2018 Reads

It was a pretty good year for reading, I managed to keep a habit while working on the startup.  Below is a list of what I tackled since last Winter.

Screen Shot 2018-12-08 at 2.09.06 PM.png
Still from Van Dyke’s “An Album of Fluid Motion”


I got pretty obsessed with fluids earlier this year.  As a pilot I wanted to sharpen my understand of lift and how it works, and while in the process I uncovered the inspiration for a talk I gave in May at Refactor Camp.

I read most thoroughly through the works by Anderson and Vogels, and selectively pecked through the rest.  I can now give a pretty good and accurate explanation for how wings work.  Hint: start from the idea that a moving wing has created a ‘void’ behind it as it moves through the air and build your intuition from there. Ignore anything to do with air ‘speeding up’ on top of the wing and instead think of volumes and displacement.

History of Aerodynamics, John Anderson

This is a fascinating book, full of both science and drama.  All throughout history there have been those who thought something was impossible (usually scientists) and those who tinkered anyway (engineers).  Once an invention overturned a previous notion of impossibility, scientists went to work explaining it.  This played out for fluid dynamics + airfoils for hundreds of years, and Anderson does the right amount of writing about it.

Life in Moving Fluids: The Physical Biology of Flow, Steven Vogel

Another fascinating book about fluids except with mother nature as the guide.  All kinds of life, from the smallest bacteria to the albatross, has adapted itself to a life in fluid, be it water or air.  Vogels seems to cover all of them, whether seed, trout, or sperm.  It’s a fun read at the intersection of biology and physics that will show you why a trout is the perfect airfoil shape and how a spider can soar.

An Album of Fluid Motion, Milton Van Dyke

Beautiful album book of various fluid flows.  There’s a pdf version here.

Turbulence: The Legacy of A. N. Kolmogorov, Uriel Frisch

Turbulence is an important concept to understand in fluid dynamics.  Although Frisch gets a bit technical and math-y, you can grok much of the beginning explanation and setup. It was fun launching off from this and thumbing through Mandlebrot’s Misbehavior of Markets: A Fractal View of Financial Turbulence and The Fractal Geometry of Nature.

Understanding Aerodynamics, Doug McLean

Probably the best, most comprehensive, detailed, and up-to-date book on flight you can find today.

Understanding Flight, David Anderson and Scott Eberhardt

Mostly a lite version of McLean.

Entrepreneurship / Leadership

Naval Leadership: Voices of Experience

I’ve owned this book for a few years and always enjoy revisiting it for good reminders of proper management and leadership.  The sections on delegation and supervision are gold.

Eleven Rings, Phil Jackson

Good read… I like Phil’s style and the way he went about building mindful teams.

Am I Being too Subtle?, Sam Zell

Good autobiography of a smart and quirky entrepreneur.

High Growth Handbook, Elad Gil

Some good stuff in here.

George Marshall: A Biography, Debi and Irwin Unger

Marshall has been lauded as the greatest American since George Washington… the Ungers take a much more sober view of his contributions.  While his character was undoubtedly flawless, his track record of decisions show he made quite a few missteps (but who never did?).  Still, I loved getting a view of this era of American history (US military pre-WWII, pre-communist China, and post-war Europe) through Marshall’s eyes and actions.

Longitude: The True Story of a Lone Genius Who Solved the Greatest Scientific Problem of His Time, by Dava Sobel

I read this fairly short book on my Kindle and loved it.  Just like Anderson’s History of Aerodynamics, this provides a true story of the heroes and villains that surround the development of a novel technology.  Whenever I read works like this I always think about current technological developments and wonder who the stubborn bastards are that’ll be left on the wrong side of history.

Just for Fun

Inside Moebius, Jean Giraud

I loved Moebius’ work in The Incal and enjoyed flipping through this more auto-biographical work.  Very different from his usual and not for everyone.

Thrawn: Alliances, Timothy Zahn

I’m a sucker for the Thrawn storyline and devoured Zahn’s latest over a weekend.

Foundation, Isaac Asimov

An important work of science fiction I’d never read.  Quick and fun read.


The Ascent of Money, Niall Ferguson

Great historical account of money that starts with ancient gold and silver and runs up through the US housing crisis.  It was most recently published in 2009 and so doesn’t contain anything about Bitcoin, though the author wrote something last year.

Networks, Crowds, and Markets, David Easley and Jon Kleinberg

Great ‘textbook’ that’s not too dense.  Rich with a lot of models and background for anyone who wants to think about networks, the internet, and aggregate human behavior.  I haven’t read it all yet but hope to spend more time with it someday.  This was one of the many great books that are regularly recommended by @arbedout.

Personal Interest

Behavior: The Control of Perception, William Powers

Powers was an engineer who specialized in control systems and cybernetics, who took those ideas and applied them seriously to psychology and how our brain works.  I’ve always been unimpressed with the large gap between our theories of neurons and psychology and Powers does the best job I’ve ever seen at filling it.  He sketches out several layers of theory that one might equate to wiring diagrams for how our neuronal control systems work.

His most important yet subtle insight is that humans don’t really control their ‘behavior’ in the way we usually mean it, but that instead we control for our ‘perceptions.’  Because our senses are our only means of accessing our bodies and the outer world, our nervous system acts like a machine that acts to bring about the desired state of sensory input.  Like the thermostat that turns on heat or cold depending on the temperature, our brain is like: Stomach telling you it’s low on food?  Change behavior until we’re no longer getting that signal.

It seems simple on the surface, but it’s a powerful paradigm that allows models from traditional control theory to be applied in areas of psychology that never were before.  Powers was really ahead of his time and unfortunately ignored by most of traditional psychology when his theories were published in the 1970s, but these days it’s arguable that he was barking up the same tree as our cutting edge theories around predictive processing and Friston’s Free Energy Principle.

This was one of the most interesting books I’ve ever read.  It can be a bit dense and is not for everyone, for a more full review than my blurb you can read this post by Scott Alexander about the book and one or two of his followups.

A Thief of Peirce, Walker Percy and Kenneth Laine Ketner

I have a personal obsession with Peirce, and have been delighted to discover in recent years that Walker Percy was also a big fan.  This book is a collection of letters between Percy and Ketner, a leading Peirce scholar.  The title comes from a reference by Percy in one of his letters that he’s borrowed a lot of his ideas off of Peirce’s writing.  Good book for any semiotic fans out there.

