Things take time.

  • Nintendo fairly famously was born in 1889, and the modern incarnation — Yamamuchi Nintendo & Co., LTD — was established nearly fifty years later, in 1933. They spent forty years selling playing cards, then another decade operating merely as a distributor of electronics before coming out with their first piece of electronic hardware.
  • The Lego Group began in a Danish workshop in 1932; it took them 26 years until a confluence of technology, iteration, and luck led them to what we now refer to as a Lego. (Er, sorry — a Lego brick.)
  • Nike spent eight years merely re-selling (literally, not figuratively) Onitsuka shoes to a U.S. audience.
  • Gates and Allen ran Microsoft as what was essentially a freelance firm for eight years, too, before scoring a contract with IBM (and even that took an additional two years to be parlayed into MSDOS.)

(There are, of course, some companies that like Athena sprout fully-formed from the head of their creators — Amazon and TSMC come to mind.)

When we build hagiographies of the companies we love (or at least find most interesting), it can be tempting to draw clean, neat, satisfying arcs and fast forward through the boring eras that do not inform our modern understanding of those organizations.

But neither the Nike Cortez nor the Lego System 236 Garage with Automatic Door came from the first decade of either company’s existence.

Part of success is staying alive long enough to have the right kinds of things happen to you all at once.


Chalk this one up right next to Scott Pilgrim Takes Off in the annals of "okay, maybe recycling IP isn't that bad after all", though I think the Tom Ripley persona is less like, say, Star Wars, and more something like Macbeth or James Bond — an archetype, a narrative playground through which directors and actors can create their own adventures and make their own bold statements.

And talk about a bold statement! Showrunner Steven Zaillian (who was not a name I was familiar with coming into the premise but was responsible for writing many parts of what I would consider the "elevated normcore dad canon": Schindler's List, Gangs of New York, Moneyball, Clear and Present Danger). This is as auteurly as one can imagine from a miniseries, with every cent in the budget sumptuously accounted for.

This is beautiful, captivating television. There's a lot to return to, and it's powerful in its first strokes. What more [1] can you want?


  1. Besides, perhaps, maybe one or two less plot points that strain incredulity? ↩︎


I have a good number of people ask me what software stack they should use. I always have a two-part answer:

  1. Use what you're familiar with. If there's something that you've spent a good amount of time using, stick with that one.
  2. Rails. People are usually surprised when I say this because I don't use Rails, and while I spent some time writing Ruby when I was at Stripe, I would not consider myself an aficionado by any means.

My answer is motivated by a melange of various inputs. When choosing a software stack, you want something that:

  • is commonly used, so you can easily hire and onboard folks and find resources without having to pull teeth.
  • is battle-tested and has been around for a while, ensuring there's a lot of prior art, and you don’t have to worry about living at the bleeding edge.
  • has a robust and productive third-party ecosystem with packages dedicated to solving the problems you're going to run into as you get a SaaS off the ground.
  • is dynamic and portable in terms of hosting, so you're not tied to one or two specific infrastructure providers.
  • is productive, which of course is a squishy term that's impossible to quantify but I don't think anyone's going to really say Ruby or Rails is a hard language/framework with which to make forward progress.

Rails tackles all of these things and, in my opinion, is marginally better than everything else. I say marginally because I don't think Rails has so much more productivity inside of it that you should discard 5 years of experience with PHP, Python, or some other language that you're more comfortable with to pursue it.

But, if you are coming at the SaaS world from a complete state of "tabula rasa", Rails and the Ruby ecosystem seems like the way to go.

(Really, though, it doesn't matter. Your software stack is almost certainly not going to decide the life or death of your business.)


Welcome to spring, bona fide and humid. Lots of writing this month:

In other, non-writing news:

  • We launched Buttondown's new docs, the third iteration in eight years (the first being Notion, the second being what this new iteration is replacing.) This was largely Ben's project, and he's publishing a blog post more formally today or tomorrow on it; I'm really happy with how it turned out.
  • Went to MicroConf. Still need to write up some notes; I had a great time.
  • Busy, busy, busy. The next four months are gonna fly by.


I started Work Clean with the expectation that it would be like so many of the mediocre pieces of airport bookstore fodder in its ilk: "here's how this somewhat interesting concept in an orthogonal discipline can be applied to your life, with 200 pages of poorly edited and increasingly thin metaphors to buttress out the runtime."

And, in many ways, it is that book. But — and maybe it's where I am in my life and my increasing sense that software development is going to look more like cooking than like industrial design, maybe it's just because I really liked The Bear — I found it to be the best possible version of that book, and probably the single most useful primer on how to orient yourself around knowledge work that I've read in a long time. It is a thinly-veiled pastiche of Getting Things Done [1], but replaces much of the now-dated specifics in GTD with things that are much more modern and relatable. The prose is solid; the metaphors and too-cute anecdotes do not outstay their welcome.

It is not a life-changing book, but it (along with The E-Myth Revisited) are the two best productivity/business/personal growth books I've read in a long time, and the two that I would have very few qualms recommending.


  1. Pastiche is perhaps not the right word, as the author directly calls out GTD as an inspiration ↩︎


I chatted about Python with Mike, who was lovely (even though he's using Substack.)

Listen to the episode

Postgres' JSONB functionality is fast and useful but when I find myself dropping down from the Django ORM into SQL to do weird things, the syntax strikes me as confusing and arcane. As such, when I need to do esoteric things it takes me longer time than I'd like, and in hopes that this saves you ten minutes of Stack Overflow trawling:

SELECT id, metadata FROM emails_subscriber
WHERE jsonb_typeof(metadata) != 'object'
OR jsonb_path_exists(metadata, '$.keyvalue() ? (@.value == null)')

Given a table emails_subscriber that has a JSONB column metadata, this returns all rows in the table where metadata itself is not null but some value within metadata is null (e.g. {"foo": 3, "bar": null}).


Lots of people have spent the past few days discussing the perceived increase in difficulty in getting an entry-level programming job relative to the halcyon ZIRP days of yesteryear. I am sympathetic to new grads running into this; I am dismayed that when I ask some [1] of them what they've been doing their answer boils down to "sending out my resume to as many jobsites as possible" and "programming exercises."

