Not Once

I have never once regretted going to the gym.

Sure, it’s hard to get going, but I’ve never once walked out of the locker room and thought, “You know, I shouldn’t have done that. That was a bad idea. What a waste of time.” Never.

So many things are the same way– hard to begin, but never regretted once they’re done. It’s one of life’s little asymmetries. Likewise, so many things are regrettable in hindsight, but they take almost no effort at all to get started. Overindulgence, impulsive behavior, laziness of any type.


Other things I’ve never regretted, and their flip sides:

I’ve never regretted getting up early, but I’ve regretted sleeping in.

I’ve never regretted staying sober for a night, but I’ve definitely had too much to drink.

I’ve never regretted working hard, but I’ve regretted spending the afternoon watching Mad Men instead of working hard.

I’ve never regretted delaying sex with someone I loved, but I’ve regretted sex with someone new too soon.

I’ve never regretted play, but I’ve regretted time where my mood prevented me from being playful.

I’ve never regretted reading a book, but I’ve regretted taking the easy way out and opting for a movie or a blog instead.

I’ve never regretted writing, but I’ve regretted spending all night bouncing from distraction to distraction. I’ve felt the pain of wasting hours with nothing to show for myself.

I’ve never regretted getting in touch with someone new, but I’ve regretted missed opportunities to form a new relationship.


Why is it so hard to think ahead? Why can’t we see the end result, but we are instead stuck in a pattern of instant gratification? The answer is right in front of us, but we act like we can’t see what’s right in front of us? Why do we do this, flitting from one impulse to the other, never able to focus on the not-so-distant future?

Seneca said: “Call to ming when you ever had a fixed purpose; how few days have passed as you had planned…You will realize that you are dying prematurely.”

He’s right. Instead of focusing on the distant future, we spend out lives tossed around by these alternating forces of impulse and restraint, action and hesitation, pride and regret.

We are all like children. Or addicts.

Experience: Too Much / Not Enough

If you apply for a job today, it seems like you practically need a masters degree for an entry level position. This is true even for menial work like office administration.

During the draft in WW2 and Vietnam, and even in the military today, it’s possible to take an 18 year old and turn him into a tank operator or a pilot or a marksman within a couple years. At the very least he can be a passable soldier and a comeptant office administrator within a month or so.

It seems unheard of to hire someone with no skills to do a corporate job, yet the military shows that it’s obviously possible to train an inexperienced person to do complex tasks. So why the discrepancy? Why the overemphasis on formal education? I’ve heard it said that it’s a symptom of rampant over-education. A sort of “more college is always better” mode of thinking. The soccer mom-ificaton of society, trying to over prepare everyone for everything.

But the answer is much simpler and less ominous. It ignores that there is probability at play: military recruiting and corporate recruiting are fundamentally different because the military takes thousands of new recruits on at a time, while businesses only hire one person for the job.

The military is making small bets on a thousand horses. If one private can’t make the cut, it’s no big deal. Next, please.

Businesses don’t have that option. They’re betting big, so they want to see some security in the form of excessive degrees and experience. They need to do this to mitigate risk, to cover their asses.


Ignorance from the Outside

I remember when I first started working at Greensgrow. It’s funny now to think about it, but I assumed that because it’s an environmentally-focused organization that deals in produce, that everyone on staff would be radical environmentalists, great cooks, and knowledgeable farmers. I was nervous at first because I didn’t have any of those skills at all. So foolish!

As it turns out, you don’t need to be a good farmer to manage a farm. And you don’t need to know the difference between an Ida Red and a Red Delicious to keep inventory in stock and sell apples.

 I made a classic mistake– I was nevous because I lacked skills that I assumed were relevant, but that were actually pretty superficial. What I  had, and what they were really looking for, were less specific but more valuable skills. Leadership, responsibility, insight, humility, competence.

This can be solved by (1) being more confident and direct with my abilities, and (2) recognizing the domain independence of certain skills. If I had gone into that interview talking about how much I know about produce, they would have laughed at me. But they, like all smart people, know that the right knowledge doesn’t necessarily look like the right knowledge to outsiders.

In other words, what looks like knowledge might not be knowledge, and what looks like ignorance isn’t necessarily ignorance.

Signal and Noise, or Why I Don’t Watch the News

This is an oscilloscope. It’s measuring an electrical signal.