Drama of the Gifted Child, Alice Miller

Miller’s key idea is that many children who are “gifted” in the way of being attuned to the emotions and states of others, especially their parents, grow up losing sight of themselves and their own feelings because the feelings of others can appear so vivid and, especially while they are dependent on them, critical to their survival.  Instead of fostering a healthy amount of “me first” the child, they go through life always seeking the approval of others. It’s a good point and relates to the trend of narcissistic parents in our generation.

The Truth, Neil Strauss

I had read Strauss’ The Game when I was a teenager, and enjoyed coming full circle with this work about how he learned to embrace monogamy.

The End of Alzheimer’s, Dale Bredeson

This book, or something like it, should be required reading for every human being.  We often take for granted our healthy brains and those of close friends and family, so when we are caught be surprise by dementia or Alzheimer’s disease it’s tough to know where to look and how to act early on.  This book is about as comprehensive a guide as you can find, at least on the clinical and preventative side.

Alzheimer’s is still in the same category as cancer: we think we can explain the mechanisms that are happening when shit goes south, but we can’t pinpoint a reversal or cure.  Bredeson does a good job outlining the latest theories and a comprehensive treatment plan that’s seemed to work for his patients.  If I could sum up his advice in a few words, it reads like a lot of generic health advice: eat well, sleep well, and don’t drink too much.

Silence: In the Age of Noise, Erling Kagge

I saw this get recommended in a few places and decided to give it a shot.  The book is a healthy reminder to tune out of our environment now and then and connect with ourselves.


What to Remember When Waking, David Whyte


The Wisdom of Insecurity, Alan Watts

I didn’t get as much out of this as Watts’ Out of Your Mind.  Some helpful perspective if you suffer from lots of anxiety, I guess.

Being Human, Robert Sapolsky

This was really fun.  It’s basically a bunch of lectures by Sapolsky covering all kinds of topics from biology and psychology.  He’s brilliant.

Radical Honesty, Brad Blanton

I loved this.  It’s read by the author and while it’s great to hear his own words and voice, he didn’t use the best recording equipment everywhere or have the best editor to smooth things out.  Regardless, it’s a great message about just being more honest in life and not GAF.

Blood Meridian, Cormac McCarthy (read by Richard Poe)

I’d read Blood Meridian 10 years ago and had always wanted to revisit it again.  I heard Poe did a great job narrating this, and he really does.  This is such a violent work but it’s still beautiful writing.

Summer Reading: Complexity, Continuity, Math, and Leadership


Re-Engineering Philosophy for Limited Beings, by William C Wimsatt

This was one of the deepest and most interesting books I read all year. Wimsatt is a philosopher, but early in his career he did tours through physics and biology. This helps to ground his material in real scientific contexts, especially in the history of genetic theory.

Some favorite quotes:

  • “Why is it that academics who claim to seek the truth want to pretend that they have always had it?”
  • “The history of scientific progress and the evolution of our conceptual categories is littered with one generation’s projects and category mistakes that have become the next generation’s impossibilities and conceptual truths.”
  • “Cognitively speaking, we metabolize mistakes!”


Wimsatt is a big fan of Herbert Simon’s model of man as “satisficer,” and notes how suited heuristics are for the temporal and cognitive limitations we’re faced with. He even draws a parallel to evolutionary biology, claiming that biological adaptations also meet the definition of a heuristic.

The chapter “False Models as Means to Truer Theories” is a tour de force through the nature of models and why it’s still useful to construct them even when they may not be comprehensive or 100% true in all cases. He provides several examples from the history of genetics for how a theory that was not quite right was able to spur insights into a deeper understanding of how genes worked.

Wimsatt is very detailed and enumerates qualities and definitions for many abstract ideas that are above and beyond what I’ve typically seen. For instance, he gives a definition of a heuristic based on three qualities:

  1. “The correct application of a heuristic procedure does not guarantee a solution and, if it produces a solution, does not guarantee that the solution is correct.”
  2. Heuristics are “a cost-effective way, and often the only physically possible way, of producing a solution.”  “The application of a heuristic to a problem yields a transformation of the problem to a nonequivalent but intuitively related problem, [meaning] answers to the transformed problem may not be answers to the original problem.”
  3. “The failures and errors produced when a heuristic is used are not random but systematic. …any heuristic, once we understand how it works, can be made to fail. … This property of systemic production of wrongs answers will be called the bias of the heuristic.”

Mental Models

Wimsatt introduces several valuable mental models:

  • Robustness analysis: Something (an entity, concept, pattern or theory) is robust to the degree that it is accessible via multiple independent means. With this in mind, we might order the laws of nature by fundamentality: “the more fundamental laws will be those that are independently derivable in a larger number of ways.”
    • Wimsatt goes on to describe what’s elsewhere called thinking from First Principles: a reasoning process involving just a few short jumps from fundamental laws and principles will do much better than a long, serial chain of reasoning. “We feel more confident of objects, properties, relationships, and so forth that we can detect, derive, measure, or observe in a variety of independent ways because the chance that we could be simultaneously wrong in each of these ways declines with the number of independent checks we have.”
  • Generative entrenchment: Wimsatt’s idea of generative entrenchment is deeply tied to evolutionary processes. As organisms or systems evolve, certain changes become more critical than others because they help generate other adaptations. An example would be the emergence of RNA and DNA, which have become generatively entrenched in so much of biological life due to their unlocking of many more adaptations. Other examples would be the joint-stock company or Bitcoin (kicked off Blockchain + ICO ‘revolutions’).
    • “A deeply generatively entrenched feature of a structure is one that has many other things depending on it because it has played a role in generating them. It is an inevitable characteristic of evolved systems of all kinds – biological, cognitive, or cultural – that different elements of the system show differential entrenchment.”  Generatively entrenched features engender and result in positive feedback loops: as more things build on a platform that platform becomes more entrenched, making it more stable and unlikely to change, therefore more things get built on it, etc.
  • Perspectives and causal thickets:  These are close analogs to Charlie Munger’s latticework of mental models. When a phenomenon is complex enough that it requires multiple explanations that cross boundaries (both physical or theoretical), Wimsatt labels the multi-disciplinary view for that phenomenon a “perspective” (rather than just a single explanation from a theory of physics or biology). Wimsatt considers that there are aspects of reality that still don’t yield themselves to explanation by perspectives, these areas of reality he calls “causal thickets.”  I love this term as it calls to mind a shrub, where every branch is a theory or explanation that might be valid but is only a minor, intermingled part of the picture. Examples of causal thickets are abundant in the realms of psychology and sociology.

The Ontology of Complex Systems

I’ve always been fascinated by how nature seems to operate at levels. Why is it that we seem able to stack fields and theories on top of one another, such as Physics > Chemistry > Biology > Sociology?  Wimsatt explores why these occur in nature and complex systems. One answer has to do with the size of things in nature: because the size of something means it’s likely to interact with other things of equivalent size, our theories become robust at those levels (e.g. we have more means of proving and providing examples of a given theory at that level).