It's hard to be prescriptive when it comes to the job market — I barely remember what being a new grad was like, and even then I was a white guy who could correctly deploy "orthogonal" during the soft-skills interview, and so I try not to opine on tactical advice and instead stick to talking about my lived experience as an interviewer.

Here is one thing though that I think is so criminally under-utilized by prospective applicants that it is worth calling out: writing friction logs. Friction logs:

  • take very little time (you could dedicate five hours a week to this practice and end up with a dozen solid friction logs after a month)
  • require no specific domain expertise
  • require no financial investment
  • strengthen your product skills
  • strengthen your writing skills
  • immediately make you stand out more than every other candidate with a welterweight GitHub Pages that links to your senior project
  • provide an obvious in-road to a company that is more interesting & higher-value than yet another anodyne cover letter

Read Sebastian's terrific essay on how to write one; check out User Onboard for some higher-production value versions; go forth and log frictions.

(Putting my money where my mouth is: if you do this ten times, email me your blog and I'm happy to set up some time chatting with you and introducing you to people who work at companies that are hiring. Serious.)


  1. Not all! Some! ↩︎


Cognition, a six-month-old startup in the AI coding space just raised $175m at a $2b valuation:

Despite the skepticism surrounding Devin’s launch, the AI coding assistant has shown promising results. According to the SWE-Bench benchmark, which evaluates AI models on software engineering tasks, Devin achieved a 13.86% accuracy in resolving issues unassisted, surpassing the previous best model’s 1.96% unassisted accuracy.

I am (to put it mildly) very skeptical of their ability to defend that valuation, but I wanted to zoom out a bit and offer a small bit of advice when it comes to understanding the potential and value of tools like these:

You need to be able to taste the kool-aid they're selling you.

I feel like I am in a very weird uncanny valley of bearish on the current crop of AI-enablement tools and yet very very bullish both on the ones that I use (which is to say, Copilot) and the overall potential for the industry going foward. Why? Because every single tool I use tends to be bad, and bad in obvious ways that make me suspicious of demos.

I am quite excited for Cognition to open up their beta so I can try it out — I might eat my words, and certainly if any company can, say, double the efficiency of a median developer than they've earned a multi-billion dollar valuation. But until then, I assume that it is vaporware whose differentiation will be gobbled up by players (Microsoft, OpenAI, Sourcegraph) more well-positioned to execute at scale.


Stripe held the keynote for Sessions, their annual WWDC/re:invent-esque conference, this morning. I wanted to jot down some thoughts while they’re still fresh. (I think the changelog is the best way to poke around both the changes I’m writing about and the ones that I omitted.)

Caveat / disclosure

I am a Stripe user and shareholder. That being said, I have a public track record of being very persnickety, as evinced by the sheer number of emails I send to [email protected]:

Thank you Jeff (and every engineer who fixed one of my nits!)

Stuff I am particularly jazzed about

  • It seems very clear to me that if we were to flash-forward five years, the single most important thing shipped (though it technically soft-launched back in January, I think) was Automations. If you were to take the entirety of all payments integration code in the world and throw it into a very large graduated cylinder, you’d see a huge swath of “valuable-in-terms-of-revenue-but-cheap-in-terms-of-differentiation” code float to the top that all looks essentially like “listen to invoice.will_be_due and then send a coupon if usage is low,” and I think it is a clear and obvious area that Stripe should invest in. Automations efforts are always a very interesting exercise in prioritization and triage; the things that you can do right now are pretty limited and largely a superset of stuff that was buried in that terrifying Billing settings page, but I doubt that will be the case for long. In particular, I think the success of automations will be driven by Stripe’s ability to ingest more and more customer-level usage data and evolve past the fairly crude metadata key-value store. (Imagine, for instance, being able to spin up an automation within the dashboard that says “if someone cancelled their subscription, cited pricing as a reason, and had used the product for at least six months, offer them a 50% discount but only if they pre-pay for a year.)
  • Organizations, allowing you to group various accounts together and run aggregated analyses. A very iykyk pain, but one that I am quite excited to have solved for Third South Capital-related reasons.
  • Usage-based billing. Just an absolutely beautiful API; I am the first to whine about how convoluted the core Billing models have become in the efforts to be able to model more and more complex use cases, but this feels elegant and ergonomic.
  • Risk management with Connect. It is kind of odd to me that this not being branded as “Radar for Connect” [1], but I’m happy with the end result. Connect stuff is where I feel the most underequipped on a day-to-day basis with Stripe, and this is a strong step in the right direction.
  • Adaptive pricing, which is very boring but will instantly wipe out a solid 13% of my inbound billing questions

Things that weren’t mentioned but still jazz-worthy

Some stuff was posted in the changelog that I think is quite exciting, despite not making the “will the CFO at Mindbody care about this?” cut:

  • Sandboxes, a spiritual successor to “test mode”. Being able to arbitrarily spin up environments for end-to-end testing or contractors would be tremendously useful.
  • Connect platforms can access support cases for connected accounts, which is tremendously and immediately useful. [2]
  • Entitlements, which allow you to start pushing a bit more about your billing state machine to Stripe. [3] I struggle to think of particular use cases today in which I’d want to do this, but can think of many that I’m sure will come, like:
    • Surfacing entitlement information within the Customer Portal
    • A/B testing entitlement splits and seeing impact on upsell within Checkout

What’s still on my wishlist

  • More investment in customer portal.
  • More investment in bringing all of the small nice ships (upsells! branding! etc.) to Connect so I can enable them automatically on behalf of my users.
  • Recurring pay-what-you-want prices.
  • Programmatic access to the notes field on customers, invoices, etc.
  • A/B testing non-payment-options pieces of Checkout, such as copy or branding.

  1. I get that it’s more than that, but still! ↩︎

  2. With the caveat that I can’t use this, because it excepts “Connected accounts who are or have been connected to multiple platforms”. This, like many other things, is both incredibly frustrating and incredibly understandable, and I think leads to some pernicious incentives for platforms. ↩︎

  3. Good primer on entitlements here: https://arnon.dk/why-you-should-separate-your-billing-from-entitlement/. ↩︎


Two people who I think are smart and good both said things that I bump up against [1]:

"The software industry is rapidly converging on just three languages: Go, Rust, and JS. It would be smart to learn one of those really well, and have at least a working acquaintance with the other two."

