Thoughts on Planning (a.k.a. How to Avoid Facebook)

One of the best habits I’ve picked up recently has been to (before turning in for the evening) schedule and plan out what I’ll be doing the following day. I take fifteen or twenty minutes at night just prior to hitting the sack to review my master to-do list and block out recurring activities like weight training, writing, eating, etc., adding in well-timed boluses of administrative or one-off work as necessary.

I make sure to batch these tasks intelligently. I never sandwich administrative stuff between creative work. This approach keeps my mind nimble and uncluttered. The human brain is notoriously bad at parallel processing, so the less noise I have coming in from adjacent tasks the better.

I notice a significant decrease in productivity when I don’t plan.

There is an art and a science to planning. It’s not so important that you actually replicate the schedule you plan out, but it is important that you try your best to do so. When you’re using your idealized day as a reference point, it’s a lot harder to justify squandering time on social media sites.

What I’m getting at is that you shouldn’t feel guilty if the day as you envisioned it doesn’t go exactly as you hoped. This is to be expected and becoming an automaton is not the point of the exercise. The simple effort of trying to follow the schedule as best as possible puts you one hundred steps ahead of where you would have been had you left the day to chance.

I like a simple pad of paper and pen for mapping my schedule. I toyed with MS Outlook and Google Calendar but found them unnecessarily clunky. With more scientific evidence coming out that writing by hand stores things in memory better than typing, I stick to ink.

Happy planning!

Winning the War with Ourselves

Every day we’re at war with ourselves. Stoicism, the Hellenistic philosophy, is my most useful weapon in combatting the enemy of Resistance, the negative force that impedes our climb toward greatness.

With Jim Collins’s book Built to Last being a recent nightstand fixture of mine, while reading it, I recalled the story of Vice Admiral Jim Stockdale as told by Collins in another of his bestsellers, Good to Great. Stockdale flew the first sorties into North Vietnam and was shot down early in the conflict. He was imprisoned in the “Hanoi Hilton” for eight years.

I’ve linked to a video of bestselling author Steven Pressfield in the first paragraph. In the video, Pressfield discusses Resistance and how to overcome it. While writing this post, I also learned that he is a reader and devotee of Collins’s work. He mentions Good to Great as the second favorite book of (after Marcus Aurelius’ Meditations) Marine general Jim “Mad Dog” Mattis, who was appointed head of United States Central Command in August 2010.

While writing Good to Great, Collins had the opportunity to meet Stockdale. From their conversation, Collins took away a very important lesson he later included in the book. Stockdale related to Collins the following about his time in prison in Vietnam:

I never lost faith in the end of the story. I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.

Stockdale, however, made a point of distinguishing faith from optimism. As Collins explains:

I didn’t say anything for many minutes, and we continued the slow walk toward the faculty club, Stockdale limping and arc-swinging his stiff leg that had never fully recovered from repeated torture. Finally, after about a hundred meters of silence, I asked, “Who didn’t make it out?”

“Oh, that’s easy,” he said. “The optimists.”

“The optimists? I don’t understand,” I said, now completely confused, given what he’d said a hundred meters earlier.

“The optimists. Oh, they were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.”

Another long pause, and more walking. Then he turned to me and said, “This is a very important lesson. You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

What separates people, Stockdale says, is not the presence or absence of difficulty, but how individuals deal with the inevitable difficulties of life.

The Stockdale Paradox effortlessly captures this. It is a signature of greatness in people and organizations, corporations, even nations (think Great Britain during WWII, under the leadership of Winston Churchill). Adversity strengthens the soul and hardens the body. It strips away the noise and clutter of life and allows the mind to focus on what will have the most impact.

It’s not enough to believe you will simply survive. You must believe in your ability to prevail.

Collins never explicitly raises the issue of philosophy or Stoicism, but there it is, on paper, in one of the most articulate, actionable, understandable, applicable iterations I’ve ever seen.

Meditations by Marcus Aurelius is one of my favorite Stoic texts. In confronting the more mundane of life’s difficulties, I often refer back to the following quotation:

When you wake up in the morning, tell yourself: The people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous, and surly. They are like this because they can’t tell good from evil. But I have seen the beauty of good, and the ugliness of evil, and have recognized that the wrongdoer has a nature related to my own—not of the same blood or birth, but the same mind, and possessing a share of the divine. And so none of them can hurt me. No one can implicate me in ugliness. Nor can I feel angry at my relative, or hate him. We were born to work together like feet, hands, and eyes, like the two rows of teeth, upper and lower. To obstruct each other is unnatural. To feel anger at someone, to turn your back on him: these are obstructions.

