. They have no prestige but they are honest.

All of this reminds me of this section from 15 Ideas From Morgan Housel’s Interview with Tim Ferriss:

The optimal amount of bullshit

You had Stephen Pressfield on your show, and he was talking about a time when he lived in a mental institution. He was not a patient himself, but he lived there and he starts talking to all these people. And he made this comment that a lot of the common denominators of these people who lived in a mental institution was they were not crazy, they just could not handle or put up with the bullshit of life. They just couldn’t deal with it. And that was kind of why they ended up in the mental institution. And he said all these people were the smartest, most creative people who he had ever met, but they couldn’t put up, they had no tolerance for the bullshit of the real world. And that to me, just brought this idea that there’s actually an optimal amount of bullshit to deal with in life. If your tolerance for bullshit is zero, you’re not going to make it at all in life…

I listened to that [interview] and it was like, “Oh, see, these people could not function in the real world because they had no tolerance for bullshit.” The second step from that is, there is an optimal amount of bullshit to put up within life. And that was where this article, “The Optimal Amount of Hassle,” came from.

And I remembered I was on a flight many years ago and there was this guy in a pinstripe suit who let everyone know that he was a CEO of some company, and the flight was like two hours delayed, and he completely lost his mind. He was dropping F bombs to the gate agents and just completely making an ass of himself because the flight was delayed. And I remember thinking like, “How could you make it this far in life and have no tolerance for petty annoyance, like a delayed flight?”

And I just think like there’s a big skill in life in terms of just being able to deal with some level of bullshit, and a lot of people don’t have that. There’s another great quote that I love from FDR, who of course was paralyzed and in a wheelchair. And he said, “When you’re in a wheelchair and you want milk but they bring you orange juice instead, you learn to say, ‘That’s all right.’ and just drink it.” And I think that just having the ability to put up with that kind of stuff is, I think, really important and often lost in this age where we want perfection. We want everything to be perfect, and it never is.

[Kris comment: I have a good friend who is insanely smart and well-traveled (top 1% in both categories of everyone I know). His brother is not conventionally successful but I was curious what that brother is like. His brother is also very well-traveled in part to choosing a life in the armed forces. But my friend also described his brother as extremely smart. But…incapable of tolerating the b.s. The military life is simple in the ways he prefers. It has always stayed with me, that my friend quite explicitly described his brother as being unwilling to suffer bullshit. I often feel that “getting ahead” in a conventional sense is really just alpining sedimentary layers of compressed bullshit. When I use the word “integrated” metaphysically, a large portion of that is finding your personal sweet spot on the b.s. continuum.]

Jobs like trading and finance are especially vulnerable to bullshit because we put abstractions like price discovery, efficiency, and liquidity on pedestals. Rightfully so. In Finance Guilt, I defend these ideals. The progress of civilization does depend on them.
The problem is that whenever something is good it’s easy to rationalize its excesses beyond the point of diminishing returns. It’s hard to know when more isn’t better.

You have heard the lament that too many wicked smaht people go into finance when they should go into science. What about the genius trading quants who literally used to build weapons for Russia? I’ll leave this for the utilitarians to sort out. Meanwhile, someone who just learned to spell libertarian is hyperventilating “the market will decide”. As if the market’s outputs themselves weren’t downstream of rules set by politicians horse-trading in “the room where it happens.”

Byrne Hobart’s quote brings object-level framing to an abstract argument:

The defense of 1031 exchanges is that they encourage growth because they keep people spending money on new property developments instead of cashing out and enjoying their gains. Which embeds two assumptions:

  1. It’s generally better to tax consumption than investment, and
  2. Real estate investment is a particularly worthy kind of investment to avoid taxing.

Assumption #1 sounds true, but is circumstantial. Assumption #2, though, is hard to defend. Real estate speculation does produce jobs, but it also produces macroeconomic volatility and sometimes threatens the financial system. From a macroprudential perspective, where the goal is to reduce the odds of financial crises, it might make more sense to have 1031 exchanges for everything but real estate: sell your company, and you can roll the money into starting a new one; sell a mall or skyscraper, and you get taxed. But it’s always fiendishly hard to predict the long-term incentives created by a change in the tax code. Any tax on realizing gains, for example, is implicitly a subsidy on borrowing against appreciated assets instead of realizing those gains. If that’s true, the net effect of eliminating 1031 exchanges would be that real estate portfolios would turn over less often. If we assume that people vary in their ability to make good real estate investments, this would mean that the best such investors wouldn’t make as many discrete investing decisions, which would make prices a bit less efficient. Which might be a reasonable tradeoff: making real estate investing a less tax-optimal choice could be a fair trade in exchange for making real estate prices less reflective of their value. But it’s still a tradeoff, not a straightforward benefit. Quirks in the tax code become load-bearing over time; even if they didn’t make economic sense when they were made, the structure of the economy only makes sense in light of the tax incentives that economic actors have already responded to. If you assume that people are reasonably good at reacting to incentives—or, more plausibly, that over time the people who are good at doing this end up controlling more assets—then any change in those incentives has complicated and unpredictable results.]

Last Call

Let’s do follow-up riddles based on last week’s post. You don’t need to read last week to participate. The solutions are at the end of today’s post.

  1. In a follow-up to Another Kind Of Mean:

    You are going on a 2-mile trip. If you drive 30 mph for 1 mile, how fast do you need to drive the second mile to average 60 mph for the entire trip?

  2. A father and son get into a terrible car accident. The father is immediately killed. The boy is taken to the hospital. The surgeon looks at the boy and says “I cannot operate on him. He’s my son”.


From My Actual Life

I went camping for the first time with my family. We’ll do it again.

Solutions to the riddle:

  1. There is no speed you can travel the second mile to average 60 mph for the whole trip. In order to average 60 mph for a 2-mile trip you must travel a mile per minute. So you cannot take more than 2 minutes for a 2-mile trip. If you drive the first mile at 30 mph, you have already driven for 2 minutes.
  2. The surgeon is the boy’s mother. I fell for this riddle when I was in HS. I was reminded of it by a reader in the comments to last week’s post a Sexist Gives A Math Lesson. Here’s the thing…I’ve asked this riddle to many people, male and female. And almost everyone gets it wrong. Their mind goes to harder explanations — it’s a ghost, it’s a stepdad, etc. I’m not kidding, test this out at your barbecues today.

    You know which cohort of people gets it right? Elementary school kids. Even the boys. Do what you want with this.

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