Lately, “Design Engineer” has felt more and more like a good fit for me. Perhaps because it is deliberately cross-discipline. It satisfies my deep-seated feeling of “don’t put me in a box” while also satisfying my belief that one narrow discipline can’t produce everything necessary to create a great experience on the web.

I do not think it's coincidental that the best (smartest, most productive, have generated the most enterprise value for their employers) engineers I know describe themselves as "Developer", "Designer", "Engineer", or some other vague, generic, one-word name that belies no hint of their seniority or position in the org chart or stack of choice. (Or you can go even further, Xerox PARC-style, and call yourself a "Member of Technical Staff" — same idea applies.)

Job titles, strong opinions on technical stacks: all of these things are necessarily restrictive. If you want to succeed in your career, you need to shift your way of thinking away from framing of your work in the context of the genre of artifact you produce and towards the context of the value you produce.

Spend time with every single other department at your company; spend time with users (as much as possible); spend time reading everything that comes across your desk. Get really really good at asking clarifying questions and combining disparate threads. Then write some code — and what you write matters much less than the outcome of its deployment, because despite what anodyne publicly-posted job descriptions might tell you your job is not to write code — it is to produce value for the organization.


  1. I am being very deliberate with choosing "bump up against", here, because I don't think they are necessarily wrong nor do I think they are being prescriptive. So please don't interpret this as "these two are dummies, here's what you should do". ↩︎


I wrote last month about using weird tests. Here's another example: checking for broken internal links in our upcoming docsite redesign!

const extractInternalLinks = (content: string): string[] => {
  // Check for internal links only, in the form of [text](/path).
  const internalLinks = content.match(/\[.*?\]\(\/.*?\)/g);
  return (
    (internalLinks
      ?.map((link) => {
        const path = link.match(/\(\/.*?\)/)
          ? link.match(/\(\/.*?\)/)![0].slice(2, -1)
          : null;

        // For now, we'll filter out any images or other non-page links under
        // the assumption that they can be caught elsewhere (e.g. the build step.)
        if (path && path.match(/\.(png|jpg|jpeg|gif|svg|webp|ico|pdf)$/)) {
          return null;
        }
        return path;
      })
      .filter((link) => link !== null) as string[]) || []
  );
};

const MARKDOC_DIRECTORY = "content/pages";

// Make sure all mdoc files with internal links are valid.
fs.readdirSync(MARKDOC_DIRECTORY).forEach((filename) => {
  test("Check internal links in " + filename, () => {
    const fullyQualifiedFilename = `${MARKDOC_DIRECTORY}/${filename}`;
    const content = fs.readFileSync(fullyQualifiedFilename, "utf-8");
    const internalLinks = extractInternalLinks(content);
    internalLinks.forEach((outboundPath) => {
      const mungedOutboundPath = mungeInternalLinks(outboundPath);
      const expectedOutboundFilename = `${MARKDOC_DIRECTORY}/${mungedOutboundPath}.mdoc`;
      expect(
        fs.existsSync(expectedOutboundFilename),
        `Internal link to "/${outboundPath}" in "${filename}" does not exist.`
      ).toBeTruthy();
    });
  });
});

This is admittedly less weird than some other examples I've written about, but the core idea is the same: your test runner is a fast, ergonomic, pre-existing tool to express invariants upon your codebase, and it's easier to reach for something like this than pull in another third-party dependency.


This week marks two full years since I left Stripe and started what in retrospect is a new (and likely) final phase of my career as an independent technologist. I didn’t quite know what that would entail at the time: it turned out to be a combination of founder (my work at Buttondown) and managing partner (my work at Third South).

I wanted to put to pen some notes and thoughts for folks considering a similar such change, loosely organized by topic that people tend to ask about:

Balance

Work-life balance is, in general, worse and harder than it was previously. This can obviously vary a lot from person to person or season to season — for instance, I could probably work ~15 hours/wk if I was happy to just subsist off of my current engagements rather than wanting to actively try and grow them — but independent work largely means eschewing the safety net that larger companies afford you. I am never more jealous of my friends in industry than when they talk about taking a multi-week vacation and setting an OOO reminder because they know their team can handle it.

Flexibility

That being said, work/life flexibility is at an all-time high. I work a pretty conventional schedule most days, but even then if I have a day that I’m not feeling 100% I know I can take it easy or rest or spend my time in the garden or whatever. (At a wider-aperture level, I get the privilege of structuring my day exactly how I want it: heavily skewed towards focus work, with only a single two-hour meeting block in the late afternoons.)

Fulfillment

I am, without question, the most deeply creatively fulfilled I have been in my entire life. My work feels like an extension of my self and my ethos, in a way that feels more akin to an artisan; I feel an extremely large sense of pride and connection with what I produce and manage.

Community

It is fairly lonely relative to the digital/tangible watercoolers that defined and enhanced my time at larger companies. Most of the online communities ostensibly geared towards folks in my position are overwhelmingly oriented towards salesmanship and transactional relationships; I’m grateful to the folks who I’m able to chat with about a variety of business and business-adjacent things (thank you, Nick, Sumana, Shep, and Jo!), but I find myself missing the sense of ubuntu and camaraderie that comes from being able to chat with dozens of people about a shared mission.

Growth

I have grown more as an engineer, operator, marketer, and craftsman in the past two years than in any other stretch of my life, bar none. There’s one bit I miss of being at a large company, which is dealing with deeply cutting-edge technical problems, but my ability to analyze information, make decisions, and perform at a high-level has grown very quickly.

Money

It is really hard for me to offer a cogent, good-faith analysis that suggests independent work is, on average, going to bring in more money than working in industry. Buttondown is a very healthy and quickly-growing business, and even then its returns are less than if I had just sat in a ~750K TC FAANG-ish job for the past two years. [1]

Risk

In retrospect, this was probably the silliest concern I had when striking out alone. I don’t mean this to sound braggadocious, but I know (and most founders know) that if I decided I wanted to go back into the warm arms of industry I could send a few emails and end up a week later with a job at a company I admired.