Notice how the line is defined by many small jagged variations, but if you zoom out a little, perhaps if you unfocus your eyes a bit, you see a larger trend as well. It spikes up, then down, then back to the middle, before sinking down again. The larger, more interesting, more long-term information is the signal, and all the minute disturbances along the way are the noise.


Or another way to think of it: suppose you’re in a crowded restaurant, struggling to hear your date over the loud conversations taking place at all the adjacent tables. You have to mentally phase out all the other talking, chewing, slurping, clinking, and laughing– not easy, but possible. Signal and noise.

Nassim Taleb, in his incredible book Antifragile: Things That Gain from Disorder, makes a case for avoiding the news, mainstream or otherwise, based on this principle. It’s obvious that not all news is worth watching. So much of what we consume is overhyped and turns out to be inconsequential. We’re looking for the signal, but sometimes all we hear is noise.

Let’s imagine that during the course of a year, pieces of real, imporatant news (signal) and pieces of overhyped news that publications use to fill their pages and get viewers on slow days (noise) come in equal proportions. But what happens if you zoom in, say to every day? You suddenly can’t see the big picture, and you see less of the signal. If you’re checking news daily, you are exposing yourself to a higher proportion of noise-to-signal, maybe 95% to 5%. And if you’re a day trader or a person who refers to the front page of the NYT every few hours “to stay informed,” the proportion might be more like 99.5% noise, 0.05% signal.

The irony, of course, is that you’ll actually feel more informed. But the truth is that so much of the stuff we consume every day is meaningless and prone to exaggeration and speculation unless we can view it in the context of the long term. Watching the news crowds our brains with information that will likely be of no use, all the while giving us a false sense of understanding and “awareness” of the world.

It’s remarkable how the truly important things have a way of finding their way into my brain. I don’t watch the news, but I know all about the failings of the ACA, Justin Bieber’s arrest (OK maybe not so important), the conflict in the Ukraine, and Governer Christie’s bridge closing debacle. Like magic. Instead of following the painstaking fluctuations, I let time and distance filter out most of the noise.

Whether it’s in the news, in restaurant conversations, in physics, in your weight-loss regimen, in inventing, and in business or military strategy, this is a universal law: If you bother less with the day-to-day minutia, the longer-term trends, which are ALWAYS more important, present themselves to you more readily.

So stop watching the news.

If Everyone Hated You

Assume everyone hates you. They hate you and they don’t want you to succeed or to ever be happy. They laugh at you behind your back, and sometimes right to your face.

In Greek myth, Sisyphus was condemned in the afterlife to push a boulder to the top of the hill, but every time he made it to the top, he would slip and the boulder would roll down to the bottom. There was another myth about a man named Tantalus who stood forever in a pool a water. Within arm’s reach was the branch of a fruit tree, but whenever he reached for it, it would move away, and whenever he crouched down to drink the water, it would recede. He was condemned to eternal hunger, thirst, and frustration.

I like these stories because the tell of a type of suffering that is so different from the Christian hell– fire and brimstone and all that stuff. These stories are less direct. They’re not about intense physical pain, but rather they’re stories of deep psychological suffering. I think they’re worse. Maybe it’s because I know the frustration of a task that’s never quite finished, or the discomfort of  hunger or thirst. A long day with no time for lunch or dinner, or a tragically unsaved Word document when the computer freezes– these things are far more real and more painful to me that the thought of being skinned alive and branded by a bunch of little mustachioed red men with pitchforks.

What if your own version of hell was this: You are living life much like you are now. You have the same friends, job, home, and belongings, but everyone speaks a language that you don’t know and can never learn. And they all dislike you and you don’t know why. There seems to be nothing you can do about it. What do you do you? Do you give up and hit the bar every morning until your time on earth is used up? Do you steal some drugs and have sex with hookers for the rest of your life? Pursue an existence of pure pleasure? Or do you keep pushing ahead in spite of the impossible odds and say “fuck ’em” of allt he people who hate you, just like Sysuphus did to that boulder ever single time?


OK, now back to reality. Not everyone hates you. But sometimes it’s helpful to pretend they do, just so you can practice saying “Fuck ’em.”You didn’t need them anyway.

The Stoics had an excercise where they would imagine they already lost.

“Imangine your life is over,” Marcus said. “Now take what’s left and live it properly.”