Wimsatt spends a good deal of the book outlining a subtle position on reductionism. It’s easy for us to read books about complexity and emergence then develop a distasteful attitude for simple reductive explanations. But Wimsatt shows that reality isn’t even simple enough to contain solely reductive OR emergent phenomena. Reductive explanations still have their place in describing nature accurately.


Wimsatt believes our world is like graphs (a) or (c) above. Below, he draws the progression from simple reductionist theories, through emergence, and then causal thickets.


Extreme Ownership, by Jocko Willink and Leif Babin

A quick read on leadership principles. Aside from the Iraqi war anecdotes, which were interesting in their own right, most of the ideas are things you’ve probably heard before. But that doesn’t mean it’s not worth it to be reminded of them.

Love and Math, by Edward Frenkel

I went on a big math kick these past few months. Frenkel’s book is a good introduction to modern mathematics that isn’t too tough for a layperson. The book is worth it for his explanation of symmetry alone, although there were a few parts where he gets carried away.

Princeton Companion to Mathematics

I’ve not read anything near all of this volume, but made a dent in the first few chapters and skipped around as various topics interested me. More of an encyclopedia than something you read cover-to-cover, it’s great to have around as you’re exploring math topics.

To Predict IS NOT to Explain, by Rene Thom

Thom was an influential mathematician from the last century who invented catastrophe theory and did lots of work in topology. I have a large personal fascination with the dichotomy between the continuous and the discrete. When and where is it helpful to treat a system as analog or digital, continuous or discrete? Is reality fundamentally one or the other? While no-one can really know, I have a soft-spot for people in the predominantly continuous/analog camp, such as Thom and CS Peirce.

Peirce’s Logic of Continuity, by Fernando Zalamea

Peirce is one of my favorite philosophers and this book is an exploration and expansion of his theories of continuity. Most discussions of continuity by mathematicians stop at Cantor’s real number line (or the related Zeno’s paradox), but as Zalamea shows, Peirce’s concept of continuity is a much more metaphysical idea that goes deeper. I loved the first half of the book but struggled through the latter half, when he dives into Peirce’s existential graphs. I’m still working up to see the real beauty and utility people ascribe to these tools developed by Peirce.

Philosophy of Gesture, by Giovanni Maddalena

More Peirce-inspired, continuity-related stuff, from a philosophy/semiotic point of view. Probably not worth it if you’re not into this sort of thing. I do find it interesting that Maddelanas’ models for synthetic judgment bear a lot of similarity to Wimsatt’s perspectives and causal thickets.

Maps of Meaning, by Jordan Peterson, plus 2 dozen of his podcast episodes

I’ve not read this cover-to-cover yet, but only because I’ve listened to so many of his podcast episodes which cover a lot of the same territory. I’ve come to love Peterson’s work. I grew up with a largely Catholic upbringing, surrounded by stories from the Bible that I struggled to take too literally. Peterson offers a synthetic perspective on some of our oldest stories that bring together evolution, psychology, and historical fact. Even if we find it hard to believe in the literal tale of Adam and Eve or the fratricide between their sons, Cain and Abel, Peterson shows how these stories are generic examples of humanity’s struggle with its own limitations. These stories play themselves out over and over again across time and different cultures, so even if they may not be true as historical fact they are very, robustly true as descriptions of human nature (see Wimsatt’s definition of robustness). I can’t help but point out the parallels between his framing of chaos and uncertainty and the same Peircean continuity described earlier.

Patterns of Strategy, by Patrick Hoverstadt and Lucy Loh

I bought this book after seeing it recommended on Chet Richards’ blog. It’s another great work of synthesis that brings together theories from John Boyd, Gregory Bateson and other systems-thinkers (but not many business gurus!). I really liked their use of landscapes to visualize strategic positioning:


A Sense of Urgency, by John Kotter

A quick-read business book about urgency. I’ve thought about this a lot as it relates to distinctions between real vs. manufactured urgency, and how to increase one over the other. This wasn’t mind-blowing but still had some good reminders.

March and April Reads

The Great Endarkenment, Elijah Millgram

This is the follow-up to Millgram’s fantastic book, Hard Truths. It’s a collection of papers that were originally published elsewhere but have been edited to cohere into this one volume. While I didn’t find this book as useful to me as Hard Truths, it’s still good and is a natural extension of the topics he developed in that first volume. Millgram himself considers this to be the superior motivating frame for the ideas in Hard Truths.

Millgram’s core thesis throughout the book is that ever since the Enlightenment humankind has experienced a process of increasing fragmentation and specialization of knowledge. He characterizes humankind as “serial hyperspecializers,” a species that, in general, moves from specialized niche to specialized niche throughout a lifetime.

Specializations come and go (e.g. jobs like a switchboard operator) and within each specialization we develop unique context-specific vocabularies and frames of reference. This specialized vocabulary allows for greater accuracy and efficiency by those operating in a niche, yet represent a cost to new participants who must ramp up on a new language. Once an individual abandons a specialized niche for another they must learn yet another specialized language, but what often happens is that they instead port over pieces from the other niche. Their borrowed concepts will vary in their appropriateness for the new niche and so we will be left with partial truths via borrowed terms and frames of reference.

Throughout his work Millgram attempts to transform metaphysics into a more modern and practical tool for science and daily life. I love the path that Millgram is on and found myself nodding throughout the book. Why aren’t more practicing philosophers thinking along these same lines?

Think on These Things, Krishnamurti

I’ve been on a big ’60s guru kick lately, see Alan Watts, below. Krishnamurti is great at playing the guru who doesn’t provide direct answers but instead prompts you in an insightful way that helps you find your own answers.

My big takeaway from the book is to spend more time exploring the thorniness of a problem before jumping to solutions. For instance, if we have trouble with being late to meetings, we usually admonish ourselves and seek to find corrective behaviors rooted in self-discipline. Instead, Krishnamurti argues we should focus on why we tend to be late in the first place. If we can reach that understanding we’ll have solved our problem in mind already.

This is second-level thinking for your own self-development: instead of taking the first-level diagnosis (“I’m late because I don’t budget enough time for things”) and prescription (“let me pad meeting times by marking them 5 minutes earlier in my calendar than when they start”), spend more time taking your analysis further (“Why don’t I budget enough time for things?”). Krishnamurti’s message is that if we can get far enough along in such an analysis of why’s, down to the very bottom of it, we’ll have already solved our problem.