Identity

Even after two years, I struggle with nouns. I've finally started to kick the habit of referring to myself introductions as "ex-Stripe"; I've never loved the word "founder" or "entrepreneur", both of which strike me as having vaguely startup-ish connotations that don't feel quite correct. Even over the past six months, I've realized that folks who I'm meeting for the first time think of me less as "plucky internet person trying something new" and more as "CEO of company" [2] which is — odd. I am realizing, even now, how much of my identity and sense of self was wrapped up with being X title at Y company, and how strange it is to lose both lodestars.


A few weeks ago, I grabbed dinner with an old friend visiting from Seattle. We were chatting about how our careers had diverged over the past half-decade, and they commented:

It’s really impressive that you spent so much time when you were 25 about doing this and then you just did it. I feel like there’s so many people who joke about leaving tech and buying a farm or whatever and, you know, obviously you didn’t do that, but you still committed to a big change. How did you take the leap?

The answer I gave him — and that I’ve given a few other friends and acquaintances — was this:

When I decided to pursue independent work, I was 29 years old, with no children, a loving spouse (who was bringing in money!), a good amount of savings, and projects that I was actively excited about.

The conditions were perfect, and yet I still didn’t feel ready — my life was good, I liked my job, and it felt very risky to rock the boat and throw away what was a very good and comfortable lifestyle in favor of something new.

And yet. I knew I wanted to try something else eventually. And I kept asking myself: if not now, when? Certainly it would be harder to give up things like health insurance and a steady paycheck once I have children; certainly it would be harder to spend entire days in flow ten years from now than it would be today.

And so. It quickly became obvious in my mind that if I wasn’t going to try going independent now, then I might as well extinguish the thought forever, as the conditions for such a move would literally never be better than they were today.

And I really didn’t want to extinguish the thought forever — my dream for over a decade had been to live my life on my own terms.

And so I quit my job, and here we are.


All of this is to say: creative independence is not for everyone. My experiences may not — probably will not! — reflect yours, and my circumstances and context are probably different than yours.

But if you think it might be for you — if not now, when?


I would be remiss if I didn't end this essay with a deep note of gratitude to my wife who more than any single person pushed me to take this jump, even though it meant she'd have to deal with me being even more insufferable than I already am.


  1. This, by the way, is a good shibboleth for if a person writing online about their experience is full of shit — if they’re suggesting you should do this for monetary reasons, chances are they’re trying to sell you a course. ↩︎

  2. Albeit an idiosyncratic one! ↩︎


  • Magnuson Park on a lazy Saturday in July;
  • Golden Gardens on a rare sunny October day;
  • Top Pot (for nostalgia's sake);
  • Gasworks;
  • Taste of India;
  • Unicorn (and living across the street from it for two years);
  • the Vivace sidewalk stand (where I made my first Seattle friend, hi Shep);
  • Zig Zag;
  • coffee-walks around Green Lake;
  • Freeway Park;
  • the bar at Canlis;
  • the twice-baked almond croissant at Bakery Nouveau;
  • the live performance of the Charlie Brown Christmas soundtrack at the Cornish Playhouse;
  • Damn the Weather (and their Caesar Salad sandwich);
  • long, lovely, lazy walks/runs/rides around the Burke-Gilman;
  • the omni-present haze of pot and laughter at Cal Anderson;
  • Twice Sold Tales and Ada's;
  • 5 Point, where I had my first legal beer;
  • the University farmer's market;
  • the Arboretum;
  • Knee High, Inside Passage, and Canon (on industry nights);
  • Herkimer;
  • SBP (before it got overrun by all the UW kids);
  • Schilling, Paseo, Dick's;
  • any and every possible sporting event.

I lived in Seattle for ten years; I left because it was time to leave; every time I come back I think about staying. Seattle forever.


This could have been a much better show (and I suspect that the British show which inspired it very well might be), as I love the premise — half whodunit, half improv — but it is simply just not a good time to interact with. Feels like a series of ten-minute long webisodes with as many hits as misses.

At the very least, you can tell that the people involved are having a very good time. That's better than nothing!


A number of people have asked me in the past week why Buttondown isn't open-source, given:

  1. the love and overt financial commitment we have to open source
  2. the increasing number of "open source startups" (Cal, Maybe, Lago coming to mind)

I preface this answer with the fact that this is coming from my personal blog and not Buttondown's blog, and maybe a year from now either my philosophy or my math has changed on the matter, but the answer right now is something like the following:

  1. To be open source in a meaningful sense, the process of working on Buttondown would have to change pretty drastically.
  2. The number of users who benefit from Buttondown being open source is fairly small.
  3. The theoretical increased rate at which the product could improve is not particularly high. [1]
  4. I think running a company (even an idiosyncratic one) is a fairly distinct skillset and bag of incentives from open source maintainership, and as bad as I am at the former I think I'd be even worse at the latter.

I write the above in pencil, not pen — I think points one and three could very well change in the future. But right now I think the vast majority of startups who "go open source" do so more as a marketing tactic than as a genuine belief in open source, and I think the best way for Buttondown to "be open source" is to open source components (e.g.) and contribute financially to the software on which it relies.


  1. I find it instructive to look at Posthog's commit history. ↩︎


I admired and liked Klute but did not quite love it as much as I loved The Conversation, which I thought tackled the coming battleground of large-scale surveillance and visibility and the small-scale world of human minutiae with more aesthetic aplomb and coherent theses.

Most of my pico-criticisms are answered in Bakula's spiritual successor to Klute, The Parallax View. Absolutely dynamite performance by Beatty, two of the most memorable cinematic experiences of the past few years for me (the film-within-the-film, and the long slow shot of Hammond's corpse being driven, via golf cart, into an increasingly large number of chairs in the now-empty auditorium.)

I'm sure many comparisons can and will be drawn between this and Three Days of the Condor, but that film chooses to at least offer the viewer a glimmer of hope: that a sufficiently disciplined and idealistic protagonist can make a difference in the world. Bakula offers no hope here, and the sheer paranoia and cynicism of this film (very few questions answered; very few fears dispelled) makes me feel like it is a perfect movie for these times, when we are once again terrified of the world around us and the people who drive it.

Highlights

We all ache for the chance to be proud again.


