Farnam Street’s 2018 Annual Letter to Readers

Most public companies issue an annual letter to shareholders. These letters present an opportunity for the people entrusted to run the company to communicate with the people who own the company, the shareholders. In 2015, I started a similar tradition at Farnam Street. (2016 and 2017 letters are also available.)

Stewards of companies have a legal duty to do what’s in the best interest of shareholders. I feel a similar obligation to you. You trust me with something far more valuable than money: time.

For all of us, time is finite. Reading Farnam Street or listening to The Knowledge Project means you’re not doing something else. My job is to make sure your investment is getting an above-average return.


The Psychology of Email Lists

Our newsletter mailing list has grown to roughly 185,000 subscribers, compared to 155,000 at this time last year.

The map and the territory tell very different stories. To understand the difference, we need to understand email lists a bit better.

Email lists are the best way to reach people directly. With email, there are few barriers between the content creator and the reader. Getting into someone’s inbox is like getting into their bed: it requires an invite.

The world is full of companies that want you to sign up to their email list. These actors use pop-ups, free downloads, and other tricks to bribe you for your email. While they do this for numerous reasons, few actually concern you, the reader. They just want to sell you something.

For individuals, big email lists typically mean big egos or bigger paychecks.

Bigger egos—in the sense that the size of the mailing list is a metric by which people keep score. Sometimes this is unspoken; other times it’s fairly overt. Some comparison is natural, but there is a lot of appearance over substance going on. No one wants to be the little piggy in the straw house.

Bigger paychecks—in the sense that people use lists as a proxy for value. I’ve encountered this firsthand in 2018, while negotiating our book deals (more below). Everyone wanted to know our list size, but few wanted to know the open rate. If the list size is the map, the open rate is the territory.

The industry considers a 20% open rate to be good, for an email list of over 100,000 addresses. I think that’s terrible. It means about 20–25% of people actually open your emails, when you account for the plethora of adblockers and image loaders it means actual open rates are slightly higher than reported rates.

Our open rate used to be 35%—and now it’s about 45%. The difference is telling. A list of 150,000 with a 25% open rate reaches an effective audience of about 37.5k people per email. An open rate of 45% changes that to 67.5k per email. Clearly, not all lists are the same.

At FS, we’re not after the biggest list, just the best. We offer a one-click unsubscribe. And if it looks like you haven’t opened an email from us in a while, we will send you a few emails to see if you want to stay on the list. If you don’t engage, we’ll proactively remove you. If you miss us, you can always sign up later—and if you don’t notice, well, you’re breaking my heart.


We’re on our third or fourth iteration of domain names now.

We started with 68131 (the zip code for Berkshire Hathaway), then moved to and now While we started out as a blog or scratchpad, today we’re so much more than a blog. We’re moving our branding toward FS. Why did we move away from Farnam Street blog to In short, it was easier to type, available to us, and our friends at Automattic made it simple for us to switch.

We changed hosting companies this year. Our new hosts, Pressable, sped up the site. Most importantly, they freed me up to write, instead of spending hours a month on webhosting. If you’re looking for a webhost, they are the most competent and proactive we’ve come across.

Our relative ranking among websites continues to improve. Last year we were ranked among the 40,000 most popular sites in the world—out of hundreds of millions. As I write this we have moved into the top 33,000. And in the US, out of an estimated 200 million active websites, we rank in the top 11,000. That’s the top .006%, for those of us who are counting.

I hope to further refine the reading experience on the website in 2019, become a bit more brand-consistent, and better position FS to create something that outlives me.


I received a curious call from a reporter from the New York Times earlier this year, asking, “Why does everyone on Wall Street keep talking about you?” He found my “I don’t know” rather unsatisfying, and kept probing. The result was this profile on me. While we stayed on the most-emailed list for two full days—an eternity in the news world—the best thing about the story was that my mom doesn’t think I’m unemployed anymore.

My hometown paper also featured me in this article. Lest I get a big head, my mom pointed out that I couldn’t get ahead of “cat stops traffic” and “man walks slowly across street” to make the most-viewed stories of the day.


In 2018, we offered two public Re:Think Workshops, on Innovation and Decisionmaking. We continue to limit attendance at these events to ensure a good experience for everyone. We sold out the 2019 version of Re:Think Decisionmaking in one day. Join the waiting list so you don’t miss out on future dates!

While the feedback we get is positive beyond belief, we’ll be doing a major revamp of the content in 2019 to be released in 2020.

Our two smaller events are exceptional, but they’re not for everyone. We also require that you apply to attend these events because we need to ensure we have the right mix of people.

The first, Think Weekend, is a dinner series. We meet for a Thursday–Sunday period in a warm location during winter. The days are free time, and we have an interesting series of dinner conversations.

The second is Re:Think Europe. Here we have 10 people show up for what’s been called “the most unique experience I’ve ever had.” It’s an intense period in close quarters with ten people that start out as strangers but wind up best friends. People walk away mentally stimulated and exhausted, while making tangible progress on problems they have.

The Knowledge Project #ListenAndLearn

The Knowledge Project moved away from being “the most irregular podcast in the world” to presenting a new episode about every other week—about 25 episodes this year. Our 2018 guest list included FBI hostage negotiator Chris Voss, learning expert Barbara Oakley, Stripe CEO Patrick Collison, obstacle course super champ Amelia Boone, poker pro Annie Duke, Shopify CEO Tobi Lütke, and the CEO of the JP Morgan, Amazon, and Berkshire Hathaway healthcare initiative, Atul Gawande, to name a few. (You can find the full list here.) The lineup for 2019 looks just as good.