Very guru-y and somewhat woo, but I like it.

The Power of Gold, Peter Bernstein

This was a great account of this history of gold through the ages. Bernstein covers the basics of gold’s inherent properties that make it valuable (malleability, density, scarcity and lack of corrosion), its first use as a trading commodity and store of value, and its role in economies and state power. As an economic history it’s fantastic, but I love the qualitative stories about gold booms and busts. I’ve spent the last few years studying bitcoin and cryptocurrencies and there are a lot of parallels of investor/speculator psychology between the old and new commodities. It puts a lot of the short-termism around bitcoin’s scaling debate in perspective – gold has had plenty of multi-year crises throughout the centuries.

Shoe Dog, Phil Knight

This book has already been lauded by nearly every entrepreneur and executive I’ve talked to about it. And rightly so – it’s well-written and captures the spirit that drives me and similar people to creative pursuits like entrepreneurship. Even though it’s a recent book it should hold up for a long time.  Knight’s story of Nike’s origins and early days is the iconic entrepreneurial adventure.

Thrawn, Timothy Zahn

When Disney acquired Lucasfilm and announced they were scrapping the Extended Universe, the biggest loss was the saga of Grand Admiral Thrawn. It’s a damn shame we’ll likely never get to see this awesome character on the big screen.

Originally set in the years after Return of the Jedi, Zahn’s first Thrawn trilogy told of a brilliant Imperial strategist who attempted (and nearly succeeded) to bring the Empire back to glory after the death of the Emperor. Thrawn was a perfect blend of intelligence, strategy, and good intentions while still being the bad guy that you want to succeed. I loved his creative strategies and how he would glean insights about his enemies. Before a battle he’d draw up everything he could about an alien foe’s art and culture to glean how they might be culturally predisposed to bluff, feint, or play a conservative hand.

This book was released last month and is a prequel to Zahn’s original trilogy. It tells of how Thrawn rose through the ranks of the Empire. If none of the above sounds interesting to you I’d skip the book, but for fans of the original trilogy it’s a great dose of nostalgia.

Out of Your Mind, Alan Watts

This is a collection of lectures by Alan Watts in audio format (available on Audible if you have a subscription). I was blown away by the wisdom and modern views he was espousing back in the 1960’s and wondered why I haven’t heard more of his stuff before. All of his ideas – about anxiety, the struggle to know oneself, and the mysteries of the universe – still hold today. He’s not as cryptic as Krishnamurti and packages Eastern thought in a way that’s more easily digestible if you have a Western-educated background. You don’t have to take my word for it – Naval Ravikant mentioned reading Alan Watts in recent podcast interviews with Tim Ferriss and Farnam Street.

Stealing Fire, Jamie Wheal and Steven Kotler

Another audiobook I listened to. It’s all about how we perform under altered mind-states and how to produce them. An altered mind-state, something the authors call ecstasis, is something like a flow state or that which people experience under certain psychedelic drugs. Their message is worth heeding – that we should consider when and how we’ve seen these states in our own pasts and how to cultivate them for ourselves to better our creative work.

Hard Truths

The subject of truth has been coming up quite often these days.  More of us are concerned with the information we get from the media or the president, and rightfully have questions about what we should or shouldn’t trust.

When debating these issues we’re covering well-trodden ground by philosophers, especially in metaphysics.  Since at least the time of Aristotle, this brand of philosophy has posed questions like “what really exists?” and “what is knowable?”  A work from 2009 by Elijah Millgram, Hard Truths, explores the history of this field and provides some surprising answers.

Millgram starts his book by breaking with the historical line of philosophers on this topic. Most works from the past use a classical view of logic where true conclusions follow from true premises.  These involve statements like “if P then Q,” which allow for valid, deductive arguments so long as P is true.  If your initial premises are true, and you make valid sequential inferences, then your argument on the whole will preserve truth and remain valid.

However, outside of the clean, symbol-manipulating world of formal logic, this reasoning breaks down.  Classical logic, Millgram points out, presupposes that the premises are bivalent: they are either Fully True or Not True, with no in-between.  This assumption severely restricts the domains in which it’s safe to use this kind of model, and frustrates attempts to use it in real-world contexts.  Instead, Millgram claims that we are nearly always stuck with some form of Partial Truth in the real world.

Partial Truth is something that is true ceteris paribus (all things being equal), or true in certain circumstances.  A phrase we might typically consider to be Fully True such as “the sky is blue” is only partially true: check it out on an overcast day, or at dawn, or at night.  If you were limited to making only strictly true statements that come out true 100% of the time, you’d need a lot of hedging in your statements to make something like “the sky is blue” work: “The sky appears blue under clear meteorological conditions, with no other atmospheric disturbances (such as pollution), and only in the time period between 30 minutes after dawn and 30 minutes before dusk.”

Screen Shot 2017-02-28 at 9.10.51 AM.pngIs the sky blue?

That sentence is not easy to construct.  It takes real effort to properly hedge and guard one’s arguments against exceptions and ceteris paribus clauses.  This brings us to one of Millgrams core points: Truth, with a capital T, does not come for free.  Every time we wish to make something come out as true in a greater number of circumstances, we have real work to do in front of us.  Interestingly, Millgram points out that this work is not always conceptual, but often resembles engineering physical, real-world phenomena in order to match our assertions.

That is to say, the class of things in the world for which we can make declarative, 100% True statements are typically man-made.  A simple example would be everyday man-made items like car parts.  It’s only the case that we can say this is the proper engine bolt for a Honda Civic because thousands of man-hours of design and engineering made this True.  Only through costly design and engineering efforts are we able to state with metaphysical certainty that this is the True replacement part.


Through design and engineering work we can have True statements about everyday items.

Beyond so concrete of an example, we can look to more long-term engineering efforts, such as those that are at work in biology and cultural evolution, as providers of bivalent distinctions.  Biological evolution gave us distinctions among sexes and species, while cultural evolution gave us institutions and legal frameworks to produce bivalence around things like citizenship and property ownership.  Take time, and our ability to make clean, bivalent statements about it.  Only as a result of both real world engineering, through the invention of the clock, and cultural evolution, through adoption of timekeeping norms, are we able to take statements like “I arrived at 3pm” as true.

To summarize Millgram’s points so far: most metaphysicists and philosophers of the last several thousand years believed they could deal with the world in terms of a bivalent True or Not True attitude.  Instead, they must accept that what they are dealing with most of the time is Partial Truth.  And if you expect to be able to advance Partial Truth towards a fuller Truth, you will have to do real work: either in the real world, as in the case of manufacturing Civics, or conceptually.