Finally, our intuitions should be informed by the economic idea of “opportunity cost of time.” If a child is watching TV, they are not doing something else. Depending on what that “something else” is, TV watching may be better or worse. Many studies of this emphasize that (for example) your kid can learn letters or vocabulary from Sesame Street, but they are better at learning those things from you. That’s almost certainly true, but … [i]f the alternative to an hour of TV is [instead] a frantic and unhappy parent yelling at their kid for an hour, there is good reason to think the TV might actually be better.

via Cribsheet

We all ache for the chance to be proud again.

via The Parallax View

When I was in high school and even more insufferable than I am now, a friend and I started a tumblr called "sun words". The concept of this was to collect words that we discovered that were particularly succulent or mellifluous.

I have found myself learning more and more words recently. This is fun and good: I was worried for a while that my days of adapting and playing with the English language were largely behind me. I thought it would be interesting and illustrative to collect a list of the words I've learned recently alongside the sources from which I've gleaned them.

When I first started building this catalog, I expected the plurality to be from the NYT crossword 2, and the data appears to bear that out:

  • manuport: a natural object that has been deliberately taken from its original environment and relocated without further modification
  • parvenu: a person of obscure origin who has gained wealth, influence, or celebrity.
  • asthenia: abnormal physical weakness or lack of energy
  • hoosegow: a prison (via Fargo (Season 5))
  • stentorian: loud (via NYT Crossword)
  • ratiocination: a process of exact thinking
  • limerence: a state of involuntary obsession with another person
  • iatrogenic: relating to illness caused by medical examination or treatment.
  • sequelae: a condition which is the consequence of a previous disease or injury.
  • ostranenie: the artistic technique of presenting to audiences common things in an unfamiliar or strange way so they could gain new perspectives and see the world differently.
  • lebensraum: the territory that a state or nation believes is needed for its natural development
  • moksha: release from the cycle of rebirth impelled by the law of karma
  • quondam: that once was; former
  • lanai: a porch or veranda.
  • analphabetism: illiteracy; the inability to read and write
  • conurbation: an extended urban area, typically consisting of several towns merging with the suburbs of one or more cities.
  • metanoia: change in one's way of life resulting from penitence or spiritual conversion
  • pandiculation: the involuntary stretching of the soft tissues, which occurs in most animal species and is associated with transitions between cyclic biological behaviors, especially the sleep-wake rhythm
  • rorqual: a streamlined whale
  • quiddity: the inherent nature or essence of someone or something.
  • katabasis: a mytheme or trope in which the hero embarks on a journey to the underworld
  • axilla: the space below the shoulder through which vessels and nerves enter and leave the upper arm; a person's armpit.
  • aborning: while being born or produced
  • hormesis: a dose-response phenomenon characterized by low-dose stimulation and high-dose inhibition
  • bezoar: a small stony concretion that may form in the stomachs of certain animals, especially ruminants, and which was once used as an antidote for various ailments.
  • haruspicy: the art or practice of divination
  • geodesy: the branch of mathematics dealing with the shape and area of the earth or large portions of it.
  • buccal: Related to the cheek
  • poteen: alcohol made illicitly, typically from potatoes.
  • pentiment: an underlying image in a painting, especially one that has become visible when the top layer of paint has turned transparent with
  • volvelle: a rotating paper 'wheel chart', often found in early astronomy or mathematical books
  • diopter: a unit of refractive power that is equal to the reciprocal of the focal length (in meters) of a given lens.
  • echolalia: meaningless repetition of another person's spoken words as a symptom of psychiatric disorder.
  • amanuensis: a literary or artistic assistant, in particular one who takes dictation or copies manuscripts.
  • ochlocracy: government by mob rule
  • ferial: denoting an ordinary weekday, as opposed to one appointed for a festival or fast.
  • baksheesh: a small sum of money given as a tip, bribe, or charitable donation
  • finial: a distinctive ornament at the apex of a roof, pinnacle, canopy, or similar structure in a building.
  • sockdolager: a forceful blow
  • zhuzh: make more exciting, lively, or attractive.
  • nychthemeron: a full period of night and day
  • overmorrow: the day after tomorrow
  • allopathy: the treatment of disease by conventional means, i.e., with drugs having opposite effects to the symptoms.
  • hieratic: of or concerning priests
  • paracosm: a detailed imaginary world, especially one created by a child
  • morganatic: relating to or denoting a marriage in which neither the spouse of lower rank, nor any children, have any claim to the possessions or title of the spouse of higher rank.
  • tulpa: an object or being that is created through spiritual or mental powers
  • iatrogenic: relating to illness caused by medical examination or treatment.
  • asthenosphere: the upper layer of the earth's mantle, below the lithosphere, in which there is relatively low resistance to plastic flow and convection is thought to occur.
  • plat: a plot of land
  • armillary: resembling an armlet or bracelet: consisting of rings or circles
  • cabotage: the right to operate sea, air, or other transport services within a particular territory.
  • clerestory: the upper part of the nave, choir, and transepts of a large church, containing a series of windows. It is clear of the roofs of the aisles and admits light to the central parts of the building.
  • acedia: spiritual or mental sloth; apathy.
  • anxiolytic: (chiefly of a drug) used to reduce anxiety.
  • rhadamantine: rigorously strict or just
  • eucatastrophe: a sudden and favorable resolution of events in a story; a happy ending.
  • argot: the jargon or slang of a particular group or class.
  • geas: an obligation or prohibition magically imposed on a person
  • tonsure: a part of a monk's or priest's head left bare on top by shaving off the hair
  • gruit: a herb mixture used for bittering and flavouring bee
  • bouquiniste: a dealer in secondhand books
  • anaglypta: a type of wallpaper that has a permanent raised design
  • footling: trivial and irritating
  • quango: a semipublic administrative body outside the civil service but receiving financial support from the government, which makes senior appointments to it
  • mandinarate: a ruling class of scholars and elites
  • spatulate: having a broad, rounded end.
  • guerdon: a reward or recompense.
  • aquarist: a person who keeps an aquarium
  • moll: a gangster's female companion
  • sedevacantism: a doctrinal position within traditionalist Catholicism which holds that the present occupier of the Holy See is not a valid pope due to the pope's espousal of one or more heresies

vranyo white lies or half-lies in Russian culture, told without the intention of (maliciously) deceiving, but as a fantasy, suppressing unpleasant parts of the truth

integument a tough outer protective layer, especially that of an animal or plant.

