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 Create

If you feel like politicians don’t represent your attitudes, it is possible that you are not strange enough.

In the documentary Objectified, industrial designer Dan Formosa describes his lab’s approach to building new products:

“We have clients come to us and say, ‘Here is our average customer.’ For instance, ‘Female, she is 34 years old, she has 2.3 kids,’ and we listen politely and say, ‘Well, that’s great, but we don’t care . . . about that person.’ What we really need to do, to design, is look at the extremes. The weakest, or the person with arthritis, or the athlete, or the strongest, the fastest person, because if we understand what the extremes are, the middle will take care of itself.”

My take: This approach is currently being tested in the U.S. presidential election. We will find out whether speaking to the oddest, the angriest, and the most dogmatic at the exclusion of everyone else is a viable political strategy, or whether you really need to cater those in the middle: independents and undecideds.

More than that, this is a lesson for anybody who has something to say:

Who is your least interested audience? Who are your biggest opponents? Who loves your work? Who are your True Fans? Whether you are crafting a presentation for management, planning a protest, or starting a blog, these are the two audiences you need to consider. Shock your opposition to attention. Nerd out with your homies. No middle ground. No average users. The mean will take care of itself.

To learn about how Tim Ferriss used this principle to learn Spanish in 8 weeks, read The Four-Hour Chef.

Why We Do Better

Who wins a debate?

Who had the better argument?

Who seemed more likable?

Who showed more strength?

Who was more informed?

Who blinked less?

Who was more memorable?

Who was funnier?

Who convinced more people of their position?

Who had more empathy?

Who showed more certainty?

Of course, it doesn’t matter. Because the person that wins is the person that does the work, investigates the problems, builds the coalition, earns trust, takes responsibility for the outcome. This is the person that wins, whether they show up to the debate or not.

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 Create

“The 8 hours you need to sleep each night, are my opportunity. The time you spend with your family and friends, is my opportunity. If you’re not maxed out, if there’s still a shred of humanity left in you, then you’re just leaving your lunch on the table.”

This brilliant blog post by Elaine Ou captures a common strategy: to expand to the widest possible audience, slash your margins. Instead of making $10 per sale, make $1. Instead of $1, make 10 cents. Instead of 10 cents, raise funding to give it away for free.

We often encounter the same incentives at our own jobs. Rather than money, the margin for our work is time. Instead of leaving at 6, stay until 8. Instead of finishing at 8, work on the ride home. Instead of finishing when you arrive home, work the weekend. Slash your margins. Track your metrics. Eliminate your inefficiencies.

When your team begins talking about efficiency, it’s time to find a new team. Efficiency is an endless war, one measured in minutes and dollars saved, not in people served or missions met.

Every four years, someone sets a new swimming record at the Olympics. Efficiency is an endless war.

And what’s the opposite of chasing efficiency? Spending more time: to listen, to build relationships, to tailor, to take risks. To serve fewer, better. To add humanity to your work. The more you add, the more you keep.

Why We Fuck Up

One of the reasons we are more anxious on planes than in cars is because every time a commercial airline crashes, news outlets tell us. Heavily and graphically.

Websites, TVs, and newspapers bombard us with images of the smoking wreckage, the grieving families, the smiling faces of the lost.

We may comprehend than there are far more victims of car crashes than plane crashes each year, but their reporting is nearly inaudible, their carnage invisible. What we don’t see, we tend not to worry much about.

Perhaps, for our collective mental health, we should stop reporting on plane crashes.

Or perhaps, for our collective physical health, we should start reporting on car crashes. Heavily and graphically.

Why We Act

A friend once told me about a game he’d play to spend the empty days as a teenager in Brooklyn. He would walk out the door, pick a direction, and keep walking. Every time he reached a traffic light, he’d turn left or right at random. For hours. No destination in mind; he’d end up where he’d end up. Always somewhere new. For curiosity. For adventure. For no reason.

We are tourists, in a densely networked city of ideas, and there are tour guides at every corner. Friends. Blogs. Algorithms. Each suggesting what path to take when we reach the corner.

We tend to prefer this. We’d rather somebody hold our hand as we cross the street.

There is safety in curation.

Conversely, there is heroism in discovery.

There are few spaces left, physical or digital, where heroism is even possible. Curation and recommendation are so intrinsic to daily life that we confuse social proof for quality:

“This restaurant only has two reviews. Bad sign.”

“They’re not even on Spotify. Why would I go to their concert?”

“How helpful could this book possibly be if no one knows about it?”

This, I see, is the rare advantage of a public library: one of the last remaining spaces without tour guides. A place for heroism. A place you can turn left, turn right, turn left, hand un-held. End up where you end up. For curiosity. For adventure. For no reason.

Why We Do Better

Developing a team of risk-takers is challenging foremost because culture is a bad dog: it resists efforts to train it. Posters on the wall don’t create a team’s culture, nor do mandates, hoodies, slideshows, or mission statements.

People follow incentives, systems, and other people. So to foster your risk-takers, you must:

  • Hire people that are weird and endearing.
  • Expect modeling from the experienced people on the team
  • Give people the trust and time to test their ideas,
  • But abandon stuff that isn’t working as quickly as possible.
  • Do not get overly fixated on metrics, which almost always miss something important and ineffable.
  • As a manager, know the difference between an interesting idea and somebody throwing shit at the wall.
  • Distrust grids, bars, and spreadsheets; trust curiosity, experimentation, and people who build relationships outside of their team.

It’s trendy for companies to outwardly praise risk-takers, mad scientists, and leaners-in, those intrepid challengers of status quo. It’s less common for those companies to tolerate the uncertainty and failure that accompanies real risk.

In many companies, the biggest risk you can take as a manager is standing up for your people’s permission to fail – messily, noisily, nobly. Do that, and your fellow adventurers will take notice.

Why We Create

The insight of an experience like Snapchat is that impermanence lowers the bar to action.

First, impermanence removes the urge to get it right: beautiful, meaningful, even interesting. We spend less time fretting over our sandcastles when we know that the tide will wash them away.

Second, impermanence negates our concern for reputation. Reputation is the child of memory; when there is no record of what we made last week, who we were last year, we are free to be mercurial, absurd, idiotic. In other words, ourselves.

Knowing this, it’s worth considering where we (personally or collectively) creatively stall in other domains. The broad question: what do we not attempt, for fear of getting it right the first time, every time?

  • Fields where the initial investment cost is high
  • Fields where we will be judged/graded/evaluated, particularly publicly

Scientific research, starting a small business, switching careers, going back to school. Trying that new dance move. Giving compliments. Being honest. Raising our hands.

All subject to the tyranny of the high bar.

Perhaps we will run faster as we build ways to forget our steps.

Why We Create

The relationship between the critic and the artist mirrors the relationship between the translator and the language.

Consider: translators decode. Translators connect. They frame perspective of the speaker and contextualize within the culture of the listener. Great translators reveal depth of meaning. Beauty hidden in nuance.

Some, some garble the message. Mistranslate. Overcomplicate and over-formalize. Misread intent.

And some words are just untranslatable. You must read them in their native form. You must live as the speaker lived to hear her tongue in full.

Finally, you can communicate through a translator, but to hold a conversation you must learn the language.