I’ve found the same thing happens the more you learn about a subject. As you burrow in, the surface layers of common sense peel away until you’re left with something stranger.

Strangeness is a good thing. It means you’ve ventured into new territory, where opportunities can be found and falsehoods shed. I’d say my goal in learning anything is to try to find this zone of strangeness.

The Danger of “Obvious” Truths

If something seems “obvious” to you, it generally means one of two things: either you understand it so well that it has become intuitively grasped, or you don’t understand it at all. My experience tells me most people suffer from the latter condition.

Richard Feynman creates a window into the strangeness of reality in his explanation of magnets. To most people, the effect of a magnet is mysterious—how does it repel things without contacting them? However, as Feynman explains, this reasoning is backwards, contact forces are based on these “mysterious” action-at-a-distance principles.

Or consider something that couldn’t be more “obvious”: consciousness. I think, therefore I am. Except, as in the case of split-brain patients, I can sever the wires connecting your left and right hemispheres and turn you into two separate people. If you have an indivisible loci of consciousness, how can it be split with a scalpel?

What about the more practical context of your career? I have had several friends who are able to charge double their employment salaries, simply by changing to an independent consultant. Their work is the same, but yet everyone seems happy to pay them twice as much.

Human beings fear strangeness, so when we see things which don’t fit our “obvious” maps of reality, we have knee-jerk reactions. We try to dismiss them, as Einstein famously did in his initial rejection of quantum mechanics. Or we shoot the messengers of strangeness, claiming that these consultants are rip-off artists, or that employees are being exploited.

Rejecting evidence that the world is different from what it seems isn’t new, and it isn’t restricted to fundamentalist theocrats. We all resist the strangeness, and it takes effort to push through that.

Down the Rabbit Hole

I think my obsession with learning stems from realizing how essentially strange most things are. No, most things are not “common sense”. What we even call “common sense” is often approximations which work in specific contexts but fail outside of the realm of past experience or the intuitions endowed in human nature.

In fact, much of what we call common sense is neither common, nor sensical. We use the hindsight bias to pretend facts which come to us were apparent all along. As a result we rob ourselves of the strangeness that lies ahead.

The strangeness totally overwhelms the obvious, the unknown vastly overshadowing the known. This isn’t a defense of mysticism or a suggestion we should throw up our hands and live in ignorance. It’s the opposite—our individual ignorance actually makes the marginal value of new knowledge so valuable. Each new insight has enormous potential, so we should be much more curious than we are.

A simple insight, such as that we may have less conscious control than we realize, can have profound consequences. It suggests that the way to make changes, like getting in shape or becoming productive, isn’t by trying to be superman, but by making miniscule shifts with overwhelming focus.

Defending Old Ideas from the Assault of the Strange

Smart people often fall into a trap. Their intelligence and quick wit makes them excellent at defending their ideas. As a result, they can easily trounce the straw-man and ad hominem arguments of their dullard opponents.

These victories accumulate, and the intelligent person’s lack of defeat becomes a sign of infallibility. This creates an impassable barrier between the smart person’s ideas and the encroaching strangeness of reality. Without regular exposure to the strangeness, that person may even forget it exists.

I’m not immune to this weakness either. The only thing you can do is strive to let the strangeness come in, especially at the oblique angles, where your intellectual immune system isn’t bracing for a full-scale assault.

Moralizing Away the Strangeness

The most insidious practice to avoid dealing with strangeness is to simply declare any ideas in the wild territory as being immoral to even consider. This allows us to avoid any potential strangeness, or worse, unsettling consequences.

I find it amusing that many people who laugh at those who dismiss scientific arguments without hearing them, often quickly dismiss economic arguments on the same grounds. When an argument about economics or evolution becomes taboo to even consider, truth becomes a casualty.

Perhaps there are some areas we’d prefer to live with comfortable delusions. But the cost of self-deception is high too, so moralistic over evidentiary arguments should be sparingly applied.

Feeling Strangeness

True mastery of an idea tends to come with noticing its strangeness. Like the word you utter endlessly to hear the peculiarity of its sound, ideas begin confusing, become intuitive and end strange. This isn’t the strange that comes from confusion or frustration, but from seeing the idea from so many perspectives that you notice its sound, not just its semantics.

Fake understanding doesn’t have strangeness. It’s the memorizing of formulas and the verbatim regurgitation of arguments. When you master the chain rule of calculus through rote, you don’t actually see what is happening deeply. I know I’m starting to learn something deeply when it stops being “obvious” and begins to seem strange.

Strangeness is good, and the only way to get there is to keep learning. To keep digging deeper, even if it sometimes means venturing into a place that looks very different from where you started.

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My response may seem rude or pessimistic, but it was the truth. I’ve known this friend for a long time—long enough that we can give each other blunt feedback without taking offense—and setting fitness goals only to make zero progress was so common it was practically a ritual for him.

Instead I gave him a better plan. Why not focus on trying to just exercise regularly for one month? After that, it will be easier to keep working out even if you can’t hit a specific milestone.