As I write this we stand at 47 published episodes with over 4.8 million downloads. You should know that we’re not bound to bi-weekly episodes. Our only commitment is quality, so we don’t pre-commit to frequency or duration. Some of the shows will be 15 minutes and others will be four hours. We rarely edit conversations, unless it’s requested or we feel it’s important to protect the guest. To put things in perspective, only two or three instances come to mind. My assumption is that if I’m still interested in the conversation, you are too.

I know what you’re thinking: can you sit and talk for four hours with one person, with no interruptions? Yes! Our guests are exceptional people, and I’m a fanatic when it comes to listening and learning.

The Knowledge Project isn’t bound to have me as a host. In the future, we will explore having other hosts.

We guided TKP’s branding on a sharp turn for the better this year, and will continue in 2019. We invested a lot of money in these improvements—they don’t increase revenue for us but do make for a much better product and experience for you.

We’re likely to move away from sponsors to a listener-supported model in the near future. While we’ve had some great sponsors, like Metalab, I increasingly find that sponsors want things from me—really from you—that just don’t align with my principles.

Speaking of which, let’s talk about some of that stuff. I take your trust in FS and in me very seriously.

  • I am not paid by any company for any opinion or article posted on FS or in any public forum, including podcasts and Twitter. I receive free products all the time in the mail (over 200 in 2018!). If I use them and like them, I try to tell people about them—no affiliate links. If you’re wondering what this looks like in practice, I think I mentioned two things this year: Atoms and Bellroy. I wear the Atoms every day in the office, and Bellroy has been my wallet forever. It’s the same one I buy for my friends.
  • Farnam Street participates in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising commissions by linking to Amazon. Simply put, if you click on my links and buy anything, I earn a small commission, yet you don’t pay any extra.
  • Sponsors of our newsletter and website are not allowed to run any code that might track your internet presence. We tell them nothing about you except in broad strokes. Website sponsors operate on a percentage-of-traffic basis and do not compensate us based on page views. This reduces our incentive to increase page views and write crappy content.
  • We do not have a Facebook tracking pixel, so we’re not enabling companies to “target our audience.”
  • We don’t give out your email address to any third parties.
  • If you’re interested in sponsoring the newsletter, podcast, or website, feel free to reach out to us at [email protected] or directly to me at [email protected]


A few years ago, we started offering courses to help people with skills that make them more adaptable. We were more concerned with outcomes than income. To that end, I purchased most of the most popular online courses and took a look at how they worked, what they were selling, and how they went about improving outcomes.

Unfortunately, we didn’t learn a ton from these courses. Most university courses are theory-based, which is great but not practical. Most of the online courses offered by entrepreneurs are edu-tainment around selling stuff—like online courses. This didn’t deter us. We took a different approach, working through iterations until we hit on something that finally worked: one-on-one interaction.

If you did the homework in The Art of Focus last year, which was a daily email to me, we responded and problem-solved with you every step of the way. Most of the time it was me responding. While this wasn’t efficient or scalable, it was certainly effective. These weren’t group calls but one-on-one interaction. That was just one of the lessons that we learned about how to increase the odds people actually made changes that stuck.

Now that we know what works and what doesn’t, we can tackle a few more ambitious ideas around courses.

In our history, we’ve offered three online courses, a productivity webinar, The Art of Focus, and The Art of Reading. We’ve stopped selling two out of three of these, and will stop selling The Art of Reading in January 2019. (The Art of Focus will be available as part of the Learning Community in January, and the productivity webinar is already available to members.)

Here’s a sneak peek: we’ve  been working on a mega-course on learning for over a year. It has taken a long time to cover not only the theory behind how we learn and how your brain processes information, but how to put it into practice. The wait will be worth it! We’ll use what we learned in the previous courses to increase the odds of success for participants.

I’ve tested the concepts with a few people I’m close to, and the response I’ve gotten is nothing short of amazing. Here’s a representative sample from my testing: “Shane, no one has ever taught me how to learn. In under an hour, you changed everything from the types of questions I ask other people to dramatically increasing my ability to quickly learn…nothing will be the same again.” That’s unsolicited feedback, three months after our conversation, from a person who wanted to test the course for me and paid for it on spec. No videos, just one hour with me in a restaurant over dinner.

The Learning Community

Rest assured, we have no aspirations of running the biggest membership community on the planet, just the best. The Learning Community isn’t for everyone. Our growing Learning Community continues to collect remarkable people and includes entrepreneurs, Fortune 50 CEOs, professional coaches, athletes, GMs from all the major leagues (NFL, NBA, NHL, and MLB), students, teachers, Nobel Laureates, and bestselling authors.

The learning community isn’t about more content but better content. Not only is it a way to support what you love (FS), join our virtual reading group, get transcripts to all of our podcasts, and so much more—it’s a way to join and interact with a group of people like you, who want to get better and smarter without the shortcuts, a group that offers everything from reading recommendations to smart parenting advice. Some of my favorite moments this year, has been when someone posted questions about a book to the community forum and the author, an LC member, responded.

Importantly, if you read the website for free, it’s funded by the Learning Community. While there are some exclusives and some bonus FS content for LC members, the majority of FS content will always be free. If you find value in Farnam Street, we hope you’ll consider joining the Learning Community, or gift it to the ones you love.


Last year I wrote this:

“As many of you know, we’re huge fans of mental models. The problem is that when I set out to read about mental models years ago, there wasn’t a good source of information in one place. Where could I find timeless ideas to help me learn, think, and decide?

Farnam Street has filled that void for many, but we’ve been inundated with requests to write a book about mental models. The first volume, internally dubbed Thinking Tools, will be released soon. Rather than being a version of the website, it’s a fresh start at intelligently preparing ourselves for the world. Whether readers are high school students or newly retired seniors, this well-designed book will hopefully have a place on their shelves for generations.”