Unfortunately this doesn’t give us any clear answers for how to properly deal with truth in political discourse.  Instead, we’re stuck with partial truths flung from both sides: “immigrants are stealing our jobs!” (yes, that’s true sometimes, but…) versus “immigration is good for the economy!” (yes, that’s mostly true, but…).  If anything, an appreciation of Partial Truth might help you treat your own assumptions as less absolute, and allow for finding better compromises and empathic solutions.

I happen to think Partial Truth is an interesting metaphysical ground-layer for what goes on in early stage entrepreneurship.  I will take that up next time, when I’ll unpack some more of Millgram’s ideas from Hard Truths and his latest book, The Great Endarkenment.

January & February Reads

2017 has been off to a good start, books-wise.  Here are some of the books I read these last few weeks:

Hard Truths, Elijah Millgram

This was a wonderful book that hits at the core of one of my long-time pet theories.  Millgram gives us a very readable work of modern philosophy that dresses down much of the last century’s work by metaphysicists.  He points to their efforts to find concrete answers to “What is true?” as misguided and doomed to fail.  Instead, we are destined to always deal with Partial Truth, except for when we take on significant efforts to re-engineer the world or our conceptual apparatus in order to give us the ability to make True statements.  Even then, we’re still often left with having to decide what is “true enough” for any given problem or context.  Millgram points out that this is the problem area philosophers of metaphysics should instead focus on (what true enough means in different domains, etc), and they should redefine the field as one of “intellectual ergonomics.”  I’ll be borrowing from this book for a long time.

Algorithms to Live By, by Brian Christian and Tom Griffiths

I listened to this on audiobook but I’ve preordered the paperback to have a physical copy.  I love this kind of stuff.  The authors cover a lot of research from math and computer science over the last century around optimal decision making, a sexy topic for any engineering-minded person.  It turns out a good amount of the heuristics we all use naturally for situations are also the ideal mathematical choices – a win for natural evolution.

John von Neuman, Norman Macrae

I didn’t know much at all about John von Neumann before reading this book.  I’m so glad I do now, what an amazing man.  There’s probably too much fetishizing about his prodigious intellect out there, even if it’s deserved, but he was otherwise a very well balanced and likable man.  For over a decade he was like the unicorn CTO for the US Armed Forces – equally brilliant and practical.  Beyond his contributions to US weapons technology and strategy, he sparked research and progress in a lot of other areas, especially the modern computer.  His approach there is remarkably similar to the open source movement of our modern area: he made sure his teams’ discoveries in the process of building one of the first computers was always published in the public domain and available for borrowing and improvement.  I do wish the biography went into more technical detail, at least at par with Isaacson’s Einstein biography, but this seems to be the best biography of him we’ve got.

This book paired nicely with Dan Carlin’s most recent Hardcore History episode, Destroyers of Worlds.  It’s another excellent episode that’s about the world-wide race to posses nuclear weapons and how that changed geopolitics forever.  Macrae’s biography gives added color about how decisions were made behind the scenes, especially as so many of them were a result of Von Neumann’s recommendations.

The Art of Learning, Josh Waitzkin

Great book on skill development, inspired by Watizkin’s time as a young chess prodigy and his foray into Thai Chi.  Last year I began learning to play the piano and how to swim, and it’s been helpful to have read this book (and The Inner Game of Tennis) as guideposts on the learning process.  A lot of great reminders in here about what it means (and takes) to perform well in any domain.

“The key to pursuing excellence is to embrace an organic, long-term learning process, and not to live in a shell of static, safe mediocrity.  Usually, growth comes at the expense of previous comfort or safety.”

The Trauma of Everyday Life, Mark Epstein

A great book by a psychiatrist who traces Buddha’s life and draws parallels to typical dilemmas and traumas we are all faced with.  There is a lot of wisdom in here, and it pairs well with a bunch of other stuff I’ve read recently, like Waitzkin’s book and Harris’ 10% Happier.

The Hitchhikers Guide to the Galaxy, Douglas Adams

A classic work of fiction that was a fun change of pace.  I bought the “ultimate” edition, with all the follow-on books, although I gave up halfway through – I could only take so many zany mishaps and adventures.

The Warded Man, Peter Brett

Fun work of fiction that helped fill my craving for good fantasy fiction after reading Patrick Rothfuss’ books last year.

The Dip, Seth Godin

Fast read about when it’s worth pushing through hard phases of any project.  If you find yourself asking questions about whether it’s worth quitting a project or not, you might pick this up to add some perspective.

Bias As Superpower: Using Your Cognitive Bias To Become Smarter

Anyone who studies psychology and looks to improve their thinking has come across cognitive biases: our tendencies to think in ways that deviate from rationality or good judgment.  It’s worthwhile to peruse them and understand them, but it would be a mistake to claim that we have to avoid them completely in order to be a rational person.

As an example of what I mean, I want to explore the difference between learning and confirmation bias, and whether there is in fact any difference.  When you look at the processes involved in each, as I’m about to outline, it’s clear that there is some strong similarity between the two.  Looked at this way, I think there are some interesting takeaways for anyone interested in constant learning and self-improvement.

What is Learning?

There are a lot of different models of the learning process, but let’s take a simple one.  In this version, teaching and learning involve a process of advancing one’s state of knowledge through the mastery of small topics (or lessons) that get successively harder or more complex.

Take math skills as an example.  Students generally progress from counting and simple arithmetic to functions and algebra, then basic geometry, before finally moving to more complex formulas, trigonometry and calculus.

If you were a tutor responsible for ushering a student along that path, your teaching process would look something like this:

  1. Assess the student’s current state of knowledge
  2. Give lessons and assignments that are just within grasp of their current state of knowledge
  3. Repeat

A good tutor will devise every lesson as in a sweet spot of not too close yet not too far from the student’s state of knowledge (i.e. proceed from 8th grade algebra to 9th grade geometry, not straight to college level calculus).  Too close and the student is not learning fast enough, too far and they will struggle to keep up.

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In this way, each lesson builds on prior knowledge in as efficient way as possible.  Each lesson should confirm and incrementally advance the student’s state of knowledge.  I argue that this doesn’t read much different from the standard description of confirmation bias.

Confirmation Bias

Let’s examine a few of the common definitions of confirmation bias:

  • “A confirmation bias is a type of cognitive bias that involves favoring information that confirms previously existing beliefs or biases.” [link]
  • “[Confirmation bias] is the tendency to search for, interpret, favor, and recall information in a way that confirms one’s preexisting beliefs or hypotheses, while giving disproportionately less consideration to alternative possibilities.” [link]

A classic example would be someone who believes in astrology – that the positions of stars and planets have predictive bearing on earthly events.  If this person is exhibiting confirmation bias, they will interpret any correlation between an astrological event and a borne-out prediction as evidence that astrology works, while avoiding possible conclusions to the contrary.

