How To Think by Alan Jacobs

How to think by Alan Jacobs

Fair warning, this is not a book for those looking to sharpen their thinking skills just to win more arguments. On the contrary, this book helps one recognize that losing may be just as valuable. That thinking well is not a joyful or direct path. Or, that what we believe to be the attributes of an “open mind” is more likely to be just a different form of a “closed mind” validated by a different group. Thinking is all about learning to do the uncomfortable, and if one can understand how thinking works, one may become a better thinker over all. To posit those theories, and many others like it, Alan Jacobs deals with optimism, community, solidarity, truth, social affiliation, kindness and vice by asking how they blend or contradict one another.

I especially love the fact that the book is current, and cites examples from events familiar to global state of consciousness. It helps that the author is as unbiased as a person could be, while still able to make sharp and concise points, and because of that, no other book is as important for any affiliation or creeds to benefit. In our polarized, highly emotional world, it’s refreshing, and necessary. As current as he is, he is no stranger to the history of thinking. From Luther, to T.S. Elliot, to Kannanman his references aren’t always made to simply validate, but to argue against, assert, or deconstruct the art and science around thinking.

It’s easy to assume the social conscience of the world is more worse for ware now than ever before, and the new phenomena of the internet and social media is mostly to blame. Instead of leaning into that assumption, Alan offers some perspective look back to early writers, like a quite T.S. Elliot who said, “The vast accumulations of knowledge—or at least of information—deposited by the nineteenth century have been responsible for an equally vast ignorance. When there is so much to be known, when there are so many fields of knowledge in which the same words are used with different meanings, when everyone knows a little about a great many things, it becomes increasingly difficult for anyone to know whether he knows what he is talking about or not. And when we do not know, or when we do not know enough, we tend always to substitute emotions for thoughts.” That is surely something as appropriate today as it was 100 years ago.

There are quite a few gems sprinkled throughout the book that can get the wheels churning. Like how Alan challenges his readers to separate a single thought from all the context and emotion laid around it. For example, “A madman is not one has lost reason … a madman is one that has lost everything but reason.“ Indeed, the separation of fact, from emotion, or affiliation, let’s facts get tangled up into a single, lump of subjective “truth”. That affiliation and process of lumping makes it easier for us to turn every “neighbor” into what Alan Jacob’s called the “Repugnant Cultural Other” AKA  “RCO”. When more and more people are classified as an RCO based on a discrete piece of truth we decide to focus on, then we fail to allow ourselves to learn, or accept, anything else form them. As Alan puts it, “If that person over there is both ‘other’ and ‘repugnant’, I may never discover that that person and I like the same television program, or like the same books (even if not for the same reasons), or that we both know what it’s like to nurse someone through a long illness. All of which is to say, that I may forget that political, social and religious differences are not the whole of human experience.” That posit is very much a reality with the current collective human psyche. It does in fact feel as though more and more of us are at odds with our neighbors, and we are so with less and less information to guide it.

Of course separation via classifying others as an RCO goes well beyond politics and social media. As both an academic and a christian, Alan adds religion to the ring by noting, “When I hear academica talk about christians I think, ‘that’s not quite right. I don’t think you understand the people you think your disagreeing with’, and when I listen to christians talk about academics I have the precisely the same thought.”

Why do we decide to stick to a bandwagon, against all evidence to steer us away, or care to even search for a deeper truth? Alan quotes Robinson to underline this part of the human condition at play. “It is a great example of our collective eagerness to disparage without knowledge or information about the thing disparaged when the reward is the pleasure of sharing an attitude one knows is socially approved.” Alan continues, “Why would people ever think, when thinking deprives them of the pleasure of sharing an attitude one knows is socially approved? If you want to think, then you have to shrink that hypertrophic need for consensus.”

Where academia is concerned, Alan pulls a quote from Jeff Schmidt’s to assert that education is not necessarily an avenue e toward greater thinking either. In “Disciplined Minds” Schmidt says, “Academia and high-racking professions are good at maintaining “ideological discipline”… people who do well … tend to have “assignable curiosity”, which is to say, they are obediently interested in the things they are told to be interested in.”

Though, there are some academic environments that are created to nurture true thinking. Alan tells an anecdote from the Yale Political Union debate club. As he observed at Yale, you are scored not just by wins, but by the number of times you flip your beliefs mid-debate. love how that metric aligns with not the speaker ability to power their will on others, but in the power and flexibility of being a good, open minded, listener.

This is one of my favorite books I’ve read this year and a great supplement to the best selling books Thinking Fast and Slow and Blink. It is well worth the time so, after each chapter, sit back, and push embrace “How to Think” better.

[Video Excerpt] Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel by Rolph Plots

I heard about this book from Tim Ferriss’ podcast. In it, Tim dedicated an entire show to the author’s reading of this book. It got me hooked.