I have to eat those words. And I have some other confessions to make.

Writing a book and publishing a book are two very different things. The writing was done and fully edited in May. However, then we had to learn how to actually publish a book. That’s where the time and effort really come into play. There are a lot of publishing decisions around books—everything from typeface and layout to paper and design. You have to decide on the style, not just for one book but for the planned series of 5. Then you have to decide where to print, how to sell them (it’s not as easy as sending them to Amazon), how many to print, whether you want electronic copies, audio, and a host of other things.

Let’s talk a little about the series of books that we’re publishing under Farnam Street: The Great Mental Models.

The first physical book was designed from the beginning to be a beautiful reference book. In a world of disposable books, I didn’t want this to be a book you bought and threw away. I wanted to be the last book on your bookshelf.

Just because we’re self-publishing doesn’t mean we can’t have a world-class team. Our creative director for the project, Morgwn Rimel, came by way of setting up the School of Life. We love working with Flok Design, an international design firm based in Germany. Illustrator Marcia Mihotich is insightful—we love her style. We also had a great editor, Néna Rawdah, and proofreader Karina Palmitesta.

While we self-published to maintain control over the content, thanks to the team above it will look and feel better than most traditionally published books in every way. If you’re curious as to what it looks like on the inside, you can see here and here.

There is some bad news, if you’re eager to get your hands on a physical copy. We’re only printing 3000 physical copies.

The reaction from my agent was telling.

“Shane, so let me understand this right, if you had demand for another 1k books you wouldn’t print more?”

“Not unless something changes.”

“So you don’t want to make more money.”

“Not off the physical book.”

[Two minutes of silence.]

“I’ve never heard that before.”

I don’t have an easily explainable answer to why only 3k hardcovers, so I won’t even try to explain it. Learning Community members will know about the physical copies first and get first dibs.

Why will I be able to get an audio copy before eBook copies?

Long story short: Audible came to us and said they wanted to partner with us, and offered us a lot of distribution and promotion. Helping more people with critical thinking outweighs having the physical and print books out sooner. We’re excited to work with Stacy Creamer and the team at audible.

I am hesitant to sell the print and electronic rights, because I think holding them gives us flexibility in the future. I want all the content to eventually be free, because that helps our mission of equalizing opportunity: the people who can’t afford books arguably need access to thinking tools more than the people that can. And we want to experiment with things that would have been really hard to do with a traditional publisher.

The FS brand carried the day at every meeting we had with people interested in the audio rights. There wasn’t a person we talked to who wasn’t familiar with FS, and in every room where it was pitched, people said, “I love that website.” That helps.

In short, the mental models books are coming. The first draft of the second book is almost done. The books will come out as soon as I can get them to you without sacrificing quality or distribution. As soon as we know more I’ll let you know.

A Trade Book

I signed a book deal with Penguin Portfolio for a trade book and am beyond excited to be working with the team there, especially Niki Papadopoulos. I’ve wanted to work with Niki ever since she came to one of our events four years ago. While this contract was for one book, I have four high-quality and unrelated book ideas in the queue.

Stay tuned.

Team Farnam

Perceptive readers know there is more to Farnam Street than just me. While I might be the face of FS for now, the site you are reading is increasingly about a team of people.

The team includes Rhiannon, who is a full-time staff writer and my right hand, working with me on the mental models books. Devon is our jack of all trades, doing most of our copy for courses, marketing emails, and podcast production. Bri is my part-time assistant.

Next year, two more will join the fray: one person in January to help us research, and another person in October to lead the team to the next level. I wasn’t looking for people, but the opportunity arose to hire two amazing humans, so I pounced.


I want to thank our website sponsors Royce Funds, Tulco., and Greenhaven Road Capital. I’d also like to thank our podcast sponsors Metalab, HeathIQ, and Inktel. If you’re interested in sponsoring us, send me an email at [email protected]

A Better Way to Sell Your Business

If you’ve built a profitable business with a reputation for fanatical customer service, I’m interested in becoming your partner.

Through Syrus Partners, a company we started to mirror Berkshire Hathaway on a micro scale, we made several investments last year. They included Mealime and Paragon Intelligence—where my background comes in handy.

We’re looking to partner with companies that have a reputation for honest and fair dealings, consistent earnings, good returns on capital, and straightforward business models. As an investment partner, we’re not interested in flipping the business, taking control, or leveraging it up. We bring permanent capital, simple and fair deals that can close in 4–8 weeks, and a reputation for letting you do your thing. We’re always available to help with anything—our team consists of people with world-class experience in marketing, branding, sales, and technology, not to mention an extensive Rolodex. Simply put, we offer as much or as little help as you want. We want you to keep doing what you’re doing.

We’re not VC, so please no pitches for business ideas. If you’ like to explore selling all or part of your business to a trustworthy and long-term partner, send an email to [email protected] with all relevant details.

Thank you.

We continue to put one foot in front of another and reinvest the proceeds from the Learning Community to create the best content we can.

Next year we’ll get back to more variety of content. There will be a mix of deep dives on topics as well as explorations. In short, back to our roots. We lost a bit of focus on that in 2018, which is entirely on me.

There is much good to come from FS in the new year. I look forward to continuing to learn with you. Thank you for reading and supporting us.






Why Small Habits Make a Big Difference

James Clear’s book Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones explores an interesting subject, on the compounding nature of the long game. While everyone is looking for big gains—the proverbial get rich quick scheme—there is a space that’s not getting much attention.

Those who understand compound interest can make it work for them and those that don’t understand it spend much of life trying to get out from its shackles. When we think of compounding we typically think of finance and positive returns, as in “good compounding.” But compounding just reinforces what’s already happening — good or bad.  There is no judgment. And compounding works outside of finance. So while we can compound money positively and negatively, we can compound ourselves as well.