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Putting Them Together

Compare those definitions of confirmation bias to our prior statement about efficient tutoring / learning:

  • Tutoring and learning involve the presentation of information in such a manner that confirms and extends the students’ existing knowledge in as efficient way as possible.

See the difference?  No?

With such a close definition, it’s actually hard to distinguish when you are really doing one or the other:

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In some sense, when you’re looking to make good headway in a new subject area, you want there to be some confirmation bias.  Otherwise you’re not learning in an integrative way, you have random facts disconnected by miles of ignorance, and your payoffs to learning might be too far out to be immediately useful.

The Sweet Spot

We can map any point in that Venn diagram to one’s “slope of learning” as they try to progress in a subject area or grasp a new piece of information.  We can base this slope on the subjective rating by the individual for how easy or hard it is to understand the new piece of knowledge.

We’ll use a ski slope metaphor for how cognitively burdensome it is to integrate a new piece of knowledge or fact:

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If you stick to the green Hard Going slope you will make slow progress, but the difficulty may help reassure you that you’re not just combing over territory you’ve already covered.  If you stick to the Easy Going path, you may move a lot more quickly towards tangible intellectual progress, but it is likely to be incremental at best.

Confirmation bias is still learning, it’s just learning in a way that most economizes cognitive effort.

So as you learn new information you should ask yourself: how cognitively challenging was it to integrate that new piece of knowledge?  What slope do I perceive myself as on?  You can use this as a litmus test for how likely it is that you’re doing real hard learning, or simple confirmation.

Knowledge Economies of Scale

There’s another paradox that comes after this process picks up steam.  Take someone like Tyler Cowen.  Wikipedia identifies him as an economist, but as his interviews and blog make clear, his knowledge is much broader than that, covering a wide field in areas like sociology, psychology, and global culture.

We might imagine that his personal “Knowledge Cloud,” inside the space of all possible knowledge, looks something like this:

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Let’s pretend there are economies of scale at work in knowledge acquisition.  This means that the more knowledge you have in your initial repertoire, the easier it is to bring in knowledge that directly neighbors it.

In the case of some new idea at the crossroads of sociology and economics, Tyler Cowen’s effort to grasp that idea might look like this:

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Now take someone else with a very different background, like Elon Musk.  Elon’s knowledge cloud, and his effort required to grasp the same concept, might look like this:

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Now we have a scenario where the “ski slopes” for each individual differs greatly, for that particular new idea:

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Tyler’s slope is much closer to what we’d be tempted to call confirmation bias.  But is it still confirmation bias?  Is it a bad thing?  Can we accuse domain experts that publish and adopt research at the cutting edge of their field as simply engaging in confirmation bias?

Bias Bad, no Bias Good

I don’t pretend to have the answers here, though I think this is a much richer description of what we mean when we talk about confirmation bias.  Confirmation bias is always at or near the top of any list of cognitive biases, and it makes sense why this is so.  We are learning all the time and we’ll mostly gravitate towards the easy slope, towards learning with the least effort or in the most economical way.

If people continually economize their learning, they will build models solely based on what’s the least cognitively burdensome knowledge for them to acquire.  That’s a big way to miss out on other important models, and why we should recognize confirmation bias as a potential pitfall.

But if we take the simple approach that says “I shall not commit any of the biases on this list,” we are misunderstanding what that list is telling us.  Behind every “bias” is some truth to the way we operate, some core insight about how we evolved as intelligent beings.  It would be a shame to turn our backs on thousands of years of evolution just because we have a fetish for what’s supposedly rational.  Instead of fighting ourselves and seeking to rid oneself of biases, you might try to take the idea a little deeper and use it to work with, instead of against, your brain.

What I read in 2016

2016 was an excellent year for reading.  IMG_20161206_164236.jpg

All of the books were great.  Below are some brief summaries.

Unique and worthwhile: (these titles are excellent and don’t appear on many other lists)

Peripheral Visions, by Mary Catherine Bateson

A really great book by the daughter of the famous anthropologist, Gregory Bateson.  She’s a brilliant researcher and writer in her own right, and in this work she examines many of the cultural norms across the world around learning, tolerance, and perspective.  A few choice quotes:

“We reach for knowledge as an instrument of power, not as an instrument of delight, yet the preoccupation with power ultimately serves ignorance.  The political scientist Karl Deutsch define power as ‘the ability not to have to learn,’ which is exemplified by the failure of empathy in a Marie Antoinette or the rejection of computer literacy by an executive.  Ironically, in our society both the strongest, those who have already succeeded, and the weakest, those who feel destined for failure, defend themselves against new learning.”

“The pitfall of fundamentalism… is that when some item is held constant while the context varies, constancy is an illusion, and those who resist change often suffer themselves.”

“Sometimes you meet people who have learned their way around the culture of the ‘other’ well enough to have access to a second way of seeing the world.  They then have a unique capacity to pick and choose among behaviors and assumptions that would otherwise have remained unquestioned, and even to invent new ones.”

The Sign of Three, edited by Umberto Eco and Thomas Sebeok

I have a private obsession with semiotics and in particular, Charles Sanders Peirce, one of its founders. This book is a collection of somewhat academic essays by scholars about the practice of abductive reasoning, something Peirce defined.  Abductive reasoning is different from deductive or inductive reasoning, in that you’re required to make a leap from observations/data to a theory, with no guarantee that your hypothesis is correct.  It’s the real process behind Sherlock Holmes’ methods, or any good hypothesis in the Scientific Method.

The discussions in the book range from detecting art forgeries, the methods of Sherlock Holmes and Dupin (the detective in Poe’s Murder in the Rue Morgue), Voltaire’s Zadig, and of course, Peirce himself.  Much of it was used as inspiration for my post on Ribbonfarm.

Charles Sanders Peirce, by Joseph Brent

Peirce lived something of a tragic life.  He was an early prodigy but had habits and a communicative style that put him at odds with many of his contemporaries, who often worked to block him from academic posts or opportunities.  Thus, much of his work was left to relative obscurity, even though he was a very modern thinker with idease that are at the core of present day probability theory, psychology, physics, mathematics and logic.

The Systems Bible, by John Gall

Though it’s a bit quirky, this is a great book and summary of practical advice when dealing with systems of all kinds.

Great: (these are a little more esoteric, while still good)

Reasoning and the Logic of Things, by Charles Sanders Peirce

One of the few accessible compilations of Peirce’s work.