The problem with my friend is a general one. Self-help books and our overly self-esteem obsessed culture tells people that they can do anything. That everyone is the smartest, strongest and most beautiful person. The only problem is, we’re not.

You’re Lazier, Weaker and Dumber Than You Think

I believe, on the whole, confidence is a good thing. It may even be the case that even being irrationally overconfident is a good thing. Narcissistic people do better in job interviews, and many of the worlds most productive people had egos bordering on megalomania.

The reason confidence works is that it is usually in the abstract. Genuine confidence is hard to fake consistently, so being overconfident in the abstract leads people to believe it’s justified.

This advantage of confidence may explain why people are so overconfident. Despite the media cries about low self-esteem, most people tend to believe they’re above average in everything. In fact, there’s some evidence that the more realistic self-estimate is associated with depression. Evolution may have hardwired us for our own self-deception.

The weakness of confidence is when you’re forming concrete, short-term plans. These occur on such small timescales that you’re unlikely to reap any of the benefit of your inadvertent boasting, so being too ambitious can actually hurt you.

My friend’s fitness goal is a clear example. He, like most people, was overconfident about his ability to make behavior changes in a short time. By trying to accomplish much less in the short-term, his chances for lasting long-term change goes up dramatically.

You’re Not Really in Control

Think of any recent action you took: reading this article, taking a shower, eating breakfast. Now ask yourself, who decided to take that action?

Obviously you did. The entire principle of consciousness is that we’re agents, aware of and responsible for our own actions. Aside from rare cases of extreme intoxication or psychological disturbance, we generally suggest people are the causes of their behavior.

But this grip of control over our actions may be more illusory than we’d like to admit. Cognitive scientists are just beginning to discover that many of the reasons why we take particular actions are simply made up. The conscious mind may be less of a causal force and more of a storyteller, fabricating explanations for behavior which is dictated at an unconscious level.

An interesting experiment provides insight into this frightening reality. A split-brain patient is someone who, usually as a treatment for extreme epileptic seizures, has had their corpus callosum severed. Those are the interconnections between the right and left hemispheres of the brain.

In the experiment, the patient was shown two images, one to the left hemisphere and one to the right hemisphere of the brain (each eye is wired to separate hemispheres). In this case, a picture of a snowy driveway and a picture of a chicken.

The patient was then asked to pick an image corresponding to the scene. The left hand (connected to the right hemisphere) pointed to a shovel, matching the snowy driveway. When asked about this choice, the more verbal left hemisphere said that it was because the shovel could be used to clean out the chicken shed. The left brain had no access to the picture of the driveway, so when asked what caused the right brain’s response it simply made something up.

This experiment suggests many of our conscious decisions are actually stories created after the fact. We make a decision, and then our conscious mind weaves a story to explain it, even if the true motives are unknown.

How Recognizing My Feebleness Changed My Life

This may sound depressing, but it doesn’t have to be. Knowing that your conscious control is weak is actually tremendously helpful. It means that instead of constantly chastising yourself and making excuses when you fail, you can uncover and tweak the true generators of your behavior.

For me, the biggest change in my life happened when I stopped trying to accomplish everything at once. I realized that I’m actually incredibly lazy—most of what I do has to do with habits and trivial stimuli, rather than deep thoughts.

Instead of trying to change every behavior at once, I would pick something incredibly small and simple and focus on it for an entire month. Even that can be difficult, but it meant I could make a change almost habitual before I tried something else.

In my short-term to-do lists and projects I strive to be modest. My agenda is usually far less ambitious than my friends, even in cases where my track record is better than theirs.

What About Optimism and Ambition?

I believe optimism, hope, ambition and all that general self-help pabulum work best as far beliefs. That is, being overconfident works best when it is a generalized ideal you use to think about the long future, not when you’re planning your to-do list tomorrow.

The truth is, most people make two errors in their judgement. They are overly optimistic in the short-term, because inherent overconfidence and the illusion of control convince them they can achieve more than they can. But people are also too unimaginative about the future—we tend to imagine the future as mostly resembling the present.

I suggest two cures: first, acknowledge your short-term laziness more. If you know you’re lazy, you can work around it. Most people don’t because we like to think of ourselves as being industrious and in control, not easily manipulated automatons. Second, be more imaginative about the future, even small ripples can turn into big waves over time.

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I also try to avoid hyping entrepreneurship too much. It’s incredibly hard work to get established, there are no guarantees of success and you’ll face tons of discouragement. There are many less dramatic professions which nobody hypes, but many people would be happy in.

Those caveats aside, I can be honest: the decision to start my own business was easily the best decision I’ve made in my life. No other decision really even comes close.

I loved building it when it was just an idea, and I love running it now that it is my reality. I’d like to write more, but it would end up sounding like a Hollywood cliché, so I’ll leave it at that.

No, my experience isn’t universal. I was successful; many aren’t. It’s a virtue of the selection bias that I get to tell you I’m happy with my choice, but the disillusioned former entrepreneurs don’t have a soapbox to balance my rhetoric.