The neutrality of compounding is what makes it interesting — as we can get it work for us. If we can replace a negatively compounding habit or mental discipline with one that’s neutral or positive, we instantly get better. And if we can accelerate positive compounding, we can really see the results.

Tiny, nearly imperceptible changes can make a huge difference when you factor in time.  As the graph above demonstrates, the difference in tiny changes is astonishing.

Clear writes:

Here’s how the math works out: if you can get 1 percent better each day for one year, you’ll end up thirty-seven times better by the time you’re done. Conversely, if you get 1 percent worse each day for one year, you’ll decline nearly down to zero. What starts as a small win or a minor setback accumulates into something much more.

Habits are the compound interest of self-improvement. The same way that money multiplies through compound interest, the effects of your habits multiply as you repeat them. They seem to make little difference on any given day and yet the impact they deliver over the months and years can be enormous. It is only when looking back two, five, or perhaps ten years later that the value of good habits and the cost of bad ones becomes strikingly apparent.

When we watch people make small choices, like order a salad at lunch instead of a burger, the difference of a few hundred calories doesn’t seem to matter much. In the moment that’s true. These small decisions don’t matter all that much. However, as days turn to weeks and weeks to months and months to years those tiny repeatable choices compound. Consider another example, saving a little money right not won’t make you a millionaire tomorrow. But starting to save today makes it more likely you will become a millionaire in the future.

Our brains have a hard time intuitively understanding time, compounding, and uncertainty. All of those things conspire to work against us when it comes to habits and mental disciplines. Why choose to save $20 today when I could buy a bottle of wine and have instant pleasure? Our minds do not easily realize that $20 saved today could be $100 in the future. And if we do save the money, there is no certainty that it will compound positively, it could, after all, compound negatively and I end up with $15. Now you can begin to see why it’s easier to just live in the moment and do whatever you want.

Clear writes:

But when we repeat 1 percent errors, day after day, by replicating poor decisions, duplicating tiny mistakes, and rationalizing little excuses, our small choices compound into toxic results.

As an entrepreneur, I’m always looking for opportunities. The opportunities that interest me the most offer superior returns, low risk, and a long duration. Just as investing in companies can give you the opportunity to find all three, so does properly investing in yourself. Habits and mental disciplines are controllable, offer enormous opportunity for returns, have extremely low risk, and you can use them for the rest of your life. More importantly, they allow you to diverge from the herd and advantageous divergence is the name of the game.

Love, Happiness, and Time

How many of us regard love and happiness as a place? A box to tick off, a destination we get to? We often conceptualize these two things as goals. Is this responsible for why we are so devastated when they leave after being in our lives for a while?

What do love and happiness have to do with time?

Recently I read The Order of Time, by Carlo Rovelli. In it he writes,

We can think of the world as made up of things. Of substances. Of entities. Of something that is. Or we can think of it as made up of events. Of happenings. Of processes. Of something that occurs. Something that does not last, and that undergoes continual transformation, that is not permanent in time. The destruction of the notion of time in fundamental physics is the crumbling of the first of these two perspectives, not of the second. It is the realization of the ubiquity of impermanence, not of stasis in a motionless time.

This passage, in particular, gets me thinking. By this point in his book, Rovelli has brought me to “a world without time.” Thanks to his writing skills, I am comfortable being there. Time reveals itself to be part of the human condition, not the physical world.

Rovelli continues:

The difference between things and events is that things persist in time; events have a limited duration. A stone is a prototypical “thing”: we can ask ourselves where it will be tomorrow. Conversely, a kiss is an “event.” It makes no sense to ask where the kiss will be tomorrow. The world is made up of networks of kisses, not of stones.

Will it be more rewarding and useful to conceptualize love and happiness like time? An event, not a thing. A kiss, not a stone.

If you think of love like a stone—to be fair, we often do—it is a thing that you attain. You may have an expectation that it will persist and continue to exist. So when you and your partner fight, and it seems the love disappears for an evening, you panic. The love is gone! The thing that connects you wasn’t permanent at all. What does that say about your relationship?

If we change our thinking to love being an event, like a kiss, then a burden is lifted. It’s an event we experience with our partners many times, but not always. And then we can focus on creating the conditions that the event of love requires, even if it might not come to pass every moment of every day.

Rovelli has more to say:

On closer inspection, in fact, even the things that are most “thing-like” are nothing more than long events. The hardest stone, in the light of what we have learned from chemistry, from physics, from mineralogy, from geology, from psychology, is in reality a complex vibration of quantum fields, a momentary interaction of forces, a process that for a brief moment manages to keep its shape, to hold itself in equilibrium before disintegrating again into dust…gradually, an intricate knot in that cosmic game of mirrors that constitutes reality.

Even a stone, the most “thing-like” of things, is fleeting, its definition multilayered and dependent on my perception.

Perhaps it is useful to consider happiness the same way. It’s not something we achieve in perpetuity, an object external to ourselves, as if we could just find it and break off a chunk to keep with us forever. Its existence is bound with our ability to experience it.

“I remember one morning getting up at dawn. There was such a sense of possibility. You know, that feeling. And I…I remember thinking to myself: So this is the beginning of happiness, this is where it starts. And of course there will always be more…never occurred to me it wasn’t the beginning. It was happiness. It was the moment, right then.”

— The Hours (screenplay by David Hare)

As with love, we can reconfigure happiness into an event. It happens. It holds itself in equilibrium for a moment and then disintegrates.

Right now it is fall. Outside my window I am super lucky to witness the unrelenting biological changes that produce such spectacular leaf colours every year. It’s a moment that keeps its shape for a small part of the year. As I get older, I make sure to take the time each October to pay attention and enjoy it.

