When Experience Makes You Stop Taking Shots

Aug 9

9 min read

Updated: Oct 29

There is a very easy way to look smart. Bet against everything. Say the numbers are not there, say we have seen this before, then wait. Most of the time something goes wrong and you get to say, see. The critic has a real statistical advantage. Most swings do not become hits. Most shots do not become goals. That advantage does not make anyone a leader. Leadership has to create a future before there is any evidence the future will arrive. In Episode 384, Edge of the Napkin #48, I work through what happens to experienced entrepreneurs when the evidence piles up. Wisdom becomes caution. Caution becomes protection. Protection means fewer shots. The person with the most capacity to take a meaningful shot becomes the person least willing to miss. Here is how I think about getting the puck back.

From Edge of the Napkin, Episode 384 of Paper Napkin Wisdom.

The intelligent person's trap

The critic gets to wait. The person trying has to move first.

That is a pretty good game, and there are lots of ways to win it. Predict the new thing will not work, and most do not. Say the new product will not take off the way anyone hopes. Call the new hire ordinary before anyone finds out, and you could be right. Bet the team misses a goal somewhere this quarter, because they will. You can build an impressive record that way.

Sometimes skepticism protects us. Then there is a point where skepticism becomes an identity, and the person starts needing the world to disappoint them, because disappointment proves how perceptive they are. I do not want to live that way. I certainly do not want to lead that way.

For someone who has been building a long time, this gets harder, not easier. You have the receipts. You have watched partnerships tear apart. You have watched great people make terrible decisions, and maybe made a few yourself. You have lost customers you thought were yours forever. You have made bets that did not work.

Those experiences teach something useful. Risk is real. They can also teach something more dangerous. They can teach us to stop shooting.

I notice the relief underneath that. When I build a detailed case against something before ever testing it, there is a small feeling of permission not to try. That relief is information too. Sometimes the thing I am calling wisdom is the comfort of not having to risk being wrong again.

Confidence is believing you are still allowed to shoot

A .300 hitter in baseball gets a hit three times in ten official at-bats. That is exceptional. It also means one of the best hitters in the game walks back to the dugout hitless roughly seven times out of ten.

Bring that standard anywhere else and it sounds absurd. Pretty good day, honey, I failed 70 percent of the time. Nobody would know what to do with that. Review an executive the same way and the sentence falls apart. She gets it wrong seven times out of ten, let's give her a massive contract.

The game is not built around avoiding failure. Failure is built into the game. The athlete's job is not to eliminate it. The athlete's job is to remain able to perform after it.

Hockey makes it plainer. Elite scorers miss on the enormous majority of shots they take. The puck gets saved, goes wide, hits a post, gets deflected. Then Ovechkin gets the puck again. And he shoots.

What interests me is not the release or the positioning or the skating. It is what happens inside someone who has taken thousands of shots that did not go in and still wants the puck.

That is where my definition of confidence comes from, and I like it more as time goes on:

Confidence is believing that I'm still allowed to shoot after I miss.

It removes performance from confidence. I don't need the result to prove I belong. The market doesn't have to validate the idea before I test it, and the last attempt doesn't have to have worked before I make the next one. I can survive information, and that's powerful.

Maybe confidence is not the absence of doubt. Maybe it is reducing the authority doubt has over action.

Failure is information until we make it identity

Most ambitious people already have a commitment to winning. Entrepreneurs certainly do. Something has to sit underneath that, and it is a commitment to failure.

That sounds wrong at first. Failure is the admission price for anything where the outcome is not guaranteed. And if the outcome is guaranteed, I am probably nowhere near my edge.

The commitment is not to lose carelessly, and it is not to repeat the same mistake for years and call it perseverance. It is to stay in relationship with a miss long enough to learn from it. Fail small. Keep it cheap where you can. The miss has to arrive early enough that the information still helps. Then look, learn, change, try again.

Failure alone does not create wisdom. Some people fail for twenty years and learn almost nothing. Learning requires attention.

Most of the suffering I have created around my own misses did not come from the miss. It came from what I made the miss mean about me.

This gets especially dangerous after you have succeeded. When you are starting, failure is expected. Nobody thinks you know everything, not even you. After you have built something real, people expect you to know, and you expect yourself to know. Identity attaches to competence. I know how to build, I know how to sell, I know how to read people.

Then a chapter changes. Something that worked for twenty years stops working. A beginner can say, I didn't know, I'm just beginning. The experienced entrepreneur hears something else. I should have known better. I waited too long.

That sentence can become a prison. Once I believe I should already know, a failed experiment stops being information and becomes evidence that I am losing something. So I protect the record. I protect the reputation. And I shoot less.

Belief before evidence, not belief instead of evidence

The line that sits underneath this whole episode came from a show I was watching. Susan Duffy in Reacher tells her partner she does not care about the percentages. Good shit can still happen.