I can’t tell you to start a business, or even whether you should. But if you feel the uncontrollable urge to go out and create something in the world, you should at least be serious about that desire. That means being aggressive about learning as much as you can about what makes it possible for some people to succeed at it.

The $100 Startup

My friends Adam Baker and Karol Gajda have put together an amazing package of resources for entrepreneurs, in support of Chris Guillebeau’s new book, The $100 Startup. It’s been a frenzied discussion all over the blogosphere, so you’ve probably already read about it.

The book is included, and it takes an extremely pragmatic approach to running a business. Chris actually went out and selected over 2000 actual lifestyle entrepreneurs to interview about their success. It’s about actual people, not abstract theory.

I’m already biased on this issue, so I decided to affiliate with Chris, Adam and Karol to help promote the package here. If you buy the package through my link and email me the receipt, I’ll forward you a copy of my book—Think Outside the Cubicle, which is aimed at productivity for entrepreneurs.

The offer is time-limited since an unfortunate artifact of the book publishing process is that the lifetime sales of a book depend heavily on its initial promotion. If you want to get the offer you should take advantage of it now, since the discount is incredibly steep for only a short time window.

I can’t tell you what your experience will be. But as I look out from my window onto one of the most beautiful cities in the world, working only on projects of my own desire and having nearly complete freedom, I realize how different my life could have been if I hadn’t taken that chance.

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“I can live with doubt and uncertainty. I think it’s much more interesting than live with answers which might be wrong. I have approximate answers and different degrees of certainty about various things, but I’m not absolutely certain of anything.”

Thinking in uncertainties is unnatural. Like reading, arithmetic or operating computers, it is a learned skill, not something that comes imbued in our mental hardware. But uncertainties is all there ever is, so it is a useful skill, even if it doesn’t come installed at birth.

Most people intuitively understand that some things are uncertain. You can see the weather forecast predict a 75% chance of rain. Yet, if it doesn’t rain tomorrow, you’ll hear people say that the weather report was wrong.

The weather report wasn’t wrong, your belief was. By rounding up the probability of .75 to 1, you made the error by reasoning in certainties.

Uncertainty is the Only Correct Way to Think

Weather is a trivial example. You’ll see the same fallacious reasoning in the abundant comments on my article on atheism. I get many critical commenters saying that I’m being irrational for rejecting the idea of a god without proof.

The very nature of their comment betrays a more fundamental ignorance—those people can’t reason in uncertainties. I don’t reject anything, I simply declare that with the evidence available to me, the proposition is unlikely. I can’t put an explicit percentage like the weatherman, but I’m making the forecast that there probably isn’t a god.

What if new evidence comes to me in the future, suggesting higher intelligence? I would adjust my relative uncertainty to be more in favor of the possibility. That doesn’t make my original judgement unjustified, since I had always included the possibility of new evidence changing my original position.

Many people have a false notion of reasoning that suggests if something is uncertain, they are free to believe what they want. While you’re always free to believe anything, including falsehoods, that doesn’t mean they are justified. My claim is that uncertainties, which are weighted appropriately, are the only justifiable beliefs to have.

For many things in life, the uncertainty is so small we can ignore it. I don’t regularly consider the possibility that gravity will cease to function and I’ll float into space because the doubt is miniscule. But just because we can ignore uncertainty in practical contexts doesn’t mean we can omit it wholesale.

Texas Hold ‘Em Logic

Poker is a fantastic game to train you in this counter-intuitive way of thinking about uncertainty. Good players quickly learn that there is a difference between winning and making correct decisions. Many novice players bet incorrectly on hands will sometimes win, but that doesn’t make their decisions justified.

Being a good player means being able to reason in uncertainties. Good players also realize that this uncertainty doesn’t afford them the luxury of being able to decide to believe whatever they want to. Ultimately, a 50% chance of winning a particular hand just that—50%. Believing anything other than this uncertainty is wrong.

Realizing that uncertainty exists encourages players to think not just which decisions paid off, but which decisions were valid strategies from the available evidence. Few other activities will train you in the difference between a valid argument with a false conclusion and an invalid argument with a true conclusion than poker.

Degrees of Belief

I like the poker example because it shows why thinking in uncertainties is useful. If you can’t think in uncertainties, you’ll lose a lot of money playing poker. Similarly, failing to think in uncertainties means you’ll almost certainly make bad decisions in your life.

The challenge is that uncertainties are rarely calculable like they are in games of chance. This is why I think in terms of qualitative degrees of certainty, rather than trying to pin down beliefs to 1%, 50% or 99%.

For example, if I get gossip about a friend which has been buffered through many sources, I put hazy certainty on that knowledge. Is it 75%? 60%? 50/50? Who knows? But it’s mentally labelled with an ambiguous quality.

What if I read a single scientific study about a phenomenon in psychology? Again, the exact percentage of uncertainty is probably too difficult to calculate, but I can put it as being more reasonable than speculation, but less certain than a truth confirmed repeatedly.