Could we enjoy happiness more if we consider it the same way? It may sound odd to say that, because who doesn’t enjoy happiness? But there seems to be an eternal struggle with happiness. When it goes, it hurts. Sometimes, when it comes back, it’s bittersweet, because we know it will go again.

The idea of time being an event, and how we experience it, relates, I think, to fundamental conceptions of happiness and love. Time, source of much of our anxiety and sadness, can be understood as a momentary holding together of a set of factors that we experience because of how we are built. I think we can consider love and happiness the same way.

Rovelli explains it this way:

And we begin to see that we are time. We are this space, this clearing opened by the traces of memory inside the connections between our neurons. We are memory. We are nostalgia. We are longing for a future that will not come. The clearing that is opened up in this way, by memory and by anticipation, is time: a source of anguish sometimes, but in the end a tremendous gift. A precious miracle that the infinite play of combinations has unlocked for us, allowing us to exist. We may smile now. We can go back to serenely immersing ourselves in time—in our finite time—to savoring the clear intensity of every fleeting and cherished moment of the brief circle of our existence.

Battling Entropy: Making Order of the Chaos in Our Lives

“Nor public flame, nor private, dares to shine;
Nor human spark is left, nor glimpse divine!
Lo! thy dread empire, Chaos! is restored;
Light dies before thy uncreating word:
Thy hand, great Anarch! lets the curtain fall;
And universal darkness buries all.”
― Alexander Pope, The Dunciad


The second law of thermodynamics states that “as one goes forward in time, the net entropy (degree of disorder) of any isolated or closed system will always increase (or at least stay the same).”[1] That is a long way of saying that all things tend towards disorder. This is one of the basic laws of the universe and is something we can observe in our lives. Entropy is simply a measure of disorder. You can think of it as nature’s tax[2].

Uncontrolled disorder increases over time. Energy disperses and systems dissolve into chaos. The more disordered something is, the more entropic we consider it. In short, we can define entropy as a measure of the disorder of the universe, on both a macro and a microscopic level. The Greek root of the word translates to “a turning towards transformation” — with that transformation being chaos.

As you read this article, entropy is all around you. Cells within your body are dying and degrading, an employee or coworker is making a mistake, the floor is getting dusty, and the heat from your coffee is spreading out. Zoom out a little, and businesses are failing, crimes and revolutions are occurring, and relationships are ending. Zoom out a lot further and we see the entire universe marching towards a collapse.

Let’s take a look at what entropy is, why it occurs, and whether or not we can prevent it.

The Discovery of Entropy

The identification of entropy is attributed to Rudolf Clausius (1822–1888), a German mathematician and physicist. I say attributed because it was a young French engineer, Sadi Carnot (1796–1832), who first hit on the idea of thermodynamic efficiency; however, the idea was so foreign to people at the time that it had little impact. Clausius was oblivious to Carnot’s work, but hit on the same ideas.

Clausius studied the conversion of heat into work. He recognized that heat from a body at a high temperature would flow to one at a lower temperature. This is how your coffee cools down the longer it’s left out — the heat from the coffee flows into the room. This happens naturally. But if you want to heat cold water to make the coffee, you need to do work — you need a power source to heat the water.

From this idea comes Clausius’s statement of the second law of thermodynamics: “heat does not pass from a body at low temperature to one at high temperature without an accompanying change elsewhere.”

Clausius also observed that heat-powered devices worked in an unexpected manner: Only a percentage of the energy was converted into actual work. Nature was exerting a tax. Perplexed, scientists asked, where did the rest of the heat go and why?

Clausius solved the riddle by observing a steam engine and calculating that energy spread out and left the system. In The Mechanical Theory of Heat, Clausius explains his findings:

… the quantities of heat which must be imparted to, or withdrawn from a changeable body are not the same, when these changes occur in a non-reversible manner, as they are when the same changes occur reversibly. In the second place, with each non-reversible change is associated an uncompensated transformation…

… I propose to call the magnitude S the entropy of the body… I have intentionally formed the word entropy so as to be as similar as possible to the word energy….

The second fundamental theorem [the second law of thermodynamics], in the form which I have given to it, asserts that all transformations occurring in nature may take place in a certain direction, which I have assumed as positive, by themselves, that is, without compensation… [T]he entire condition of the universe must always continue to change in that first direction, and the universe must consequently approach incessantly a limiting condition.

… For every body two magnitudes have thereby presented themselves—the transformation value of its thermal content [the amount of inputted energy that is converted to “work”], and its disgregation [separation or disintegration]; the sum of which constitutes its entropy.

Clausius summarized the concept of entropy in simple terms: “The energy of the universe is constant. The entropy of the universe tends to a maximum.”

“The increase of disorder or entropy is what distinguishes the past from the future, giving a direction to time.”

— Stephen Hawking, A Brief History of Time

Entropy and Time

Entropy is one of the few concepts that provides evidence for the existence of time. The “Arrow of Time” is a name given to the idea that time is asymmetrical and flows in only one direction: forward. It is the non-reversible process wherein entropy increases.

Astronomer Arthur Eddington pioneered the concept of the Arrow of Time in 1927, writing:

Let us draw an arrow arbitrarily. If as we follow the arrow[,] we find more and more of the random element in the state of the world, then the arrow is pointing towards the future; if the random element decreases[,] the arrow points towards the past. That is the only distinction known to physics.

In a segment of Wonders of the Universe, produced for BBC Two, physicist Brian Cox explains:

The Arrow of Time dictates that as each moment passes, things change, and once these changes have happened, they are never undone. Permanent change is a fundamental part of what it means to be human. We all age as the years pass by — people are born, they live, and they die. I suppose it’s part of the joy and tragedy of our lives, but out there in the universe, those grand and epic cycles appear eternal and unchanging. But that’s an illusion. See, in the life of the universe, just as in our lives, everything is irreversibly changing.