Usually with books I review I’ll append all the excerpts I’ve highlighted from my Kindle into the my blog post. For this book however, I found myself highlighting almost every sentence. He really nails the philosophy of long term travel including the feelings, challenges and rewards that come with . I’ve thought about writing my own philosophical experiences down, but why build when you can buy, right?!

This guy is like the Confucius of travel.

Here is a short 4-minute excerpt from Tim’s podcast, and here is the book on Audible and Amazon if you end up getting hooked too.

Long-term travel doesn’t require a massive “bundle of cash”; it only requires that we walk through the world in a more deliberate way.

This deliberate way of walking through the world has always been intrinsic to a time-honored, quietly available travel tradition known as “vagabonding”.

Vagabonding involves taking an extended time-out from your normal life — six weeks, four months, two years — to travel the world on your own terms.

But beyond travel, vagabonding is an outlook on life. Vagabonding is about using the prosperity and possibility of the information age to increase your personal options instead of your personal possessions. Vagabonding is about looking for adventure in normal life, and normal life within adventure. Vagabonding is an attitude — a friendly interest in people, places and things that makes a person an explorer in the truest, most vivid sense of the word.

Vagabonding is not a lifestyle, nor is it a trend. It’s just an uncommon way of looking at life — a value adjustment from which action naturally follows.

And, as much as anything, vagabonding is about time — our only real commodity — and how we choose to use it.

In Pamplona The Sun Also Rises

My self-improvement/educational books began getting dry and it was time to learn more indirectly by ingesting some classic novels again. It may seem pretty naive of me looking back, but when I picked up a copy of Hemingway’s The Sun Also Rises I had no idea how relevant it would be to our trip. I’ve read a couple of Hemingway’s books before and loved their balance between simplicity and great emotional depth.

As many of you seem to already know, the majority of the Sun Also Rises is based out of Pamplona, Spain. There, Hemingway’s characters find themselves in a bizarre love (or loveless) story entangled within its now famous annual fiesta of San Fermin and the Running of the Bulls. As it turns out, Hemingway’s story is exactly what gave the Running of the Bulls international popularity. Today San Fermin is now the largest festival in the entire world which he himself attended nine times in his life.

As Jake (the main character in the book) drew closer to his visit to Pamplona, I in turn drew closer to mine. I arrived with about twenty more pages to go and find it fitting to finish the book while I’m here.

It is amazing to walk the very same streets that he made famous in the novel. In some ways I feel like I’ve been here before – seventy years or so ago. Before we began doing research online for our standard “things to do” list, I surprisingly already knew when the rockets would go off, where the bulls would run and a general idea of what to expect in the chaos. I would never have thought a novel would make such a great travel guide! It is such an unforgettable feeling to experience a town in two ways such as this and I am excited to enjoy the festival only 24 hours away!

Off to finish the book and start my very own version of the experience. (I’ll add notes about the book in a later update.)


Creativity Inc. by Ed Catmull

I really enjoyed reading this book! Not only did it have the insight into how a successful entrepreneur created his empire, but it is a story of how a pioneer gave birth to an entirely new industry. To add to the storyline you’ll get a behind the scenes look into the making of some of the classic pixar movies like “Up”; interactions with the late, great Steve Jobs; a look into a merger with one of the largest culture-driven companies in history, Disney; sprinkled in with nerdy facts like who invented anti-aliasing and where the name Pixar came from. It wasn’t like many business books out there, but, then again, I wouldn’t expect less from a book written by Ed Catmull with the word “creativity” in the title.

One thing I am skeptical about is how his glowing positive outlook on all the events and outcomes that transpired actually trickled down emotionally to the average employee. Having been on both sides of the founder/employee persona I  know it is easy to relishes your triumphs while realistically most people don’t care as much as you think. At times the book sounds a bit “let them eat cake” esque. That being said, I don’t think it takes away from the stories and points he makes. After all, he did create a billion dollar company, a trillion dollar industry and many award winning films along the way – so I still think his advice is sound 😉

Based on the above you may think I would say he lacked humility in the book, that’s not quite what I am saying. One thing I enjoyed immensely is how upfront he was about where things went wrong and how he pushed his ideal of creating a candid work environment. I just wonder how everyone else responded to the ideals in the day-to-day.

Throughout the book Ed does a great job giving the reader what they are ultimately looking for: tips. He summarizes many of his stories as concise lessons and at the end of the book he literally creates a list of overarching tips he believes are important. What can I say, the man knows how to tell a story. Definitely a must read.

Related Books with Similar Themes:

Some of my Kindle Highlights, with notes, from the book:

Mistakes aren’t a necessary evil. They aren’t evil at all. They are an inevitable consequence of doing something new (and, as such, should be seen as valuable; without them, we’d have no originality).