I try to apply the same metrics of uncertainty to my own pet theories and ideas. Holistic learning is popular here and there have been scientific studies which suggest it may be right. But I’m not under the misconception that a reasonable hypothesis is equivalent to a theory which has been rigorously tested.

Knowing something to the confidence that you can safely ignore uncertainty is extremely difficult, perhaps impossible for many domains of knowledge. It’s the ability to make use of the abundant circumstantial evidence and reasonable hypotheses which allows us to function, but at the same time realize that they don’t amount to unquestionable proof.

What About Healthy Delusions?

Am I contradicting myself from last week, where I suggested that some delusions (believing things which aren’t justified) is useful? It’s a finer point, but because it might confuse, I’ll try to clarify.

Some beliefs are useful but unjustified. Overconfidence with women is a possible example. Even if I have no evidence to show I’m the most desirable candidate, consuming myself in an irrational belief of confidence may improve my success.

There’s two ways these instrumentally rational beliefs fit into the uncertainty scheme I’ve presented. First, if I “irrationally” believe I’m good with women, and that makes me good with women, then the belief was actually justified. Such self-fulfilling prophecies may be cases of apparent irrationality which aren’t.

Perhaps thinking I’m Casanova makes me better with women, but not to the degree I believe it. In this sense, the instrumentally rational belief is useful, but technically unjustified. This is an example of a healthy delusion where it might be beneficial to believe a lie. That doesn’t make the lie true, or that unjustified beliefs suddenly become justified, simply that some degree of self-delusion may be advantageous.

Uncertainties are the only valid way of reasoning, in that they maximize true beliefs. However, there may be exceptions where maximizing true beliefs conflicts with other goals.

The Inescapability of Doubt

Once you accept that certainty is just a useful simplification, and that uncertainties are the only correct way to reason about things, life becomes much easier. Doubts, fears and worries still exist, but they stop being unnatural entities that need to be avoided, but qualities of reality that should be embraced.

Instead of avoiding doubt, learn the skills to work within it. There are many good algorithms for making smart decisions, given uncertain situations. Familiarity defeats fear. If you get in the habits of reasoning with uncertainties, doubt becomes a tool, not just an anxiety.

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Depressive realism is a phenomenon where, in some cases, depressed patients can view the world more accurately than the mentally healthy. In one study, participants were asked to rate their degree of control over a light bulb. Non-depressed participants believed they could control the light, even though its sequence was pre-programmed. Depressed patients accurately reported their level of control.

In another paper, psychologists argue that overconfidence maximizes evolutionary success. Read that again: not just confidence, but overconfidence. Success is implicitly coupled with embracing a delusion that you’re better than you actually are.

Findings such as these suggest that many of the cognitive biases humans exhibit aren’t design flaws but purposeful features.

Do We Delude Ourselves to Manipulate Others?

Human beings are social creatures. In addition to serving our own needs, we need to be aware of the impression we make on others. If you’re at a dinner party and served a dish you dislike, most people wouldn’t complain about it to the host. Our immediate desire to not eat the dish is put into conflict with being polite.

Robin Hanson speculates that the brain evolved a capacity for managing these conflicting needs. Use “near” modes of thinking, which are detail-rich and pragmatic, when you’re executing personal goals, and use “far” modes of thinking, which are more abstract and idealistic, when social impression matters:

“And this seems to be just what the human mind does. The human mind seems to have different “near” and “far” mental systems, apparently implemented in distinct brain regions, for detail versus abstract reasoning. …

“These different human mental systems tend to be inconsistent in giving systematically different estimates to the same questions, and these inconsistencies seem too strong and patterned to be all accidental. Our concrete day-to-day decisions rely more on near thinking, while our professed basic values and social opinions, especially regarding fiction, rely more on far thinking.”

This near/far mechanism might explain why we are deluded in the ways we are. Our biases aren’t hardwired merely because reality is uncertain, but because they allow us to manipulate the impressions we create subconsciously.

Note that this explanation of self-delusion is quite different (and much darker) than the typical reasons for optimism and confidence. Perhaps it’s safer to believe overconfidence and excessive optimism are because of self-fulfilling prophecies or ridiculous metaphysical theories, than possibly manipulative social tactics.

Lies and Happiness

The near/far dichotomy is no better represented than in discussions on happiness. I’ve shared previously Daniel Kahneman’s work showing that what we call happiness is really two different things.

When I think about what makes me happy, I think of meaningful work, travel adventures and dating exciting women. But do they actually result in my happiness, or are they far-view representations which project a good social image?

Being happy in your life and being happy about your life are two separate things. They may be correlated, but there are plenty of situations which put them in conflict. Some studies suggest having children is an example of such a tradeoff—most couples are glad they had kids, but were less happy while raising them.

Imaginary Control

Another prominent area of self-delusion is self-control. Namely we are convinced we have control over much of our behavior, even when our experiences repeatedly show us otherwise.

One of the reasons I became such a fan of habit training was simply that it acknowledged how incredibly weak our willpower is. If our actions run on autopilot 95% of the time, doesn’t it make sense to learn how to reprogram the autopilot?