matutinal of or occurring in the morning.

shufti a look or reconnoiter, especially a quick one.

mahout a person who works with, rides, and tends an elephant

hob a flat metal shelf at the side or back of a fireplace, having its surface level with the top of the grate and used especially for heating pans.

pied having two or more different colors.

mandamus a judicial writ issued as a command to an inferior court or ordering a person to perform a public or statutory duty.

eigengrau the uniform dark gray background that many people report seeing in the absence of light

hegira an exodus or migration

bracken a tall fern with coarse lobed fronds, which occurs worldwide and can cover large areas.

gastrique caramelized sugar, deglazed with vinegar or other sour liquids, used as a sweet and sour flavoring for sauces

mittelstand a group of stable business enterprises in Germany, Austria and Switzerland that have proved successful in enduring economic change and turbulence

strix in the mythology of classical antiquity, was a bird of ill omen, the product of metamorphosis, that fed on human flesh and blood

souq A street market, particularly in Arabic- and Somali-speaking countries; a place where people buy and sell goods; a bazaar.

favela a slum or shantytown located within or on the outskirts of the country’s large cities

coracle a small round boat made of wickerwork covered with a watertight material, propelled with a paddle

atelic showing an action or happening as being unfinished

ignosticism the philosophical position that the question of the existence of God is meaningless

mawkish sentimental in a feeble or sickly way

leveret a young hare in its first year

orgone a supposed sexual energy or life force distributed throughout the universe that can be collected and stored (in an orgone box) for therapeutic use

grook a form of short aphoristic poem or rhyming aphorism

choreomania n uncontrollable urge to dance, especially in a frenzied, convulsive manner

spoor the track or scent of an animal

geognosis knowledge of the world

scaffa a cocktail prepared at room temperature

segigniorage revenue or a profit taken from the minting of coins, usually the difference between the value of the bullion used and the face value of the coin.

veridical coinciding with reality

dipsomania alcoholism, specifically in a form characterized by intermittent bouts of craving for alcohol.

nullifidian a person having no faith or religious belief.

ectopic in an abnormal place or position

banlieue a suburb of a French city, especially Paris.

gurn to make a grotesque face

apposite apt in the circumstances or in relation to something.

genetrix a female parent; a mother

ischemia an inadequate blood supply to an organ or part of the body, especially the heart muscles

narthex an antechamber, porch, or distinct area at the western entrance of some early Christian churches

parataxis the placing of clauses or phrases one after another, without words to indicate coordination or subordination, as in Tell me, how are you?

allograft a tissue graft from a donor of the same species as the recipient but not genetically identical

chrism a mixture of oil and balsam, consecrated and used for anointing at baptism

modiste a fashionable milliner or dressmaker

glasnost the policy or practice of more open consultative government and wider dissemination of information

jalopy an old car in a dilapidated condition

chiaroscuro the treatment of light and shade in drawing and painting.

hosanna an expression of adoration, praise, or joy

excursus a detailed discussion of a particular point in a book, usually in an appendix.

quadrille a square dance performed typically by four couples and containing five figures, each of which is a complete dance in itself.

apperception the mental process by which a person makes sense of an idea by assimilating it to the body of ideas he or she already possesses.

paternoster an elevator consisting of a series of linked doorless compartments moving continuously on an endless belt.

sumptuary relating to or denoting laws that limit private expenditure on food and personal items

catafalque a decorated wooden framework supporting the coffin of a distinguished person during a funeral or while lying in state.

oneiromancy the interpretation of dreams in order to foretell the future.

apricity the warmth of the sun in winter

oology the collection and study of birds' eggs especially in relation to their shape and coloration

terroir the complete natural environment in which a particular wine is produced

nephology the study or contemplation of clouds

txoko a typically Basque type of closed gastronomical society where men come together to cook, experiment with new ways of cooking, eat and socialize

yegg a burglar or safecracker

marotte a prop stick or sceptre with a carved head on it

aubade a piece sung or played outdoors at dawn, usually as a compliment to someone

chrestomathy a selection of passages from an author or authors, designed to help in learning a language.

holon something that is simultaneously a whole in and of itself, as well as a part of a larger whole

feve a small trinket hidden in a king cake or similar dessert

scopophilia pleasure in looking; in Freudian psychoanalytic theory, an infantile instinct

apoptosis the death of cells which occurs as a normal and controlled part of an organism's growth or development.

hebetude the state of being dull or lethargic

deixis the function or use of deictic words, forms, or expressions.

pycnocline a layer in an ocean or other body of water in which water density increases rapidly with depth.

hircinous Of, or pertaining to goats; hircine

bogatyr a stock character in medieval East Slavic legends, akin to a Western European knight-errant

antinomy a contradiction between two beliefs or conclusions that are in themselves reasonable; a paradox.

adipose fat

propinquity the state of being close to someone or something; proximity.

sere (especially of vegetation) dry or withered

anosognosia a condition in which a person with a disability is cognitively unaware of having it due to an underlying physical condition

arrogate take or claim (something) without justification.

chiton a marine mollusk that has an oval flattened body with a shell of overlapping plates

hapax a word that only appears once in a work of or genus of literature or in a body of work by a particular author

etiology the investigation or attribution of the cause or reason for something, often expressed in terms of historical or mythical explanation.

polysemy the coexistence of many possible meanings for a word or phrase

slew to turn (something, such as a telescope or a ship's spar) about a fixed point that is usually the axis

berm a flat strip of land, raised bank, or terrace bordering a river or canal.

gantry a bridge-like overhead structure with a platform supporting equipment such as a crane, railroad signals, lights, or cameras.

mare large, dark, basaltic plains on Earth's Moon, formed by ancient volcanic eruptions

latibulate to hide oneself in a corner

enconium a speech or piece of writing that praises someone or something highly.

xerophagy the practice of eating dry food, especially food cooked without oil

interstice a space that intervenes between things

figurant one that figures in a scene without speaking or without taking a prominent part

demotic denoting or relating to the kind of language used by ordinary people; popular or colloquial.

teratogen an agent that can disturb the development of the embryo or fetus

fictile capable of being molded; made of earth, clay, etc.; by a potter.