In his play Arcadia, Tom Stoppard uses a novel metaphor for the non-reversible nature of entropy:

When you stir your rice pudding, Septimus, the spoonful of jam spreads itself round making red trails like the picture of a meteor in my astronomical atlas. But if you stir backwards, the jam will not come together again. Indeed, the pudding does not notice and continues to turn pink just as before. Do you think this is odd?

(If you want to dig deeper on time, I recommend the excellent book by John Gribbin, The Time Illusion.)

“As a student of business administration, I know that there is a law of evolution for organizations as stringent and inevitable as anything in life. The longer one exists, the more it grinds out restrictions that slow its own functions. It reaches entropy in a state of total narcissism. Only the people sufficiently far out in the field get anything done, and every time they do they are breaking half a dozen rules in the process.”

— Roger Zelazny, Doorways in the Sand

Entropy in Business and Economics

Most businesses fail—as many as 80% in the first 18 months alone. One way to understand this is with an analogy to entropy.

Entropy is fundamentally a probabilistic idea: For every possible “usefully ordered” state of molecules, there are many, many more possible “disordered” states. Just as energy tends towards a less useful, more disordered state, so do businesses and organizations in general. Rearranging the molecules — or business systems and people — into an “ordered” state requires an injection of outside energy.

Let’s imagine that we start a company by sticking 20 people in an office with an ill-defined but ambitious goal and no further leadership. We tell them we’ll pay them as long as they’re there, working. We come back two months later to find that five of them have quit, five are sleeping with each other, and the other ten have no idea how to solve the litany of problems that have arisen. The employees are certainly not much closer to the goal laid out for them. The whole enterprise just sort of falls apart.

It reminds one distinctly of entropy: For every useful arrangement of affairs towards a common business goal, there are many orders of magnitude more arrangements that will get us nowhere. For progress to be made, everything needs to be arranged and managed in a certain way; we have to input a lot of energy to keep things in an ordered state.

Of course, it’s not a perfect analogy: We have to consider the phenomenon of self-organization that happens in many systems, up to and including human organizations. Given a strong enough goal, a good enough team, and the right incentives, perhaps that group wouldn’t need a lot “outside ordering” — they would manage themselves.

“The … ultimate purpose of life, mind, and human striving: to deploy energy and information to fight back the tide of entropy and carve out refuges of beneficial order.”

— Steven Pinker

In practice, both models seem to be useful at different times. Any startup entrepreneur who has stayed long enough to see a company thrive in unexpected ways knows this. The amount of diligent management needed will vary. In physics, entropy is a law; in social systems, it’s a mere tendency — though a strong one, to be sure.

Entropy occurs in every aspect of a business. Employees may forget training, lose enthusiasm, cut corners, and ignore rules. Equipment may break down, become inefficient, or be subject to improper use. Products may become outdated or be in less demand. Even the best of intentions cannot prevent an entropic slide towards chaos.

Successful businesses invest time and money to minimize entropy. For example, they provide regular staff training, good reporting of any issues, inspections, detailed files, and monitoring reports of successes and failures. Anything less will mean almost inevitable problems and loss of potential revenue. Without the necessary effort, a business will reach the point of maximum entropy: bankruptcy.

Fortunately, unlike thermodynamic systems, a business can reverse the impact of entropy. A balance must be struck between creativity and control, though. Too little autonomy for employees results in disinterest, while too much leads to poor decisions.

Entropy in Sociology

Without constant maintenance from individuals and dominant institutions, societies tend towards chaos. Divergent behavior escalates — a concept known as the “broken windows” theory.

Sociologist Kenneth Bailey writes:

When I began studying the notion of entropy it became clear to me that thermodynamic entropy was merely one instance of a concept with much broader applications … I became convinced that entropy applied to social phenomena as well.

One example of what happens when entropy increases unchecked occurred in the Kowloon Walled City. For a substantial length of time, Kowloon was abandoned by the government after the British took control of Hong Kong. At one point, an estimated 33,000 residents were crammed into 300 buildings over 6.4 acres, making Kowloon the most densely populated place on earth. With no space for new construction, stories were added to the existing buildings. Because of minimal water supplies and a lack of ventilation (no sunlight or fresh air reached lower levels), the health of residents suffered. A community of unlicensed medical professionals flourished, alongside brothels and gambling dens.

With no one controlling the city, organized crime gangs took over. It became a haven for lawlessness. Though police were too scared to make any attempts to restore order, residents did make desperate attempts to reduce the entropy themselves. Groups formed to improve the quality of life, creating charities, places for religious practices, nurseries, and businesses to provide income.

In 1987, the Hong Kong government acknowledged the state of Kowloon. The government demolished and rebuilt the city, evicting residents and destroying all but a couple of historic buildings. Although reasonable compensation was provided for ex-residents, many were somewhat unhappy with the rebuilding project.

Looking at pictures and hearing stories from Kowloon, we have to wonder if all cities would be that way without consistent control. Was Kowloon an isolated instance of a few bad apples giving an otherwise peaceful place a terrible reputation? Or is chaos our natural state?

Needless to say, Kowloon was not an isolated incident. We saw chaos and brutality unleashed during the Vietnam War, when many young men with too much ammunition and too few orders set about murdering and torturing every living thing they encountered. We see it across the world right now, where places with no law enforcement (including Somalia and Western Sahara) face incessant civil wars, famine, and high crime rates.

Sociologists use an intuitive term for this phenomenon: social entropy. Societies must expend constant effort to stem the inevitable march towards dangerous chaos. The reduction of social entropy tends to require a stable government, active law enforcement, an organized economy, meaningful employment for a high percentage of people, infrastructure, and education.