The illusion of control is also a socially instrumental delusion. We talk about the need for more healthy food choices, but continue to eat greasy burgers, because we want to impress upon others our health-consciousness, even if the actual details of being healthy are too difficult for us.

Lies, Love and Sex

Perhaps unsurprisingly, no area is more full of self-delusions than sex, love and dating. Men fake confidence and feign indifference. Women claim to prefer equal partners, but respond to dominance. Men claim to want to date women near their age, but really prefer 21-year olds.

I don’t think I need to convince anyone that irrationality and subconscious motivations abound in dating (for both genders). But I think a more interesting question is how useful is awareness of those self-delusions? Are we happier creating pleasant narratives for our more basic drives, or by understanding them fully even if we don’t like what they describe?

How Much Self-Delusion is Healthy?

The prospect that some irrationality is a good thing is an unnerving one. It suggests that merely knowing how the world works is not enough, but that even with that knowledge, it’s useful to believe falsehoods or exaggerations in specific areas.

What is the solution to this problem? Is it to learn the truth, but foster internal contradictions when they might be useful? Or is it to try to be as rational as possible, accepting that self-delusions will naturally creep in where appropriate as designed by your mental hardware?

These ideas raise more interesting questions than they provide answers, which is a sign they are worth thinking about.

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• “Without credentials at the end, a university education is meaningless.”
• “You can’t learn without guidance from instructors.”
• “College is mostly about forming a network, not passing exams.”
• “Self-education only works if you’re exceptionally bright or dedicated. Most students need school.”

It’s hard to argue with these objections because they’re all at least partially correct. The signalling benefit of credentials is a major reason to go to school. Access to instructors and peers facilitates learning.

What irks me isn’t that these objections don’t have a grain of truth, rather it’s the presumption that they matter. Formal education is a package including many useful elements. The assumption underlying these arguments is that by missing just one component of the college experience, any alternative is rendered invalid.

The current educational system is a fixed menu. You get the campus, classes and hefty bill at the end, whether or not you wanted all those things. The world doesn’t need a wholesale replacement of college, but à la carte options.

More Options, Not Perfect Substitutes

The North American system for education is an inherently elitist one. High tuition and extremely rigorous acceptance processes are filters designed to weed out people who can’t pay or perform.

This isn’t necessarily a flaw. Even if tuition prices continue to escalate to making college a questionable choice for some, it does have the advantage of allowing the brightest to excel. Nobody ever got fired for hiring Harvard grads.

The problem with an elitist system is when there’s only one option. Don’t fit the archetype the system was designed for? You’re out of luck.

The European system is more accessible, with some countries even completely subsidizing the cost of tuition. But while that may be attractive to some, it’s a distant economic and political reality for most of the world. What’s more, education reform doesn’t need to come from the top-down, it can grow from the bottom-up.

Could OpenCourseWare Be the A La Carte Solution?

MIT’s OCW has been around for over a decade. Yet we don’t see people touting courseware “diplomas” on their resume. Perhaps this is a sign that the objectors are correct, that self-education is missing some key ingredient which prevents it from competing.

I think that’s a hasty interpretation. While the technology to offer world-class education for free has developed quickly, cultural norms take much longer to shift. This is especially true of education, which is often entrenched in decades-old HR procedures and professional accreditation boards.

Instead, I see online education as quickly becoming a robust alternative to college, but it may take longer to change the cultural assumptions underlying what it means to be educated.

Why I’m Convinced Online Education is the Future

For me, I was convinced after only one class: Linear Algebra. This was one of the few classes I’ve done as part of my MIT Challenge which I had already studied in university.

What I discovered was that the MIT’s free course was better taught, more robustly supported and more entertaining than the course I had paid tuition for in school. Far from being an inferior option, MIT’s free version was unequivocally better.

One class doesn’t prove a generalization, but I want it to throw doubt on the common intuition that cheap inherently means lower quality. Wikipedia is completely free, but the scope (and possibly accuracy) is better than Encyclopaedia Britannica.

I may not have every resource an MIT student has. But I have quite a few, and often those resources are better than those from a less prestigious school.

What About Credentials?

The strongest argument I’ve heard against self-education is the lack of credentials it generates. Bryan Caplan presents an extreme version of the argument, which claims that the signalling benefits of education is almost all of its value.

I’m not persuaded by the cynical view that the knowledge in a degree doesn’t matter. But the inability to demonstrate knowledge you haven’t paid for is a major current weakness of self-education.

I stress current because I don’t believe it will always remain so. Already MITx and Stanford have begun offering certification for individual courses for free. Even lacking that, I’ve heavily documented my own MIT Challenge, suggesting that an educational portfolio of projects and exams might be a possible alternative.

Ultimately credentials have only the value we imbue them in a society. If a significant group starts to signal their intelligence, knowledge and skills in a different fashion, the world will adjust. I already know programmers who say their GitHub accounts are more important for their career than their formal credentials.