Everything and More, by David Foster Wallace

A fantastic guide to modern mathematics, tracing the story of infinity throughout the ages.

Thinking and Deciding, by Jonathan Baron

Worth pushing through.

The House of Morgan, by Ron Chernow

Awesome history of global finance.  Chernow picked the perfect thread to follow in order to give maximum resolution to the big trends and shifts.

Charles Schwab, by John Kador

Good read on the history of Charles Schwab, the brokerage firm.  Almost all of their struggles (capital needs, regulatory pressure, technology changes, etc.) rhyme with what the current fintech space struggles with.  It can read at times like it came from the Schwab marketing department, but Kador pulls no punches when it comes to pointing out flaws in Schwab’s culture or decision making through its history.

Well covered elsewhere: (great books which you can find recommended practically everywhere)

The Snowball, by Alice Schroeder

Damn Right, by Janet Lowe

Both of the above are great biographies of two amazing individuals (Warren Buffett and Charlie Munger).

Infinite Jest, by David Foster Wallace

In talking about the ending for this book, Wallace said “it’s supposed to stop and then kind of hum and project.”  I definitely felt that for days after I read this book.  It’s deeply human, modern, and a fun read.

Foucault’s Pendulum, by Umberto Eco

I wrote something about this.

The Name of the Wind and The Wise Man’s Fear, by Patrick Rothfuss

Great fiction – sort of a cross between Game of Thrones and Lord of the Rings.

The Inner Game of Tennis, by Timothy Gallway

Great book about performance.  Fast read.

I also listened to some great audiobooks:

The Graveyard Book, by Neil Gaiman

Fun, fast bit of fiction.  You may try to call it a kids book but it’s still great.

Caesar, by Adrian Goldsworthy

I’ll never forget the period I read/listened to this in: I rewatched HBO’s Rome and played Total War: Rome II, which has a “Caesar in Gaul” campaign you can play.  Totally fun way to immerse oneself in a subject.

Born Standing Up, by Steve Martin

Funny, of course.  Also a great story about hustle and working on one’s dream.

Kitchen Confidential, by Anthony Bourdain

More hustle.  My favorite part is Bourdain’s story about how he got into food – out of childhood spite.  During his childhood, on a family summer vacation in France, Bourdain and his brother acted like punks all the time.  His parents got so fed up with it that when they went to eat at the world’s best restaurant at the time, they left Anthony and his brother in the car for the whole 2-3hr meal.  That whole time Anthony stewed “what could be so good in there, that I can’t have it?!?  I’ll show my parents, I’ll show everyone – I’ll be the best food-lover there is!”

The Subtle Art of Not Giving a F*ck, by Mark Manson

Great book, don’t let the title fool you.  There’s more to Mark’s message than being carefree.  I picked up a lot from this book.

The Power of Vulnerability, by Brene Brown

More great content for self work.  This isn’t a book per se but a recording from one of her courses.  It’s packed with a lot of wisdom and ways to become more emotionally intelligent.  I intend to listen to this again someday.

The Upside of Your Dark Side, by Robert Biswas-Diener and Todd Kashdan

Good focus on an issue that the two previous titles cover – how our weaknesses or “bad” emotions (like anger) can be better harnessed.  You can skip this one if you were to read those others, but it’s still an important topic.

10% Happier, by Dan Harris

Really entertaining.  Dan does a great job discussing his struggles and approaching meditation in a way that most of us (who might be skeptical) probably would.  He’s a self described neurotic/worry-wart, and was afraid meditation and mindfulness would cause him to lose his “edge” he perceived he had from worrying.

Eco’s Pendulum

By strange coincidence, on Friday I finished Umberto Eco’s novel Foucault’s Pendulum and the next day I woke up to the news of his death at 84 years old.  I really enjoyed the novel (his second, published in 1988) and wanted to explore my reactions and lessons I drew from it.  I’m going to cover real plot spoilers, so don’t read on if that’s not your thing.

The book’s plot follows a narrator, Casaubon, and two of his colleagues at a publishing house where they’ve been publishing books on the occult and similar subjects.  As a joke and a lure to attract more of these authors, the protagonists fabricate an elaborate Plan that weaves together many of the crazy threads they find in the manuscripts sent to them.  For many years they had mocked the conspiracy theories they found in these manuscripts until finally, with the creation of their own Plan and evidence of murder and death threats regarding it, they begin to believe in it themselves, and it becomes their undoing.

In part, Foucault’s Pendulum is a critique on those who would take history, stories, and literature too seriously in their quest to find connections and interpret hidden reasons and intentions behind events.  So it should be with a sense of irony that any of us attempt to read more into Eco’s work, probing beneath the surface, but nonetheless, as we’ll discuss, this kind of process can be very rewarding and is ultimately a key to innovation and the improvement of our real understanding of the world.

The biggest metaphor that runs wholly throughout the novel is that of the pendulum.  The pendulum is obviously important on the surface: the novel’s title comes from the invention of Léon Foucault, whose device was the first to demonstrate the earth’s rotation without relying on celestial observation.  His instrument is basically a large pendulum, big enough that its path can be easily traced and observed for slight changes as the earth rotates throughout the day.  Casaubon, lost in a sea of conspiracy theories and falsehood, fetishizes Foucault’s invention as a demonstration of a fixed point of reference.  Wobbling around in the multitude of false connections he and his partners have made, Casaubon longs for the ability to look up and see himself attached to something fixed.  Casaubon’s observations reveal the obvious fragments of what Eco is trying to tell us: that we can look for fixed points of truth when lost, that we long for that fixed point in the universe to tell us we’re okay, or that science may hint at where we can find truth and fixed points in life.

But that only scratches the surface!  I don’t know of anyone who has really examined all the ways in which you can spot a pendulum operating throughout Eco’s work.  There are several in the plot structure alone: from how the first and last few chapters take place in the Conservatoire, with the bulk of the plot in the middle; Casaubon’s time in Brazil, where he escapes from his occult readings, only to be interrupted by a ritual that preempts his return to Milan; as well as Casaubon’s back and forth between his work on the Plan and his relationships and wife’s pregnancy.

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Examples of the pendulum throughout the novel Foucault’s Pendulum.

Beyond the concrete plot movements, our protagonists are constantly struggling with the choice between two opposite sides of a pendulum: to believe or disbelieve a theory, to decide whether a claim is truth or conjecture, to trust a surface explanation or seek hidden meaning, and whether to act with bravery or cowardice.  For much of the book our heroes swing back and forth between decisions on either side of this spectrum, but inevitably their aggregate choices begin to favor one side, setting them on their spiral towards doom.