Seneca said something similar:

“Set aside a certain number of days, during which you shall be content with the scantest and cheapest fare, with coarse and rough dress, saying to yourself the while: ‘Is this the condition that I so feared?’

These exercises force you to accept the absolute worse case scenario– death, poverty, alienation– as a given, and then proceed from there. Accepting the worst. Assume you already lost, and the move on.

Because once you do that, fear ceases to exist. You are able to see the advantages of every situation and seize them with both hands. You don’t hesitate so much. Your regrets are dead in the water, and you are moved to action.

People Who Read Chomsky

A person said to me in casual conversation this week:

“I don’t understand why people watch reality TV. Why don’t more people watch TV documentaries about great people, like Noam Chomsky?”

I had to laugh. This is a person who doesn’t understand how knowledge works. Her implication is that people who pay attention to academics like Chomsky are better off that regular folk. It’s self-evident, she seemed to say, that readers of his work are more intellectual, more cultured, are more in tune with the world around them. Superior in every way. As if Mr. Chomsky’s research has the built-in ability to improve the lives of every person in the world, if they’d only pay attention. And that reality TV has fundamentally less merit.

On the one hand I agree with her. She’s not really talking about Noam Chomsky specifically — all she’s saying is that if more people had the habit of thinking with depth and logic and empathy as Mr. Chomsky does, then the world would be a better place and everyone would be happier. And that might be true.

But on the other hand I disagree with her strongly. This is a person who thinks that the point of education is to assemble as many facts as possible. She thinks the hallmark of smartness is the ability think abstractly and end lots of words with “-ism” and “-ivity”.

She’s an idiot, and she’s missing the point. Life is about assembling as much knowledge that is specific to your own circumstances as possible. It makes no difference whatsoever if you find beauty and insight in Miley Cyrus, in Dostoyevsky, or yes, even Noam Chomsky.


Diligence is a word I’ve been thinking about. My definition of it goes something like this: Dilligence is the ability to follow through with tasks that you are assigned, either from  yourself or others. It is the determination to see something through to conclusion without second-guessing, rethinking, or fear.

It’s similar to ambition and equally important, but like so many things the devil is in the details. Ambition is the desire to do great things with your life. Dilligence is the follow-through. You can strive for and expect great things to come of your life, but if you never get around to doing the work, you will lose.

Plans are only good intentions unless they immediately degenerate into hard work.

-Peter Drucker, management guy

Luck, Skill, and What Happens When You Toss a Coin 10 Times

Look at this chart– it’s a simulation of 20 people flipping a coin ten times. Let’s call it the World Series of Flipping. Heads are worth +1 point and tails are worth -1 point.

Screen Shot 2013-12-22 at 1.28.34 AM

Just as you would expect, some contestants did better than others. The spread is approximately symmetrical– about 3 people scored very high, about 4 scored very low, and the rest were more-or-less average. Of those, some were above 0, some 0, but they were overall unremarkable compared to the big leaders and big losers.

Suppose the World Series of Flipping is a multi-round game. The winners get to keep on playing, but once a contestant gets caught with a score of -1 or lower, he becomes a loser.  Losers have to collect their things and go home.

So here is what happens when we remove the losers:Screen Shot 2013-12-22 at 1.30.30 AM

Now we expand it to remove the unoccupied negative space:

Screen Shot 2013-12-22 at 1.29.23 AM

The symmetry of the first image disappears, and this paints a very different picture of the outcome. Rather than an even distribution of some failures, some successes, and most mediocrity, we just have a few winners with the rest being non-winners who are still in the game.

Why is this misleading? Consider this: if you were to take the results of the first round, remove the losers like we did, and run it again, remove the losers again, and so on, you would end up with just one or two winners. You would then be inclined to look at one of the long-term winners and, judging by their impeccable track records compared to their failed competitors, logically conclude that they are more skilled at tossing coins. You might even be tempted to suggest that he is more likely to toss heads in the future than the others.

But that’s obviously wrong– this was a purely probabilistic exercise. No one competitor is any more skilled than another. Each one, regardless of his track record, has a 50/50 chance of flipping heads next round, and hence a 50/50 chance of coming up as a loser in the long run. But that’s not always how it seems.

Like the World Series of Flipping, life is a game made up of many rounds. The lucky ones, as long as they keep living, get to keep on playing, and the unlucky ones get weeded out.