However, the line between controlling entropy and suppressing people’s liberty is a thin one. Excessive control can lead to a situation akin to Foucault’s panopticon, wherein people are under constant surveillance, lack freedom of speech and movement, are denied other rights as well, and are subject to overzealous law enforcement. This approach is counterproductive and leads to eventual rebellion once a critical mass of dissenters forms.

“Everything that comes together falls apart. Everything. The chair I’m sitting on. It was built, and so it will fall apart. I’m going to fall apart, probably before this chair. And you’re going to fall apart. The cells and organs and systems that make you you—they came together, grew together, and so must fall apart. The Buddha knew one thing science didn’t prove for millennia after his death: Entropy increases. Things fall apart.”

— John Green, Looking for Alaska

Entropy in Our Everyday Lives

We have all observed entropy in our everyday lives. Everything tends towards disorder. Life always seems to get more complicated. Once-tidy rooms become cluttered and dusty. Strong relationships grow fractured and end. Formerly youthful faces wrinkle and hair turns grey. Complex skills are forgotten. Buildings degrade as brickwork cracks, paint chips, and tiles loosen.

Entropy is an important mental model because it applies to every part of our lives. It is inescapable, and even if we try to ignore it, the result is a collapse of some sort. Truly understanding entropy leads to a radical change in the way we see the world. Ignorance of it is responsible for many of our biggest mistakes and failures. We cannot expect anything to stay the way we leave it. To maintain our health, relationships, careers, skills, knowledge, societies, and possessions requires never-ending effort and vigilance. Disorder is not a mistake; it is our default. Order is always artificial and temporary.

Does that seem sad or pointless? It’s not. Imagine a world with no entropy — everything stays the way we leave it, no one ages or gets ill, nothing breaks or fails, everything remains pristine. Arguably, that would also be a world without innovation or creativity, a world without urgency or a need for progress.

Many people cite improving the world for future generations as their purpose in life. They hold protests, make new laws, create new forms of technology, work to alleviate poverty, and pursue other noble goals. Each of us makes our own efforts to reduce disorder. The existence of entropy is what keeps us on our toes.

Mental models are powerful because they enable us to make sense of the disorder that surrounds us. They provide us with a shortcut to understanding a chaotic world and exercising some control over it.

In The Information: A History, a Theory, a Flood, James Gleick writes,

Organisms organize. … We sort the mail, build sand castles, solve jigsaw puzzles, separate wheat from chaff, rearrange chess pieces, collect stamps, alphabetize books, create symmetry, compose sonnets and sonatas, and put our rooms in order… We propagate structure (not just we humans but we who are alive). We disturb the tendency toward equilibrium. It would be absurd to attempt a thermodynamic accounting for such processes, but it is not absurd to say we are reducing entropy, piece by piece. Bit by bit … Not only do living things lessen the disorder in their environments; they are in themselves, their skeletons and their flesh, vesicles and membranes, shells, and carapaces, leaves, and blossoms, circulatory systems and metabolic pathways—miracles of pattern and structure. It sometimes seems as if curbing entropy is our quixotic purpose in the universe.

The question is not whether we can prevent entropy (we can’t), but how we can curb, control, work with, and understand it. As we saw at the start of this post, entropy is all around us. Now it’s probably time to fix whatever mistake an employee or coworker just made, clear up your messy desk, and reheat your cold coffee.

How Can I Use Entropy to My Advantage?

This is where things get interesting.

Whether you’re starting a business or trying to bring about change in your organization, understanding the abstraction of entropy as a mental model will help you accomplish your goals in a more effective manner.

Because things naturally move to disorder over time, we can position ourselves to create stability. There are two types of stability: active and passive. Consider a ship, which, if designed well, should be able to sail through a storm without intervention. This is passive stability. A fighter jet, in contrast, requires active stability. The plane can’t fly for more than a few seconds without having to adjust its wings. This adjustment happens so fast that it’s controlled by software. There is no inherent stability here: if you cut the power, the plane crashes.[3]

People get in trouble when they confuse the two types of stability. Relationships, for example, require attention and care. If you assume that your relationship is passively stable, you’ll wake up one day to divorce papers. Your house is also not passively stable. If not cleaned on a regular basis, it will continue to get messier and messier.

Organizations require stability as well. If you’re a company that relies on debt, you’re not passively stable but actively stable. Factoring in a margin of safety, this means that the people giving you the credit should be passively stable. If you’re both actively stable, then when the power gets cut, you’re likely to be in a position of weakness, not strength.

With active stability, you’re applying energy to a system in order to bring about some advantage (keeping the plane from crashing, your relationship going, the house clean, etc.), If we move a little further down the rabbit hole, we can see how applying the same amount of energy can yield totally different results.

Let’s use the analogy of coughing.[4] Coughing is the transfer of energy as heat. If you cough in a quiet coffee shop, which you can think of as a system with low entropy, you cause a big change. Your cough is disruptive. On the other hand, if you cough in Times Square, a system with a lot of entropy, that same cough will have no impact. While you change the entropy in both cases, the impact you have with the same cough is proportional to the existing entropy.

Now think of this example in relation to your organization. You’re applying energy to get something done. The higher the entropy in the system, the less efficient the energy you apply will be. The same person applying 20 units of energy in a big bureaucracy is going to see less impact than someone applying the same 20 units in a small startup.

You can think about this idea in a competitive sense, too. If you’re starting a business and you’re competing against very effective and efficient people, a lot of effort will get absorbed. It’s not going to be very efficient. If, on the other hand, you compete against less efficient and effective people, the same amount of energy will be more efficient in its conversion.