Nothing is Irreplaceable

Very few things in an undergraduate education couldn’t be replaced by a free courseware platform. Lectures? Recorded video. Networking with peers? Skype, online forums and local meet ups. Credentials? Free certification or educational portfolios.

I don’t think online self-education will replace college in its entirety. But it doesn’t have to. The world doesn’t need a perfect replica, but more choices. When Stanford offered its AI class free to the public, over 50,000 people signed up. This is just the start.

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The idea of 10,000 hours evokes the sense that mastery is mostly a process of endlessly slogging away at a craft. What’s interesting about this is that the research from which the idea is based doesn’t actually support this. Practice is essential, but not all practice matters.

Anders Ericsson’s research (which inspired the Gladwell meme) shows that hitting plateaus is common in skill development. Far from being a steady linear progression, mastery comes in bursts.

There are many causes of plateaus but a major one seems to be routine. Sticking in the same habits, whether it’s writing, programming, design or business often results in failing to progress, despite investing a lot of time.

The Catch-22 of Habits and Mastery

This leads to an interesting paradox. On the one hand, good habits are essential for building skill. If you’re not regularly showing up, every day, how can you possibly hope to invest the thousands of hours of practice needed to get good? Yet those same habits also have the cost of potentially stalling your improvement.

The concern isn’t hypothetical. As Benny Lewis explains in his quest to speak Mandarin after only three months’ practice in Taipei, it’s easy to settle on a local maxima of improvement in languages:

“One of the key factors of ensuring fast progress [in my mission to learn Mandarin] has been that I have changed my approach entirely every week.”

The obvious challenge is how do you simultaneously balance the need for having baseline habits to ensure you practice regularly—while avoiding the possibility of wasting months of work without improvement because your process is stale?

How Do You Become a Better Writer After 900+ Articles?

I find myself asking these questions about my writing. I’ve definitely improved as a writer these past six years. But after having written nearly a thousand articles, how much more can I expect to improve by writing more blog posts to this website?

It’s easy to want to be a better writer. But taking the steps to push through your comfort zone is a different challenge entirely.

What would those steps even look like? Would it mean trying to write in a new medium, such as a published book or journalistic column? Would it mean deliberately forcing a change in my writing process? Applying the theories of skill development can often be tricky in practice.

The promise of habits is that you can automate chunks of your behavior so that willpower isn’t necessary in the long-run. What happens when the behavior you want is to continually break your routine? How can you sustain deliberate instability?

The Perpetual Tension of Getting Good

You might ask whether these are things worth being concerned over at all. Why worry about pausing along the road to mastery? Why not just enjoy process and avoid the strain?

It’s popular to laud intrinsic motivation and passion, and then conclude that if you’re not in a persistent state of Zen-like calm in your work then you’re doing something wrong. When I suggested that occasional burnout wasn’t such a bad thing, I got dozens of rebuttals that stress was a demon to be avoided at all costs.

The truth is, the psychology of stress shows that it’s neither all good or bad. Prolonged distress can be harmful. But there’s also positive stress, or eustress, which is healthy.

I think the paradox of mastery shows the inevitability of some form of tension if you want to excel at something. Persistent, intolerable stress is probably bad. But alternatively, staying comfortable in your routine is not best either.

It may even turn out that this tension is a prerequisite to having work you’re passionate about. Being passionate about your work also means you care whether you do it well. How can you be passionate about your craft if you’re indifferent to striving in it?

Is Living Well a Process of Mastery?

Mastery applies to the specific disciplines of your work, but it also applies to your life. In some ways, living well is a skill. Like any skill, it relies on not just broad principles, but nuanced wisdom that comes from unique experiences.

If the life-as-a-skill metaphor holds any weight, then the idea of persistent tension and the paradox of habits apply as well. In that case, there’s probably a degree of tension—of disrupting your habits as much as building good ones—that underlies a successful life.

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Instead, I asked him what books he had read on building a remarkable career. To my surprise, he said he hadn’t read any.

This is a surprise, because I can’t think of any entrepreneurs that don’t have at least one or two favorite books on building a business. When I first got the idea of starting a business, I was voracious, reading everything I could on sales, entrepreneurship and marketing. If 80% of businesses failed, I wanted to know everything I could to be in the minority of success stories.

But becoming a successful architect is no less difficult than starting a business. Then why hadn’t my ambitious and capable friend read a single book on starting a career?

Most Career Advice Sucks

The problem is that most career advice sucks. While books on entrepreneurship are varied and numerous, most career advice falls into one of two categories: “follow your passions” and “use your network.”

Telling someone to simply follow their passions is a nice thought, but supremely unhelpful (similar to the entrepreneurial mantra to “just start something”). What if you don’t know what your passions are? Or if your passions can’t earn you a living?

Similarly, telling someone to use their network is empty advice. What does that mean exactly? Should you be spamming your Facebook friends for job opportunities?

There are some good writers on career issues, but their ideas tend to be a minority in a sea of easy affirmations about following your passion.

Maybe Employees Should Think More Like Entrepreneurs?