harridan an angry and unpleasant woman

concupiscence strong sexual desire; lust

picayune of little value or account; small; trifling

formulary an official list giving details of medicines that may be prescribed.

hybristophilia sexual interest in and attraction to those who commit crimes

widdershins in a direction contrary to the sun's course, considered as unlucky; counterclockwise.

pullulate to send forth sprouts, buds, etc.; germinate; sprout

factotum an employee who does all kinds of work.

gasconade extravagant boasting.

muliebrity womanly qualities; womanhood.

callipygian having well-shaped buttocks

meretricious apparently attractive but having in reality no value or integrity.

cloche a small translucent cover for protecting or forcing outdoor plants.

nictitate to blink

battement a movement in which one leg is moved outward from the body and in again

dissimulation concealment of one's thoughts, feelings, or character; pretense

ruction a noisy fight

propitiation the act of appeasing or making well-disposed a deity, thus incurring divine favor or avoiding divine retribution

lazarette a small compartment below the deck in the after end of a vessel, used for stores.

lordotic having an increased inward curving of the lumbar spine

bafflegab incomprehensible or pretentious language, especially bureaucratic jargon.

tonneau the part of an automobile, typically an open car, occupied by the back seats

redolent exuding fragrance : aromatic

snee to cut or thrust with a knife, esp when fighting

agnate a relative whose kinship is traceable exclusively through males

wainscott line (a room or wall) with wooden paneling

ariose characterized by melody; songlike

sangfroid composure or coolness, sometimes excessive, as shown in danger or under trying circumstances.

erumpent bursting forth or through a surface

mell to blend; mix; meld. to meddle; concern oneself

thurible censer

aureate denoting, made of, or having the color of gold

transom a strengthening crossbar, in particular one set above a window or door

febrile feverish

travois a type of sledge used to carry goods, consisting of two joined poles pulled by a horse or dog.

agential of, relating to, or expressive of an agent or agency

chaparral vegetation consisting chiefly of tangled shrubs and thorny bushes.

gamine a young woman with a mischievous, boyish charm

novena a form of worship consisting of special prayers or services on nine successive days.

oscular related to kissing

alterity the state of being other or different; otherness.

uxorious having or showing an excessive or submissive fondness for one's wife

interpellate to question (someone, such as a foreign minister) formally concerning an official action or policy or personal conduct

oriel a projection from the wall of a building, typically supported from the ground or by corbels

caconym an incorrect name for something

perihelion the point in the orbit of a planet, asteroid, or comet at which it is closest to the sun

pettifogging placing undue emphasis on petty details

agnotology the study of deliberate, culturally-induced ignorance or doubt, typically to sell a product or win favour

ontogenesis the development of an individual organism or anatomical or behavioral feature from the earliest stage to maturity

hiatal of, relating to, or involving a hiatus

hamartia a fatal flaw leading to the downfall of a tragic hero or heroine.

salubrious favorable to or promoting health or well-being

canticle a hymn or chant, typically with a biblical text, forming a regular part of a church service.

sacristy a room in a church where a priest prepares for a service, and where vestments and other things used in worship are kept.

cay a low bank or reef of coral, rock, or sand

palooka a stupid, clumsy, or uncouth person

deontic relating to duty and obligation as ethical concepts

tatterdemalion a person in tattered clothing; a shabby person

pythonist a person who professes to prophesy through some divine or esoteric inspiration

ataraxy a state of serene calmness

sybarite a person who is self-indulgent in their fondness for sensuous luxury

snood an ornamental hairnet or fabric bag worn over the hair at the back of a woman's head

peripatetic traveling from place to place, in particular working or based in various places for relatively short periods.

antrum a natural chamber or cavity in a bone or other anatomical structure

aneuploidy the presence of an abnormal number of chromosomes in a cell, for example a human cell having 45 or 47 chromosomes instead of the usual 46

passerine relating to or denoting birds of a large order distinguished by feet that are adapted for perching, including all songbirds.

rill a small stream

gouache a method of painting using opaque pigments ground in water and thickened with a gluelike substance.

friable easily crumbled

panegyric a public speech or published text in praise of someone or something

efflux something given off in as or as if in a stream

tenebrous dark; shadowy or obscure

doyenne a woman who is the most respected or prominent person in a particular field

chiral asymmetric in such a way that the structure and its mirror image are not superimposable

solecism a grammatical mistake in speech or writing

exaptation a trait that has been co-opted for a use other than the one for which natural selection has built it

lustic vigorous; jovial

voluptuary a person devoted to luxury and sensual pleasure

bedizen dress up or decorate gaudily.

locavore a person whose diet consists only or principally of locally grown or produced food.

ostinato a motif or phrase that persistently repeats in the same musical voice and/or pitch

martinet a strict disciplinarian, especially in the armed forces.

attar a fragrant essential oil, typically made from rose petals.

apophasis a rhetorical device wherein the speaker or writer brings up a subject by either denying it

belletrist a person who writes essays, particularly on literary and artistic criticism, that are composed and read primarily for their aesthetic effect

psychosphere the sphere or realm of human consciousness

clowder a group of cats

ort a scrap or remainder of food from a meal

afflatus a divine creative impulse or inspiration

desacralize to divest of sacred qualities or status

apophenia the tendency to perceive meaningful connections between seemingly unrelated things

stertoreous snoring; hardly breathing

chiffonier a tall chest of drawers, often with a mirror on top.

recusancy refusal to submit to established authority

denude strip (something) of its covering, possessions, or assets; make bare

nudnik a pestering, nagging, or irritating person; a bore.

collimate make (rays of light or particles) accurately parallel

naphtha a flammable oil

threnody a lament

mishegaas craziness; senseless behavior or activity

antapex the point of the celestial sphere from which the solar system is moving

fissile able to undergo nuclear fission; easily split

dun to nag someone about paying a debt

quorate having a sufficient number of members to constitute a quorum

parimutuel a form of betting in which those backing the first three places divide the losers' stakes

graphomania the compulsion to write

pluviophile a lover of rain

remainderman the person who inherits or is entitled to inherit property upon the termination of the life estate of the former owner

fillip something which acts as a stimulus or boost to an activity.