I wrote it down right away.

Percentages matter. Data matters. Patterns matter. I am a student of all of it. The distinction is whether they become information or instructions.

Belief instead of evidence refuses to look. Belief before evidence looks directly at what is here and also knows that what is here does not contain every possible future.

Every important thing that has ever been built spent some period of time when the evidence was still incomplete. That is true of a business, a team that became great, a person who became someone they had never been. Somebody has to live there, act there, and go first. That is often the leader.

Optimism in that form is expensive. It means being the one who believes a little longer. It means looking foolish for a while. It means taking another shot after everyone watched the last ones miss. It means finding out I was wrong.

Criticism is cheap by comparison. Put ten intelligent people in a room with a new idea and they will give you fifty reasons it fails. Sometimes I need those reasons. I want the blind spot named. A strong leader does not silence disagreement. After the reasons have been heard, somebody still has to answer what we are going to attempt.

And about the odds themselves. Percentages describe populations. They do not know the individual standing in front of them. A statistic can tell me how common an outcome is, not which person will be inside the ten percent. It does not know whether someone learned from the last six misses, or whether the team changed.

People hand too much authority to probability. They hear unlikely and translate it to don't. Those are not synonyms. Sometimes unlikely is reason enough to pass, because the cost is too high. Sometimes the downside is a bruised ego, or an afternoon, or the risk that somebody sees us fail. Those are different odds, and I do not want to confuse an emotional risk with an existential one.

What this looks like in a team: the four pillars after a miss

This connects directly to the work I have been doing on Magnetic Leadership, where confidence is one of four pillars.

Confidence allows the next shot. It is the definition above, held by a leader whose identity has been tied to being the person who knows.

Congruence asks whether my actions say what I believe. It is easy to talk optimistically. We're excited about the future, we believe in the team, this is a great opportunity. Then what? If I believe in the team, did I give them real authority? Did I invest in the direction I say I am committed to? When I say a new chapter has started, did my calendar change? And if I lead differently now, what did I stop doing? There has to be a bet.

Calm is what happens in the emotional aftermath of the miss. Anybody can be optimistic after a win. The proposal gets rejected, the candidate takes another offer, the launch disappoints. Push harder, solve faster, take control. Back then I thought I was responding to the problem. Sometimes I was responding to the feeling the failure caused in me. Those are not the same thing. Calm gives failure somewhere to go. Take calm away and every miss becomes urgency, and urgency creates reaction.

Contribution takes this past me. Eventually somebody else needs the puck. This is where a lot of experienced entrepreneurs get exposed. We say we want initiative, then someone initiates something we would not have done. We say think like an owner, then they make an owner-level bet, it does not work, and we pull everything back.

Contribution asks something harder. Can I help someone learn and keep my hands off the wheel? Can I let them miss small enough to get better? If I cannot, I build a team that knows how to avoid mistakes, or at least how to avoid me finding out about them. That is a terrible trade. I do not want reckless people around me. I also do not want people who have learned that the safest career move is never taking a shot the boss already approved.

That is not leadership development. That is dependency. The goal is not a company that never makes mistakes. It is a company that can learn and keep every mistake from becoming a crisis.

Focus, align, act: five things to do this week

This is why Focus, Align, Act means so much to me.

Focus is not predicting the future. It is choosing a future worth moving toward. Align is where I notice everything inside me using yesterday's evidence to decide tomorrow's possibility. This failed before. Our industry does not work that way. Our team is not ready. I can hear that voice and respect the experience that created it, then ask whether it gets a deciding vote. Sometimes the answer is no.

Then act. Take the smallest real shot. There is no need for the hundred million dollar version of a thousand dollar experiment, or the thousand dollar one where ten dollars would do. Small does not mean timid. Small means the information is affordable, which lets you accumulate attempts cheaply. Thinking about the shot does not count. Planning forever does not count. Talking about becoming someone does not count.

Five places to put this to work:

The odds describe what usually happens, they do not decide what you attempt. Find one thing you have recently called impossible. Write down the actual cost and the actual risk of one small attempt.
Confidence means you can miss and still want the puck. Revisit one recent miss. Write only what it taught you. Write nothing about what it supposedly says about you.
Make the failure produce information. Before the next experiment, write down one thing you need to learn even if the outcome you want does not arrive. If I am testing an offer, can it go in front of a handful of trusted customers before the infrastructure gets built? A new role for someone can start as a contained opportunity, long before anything gets reorganized.
Let experience improve your shots, not eliminate them. Take one meaningful action this week in an area where you have no receipts proving you will succeed. If nothing surprises you anymore, experience may have become a ceiling.
Say the belief out loud and give it a consequence. Tell one person on your team what possibility you still believe in. Then make one decision that costs something if you are wrong.

Maybe it matters less whether the odds are in your favor. Maybe what matters is whether there is something in front of you right now worth taking the shot at anyway.