This is a common thought, but how he frames it as a “consequence of doing something new” was especially attractive to me.

“Get a bike that’s as low to the ground as you can find, put on elbow and knee pads so you’re not afraid of falling, and go,”

If you aren’t experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it.

Is the question being asked: Whose fault was this? If so, your culture is one that vilifies failure. Failure is difficult enough without it being compounded by the search for a scapegoat.

In a fear-based, failure-averse culture, people will consciously or unconsciously avoid risk. They will seek instead to repeat something safe that’s been good enough in the past. Their work will be derivative, not innovative. But if you can foster a positive understanding of failure, the opposite will happen.

A nice way to tweeze out the root causes that lead to a lack of innovation (on this case creativity.) A culture that grows into creating repeats and derivatives to avoid risk. Overtime, it can becomes so hidden within a culture that no one can see it. This concept comes up again when he describes the merger with Disney.

it’s easier to plan derivative work—

overplanners just take longer to be wrong (and, when things inevitably go awry, are more crushed by the feeling that they have failed).

I found a life lesson here. I am a major advocate when it comes to product development to recognize that almost no plans can be too long term since variables constantly change along the way; my playbook is often to iterate with a big picture vision. For some reason, in life outside of work, I tend to overplan a lot. And, get upset when all the work that went into planning goes awry. Until I read this passage I never viewed them side by side. For me it was eye opening.

It was as if we’d picked four talented musicians, left them to their own devices, and hoped like hell they’d figure out how to be the Beatles.

Part of our job is to protect the new from people who don’t understand that in order for greatness to emerge, there must be phases of not-so-greatness

I have found some companies want it all. They want new, greatness, speed, and growth all at once. In that way they use one rule for all situations and inevitably lose the ability to grow and be creative. In their mind they are iterating away from problems – in actuality they are killing the seeds of a truly iterable future.

Making the process better, easier, and cheaper is an important aspiration, something we continually work on—but it is not the goal. Making something great is the goal.

Love that. Definitely a first principles thought that I try to remind myself of all the time. Take a step back, what is the true root problem you are solving. Then regroup.

When efficiency or consistency of workflow are not balanced by other equally strong countervailing forces, the result is that new ideas—our ugly babies—aren’t afforded the attention and protection they need to shine and mature.

Each group, then, is trying to do the right thing, but they’re pulling in different directions. If any one of those groups “wins,” we lose.

Ed makes a great case for making sure you have an environment in which many cultures can exists, but they must have the same ideals and mindset. The importance of conflict in perspective is in how it can spawn new and creative ideas.

In an unhealthy culture, each group believes that if their objectives trump the goals of the other groups, the company will be better off. In a healthy culture, all constituencies recognize the importance of balancing competing desires—they want to be heard, but they don’t have to win.

The key is to view conflict as essential, because that’s how we know the best ideas will be tested and survive.

It is management’s job to figure out how to help others see conflict as healthy—as a route to balance, which benefits us all in the long run. I’m

if history is any guide, some are diligently trying to polish a brick.

It wasn’t just that the interns lightened the workload by taking on projects. Teaching them Pixar’s ways made our people examine how they did things, which led to improvements for all.

The unpredictable is the ground on which creativity occurs.

Which meant that the people working on Up had to be able to roll with that evolution without panicking, shutting down, or growing discouraged. It helped that Pete understood what they were feeling.

“It wasn’t until I finished directing Monsters, Inc. that I realized failure is a healthy part of the process,” he told me. “Throughout the making of that film, I took it personally—I believed my mistakes were personal shortcomings, and if I were only a better director I wouldn’t make them.” To this day, he says, “I tend to flood and freeze up if I’m feeling overwhelmed. When this happens, it’s usually because I feel like the world is crashing down and all is lost. One trick I’ve learned is to force myself to make a list of what’s actually wrong.

It also helped that Pete never lost sight of his mission on Up, which was to drill down to the emotional core of his characters and then build the story around that.

“I feel like the only reason we’re able to find some of these unique ideas, characters, and story twists is through discovery. And, by definition, ‘discovery’ means you don’t know the answer when you start.

For many people, changing course is also a sign of weakness, tantamount to admitting that you don’t know what you are doing. This strikes me as particularly bizarre—personally, I think the person who can’t change his or her mind is dangerous. Steve Jobs was known for changing his mind instantly in the light of new facts, and I don’t know anyone who thought he was weak.

This was an interesting bit of insight. I have personally seen people change their mind at work and to many (often including myself) it called in to question our ability to trust their judgement. With this section I took a different tune. If you can’t change your mind you can’t make those important mistakes and learnings. With those I was particularly close to we changed one another’s minds all the time – and I actually enjoyed the feelings and perspectives it gave me. So, how do you create a trusting culture where anyone can make claims and change their mind without consequence? Something to think about.