Perhaps some of the blame in lousy career writing is due to the extreme shift in the accepted norms on employment. In my parents generation, you traded loyalty for lifelong employment. Today, I have friends in their mid-twenties who have already switched firms several times.

This liquidity in the employment contract also means employers are less willing to carefully guide your professional development. As my friend discovered when looking for his first job, HR managers wanted concrete skills, not just “potential” and a university degree.

These are new challenges for this generation of employees, but they’re the same challenges entrepreneurs have always faced: how do you take intelligent risks? What constitutes a useful network? How do you market yourself and pick the right abilities to develop?

The Startup of You

This is exactly what Ben Casnocha and Reid Hoffman have done in their book, The Startup of You. The thesis is that you should think like an entrepreneur, even if you never want to start a business.

Readers here will note I’ve been a fan of Ben’s writing for some time. Aside from having staggering career acceleration (started his first company at 13, best-selling author and speaker in his early twenties), he is able to give thoughtful analysis to complex topics, instead of resorting to cheap platitudes.

Here’s some gems I found while reading the book:

• ABZ Planning. Having a plan is great, but you won’t feel comfortable taking risks if you don’t have a safety net. Best-case/worst-case style planning is classic entrepreneurship, but rarely applied to career leaps.
• Cultivating allies and weak ties. Networking is a prominent topic, but unlike most pundits advocating conferences and business cards, the book goes into great detail on which relationships you should build, start or even let fade.
• Competitive advantage, not just passions. Passion is great, but it’s just one factor in having a great career (earning a living is another one!)
• Who you know is the what you know. We’ve all been told, “It’s not what you know, it’s who you know.” But more emphasis on this book is put on the proposition that your network can be the source of your intelligence.

The book stays aspirational without sacrificing nuance. I get a lot of books to review in the mail, but fewer I’ve actively sought out. If you’re trying to build a remarkable career, this book is a must-read resource.

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I’m nearly at the halfway point of my challenge to learn MIT’s computer science curriculum in 12 months. I decided to put together a short video explaining what my daily routine looks like, and also share some of the tactics I’ve been using to learn at a faster pace.

Learning MIT at 4x the Pace

After having completed a degree at a regular university, I was surprised to find that learning faster is actually easier if you’re not in school. There are a lot of methods I’ve been able to use to speed up the process which are cumbersome in a normal academic environment.

Are these speed ups legitimate? After all, if an actual MIT student has access to everything I do, how could I possibly learn faster using fewer resources? To explain how that’s possible, let me explain how the challenge works.

From the beginning, my goal was to pick a basis of evaluation that could get close to MIT’s actual curriculum. In the end, I settled for final exams and programming assignments. It’s not perfect, but my goal was to get as close as possible to the evaluation MIT uses, while being flexible in how I actually learn the material.

You may argue that, as evaluation tools, these miss some elements of learning, but I’d say they’re a pretty good approximation. They account for the majority of an MIT student’s GPA and they cover the almost everything taught.

The advantage of a non-traditional learning method isn’t in what it includes, but what it leaves out. With a fairly quick evaluation method, I can be more creative in using assignments, lectures, recitations and problem sets to extract the majority of the value in substantially less time.

Learning Hacks

Despite being the main vehicle for scientific progress, universities are hardly a model of pedagogic excellence. The standard teaching format in most schools has changed little in the last few hundred years, despite new scientific results showing those methods are often inefficient.

Hacking Lectures

A simple example of this is the lecture format. I can extract huge time savings by not watching lectures at their normal speed. By speeding up the lecture to 1.5-2x the pace, I can save nearly 20 hours of work, with just one change. (Note: you can do this by downloading the lecture, then using VLC Player to speed up the playback rate)

Yes, this makes lectures harder to follow, but because I can rewind and rewatch, that isn’t a big problem. If you’re taking a class you’re properly prepared for, it should only be minor sections that cause confusion—why not carefully rewatch those sections and speed up the rest?

Turn Assignments into Deliberate Practice

Assignments and problem sets are another area that can be hacked. Research shows immediate feedback and targeted practice are essential elements in rapid skill building. So why do the assignments in-order and wait weeks to get your results?

I usually do assignments out of order, focusing on questions on the hardest possible topics, or on the core skills I sense I need to master most. I also check the solutions immediately after working on a problem, to improve the feedback mechanism.

Under this view, assignments are all about preparing you and serving as an outlet for deliberate practice, not just busywork that needs to be completed.

Recursive VS Iterative Learning

Most students learn in an iterative fashion—take lesson one, master it, then move onto lesson two. The academic system basically enforces this method of learning since lessons and homework are trickled out in lockstep.

There are two weaknesses with this approach. First, you don’t get to see how early concepts are going to be applied to later ones. Second, it doesn’t allow you to invest your time in the topics you find most challenging, instead you conform to the pace of the group.

I prefer a recursive strategy. First I “learn” the entire course material, which usually doesn’t mean I’ve mastered it, but I understand the basic principles. Then I recursively deepen my understanding on harder topics until I’ve mastered it. This deepening can be done by deliberate practice in problems as mentioned previously or by using intuition-generating methods like the Feynman Technique.

