Why We Do Better

We learn the most from the events we are least prepared for. Assuming, of course, that we survive the initial collision.

In his essay on the wisdom of lifting barbells, Nassim Taleb applies the principle of tail risk to strength training. Our bodies get stronger not from the monotonous humdrum of routine activities (rising from bed, sitting in a car, sitting in the middle row at team meetings, walking to our car, etc.), but from exposure to infrequent extremes: lifting weight off the ground at the very edge of our muscular and skeletal capacity.

He uses the analogy of weight-testing a bridge:

“You will never get an idea of the strength of a bridge by driving several hundred cars on it, making sure they are all of different colors and makes, which would correspond to representative traffic. No, an engineer would subject it instead to a few multi-ton vehicles. You may not thus map all the risks, as heavy trucks will not show material fatigue, but you can get a solid picture of the overall safety.”

Frequent, trivial insults chip away at a system (low back pain, carpel-tunnel, etc.). Rare, intense shocks may strengthen them.

For the past decade, Millennials have faced a glut of minor knocks but, outside of the 2008 U.S. recession, relatively few cultural hammers. Despite being the savviest participants in social media, the most connected and technologically capable, and having the broadest access to education and global impact, commentators describe the average Millennial as sheltered, anxious, and timid.

It makes sense that a generation insulated from failure and conflict would popularize the concept of microaggressions: frequent, trivial insults that chip away at self-esteem and dignity. And, like a overactive immune response, the battle against microaggressions has not strengthened Millennial political or social clout.

To the majority of voting Millennials, the election of Donald Trump was a tail event: an unthinkable catastrophe, an existential threat made concrete.

A macroaggression.

What if that was exactly what the generation needed? An extreme event that would organize, mobilize, and strengthen the entire system? What if the most connected, most educated generation was also the most politically engaged?

We learn the most from the events we are least prepared for. Assuming, of course, that we survive the initial collision.

Why We Do Better

If free food doesn’t excite you, nothing will.

That’s about the least you can care about something. If an event boasts of free pie, you know they are in a low-care business. The conference room might be packed, but 99% people are just there for the food. When the food runs out, or the organizers ask people commit to anything (anything), the attendees will flock to the exit.

And of course, you avoid opportunities like that because you’d rather spend your time on something that you care about, pie-or-no-pie.

So that’s one end of the Care Spectrum. What would sit at the other end? What is the opposite of free pie?

How about a punch in the face?

Very few people would show up to an event that boasts it will punch every attendee in the face. In fact, let’s assume this event is extremely expensive as well. You might pay several thousand dollars to attend this event, and you will be punched directly in the face an uncertain number of times.

Very few attendees, indeed. But you can bet that whatever this event is about, the attendees care a whole hell of a lot about it. Whoever these attendees are, they are the experts and nerds, the pioneers and changemakers.

We all want to make a difference, until we get punched in the face a few times.

You might know exactly what you want to do. You might even be great at doing it.

But the question is, what are you willing to take hits for? Because this isn’t the end of the Care Spectrum: it’s the new beginning. This is the least you can care and still make a difference.

Which conferences do you show up for, punch or pie?


Want to learn more about how to care (and more importantly, not care) about the right stuff? Check out Mark Manson’s  The Subtle Art of Not Giving a Fuck.

Why We Do Better

(They will say)

“All things in moderation.”

No. No!

Moderation is dull stress, joint pain, compromise, boredom, homogenization, mediocrity. Carpel tunnel. Weak opinions. Dad bods.

No. All things in extremity. In small amounts. At random intervals. Sprints, not jogs. One square of the darkest chocolate, not a bar of Nestle.

We ignore the lesson that taps us gently on the shoulder every day. It is the moment that smashes us, breaks us, and ejects us into the atmosphere that travels alongside us forever. Not the daily bumps, but the rare stabs – deep enough to leave scars.

No, no things in moderation. Feast, then famine.

Why We Fuck Up

“Well it’s a short life and if you keep repeating your success, you’re living a shorter time. In other words, you’re going to end up looking back on your life in sections, not in years.”

-Louis CK, in conversation with Marc Maron

Here’s an illustration of how perception and memory work. Read these two 9-digit sequences:



Wait 30 seconds and try to recite the sequences without peeking. The first is far easier to remember because we detect an obvious pattern – four hundred, five hundred, six hundred. We can reduce nine digits of information into three ‘chunks’.

Our experiences work the same way. We don’t remember every moment of every day. We chunk batches of moments together: the time spent making and eating breakfast, sitting in the car to work, checking email, the first meeting of the day, etc. The more varied our days are, the fuller we perceive them to be; nevermind that each day consists of the same number of moments.

The temptation, as we age, is to hew closely to the experiences we find most agreeable. We stick with the easy, the comfortable, the stable. The job we’ve figured out. The neighborhood we can map out in our head. The familiar shape of our Saturdays.

Routine is an opioid, not a stimulant.

Warm in its embrace, we startle awake decades later, wondering “where did the time go?”

Why We Act

In another life, I taught Psych 1 section to freshmen. I’d open each discussion session with an open-ended question to whet their curiosity about the day’s subject. Following a lecture on emotion, I posed this question to the class:

If you could get rid of any emotion, what would it be?

Can you guess the most popular answer in the group? The nearly unanimous response?

Take a few moments to think.

The emotion they wanted to snuff out, by miracle or by pill, was jealousy.

The voice that whispers you are not enough.

Why We Do Better

Screen Shot 2016-04-09 at 5.14.32 PM

This is one of my favorite comics, and there are two ways to interpret it: the fool reading and the monk reading.

The fool reading sees Mr. Dog ignorant or stubborn in the face of obvious catastrophe. Dog is each of us: happily, stupidly plodding deeper into the jungle despite every sign that we should turn back.

It’s Jeb! continuing his campaign after Please Clap. It’s Wile E. Coyote busily cycling his legs even though the cliff ended meters back. It’s staying at the shitty job or with the shitty person long after they’ve revealed their toxicity.

This is a valid and vital lesson, though like the Rubin vase, a second impression emerges from its contours.

This interpretation is best explained by an anecdote told by Josh Waitzkin about playing in the rain with his son:

“Parents have this language around weather being ‘good’ or ‘bad’. Whenever it’s raining you hear ‘it’s bad weather, we can’t go out,’ or ‘it’s good weather, we can go out.’ So that means we’re externally reliant on conditions being good in order to have a good time. So [my son] Jack and I never miss a single storm. I don’t think we’ve missed a single storm, rain or snow, going outside and romping in it. We developed this language around how beautiful it was, so now whenever it’s a rainy day Jack says ‘look Dada, it’s such a beautiful rainy day.’ ”

From birth, we are taught to label things as good or bad – our emotions, our physical sensations, our successes and failures. In short order, we learn to dread all that we call ‘bad’ and flee from its presence.

The truth, as Waitzkin points out, is that much richness in life comes from sitting in discomfort. In doing so, we gain mastery over ourselves. We hear depth and beauty when before we heard noise. Both courage and wit grow well in this soil.

The truth is, all that we call genius comes down to being able to sit in the fire and say, “this is fine.”

That is the monk reading.