Mental Pivot #21: Irony, Stoicism, Checklists

Pagliacci, irony, and assumptions, Ward Farnsworth’s practical guide to Stoicism, and a humble tool for reducing error.

I rarely see irony discussed by those interested in topics like mental models, but I hold irony in high esteem as a thinking tool. Contemplating the lessons of irony—especially in fiction—reminds me to keep my assumptions about the world in check.

One helpful definition comes from Matt Bird (The Secrets of Story) who defines irony as “any meaningful gap between expectation and reality.”

Irony reminds me that things aren’t always what they seem. Irony compels me to reassess what I know and why I know it. It teaches me that the world is more complicated, nuanced, and unexpected than I can imagine. Irony lulls me into assuming one possible outcome (the expectation), only to surprise me when it reveals a plausible alternative (the reality).

Alan Moore’s 1987 graphic novel, Watchmen, contains one favorite example of irony. Early in the story, the narrator recounts a classic tale (in his oddly clipped verbal manner):

Heard joke once:

Man goes to doctor. Says he’s depressed. Says life seems harsh and cruel. Says he feels all alone in a threatened world where what lies ahead is vague and uncertain.

Doctor says, “Treatment is simple. Great clown Pagliacci is in town tonight. Go and see him. That should pick you up.”

Man bursts into tears.

Says, “But doctor, I am Pagliacci.”

Surprised? I was.

Granted, there's no surprise without my wrong-headed assumptions. These assumptions form quickly and thoughtlessly as I read. Specifically:

  • The narrator says he is telling a joke, so I expect a good laugh.

  • I assume doctors know what they’re talking about. When this doctor offers a remedy, I expect it to work for this patient.

  • The great clown Pagliacci is a master of comedy. I expect him to be the happiest guy on Earth.

In hindsight, I see the layers of irony:

  • The so-called joke delivers a punchline, but without laughter.

  • The doctor’s surefire solution encounters the one unlikely scenario in which his advice is guaranteed to fail.

  • The “great clown”, a paragon of mirth, is beset by crushing sorrow. Despite his skill at bringing joy and laughter to others, he cannot provide the same for himself.

The irony of Pagliacci toys with my expectations and exposes gaps in my thinking. It highlights my mental blindspots and failures of imagination.

You might ask, to what end? Is there value in irony beyond the shock value? Are there useful lessons to be drawn?

I think so. Consider the following ways I might recalibrate my thinking:

  • I trusted the narrator. I took his word that I was hearing a joke at face value. Note to self: people say one thing and mean another all the time. Statements can be unreliable or misinterpreted.

  • Like the doctor, I failed to ask important questions about the patient up front: Who is this man? What is his name? What does he do? How differently this scene might have played out with the right question. To be fair, I’m glad the doctor didn’t ask those questions—it would result in an entirely different story! But the point stands: there was a failure of curiosity from both the doctor and me.

  • I failed to imagine a low-probability outcome. The possibility that the patient was Pagliacci was low, but not zero. I’ve read Taleb and his warnings about improbable events. Alas, I ignore this advice all the time.

  • I made a superficial judgment based on a weak factual observation. Just because clowns and comedians are funny doesn’t mean they are funny 24/7, nor are they immune to sorrow. People—including well-written fictional ones—are multi-dimensional.

Not all ironies yield so much grist for thought. But be on the lookout for those significant examples with meaningful gaps between expectation and reality. Not only will they surprise you, but they might present a welcome opportunity to examine your thinking and question your assumptions.

Now onto the updates...


What’s New on the Blog:

1. Book Notes: “The Practicing Stoic” by Ward Farnsworth

This is a wonderful introduction to the wisdom of the ancient Stoic philosophers. The Stoics wrote about a range of topics, but Farnsworth’s focus is their ethical teachings, the consideration of right and wrong behaviors and the meaning of the good life.

Farnsworth interweaves his modern-day perspective on the practice alongside excerpts of translated source material from Seneca the Younger, Epictetus, and Marcus Aurelius.

What I’m reading next: How Innovation Works by Matt Ridley. You can get a sampling of Ridley’s ideas from a 2-part podcast with Naval Ravikant (Part 1 and Part 2) or this EconTalk interview with Russ Roberts.


