Breakthroughs, Skills, and Adaptations

Two of my favorite writers are Tyler Cowen and Cal Newport.

Tyler Cowen is one of the most influential bloggers on earth. In addition to being a Harvard-educated economist, he’s created a multi-media intellectual empire for himself at George Mason University, with a podcast, blog, lecture series, online university, columns at Bloomberg, and tentacles all over print and audio media. As an example of the scope of his influence, reading Cowen’s blog is the first part of Malcolm Gladwell’s morning routine.

Cal Newport is one of the youngest tenured professors at Georgetown University, where he teaches computer science and is widely published on topics that are far beyond the scope of my intellect. But that’s not how I know about him. I know him from two of his books: So Good They Can’t Ignore You and Deep Work, both of which I consider among the most important books on how to approach work that I’ve ever read. Whenever I meet anyone who seems to be in a professional funk, if I suspect they might be open to suggestion, I do everything I can to steer them to Cal Newport’s books. Reading his first book was essential to helping me choose a path for my business, and reading the second has been equally helpful me to get it where I want it to be.

Tyler Cowen is an information omnivore (he wrote a book about just that topic, actually, called Age of the Infovore), consuming insane amounts of information from diverse print and online sources. He often cites as one of the keys to his success the fact that he is incredibly responsive to email. According to Age of the Infovore, he checks his email every five minutes. And despite having a massive online following, he answers every single email he gets.

Cal Newport’s approach is about as different from Cowen’s as you could get. He might be described as a borderline Luddite who teaches computer science. More specifically, he thinks that social media, email, and instant messaging apps are intellectual scourges to be avoided at all costs. According to Newport, to create work that has real value, you need to concentrate for long periods of time. Every time we check Facebook or email, it completely destroys our concentration, causing us to shift our focus in a way that is impossible or nearly impossible to retrieve. Newport thinks the best way to succeed is to purge our lives of the constant hum of pings, notifications, and feeds trying to steal our precious attention resources. To succeed in a modern economy where attention is a scarce resource, we must create and cultivate an environment every day where true, deep work is possible without interruption.

Both Cowen and Newport are writers and intellectuals at the absolute pinnacles of their fields. But their approaches seem diametrically opposed to each other. So who is right? Which approach is better—deep work or constant, unrelenting media consumption?


I’m reading a book right now called What Works for Whom? It’s by a couple of English academics that specialize in psychotherapy research. The book digs into which types of psychological and psychiatric interventions work for which types of psychological problems. Here’s an excerpt:

Summarizing quantitative review of outcomes for MDD [Major Depressive Disorder], it seems clear that psychological therapy has benefit over no therapy, though when active therapies are contrasted, differences between them are less clear. Although there are indications that CBT [Cognitive Behavioral Therapy] is superior to less structured forms of psychotherapeutic intervention, it is worth noting that this conclusion appears less robust when the contrast treatment is credible and theory-grounded.

The overarching lesson I’ve taken from the book is that the aggregated data show that techniques that work for one type of problem do not necessarily work for others. Not exactly a Eureka! insight, but worth noting.

CBT and inter-personal therapy work well for depression but have not shown to be effective as a treatment for substance abuse. What works for anxiety is not an effective treatment for anorexia. And so on.


Have you ever finished a book or a TED talk and thought to yourself: “This is it! This is the key to what I’ve been looking for! If I just do X or don’t do Y, all of my problems will go away!” And then after a few hours or days, the magic solution fades from memory and life goes on as normal?


There’s no shortage of people out there who are in the business of selling us on breakthroughs.

A breakthrough is an event or realization that forever changes your life. Before this moment, you were one, lesser version of yourself. And after this moment, you’re a better, improved version of yourself.

If a weekend or a conference or a person were truly capable of making you a better person, it’d be hard to quantify just how much money that would be worth. But if they were real, the sellers of breakthroughs could probably just name their price. And even if it might be real, plenty of people would be willing to take a gamble and spend a small fortune on the off chance that it might do the trick.


Last year, I found this blog on fake insights by David Chapman. It’s wonderful. For me, it was a breakthrough on why most breakthroughs aren’t really breakthroughs.

Most of the time, according to Chapman, when we are sold on the idea of having an insight it’s because we’ve been tricked into finding an easy solution to what seemed like an artificially hard problem. By solving an easy problem masquerading as a hard problem, we are tricked into believing that we have somehow achieved mastery with relatively little effort. Perhaps all it took was a slight tweak in direction or mindset.

Ultimately, most breakthroughs are an artificial sleight of hand. The ability to solve one problem doesn’t necessarily mean that you have the power to solve another, unrelated problem. There is no magic key that lets you open all doors.


I’ve spent most of my life searching for simple, overarching rules that might help me live a better life. An intellectual golden ticket, of sorts.