The depth of Stoic thought fills books and spans generations, and has influenced modern day leaders like President Bill Clinton, who named it his favorite book. I hope you get the chance to explore this wonderful school of philosophy and learn from it. I certainly have.

Musings on Entrepreneurship

The internet is an agent of change, the catalyst of the 24/7 news cycle and the unprecedented capriciousness of global financial markets. Social media eliminated barriers to market entry, reduced start-up costs and gave entrepreneurs comprehensive access to their buyers. In whole, the web has provided a low-cost, low-capital platform for enterprising individuals to build the business of their dreams.

Folks who, twenty years ago, would have never thought of themselves as business people now, by virtue of these changes, must do just that. Writers can no longer just be writers. Artists can no longer just be artists. The countering forces of technology have subsumed the once critical role of PR in the media. The publishing industry, too, is struggling to maintain its purpose in an unfamiliar environment. Those not on the technology bus ignore these trends at their own peril.

It may be that we’ve reached a point where the distinction of being “online” has lost its utility. As Wall Street Journal technology columnist Walter Mossberg once told consulting guru Alan Weiss, “Just as you don’t announce you’re plugging into the electric grid when you use a hair dryer or television, we’re also going to stop saying we’re ‘going online’ because we’ll be online at all times.”

To sustain an existence in this new economy, a paradigm shift is in order. For many, the paint-by-numbers methodology of working one’s way up the corporate hierarchy is no longer a viable career path. Today, there is opportunity at every turn. The cost to break into the consciousness of potential customers has reached zero. You and your brand can be anywhere. The only cost is time.

This creative destruction has merited a shift toward irregularly distributed consumer markets, where if an enterprise can sustain “1,000 True Fans” and secure a “Long Tail” niche, the business, if managed properly, can prove remunerative.

Yet despite all this, the principles of good business remain unchanged. The guiding norms and rules of our economy have stayed largely the same. Decades of focused learning and research on best practices are, sadly, getting thrown out the window, replaced with flavor of the day thinking. Time will reward those who have learned from the ones who came before them. Master the fundamental principles of business and you will thrive.

Every industry will always be faced with new competitors, new technologies and new challenges. But it is those businesses that can maintain their core while adapting to a changing environment that will succeed. By planning ahead, by setting a strategy and working backward from that perceived future as to how the company will look, act, and feel, you can begin taking the actions today that will predispose you to success tomorrow.

Trial and Error

Economist Tim Harford has catapulted to the top of my “must-read” list. His new book, Adapt: Why Success Always Starts with Failure, espouses the virtues of the trial and error process in our increasingly complex world. Despite playing an indescribably critical role in our daily lives, we often fail to perceive the complex systems that surround us. In this video, Tim expounds on a task that, at face value, seems reasonably doable—the creation of a toaster from scratch—to illustrate how decentralized and impenetrable our market economies can be.

This got me thinking about all of the systems we help construct, become a part of, or benefit from. Even the writing of this blog post brings together innumerable systems of wide-ranging complexity, from the nascent thought processes that inspire these words to their delivery and publication across the internet. It behooves us to better understand the systems that surround us, so we may help improve them in an effort to make our world a better place.

Mental Models and Multidisciplinary Growth

One of the things I struggled with while in graduate school was the idea that academic disciplines were mutually exclusively, wholly incompatible frameworks for understanding the world. This concerned me deeply. Some of the world’s greatest discoveries have come about due to people taking things that, at first glance, have nothing in common and smashing them together. For example, chocolate and peanut butter. Or heck, peanut butter and jelly. That’s pure comedy right there, until you taste the result.

In today’s world, things are changing with such rapidity and force that the jobs of today likely won’t exist in ten years. If you limit your study to a single discipline you risk siloing your knowledge and becoming an ossified, outdated unit of human capital. I understand the need for disciplines within academia. It helps define intellectual borders, it keeps everyone on the “same page” so to speak, and gives a sense of orderliness and predictability to academic debate. The problem is, outside the exclusive realm of theory there’s this thing called the real world, and it tends to intervene in a damningly unforgiving way.

I think a better approach is something along the lines of what Charlie Munger of Berkshire Hathaway suggests. There’s an element of the Pareto principle in his philosophy. He advocates the broad acquisition of knowledge across numerous domains that can then be applied to any number of situations. This is similar to what Bruce Lee espoused while developing his self-defense system of Jeet Kune Do, the whole “absorb what is useful and discard the rest” approach to education. In Munger’s words:

[T]he first rule is that you can’t really know anything if you just remember isolated facts and try and bang ‘em back. If the facts don’t hang together on a latticework of theory, you don’t have them in a usable form.