2. A Checklist to Reduce Errors (Specifically for My Newsletter)

I’ve reached the point where I’m making silly mistakes in this newsletter regularly. My apologies dear readers. It’s time to reduce that error rate (I can’t guarantee zero, but I can do better). 

Checklists to the rescue?

Checklists are basic, simple, and sometimes tedious. They’re also a great way to reduce avoidable errors. Noted surgeon and author Atul Gawande is a big proponent (see The Checklist Manifesto). If checklists are good enough for the life-or-death medical situations Gawande talks about, they’re certainly good enough for this hobbyist writer. 


Articles & Podcasts of Note:

  • Afraid of the Wrong Things (podcast): The Hidden Brain podcasts examines our inability to properly assess risk. This conversation touches on a wide range of ideas: the availability heuristic, emotion, cumulative vs marginal risk, linear vs exponential growth, control, personal narratives, and psychic numbing.

  • The Essential Weekly Review: David Sparks urges us to slow down and reflect regularly. Damn straight.

  • How to Be Clear: Giles Turnbull’s focus is business writing, but this is a message that never gets old for anyone interested in clear communication.

  • How to Read More: Ryan Holiday delivers 8 reasons to read more (motivation) along with 7 strategies for making it happen (the practical tips).

  • Jason Zweig—Psychology, History, and Writing (podcast): Conversation with the WSJ writer (The Intelligent Investor) and host Jim O’Shaugnessy. The host’s son Patrick O’Shaugnessy has the better known podcast (Invest Like the Best), but I prefer the tone, pacing and guests on Jim’s show, Infinite Loops.

  • Newsletters: Is this Progress?: Robin Rendle’s rant is a kind of picture book for adults; I’m as intrigued by the presentation as I am by the content. The vintage illustrations are evocative.

  • The Power of Opposites: Larry McEnerney explores the benefits and pitfalls of oppositional language (akin to binary thinking). On one hand, opposition is persuasive in its clarity. On the other, opposition results in oversimplification whose hides nuance and complexity.

  • Technological Stagnation: Why I Came Around: Jason Crawford of The Roots of Progress blog considers the “stagnation hypothesis” which posits a significant slowdown in scientific, technological, and economic progress since 1970.

  • Who Will Control the Software the powers the Internet?: Per A16Z’s Chris Dixon, “...the pendulum is swinging back to an internet governed by open, community-controlled services.” He’s bullish on blockchain, cryptocurrency, and community-owned services.


Odds & Ends:

  • ARK Investments 2021 Big Ideas Report offers an overview of important (and financially lucrative) tech trends replete with graphs, charts, and data. Big ideas include Deep Learning, Virtual Worlds, Cryptocurrency, Automation, Gene Therapy, and more. Cathie Wood’s investment acumen cannot be denied, ARKK is the largest actively managed ETF because of her insights.

  • I’m clueless when it comes to Twitter, so I appreciated two posts that popped up in my newsfeed this week. Both examine the topic of using Twitter effectively (something I’m trying to figure out myself). The first is a humorous piece from Stew Fortier, 7 Ways to Be Insufferable on Twitter. The second is Ivan Mir’s strategy for using Twitter without losing your mind: My Setup for Using Twitter without Hating It.

  • I’ve been noticing more titles from the MIT Press Essential Knowledge series while browsing at my local bookstore. These are concise introductory texts on a variety of topics including technology, science, arts, and culture. There aren’t as many titles as the Oxford Very Short Introduction series (which was highlighted Issue 19), but I like the topics MIT covers. I’m particularly intrigued by this series title: Irony and Sarcasm: A Biography of Two Troublesome Words.

  • Lastly, since irony was the topic du jour, I have a few additional resources for the interested:

    • Matt Bird video on irony: Bird dissects the many layers of irony in this analysis of Disney’s Mulan.

    • The Three Most Common Uses of Irony: Long-running web-comic The Oatmeal offers this hilarious and insightful send-up on irony.

    • What Irony is Not: “A handy guide to distinguishing the notoriously slippery concept from its distant cousins coincidence, satire, parody, and paradox.”


Acknowledgements: Thank you to the good people at the Compound Writing Group who reviewed and provided feedback on the early draft for this week’s newsletter: Piyali MukherjeeAdam TankLyle McKeanyTom White, and Yishi Zuo


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