And the more I read, the more convinced I am that there are no one-sized-fits-all formulas for how to live your life—no perfect plans for how to shape your schedule, your work-life routine, or pretty much anything else. No life hack works for everyone equally well. For each of us to maximize our talents, we must maximize self-knowledge by paying attention to our own internal signals, while incorporating lessons from those around us to the extent they might be helpful. And even then, we still have to adapt to every new wrinkle that life throws at us. And this will never end.


If you look up directions on Google Maps, there are usually three or four different options for how to get to your destination. Google will point you to the fastest way and then give you options for alternative routes. Perhaps you want to pick a more scenic option or avoid the highway. But if you go pretty much anywhere else other than those three or four routes, you’re going to end up going the wrong way. There is more than one way to get where you want to go, but there are infinitely more routes that will take you the wrong way.


I think life is like this, except to date there is no Google Maps service that is able to provide objective directions for how to get where you’re going—and where not to go.

There are lots of books and videos and Ted talks and inspirational seminars where people sell you on the idea that they can tell you how to live your life.

But as is obvious when you read books like What Works for Whom? neurodiversity is a real thing. There are plenty of 500-page academic treatises that will send your mind spinning with details of how effective strategies in one arena will be totally unsuccessful in another. Effective strategies for beating markets won’t help you in your family life. Warren Buffet’s wife left him to be with her tennis coach.

So it goes.


A few years ago I ran a couple of 100-mile races. I’ve heard some other people who have run 100-mile races say that after they have run a 100-mile race, it makes everything else they do in life much easier. As in, after running 100 miles, they know they can accomplish anything.

I’m skeptical of this. After I ran 100 miles, I just knew that I could run 100 miles. I didn’t find it easier to find meaning and purpose in my work. I didn’t find that my relationship struggles had changed. The problems I had in life before I had run 100 miles were more or less the same problems I had after I had run 100 miles.


A while back I wrote this piece called “Metarules for Games,” wherein I tried to come up with a set of overarching practices for how to approach new games. I re-read it recently, and I think it’s interesting and useful for people who like to play games, at least up to a point. It’s an exercise in how to think about games generally, but if you read it, at best, it might only provide a marginal advantage in games over someone who had not read it.

Reading “Metarules for Games,” won’t make you a chess master. To do that, you would need a base level of intelligence, plus many thousands of hours of practice and intense study. Being a chess master isn’t about breakthroughs. It’s about developing skills over years of work and then making successful adaptations during individual games. In the same vein, reading “Metarules for runners” won’t make you a 4-minute miler. Reading “Metarules for investors” won’t make you a billionaire (or a millionaire or even a thousand-aire). That’s just not how it works.


There are popular writers—Tim Ferriss in particular comes to mind—who specialize in studying and decoding habits of success. The idea is that if we learn certain overarching rules, certain patterns for how to organize our lives, that we might find a shortcut in a path to success and high status.

This sounds to me like the business of selling breakthroughs.

This type of study breaks down when we look at people like Tyler Cowen and Cal Newport, whom I mentioned at the beginning of the post. The habits that caused Cowen’s success are the habits Newport looks to avoid. If the one habit—the practice of constantly checking email, and its opposite pair, the practice of consciously avoiding email because it is a distraction from deep, focused work—both can serve as a path to success, then perhaps we can deduce that there’s no magic breakthrough to be made just by picking one habit or its opposite. Perhaps there is relatively little utility in obsessing over the anecdotal meta-habits of intellectual titans.

Tyler Cowen is highly skilled at processing massive amounts of information. Cal Newport is highly skilled at focusing on complicated tasks that most people—even very intelligent people—could not. Both have adapted to modern circumstances to find success. Cowen has succeeded by navigating the waters of information overflow better than anyone else, and Newport by avoiding the currents and staying on shore. But, despite opposite approaches, both have found a way to make it work.


I think, in retrospect, I’ve spent far too much of my life searching for breakthroughs. It’s tempting to look for one pattern or a set of patterns that will light the way for all times and places. But that’s probably not a thing. As I hit the juicy part of middle age, I think when it comes to breakthroughs,  they are more about flash than true light.

What is far more useful is the simple cultivation of skills. Work skills, physical skills, interpersonal skills, relationship skills—super-nichey skills in your chosen field that most people can’t even pronounce but you know better than anyone else on earth. The more skills you have, the more you can help people get things done. In short, if you want to be valued, be good at a lot of things that people find valuable.

Then, it’s about adapting those skills to different environments. The world today is not the same as it was five years ago and will not be the same as it will be in five years. You might be in a wheelchair or get cancer or win the lottery, or most likely, none of the above. So each of us must constantly adapt whatever skills we possess to new environments.

Learn and cultivate skills. Adapt them to whatever new environment you might find yourself in.

Rinse, repeat. How’s that for a breakthrough?

[1] Tim Ferriss’s book is called, “Tools of Titans,” which is a way better name than “Metarules for Success.” That’s why he’s Tim Ferriss.