Sensing their compounded failure, the protagonists desperately seek an out.  It’s here that Eco introduces one of his best jokes in the book and one of the most important semiotic concepts: the power of no.

Early in the book Casaubon attempts to access his colleague’s computer, which is password protected behind the very specific phrase “Do you know the password?” After a few hours of trying the most clever combinations of words and phrases he’s sure his friend would use, out of exasperation Casaubon decides to answer the phrase literally, with NO.  This ends up being the password and is a key mirror to the final moments of the book.

The Plan, invented by Casaubon and his colleagues, once heard by the various crazies and devout occultists across Europe, sends these lunatics into a frenzy over getting access to the secret weapon the Plan is said to reveal.  In their final moments, as they are interrogated and face murder by these occultist lunatics, the protagonists realize they still have the power to use no.  “Do you have the secret location of the weapon?” “No.”

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“No” as a source of inertia for getting to the other side of the pendulum.

No is important to Eco for two reasons, the first is its power to restore agency in someone who feels they have no control.  Casaubon and friends, in their search for outside sources of truth and reference, decide they must accept any theory or connection, no matter how far fetched.  Their personal lives devolve similarly, as they accept whatever happens to them with indifference.  It’s only through their rediscovery of rejection and saying no that they realize they can swing back to a position of agency and personal standing.  By rejecting the Plan and saying no to the occultist’s query, they are able to reassert their position and identity as non-occultists.

The second way in which no is important to Eco is in how concepts acquire meaning through defining what they are not.  This is the via negativa sense, the idea from theology where you attempt to define God by reasoning about what (s)he is not.  No is used to disconnect concepts from others, to break connections and to establish boundaries.  It’s key to determining which side of the conceptual pendulum you are on.

Eco’s life is a bit of a pendulum in its own right: his writings go back-and-forth between academic publications and popular fiction.  If we leave the world of Casaubon and look to Eco’s work in semiotics, we quickly find references to the same challenges he presents in the novel.

In his chapter of the book The Sign of Three, Eco delves into the various processes of abduction.  Abduction is likened to the process of hypothesizing, or guessing, about the cause of an event after one has observed the result.  When working in a process of abduction, you entertain possible worlds that may differ from experience: “…abductions… are world-creating devices” (pg 214).

Eco goes on to give examples of the detective or scientist that operate through abduction, highlighting the different incentives for each in their respective domains.  The homicide detective, in trying to find who-dun-it, is able to entertain a wide variety of hypotheses in their process of finding the killer.  We encourage detectives to consider and not overlook any possible suspect or explanation.

In contrast, scientists may find a very different tolerance for conjecture in their domain.  The further their theories deviate from accepted dogma, the more they’ll find difficulty in funding their theories.  Science and human progress depends on radical new ideas, but it can be very hard to determine when it’s a good bet and worth proving out.



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“Scientific discoveries, medical and criminal detections, historical reconstructions… are all cases of conjectural thinking.(The Sign of Three, pg 205)

Eco doesn’t paint much of the bright side of conjecturing and world-creation in Foucault’s Pendulum.  But we find elsewhere in his work the nod towards the benefits of this process, especially for those at the boundary of some important field or line of inquiry.

Progress everywhere depends on the back-and-forth between truth and conjecture, between hypothesis and verification.  If we are to advance our present reality, we must suspend disbelief and entertain alternative worlds.  But this is not a one-way process.  It requires a delicate balance and teeter-totter, and a consciousness of the consequences.

If you’re a scientist working on a new theory, or an entrepreneur entertaining a new business idea, you would do well to read Foucault’s Pendulum for an instructive lesson in the process and consequences of letting your hypotheses run away from you.

RIP Umberto Eco (1932 – 2016)


Is this the best job for this person’s career?

One heuristic we developed at Infochimps and used in several crucial hiring and firing decisions was to ask ourselves “Is this the best job for this person’s career?”  Hiring and firing decisions can have a huge impact on an individual, affecting their livelihood and self-perception in significant ways.  Once aware of the possible grave effects of hiring a person into the wrong role, or letting someone go, it is really easy for the decision-making process to get all gummed up with emotion and sympathy.

We had a very friendly, people-centered culture at the company.  Somehow the initial reasons for letting someone go or passing on a candidate never could add up to the kind of thing you’d want to say to that person’s face.  “You don’t fit in here” or “you don’t perform to our standards” can be pretty cold-blooded words to hear, and are not likely to help the individual down their path.  We also had a standard we tried to uphold whereby every job candidate left our hiring process with nothing but good things to say (even if we turned them down), same with the folks we had to let go.

One way we found to turn it upside down and come at the problem in as people-centered way as possible, was to ask ourselves “Is this the best job for this person’s career?”  Once framed this way, it can be much easier to reach a yes/no decision on your hire/fire dilemma.

As well, many of the issues we might have had or foreseen with this person become helpful points of feedback and ways we could try to set them up for more success down the road:

  • “You don’t fit in here” becomes “We believe you’ll be happier somewhere else” – Especially in our technology industry, there are hundreds of different companies to choose from for employment, offering a huge variety of cultures that might be more in-line with what that candidate believes in.  The latter reasoning makes clear that we don’t want the person to be unhappy in our organization.
  • “You don’t perform to our standards” becomes “We think you’re earlier in your path than we need for this role, and don’t want to set you up for failure” – This acknowledges their talents and aptitude, and presents the issue in a forward-thinking, optimistic point of view.  Instead of “these are the things you lack” it is “these are the things you have yet to learn or acquire.”
  • In times of a pivot or when money is tight, “we don’t need your job anymore” or “we can’t afford you anymore” are generally neutral and non-personal explanations anyway, but these can be taken another step further and phrased as “we can no longer offer you the kind of role and challenges that would help you grow.”  Again, the spirit is that the person will move on to bigger and better things as a result of this.
  • When a choice is murky because there are two candidates, one with a lot of experience and another with less, asking yourself whether the position is a better next step for either candidate can help narrow the choice.  Maybe the more experienced candidate will find the position more humdrum and same-old, not bringing the attitude and excitement you might hope for.  Maybe they are excited and consider this a great leap for themselves – but because it’s a new industry or technology area, not because it’s a title bump.

There can be lots of ways to phrase the feedback to a candidate you pass on or someone you let go, none are perfect in every case.  I have found, however, that by simply asking the question you put yourself in the frame of mind that yields much more empathetic and helpful discussions about the decision.  Next time you have trouble deciding whether to hire a particular candidate or whether to let someone go, try it.  Ask yourself: “Is this the best job for this person’s career?”