You’ve got to have models in your head. And you’ve got to array your experience—both vicarious and direct—on this latticework of models. You may have noticed students who just try to remember and pound back what is remembered. Well, they fail in school and in life. You’ve got to hang experience on a latticework of models in your head.

What are the models? Well, the first rule is that you’ve got to have multiple models—because if you just have one or two that you’re using, the nature of human psychology is such that you’ll torture reality so that it fits your models, or at least you’ll think it does. You become the equivalent of a chiropractor who, of course, is the great boob in medicine.

It’s like the old saying, “To the man with only a hammer, every problem looks like a nail.” And of course, that’s the way the chiropractor goes about practicing medicine. But that’s a perfectly disastrous way to think and a perfectly disastrous way to operate in the world. So you’ve got to have multiple models.

And the models have to come from multiple disciplines—because all the wisdom of the world is not to be found in one little academic department. That’s why poetry professors, by and large, are so unwise in a worldly sense. They don’t have enough models in their heads. So you’ve got to have models across a fair array of disciplines.

You may say, “My God, this is already getting way too tough.” But, fortunately, it isn’t that tough—because 80 or 90 important models will carry about 90% of the freight in making you a worldly-wise person. And, of those, only a mere handful really carry very heavy freight.

I hadn’t been able to articulate specifically why academia bothered me until I came across Munger’s work. It seemed ridiculous to me how disciplines would ignore each other and posit frameworks that tried to answer everything when, in reality, they could only answer some things. Going back to finance and investing, anyone who believes you can predict human behavior with physics-like precision is deluding themselves. Compartmentalization doesn’t work if your system of understanding is being tested outside the realm of theory by the selection tests of the real world. Learning should be an exercise in understanding, not an exercise in hubris or ego.

Asking The Right Questions

Being successful often means asking the right questions. It doesn’t mean having the answers or even having answers at all.

Asking the right questions helps refine hypotheses, leads to new avenues of inquiry, and expands perspective. People have a tendency to get too caught up in having answers, and of course they believe their answers are correct. Human nature drives us to confirm our beliefs and makes us unconsciously avoid information that contradicts those beliefs. In my experience, it’s when I say, “I don’t know,” that I seem to learn the most.

If we all spent a greater proportion of our time studying the problem, conceptualizing the problem, investigating and questioning and manipulating the problem, then we’d be getting somewhere. As we acquire more answers, we stuff more knowledge into faulty, compartmentalized notions of understanding and we lead ourselves astray. If one takes a look at the financial crisis that began in 2008 and sent markets worldwide into varying states of recession, it is easy to see how, after the fact, systemic risk underpinned the unraveling of global markets and resulted in the expeditious retraction of credit.

Had risk analysts and economists and investment bankers and Wall Street quants been asking the right questions about risk, specifically system risk, the efficacy of financial models to disperse and innervate a society-wide confirmation bias on the trajectory of markets could have been attenuated. But even if the magnitude of the issue was known, with everyone making so much money I’m not sure if it would have made much of a difference.


I’ve of late been putting an inordinate amount of time into philosophical texts. My current literary victim is Nassim Nicholas Taleb and his book, The Black SwanThe Wall Street Journal noted that “he writes in a style that owes as much to Stephen Colbert as it does to Michel de Montaigne.” I would have to agree.

Taleb’s black swan is in academia also referred to as a fat tail, and is the outlier that reintroduces luck and serendipity into the social sciences. Taleb seeks to explain the high impact, “impossible” events that defy our expectations of the material world and so take on the garb of a Power Law distribution. He as well examines humanity’s psychological bias and blindness toward such rare events, and in doing so seeks to answer why we’re so susceptible and blind to them.

Broadly the cognitive bias and, more specifically, the confirmation bias prove problematic as we try to understand the world we live in. By means of naïve empiricism we bipedal thinking things have a tendency to look for instances that confirm the narratives and stories and Platonic understandings of our world. The problem of course is that if you look for confirmation you can find it almost anywhere. Taleb argues that instead of deluding ourselves into thinking we’ve just aroused evidence for our correctness, we should rather scrape and claw and unearth those instances where our method or theory or course of action fails. It’s at that juncture that we actually learn something.

I’m going to try something different this time around and throw the question out to you, my readers. When have you found yourself susceptible to confirmation bias? Or, when you have taken the empiricist’s path and avoided the confirmation bias, and sought to falsify your theory rather than confirm it?

Air Combat and Strategy

I just finished reading Boyd: The Fighter Pilot Who Changed the Art of War, a biography by Robert Coram. It’s a fantastic book, appealing in depth, in complexity, and in its treatment of Colonel John Boyd, one of the finest unsung heroes of contemporary military science.