How Can You Apply These Methods?

It might be an interesting experiment to see if there are more efficient ways to learn, but you might wonder how it’s useful. After all, if you’re an actual student, assignments and attendance are often mandatory and rarely can be done in the out-of-order, rapid-feedback ways I’m suggesting.

But imagine spending a month to do what I’m suggesting, and master the concepts of your classes using free resources from Stanford, Harvard or MIT? The rest of the semester would be significantly easier if you’d already learned 80% of the course in the first few weeks.

Not everyone can learn a class in one week, even with the methods I’m describing. But I’m certainly not 4x as smart as an MIT student, so at least some of the advantage has to be structural, not just intellectual.

Changing the Costs of Learning

I know a lot of otherwise intelligent people (typically businesspeople) that scoff at learning from a university. It’s too academic, devoid of real-world implications or theoretical for their liking.

I suspect a lot of their distaste comes from the normally high cost in time and money it takes to learn. If you could learn twice as fast, with complete flexibility and zero cost, would that change your perspective of whether learning calculus, finance or genetics is worthwhile?

When mainframes still took up a warehouse, many intelligent people couldn’t imagine why anyone would want a personal computer. Now we have them in our phones. If education were to become free and less time consuming, what would stop you from learning?

I don’t know if free education will change the world. But it has at least changed my life. I’ve already started downloading the resources for graduate classes on quantum computing and machine learning I want to take once my challenge is over, and I’m looking forward to classes in physics, brain science and biology. Why not you too?

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There’s nothing wrong with this advice. Plenty of people waste years hesitating on taking the actions they know they need to take. Maybe you’re one of those people.

But the problem with generic advice is that it tries to lump everyone’s problem into a single generalization. Although many need a kickstart, there’s also a lot of people who need to stop trying to do so many things.

Starting isn’t Useful Without Finishing

Starting interesting things is a worthwhile trait, but perhaps a more important one is finishing those things. The world is full of half-finished projects which could have been great if the fire-starter hadn’t burnt out a month or two in.

The courage to start things needs to be matched with the discipline to see them through. They’re both critical, and my guess is that you can probably assess which one you need to work on.

I suggest an alternate mantra—just finish it.

How I Went from Typically Incomplete to Persistent Finisher

When I was just getting started with plans to start my own business, ambition was never my problem. I had tons of ideas and I loved the feeling of potential for starting a new project. No, my problem was getting any of them done.

My old notebooks are filled of half-started ideas, vague projects and uncompleted dreams. It took me awhile to realize that this enthusiasm was great, but unless I was able to direct and focus it, my ideas would forever remain inside my head.

What changed was that I realized being a quick starter and rare finisher is just another form of debilitating perfectionism. Instead of sticking through the practical realities of my goals, I wanted to start again, where every idea was perfect in conception.

Once I realized that finishing, not starting, was the key, I started putting emphasis on it. I’d finish projects that had flaws, just because I had committed to finishing them. I’d try to make my existing path work instead of finding a new one. I’d start less, because I took my commitments to start more seriously.

Commit Less, Commit Stronger

One of the major shifts that helped me accomplish this was to clearly separate my experiments from my commitments. I love trying new things, and I never want to give up the sense of adventure that comes with that.

But I also don’t expect to accomplish big things on a whim alone. That takes dedication and commitment, and because I take my drive to finish what I start seriously, I don’t make those commitments lightly.

I didn’t announce the MIT Challenge publicly on my blog until a few weeks before I started it. Fewer people know that I was preparing to undertake the challenge for over a year before it began. I can remember getting feedback on the idea from Cal Newport (himself an MIT graduate in computer science) in early 2011.

I went through several rounds of experiments, including a pilot course in June and nearly a month exhaustively assembling the materials I’d need, all before making a final commitment to start the project.

My current challenge is a difficult one, and finishing isn’t always possible. But I do know that if I’m eventually defeated, there’s going to be a hell of a fight before I give in.

This doesn’t mean everything revolves around a fixed plan, or that you can prepare for everything perfectly. I had a similar commitment level to starting an online business which took over seven years of non-stop effort before it was realized. But I was also flexible. I experimented on everything from industry to business model, from headline to subscribe button. Commitment needn’t imply rigidity.

Commit Less, Experiment More

Taking commitments seriously doesn’t mean you can never try new things. I simply put them into a different mental category from my experiments. At various points in my life I’ve started karate, salsa dancing, handstand pushups, Spanish, and cooking Indian cuisine. I’m not suggesting you stop doing spontaneous, fun things.

Instead I’m suggesting that you differentiate your commitments from your experiments, and treat them accordingly. The more you separate the two concepts, the easier it is to be fun and flexible with some pursuits and be an unstoppable juggernaut in others.

Just do it is a great slogan. But if you find yourself like I did, with a notebook full of half-finished dreams, maybe telling yourself to just finish it is a better one.

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