In essence, for a change to occur, you must apply more energy to the system than is extracted by the system.


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[2] Peter Atkins

[3] Based on the work of Tom Tombrello

[4] Derived from the work of Peter Atkins in The Laws of Thermodynamics: A Very Short Introduction


There’s Seldom Any Traffic on the High Road

We’ve all been there: someone says something rude to us and our instinct is to strike back with a quick-witted comeback. That’s what many people do. It’s also a big reason that many people don’t get what they want. Consider this example from my recent travels:

“Are you dense?” the gate agent blurted to me, clearly frustrated as I asked a question she’d be asked a million times that day. Only moments before, I had been sitting on a plane to Seattle when the announcement came over the PA system that the flight was cancelled.

The instructions were clear: check with the gate agent for reassignment.  I was tenth in line. By the time I talked to her, this agent had already had to deal with nine angry customers. She wasn’t frustrated with me, but I knew that everyone else had verbally beat her up. I also travel enough to know how seldom that works. She had instructed the previous nine passengers to collect their bags, go through customs, and go to the Air Canada customer service desk for reassignment.

“I guess you’re right, I can be slow sometimes,” I said. “I’m sorry.”

Her words finally caught up with her, and she apologized. “I’m sorry, that was rude of me. I didn’t mean—”

“You’ve had a long day. People are frustrated and taking it out on you when it’s not your fault. I know how hard that can be.”

She cracked a smile, the first I had seen from her since I joined the line. And she happily found me a seat on the next flight.

She was being rude. Yes. But that wasn’t the best version of her.

When people are rude, our subconscious interprets it as an assault on hierarchy instincts. Our evolutionary programming responds with thoughts like, “Who are you to tell me something so rude? I’ll show you….”

Our instincts are to escalate when really, we should be focused on de-escalating the situation. One way to do that is to take the high road.

Say something along the lines of “I can see that.” You don’t have to apologize. You don’t have to agree with what the other person is saying. But I promise the results are magic. It’s hard to be angry with someone who agrees with you. And when there is no one to argue with and they’re the only person worked up about the situation, they will quickly feel uncomfortable and try to correct course.

Making enemies is expensive. Sometimes you don’t even realize how expensive. I saw one of those other nine passengers two and a half hours later, running to the gate to board the flight I was on. They had only just gotten through the hassle that resulted from their dealings with the gate agent—while I had grabbed a glass of wine and read a book. They had no idea how much their rudeness cost them in time and energy. It wasn’t visible to them. It was, however, visible to me.

The high road not only holds your frictional costs to the minimum, but it makes you happier. You’ll go farther and faster than others in the same situation. Sure, it involves putting your ego aside for a second—but if you think about it, this approach can often be the quickest to getting what you want.

Defensive Decision Making: What IS Best v. What LOOKS Best

“It wasn’t the best decision we could make,” said one of my old bosses, “but it was the most defensible.”

What she meant was that she wanted to choose option A but ended up choosing option B because it was the defensible default. She realized that if she chose option A and something went wrong, it would be hard to explain because it was outside of normal. On the other hand, if she chose option A and everything went right, she’d get virtually no upside. A good outcome was merely expected, but a bad outcome would have significant consequences for her. The decision she landed on wasn’t the one she would have made if she owned the entire company. Since she didn’t, she wanted to protect her downside. In asymmetrical organizations, defensive decisions like this one protect the person making the decision.

My friend and advertising legend Rory Sutherland calls defensive decisions the Heathrow Option. Americans might think of it as the IBM Option. There’s a story behind this:

A while ago, British Airways noticed a reluctance for personal assistants to book their bosses on flights from London City Airport to JFK. They almost always picked Heathrow, which was further away, and harder to get to. Rory believed this was because “flying from London City might be better on average,” but “because it was a non-standard option, if anything were to go wrong, you were much more likely to get it in the neck.”

Of course, if you book your boss to fly out of Heathrow—the default—and the flight is delayed, they’ll blame the airline and not you. But if you opted for the London City airport, they’d blame you.

At first glance, it might seem like defensive decision making is irrational. It’s actually perfectly rational when you consider the asymmetry involved. This asymmetry also offers insight into why cultures rarely change.

Some decisions place the decisionmakers in situations where outcomes offer little upside and massive downside. In these cases, it can seem like great outcomes carry a 1% upside, good outcomes are neutral, and poor outcomes carry at least 20% downside—if they don’t get you fired.

It’s easy to see why people opt for the default choice in these cases. If you do something that’s different—and thus hard to defend—and it works out, you’ve risked a lot for very little gain. If you do something that’s different and it doesn’t work out, and you might find yourself unemployed.

This asymmetry explains why your boss, who has nice rhetoric about challenging norms and thinking outside the box, is likely to continue with the status quo rather than change things. After all, why would they risk looking like a fool by doing something different? It’s much easier to protect themselves. Defaults give people a possible out, a way to avoid being held accountable for their decisions if things go wrong. You can distance yourself from your decision and perhaps be safe from the consequences of a poor outcome.

Doing the safe thing is not the same as doing the right thing. Often, the problem with the safe thing is that there is no growth, no innovation. It’s churning out more of the same. So in the short term, while you may think that the default is a better choice for your job security, in the long game there’s a negative. When you are unwilling to take risks, you stop recognizing opportunities. If you aren’t willing to put yourself out there for 1% gain, how do you grow? After all, the 1% upsides are more common than the 50% upsides. But in either case, if you become afraid of downside, then what level of risk would be acceptable? It’s not that choosing the default makes you a bad person. But a lifetime of opting for the default limits your opportunities and your potential.

And for anyone who owns a company, a staff full of default decision makers is a death knell. You get amazing results when people have the space to take risks and not be penalized for every downside.

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