In the truest sense of the word, John Boyd was a genius. Taking just a brief tour of his accomplishments, we discover he wrote the manual on air-to-air combat. Before Boyd, dog-fighting was seen as some interpretative art–like ice dancing–and beyond the realm of science.

Boyd served as an instructor at the Air Force’s Fighter Weapons School (the nomenclature and design were later copied by the Navy, hence “Top Gun,” however Boyd’s Air Force institution was the original and the real deal). At age 33, he wrote a booklet on air superiority titled “Aerial  Attack Study.” It was so revolutionary that, since the time of its release, no further advances have been made in aerial combat strategy. Boyd’s booklet was the first and last word on tactical piloting and weapons use.

Boyd later developed the Energy-Maneuverability Theory. The E-M Theory gave fighter pilots for the first time a rubric to determine the energy potential of any given maneuver at any altitude for any aircraft, whether it be their own or their enemies. Before the acceptance of Boyd’s E-M Theory, fighter jets were designed to fly fast in a straight line or fly high. The F-15 was the first to be developed with maneuverability in mind. Boyd played a critical role in its construction and design.

Later Boyd and the “Fighter Mafia,” as they were dubbed, became the most influential ad hoc group the Pentagon had ever known, and in time fathered the F-16 and the F-18. Boyd’s later works like Patterns of Conflict and The Observation-Orientation-Decision-Action Loop helped form the bedrock of the Defense Reform Movement and led to much of the strategy behind the first Gulf War.

We on occasion run into similar quandaries in our daily lives as a fighter pilot does in the sky. At times the stakes can be just as serious. So what of it? How could a fighter pilot trying to jockey a $20 million aircraft apply to such mundane matters as politics?

First, it’s important to recognize that we are all complicit in politics, whether it be the public governance type or just what happens in our family lives. Politics has come to be used as a pejorative and that proves unfortunate. If you head to Definr, my favorite online dictionary,  and search for politics, the first definition you’ll come up against is this:

politics (

n 1: social relations involving authority or power [syn: {political

Read that one carefully. First, “social relations.” By design, humans are social creatures. There are macro-sociological arguments abound that titrate from our inherently social nature our improved chances for survival and hence the broader evolutionary process. The final segment of the definition, which reads “involving authority or power,” is the crux of this deceptively simple definition.

All relations involve authority or power whether we like it our not. Relations with girlfriends, boyfriends or spouses, children, parents, pets (okay, maybe the goldfish gets a pass), trolls on the internet, or the barista at Starbucks (I need my latte now!). Politics is power.

When John Boyd developed the OODA Loop, he found a means to power for the fighter pilot. Later the OODA Loop would find its way into business and government. In aerial combat, a pilot cycles through the steps of Observation, Orientation, Decision, and Action ad infinum. He scans the airspace for enemies and, upon recognizing a threat, orients the enemy into the broader context of the air battle. Based on this synthesis, the pilot decides and acts in accordance with the provided information.

The idea  is to see what your enemy sees and get inside his OODA Loop. To be able to feint and counter-attack, to anticipate, this delineates an effective usage of the OODA Loop.

For example, let’s presume Pilot A is tailing Pilot B. Pilot B, in an attempt to lose Pilot A from his six, applies hard rudder, angles to starboard and pulls high Gs in a sharp turn that orients him perpendicular to the earth. Pilot A is in a slower aircraft and won’t be able to keep up. But Pilot A, tactically, is inside Pilot B’s OODA Loop, and through a series of quick observations and decisions, he chooses to pull hard to port to intercept Pilot B’s flight line and go for the kill.

The OODA Loop has since been expanded beyond what Boyd originally intended, and has made headway into business and manufacturing circles, amongst other trades. In power conflict, the mind is critical. More specifically, the ability the mind has to adapt and maneuver in congruency with whatever structure, ambiguity, or chaos may surround it. Boyd refers to maneuvers that disorient an opponent–those acts that innervate an opponent’s OODA Loop–as fast transients. The quicker a pilot can cycle through these loops in combat, or the faster a business can recognize and act to solve problems, the more successful each will prove to be.

In life we are forever confronted with challenges, with conflict, with social relations that demand we act. The game grows more difficult as the number of variables increase. By observing and orienting ourselves to the actions of others, we can come to a better understanding of the realities that surround us, and loose ourselves from the placid and comfortable narratives that conceal truth.

And here, it’s important to note that it is action that is what matters. Not words, but actions and the results of those actions. It’s important to make this distinction and not lull oneself into complacency through a susceptibility to outward poses. When confronted with conflict, learn to take action, and decisive action at that. As Boyd said, don’t worry about your own flanks. Instead, make your opponents worry about theirs.