unicursal relating to or denoting a curve or surface which is closed and can be drawn or swept out in a single movement

pikuach nefesh the principle in Jewish law that the preservation of human life overrides virtually any other religious rule. When the life of a specific person is in danger, almost any mitzvah lo ta'aseh of the Torah becomes inapplicable

shirr bake an egg without its shell

asperity harshness of tone or manner

gangue the commercially valueless material in which ore is found

pericarp the part of the fruit formed from the wall of the ripened ovary

pleonastic needlessly wordy or redundant (“I heard it with my own ears”)

poryphyry a hard igneous rock containing crystals, usually of feldspar, in a fine-grained, typically reddish groundmass.

syntony the state of being normally responsive to and in harmony with the environment

crypticity the condition or state of something being cryptic

quirt a short-handled riding whip with a braided leather lash

ailurophobe someone who is irrationally afraid of cats

votary a person, such as a monk or nun, who has made vows of dedication to religious service

anneal to heat something and allow it to cool slowly, in order to remove internal stresses and toughen it.

chanticleer rooster

burgess an inhabitant of a town or borough with full rights of citizenship

escheat the reversion of property to the state on the owner's dying without legal heirs

parson a beneficed member of the clergy; a rector or a vicar

ratiocination the process of exact thinking

stemwinder an entertaining and rousing speech

natant swimming or afloat

brumation a state or condition of sluggishness, inactivity, or torpor exhibited by reptiles

adumbrate report or represent in outline

dudgeon a feeling of offense or deep resentment

septentrional related to the north; northern

aileron a hinged surface in the trailing edge of an airplane wing, used to control lateral balance

antedating an example or instance of a word/phrase at a date earlier than previously known

antinomianism any view which rejects laws or legalism and argues against moral, religious or social norms

cotyledon an embryonic leaf in seed-bearing plants

crenellation the battlements of a castle or other building

engram a unit of cognitive information inside the brain

fibril a small or slender fiber

flexion the action of bending or the condition of being bent

roan denoting an animal with gray/silvery hair

spinnaker a sail designed specifically for sailing off the wind

calumny the making of false and defamatory statements about someone in order to damage their reputation; slander.

vibratiuncle a miniscule or slight vibration

bollix to bungle (ie a task)

tonsorial relating to hairdressing

gravitic of or pertaining to gravity

susurrus whispering, murmuring, or rustling.

culvert a tunnel carrying a stream or open drain under a road or railroad

quidnunc an inquisitive and gossipy person

interwork be able to connect, communicate, or exchange data

kvell feel happy and proud

piolet ice axe

muon an unstable subatomic particle of the same class as an electron

plenum an assembly of all the members of a group or committee

rodomontade boastful or inflated talk or behavior.

tref not kosher

geometer a specialist in geometry (i.e. for mapmaking or exploration)

irenic aiming at peace

egest to discharge, as from the body; void (opposed to ingest)

dolorous feeling or expressing great sorrow or distress.

autogyro a type of rotorcraft that uses an unpowered rotor in free autorotation to develop lift

neonate a newborn child

neotony the retention of juvenile features in the adult animal

quincunx an arrangement of five objects with four at the corners of a square or rectangle and the fifth at its center

neoteric new or modern; recent

ablation a procedure for restoring normal heart rhythm

clement mild and peaceful

oracular hard to interpret; enigmatic

carom strike and rebound

dysgenic exerting a detrimental effect on later generations through the inheritance of undesirable characteristics

oleaginous rich with, covered in, or heavily producing oil or grease

extirpate root out and destroy completely

suet the hard white fat on the kidneys and loins of cattle, sheep, and other animals, used to make foods including puddings, pastry, and mincemeat

offal the entrails and internal organs of an animal used as food.

syncytium a single cell or cytoplasmic mass containing several nuclei, formed by fusion of cells or by division of nuclei

funicular a cable railroad, especially one on a mountainside, in which ascending and descending cars are counterbalanced.

salvific leading to salvation

missal a book containing the texts used in the Catholic Mass throughout the year

aporia an irresolvable internal contradiction or logical disjunction in a text, argument, or theory

slatternly (relating to a woman’s appearance) dirty and untidy

chthonic concerning, belonging to, or inhabiting the underworld.

gongoozler a person who enjoys watching activity on the canals of the United Kingdom

soteriology the doctrine of salvation

trilemma a difficult choice from three options, each of which is (or appears) unacceptable or unfavourable

alimentary relating to nourishment or sustenance.

helpmate a helpful companion or partner, especially one's husband or wife.

squamous covered with or characterized by scales

dewclaw a rudimentary inner toe present in some dogs

dropsy a non-technical edema

concomitant naturally accompanying or associated

weir a low dam built across a river to raise the water level upstream

miserablist a person who appears to enjoy being depressed, esp a performer of or listener to gloomy music

autarky economic independence or self-sufficiency

slue turn or slide violently or uncontrollably in a particular direction.

elucubrate to solve, write, or compose by working studiously at all hours

toyetic potentially marketable as a toy or having merchandising potential

scripturient having a strong urge to write

lustration a rite of purification, especially washing

oryx a species of large antelopes

glabrous free from hair or down; smooth

orts table scraps

saturnine slow and gloomy

cachinnate to laugh loudly or immoderately

loge a small enclosure or booth in a theatre or arena

varietist one who varies from the norm

sestet the last six lines of a sonnet

doctrinaire seeking to impose a doctrine in all circumstances without regard to practical considerations.

impecunious having little or no money

arrant complete; utter

goldbrick invent excuses to avoid a task; shirk.

cartouche a carved tablet or drawing representing a scroll with rolled-up ends

timpani kettledrums, especially when played by one musician in an orchestra

coati a type of raccoon with a long snout and a striped tail

amphigory nonsense verse

apothegm short, witty aphorism

besserwisser know-it-all, wiseguy, wiseacre, smart aleck

enchiridion carried reference book

eunoia beautiful thinking

olio a miscellaneous collection of things

phrontistery a place for studying

selcouth strange; unfamiliar; marvelous

piste a ski run of compacted snow.

autochthonous native to the place where found (ant. allochthonous)

polity an organized society; a state as a political entity

calf a floating piece of ice detached from an iceberg.


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I'm Justin Duke — a software engineer, writer, and founder. I currently work as the CEO of Buttondown, the best way to start and grow your newsletter, and as a partner at Third South Capital.

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