We have a tendency to look at successful people and try to emulate them, and we look at less successful people and we try not to do what they did. And why not? We’re only trying to learn from our environment.

But in doing this we fall victim to a significant fallacy. We make the mistake of assuming that past performance is an indicator of future success. And the real bitch of it is that sometimes past performance really does indicate a propensity for future success, but generally we have no way of identifying when that’s true. Sometimes success is the result of competence, and sometimes it’s luck. I think usually it’s a combination, but in any case we can’t tell the difference by observing.

It gets worse: We can’t tell the difference between luck and skill when observing other people, but we also can’t tell the difference in ourselves and in our own histories. Are you successful because of a series of favorable coin tosses, or are you talented in some unknown and useful way? How could you possibly answer that?

The truth is that being lucky feels a lot like being talented. The foolish person assumes that his accomplishments are the result of hard work, dedication, and his own innate skill. But the smart person takes the opposite approach– he assumes it’s always luck and starts each day with the assumption that there is at best a 50/50 chance of absolute failure. The smart person acts accordingly in the face of this uncertainty.

Tenacity, Risk, and Failure

An entrepreneur I know is looking for investors. According to his research, he thinks he’ll be able to secure a funder for every 50 people he pitches to. Think about how much work that is– that’s 50 potential funders he needs to tap his network to identify, successfully contact for a meeting, arrange a time to meet, pitch to, and then probably not hear back for weeks or months. If he hears back, he’ll have to meet with them at the drop of a hat, even if it means hopping a train or a plane to meet. He would be a fool to miss an opportunity. He’s been doing this for months. So far he’s met with six.

Is his research accurate? It doesn’t matter. The point is that he’s willing to meet with tens, if not hundreds of eccentric rich people before he finds a single one who might help him build his business.

This is a case-study in tenacity. The ability to retain your composure, your dedication, and your sense of perspective day after day in this way is a crucial ingredient to success. This much I know. Yet so many would get discouraged far too quickly and decide that entrepreneurship isn’t really for them.

One way to manage this is to retain a sense of playfulness in the whole matter. You’re not doing anything serious, you can tell yourself. Nothing important is at stake. Life, health, or morality. It’s just business. Just money. Just work. It will make the tough decisions less tough, because they seem inconsequential, and reversible if they need to be.

Everything, from the hardest business problem to the most intimidating social situation to the knottiest math problem, can be made more solvable by acknowledging that the challenge at hand does not require boldness if it does not entail risk.

In other words, if failure and success feel equally acceptable, then the pressure it off. By asking yourself at each juncture, “What happens if I fail?” and answering honestly, failure loses its scare power. It’s probably not really that bad. Boldness becomes less heroic, and therefore less intimidating.

Jerry Seinfeld on Jokes

Jerry Seinfeld knows how to write comedy. This video gives some insight into his creative process.

Key points:

  • Work hard and revise. Repetition, editing, and rewriting is crucial for nearly any project. William Zissner says this too: The essense of writing is really rewriting. That’s why Jerry obsesses over specific words, syllables, and pacing. He knows that a good joke isn’t just a funny idea– the real art is in the  way it’s delivered.
  • Always prepare. Stand up comedy seems improvisatory. You get the impression that the performer is just rattling off thoughts as they pop into his head. Or even if you realize that he must have prepared his bits beforehand, you probably assume that he’s telling it in a laid back, off-the-cuff sort of way. But that’s not the case at all. Jerry meticulously writes down every word he says during the bit, if not the entire act.
  • Don’t tell anyone you prepared. Once the jokes are written, they’re told as if they were just made up on the spot. This is what Robert Greene says in the 48 Laws of Power: “Law 30 – Make your Accomplishments Seem Effortless”When you do this, you seem natural, at ease, and more graceful. You also command respect because you seem much more competent than if you had told everyone how hard you worked. I did this once before a job interview– scripting and memorizing the perfect response for every possible question, and then when asked I basically recited it as if  I was just making it up on the spot. They offered me a job.
  • Embrace ritual. Jerry wrote the entirety of the show Seinfeld with the same type of pen. He must have felt comforted by the habit. Smart people have consistent rituals, like a morning cup of coffee out of the same mug every day, or a sacred location, time, specific pen, a closet full of the same outfit, etc. It saves brain power for more important tasks and it instills your work with a sense of duty.

Also see Seinfeld’s excellent tip to increase your productivity.