“Better the devil you know than the devil you don’t.” For many, these are words to live by.

To be clear, I am not endorsing change for change’s sake. There are often good reasons to hang on to things that work. The wrong kind of change can endanger our projects, which is why those who oppose it are in earnest when they say that they just want to protect the companies in which they work.

When companies are successful, it is natural to assume that this is a result of leaders making shrewd decisions. Those leaders go forward believing that they have figured out the key to building a thriving company. In fact, randomness and luck played a key role in that success.

After the loss of the film, our list of priorities, in order, were: (1) Restore the film; (2) Fix our …. Notably, one item was not on our list: Find the person responsible who typed the wrong command and punish him or her. Some people may question that decision, reasoning that as valuable as creating a trusting environment can be, responsibility without accountability can undermine an expectation of excellence. I’m all for accountability. But in this case, my reasoning went like this: Our people have good intentions. To think you can control or prevent random problems by making an example of someone is naïve and wrongheaded. Moreover, if you say it is important to let the people you work with solve their own problems, then you must behave like you mean it. Drill down, certainly, to make sure everyone understands how important it is that we strive to avoid such problems in the future. But always—always—walk your talk.

If you don’t try to uncover what is unseen and understand its nature, you will be ill prepared to lead.

. If we start with the attitude that different viewpoints are additive rather than competitive, we become more effective because our ideas or decisions are honed and tempered by that discourse

Mark Twain once said, “lest we be like the cat that sits down on a hot stove-lid. She will never sit down on a hot stove-lid again—and that is well; but also she will never sit down on a cold one anymore.” The cat’s hindsight, in other words, distorts her view. The past should be our teacher, not our master.

I especially like the summary, “The past should be our teacher, not our master.” It eloquently puts the conflict between when we change from our past and when we don’t. There isn’t one answer, and that summary says it all.

An adage worth repeating is also halfway to being irrelevant.

Ed often dives into how much he is afraid of creating “rules of thumb.” He is afraid that with every repetition the meaning and reasoning is slightly lost and eventually it gets misused or becomes a crutch. He touches on a huge philosophical perspective here that I find relates to life as a whole. The fear of dogma. This reminds me of my  a but of my favorite philosopher Nietzsche  that speak of the same avoidances.

Do not fall for the illusion that by preventing errors, you won’t have errors to fix. The truth is, the cost of preventing errors is often far greater than the cost of fixing them.

Similarly, it is not the manager’s job to prevent risks. It is the manager’s job to make it safe to take them.

Trust doesn’t mean that you trust that someone won’t screw up—it means you trust them even when they do screw up.

I like the way he frames it. In essence you trust that they likely screwed up for understandable reasons. Or, in other words, they would not have screwed up had it not be for a good reason.

Protect the future, not the past.

Balance is more important than stability.

Stability is an illusion after all 😉

So Good They Can’t Ignore You by Cal Newport

51IjORMFLkLSo Good They Can’t Ignore You is a story of a man’s search for the truth behind our quest to find passion in one’s work. He uses his interviews, with those that have claimed to have found passion in what they do, to derive a thesis that he believes is THE way to find a positive work environment.

Two key take aways I had from this books are the importance of:

  1. Deliberate practice
  2. Small projects

The two make up critical pieces needed for the “10,000” hours of expertise Malcolm Gladwell made famous.  Deliberate practice specifically looks at the importance of getting a steady stream of critique for your craft while you practive. “Small projects” look at the importance of dipping your toe into side projects that help you explore your craft, while building new skills. As a tinkerer I relate to those two points immensely, though I can improve on my search for harsh outside critique. For that I often think I am my own worst enemy, but that’s just a copout.

As a book I found the writing to be a bit redundant. Not a bad book per se, and the stories and perspective on what could be a common myth to “follow your passion” are interesting, but he could have done it with a book half its size – or just a long blog post. Unfortunately, because of the way it is written, you have to work through the repetitiveness to get to the good parts. Is it a must read? In a way, yes – it is a nice supplemental to books like Outliers by Malcolm Gladwell. But, I think the cliff notes may do just as well.

His conclusion to find work you love rests of the following rules:

  1. Rule #1: Don’t Follow Your Passion.

  2. Rule #2: Be So Good They Can’t Ignore You.

  3. Rule #3: Turn Down a Promotion.

  4. Rule #4: Think Small, Act Big.

Related Books or Similar Themes:

  • Outliers

Pictures that are literally worth over a million words

Check out this cool little tool: Google N-Grams

It shows a graphical representation of the frequency words used in books over a rangeof years. It is based on on all the books google has scanned into their database to date.

This TED talk is what turned me on to the project.

The project, the tool and the lecture are all quite entertaining.
Here are some graphs I created playing with the tool. Graphic data, especially that which is based on sentiment represented by our societies authors,  gives us amazing clues into how perception and reality intersect.