Every Job Is Either A Perfectionist Game Or A Risk-Taker Game - 10/01

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📰 Today's Edition: Every Job Is Either A Perfectionist Game Or A Risk-Taker Game

School taught you a very specific way to win. Follow directions. Work hard. Ace everything inside the lines somebody else drew. Take almost no risk, and you get rewarded for doing things right.

Then you graduate, and the game quietly changes.

What made you successful in school may have very little to do with what makes you successful in a career. Plenty of people who were mediocre students are doing extremely well now. Plenty of straight-A kids are stuck.

The reason usually comes down to which game somebody is playing and whether they know it.

What are the two games?

Jobs generally break down into two groups.

The perfectionist game. You do everything right, and you're successful. Mistakes are expensive, and there's no upside big enough to cover one.

The risk-taker game. You can get most things wrong. What matters is that the things you get right are enormous.

Perfectionist roles: surgery, practising law, loaning money.

Risk-taker roles: baseball hitter, poker player, angel investor.

Obviously there are many paths to success, and success doesn't have to be financial. But it's striking how cleanly roles sort into these two buckets. The risk-takers have to take risks, because they need a big outcome to make the whole thing work.

Why is angel investing the opposite of lending money?

These two look like cousins. In both cases you hand a company money and hope more comes back. The skill sets are opposites.

An angel investor thinks in portfolio construction. You're hunting for one or two companies that knock it out of the park. If one company does 10x, that barely registers next to a company returning 100x. How big your winners are is what drives your returns. The number of wins is close to irrelevant.

Now flip to lending. Your upside is capped at the interest you charge, so you can't afford mistakes. Every borrower needs to pay you back. Your success is measured by how many wins you have, which makes lending a perfectionist game from top to bottom.

Same transaction shape. Completely different mentality.

(I've been told hippocorns make poor loan officers. Something about a horn and an inability to say no to a good story.)

Can you play both games in the same job?

Yes, and this is where it gets interesting, because the answer changes depending on how far you zoom in.

Take a product manager. On a career horizon, being a PM is a perfectionist game. You want to do well at every PM job you hold. Being amazing at one company and then bombing the next seven roles is a bad career.

Zoom into the individual tasks inside the role and the game flips.

Years ago at Google there was a PM who was outstanding. What made this person outstanding was laser focus on one thing. They were bad at, or simply ignored, most of the rest. Emails about anything outside the main focus went unanswered. They bailed on side commitments constantly.

But the one thing they owned moved the needle for Google enormously. Inside that role, they were playing the risk-taker game and playing it well.

You might handle the bedside manner differently. The point stands: you can be a perfectionist on one time horizon and a risk-taker on another, inside the exact same job.

Are you really on your one shot?

Founders get this wrong constantly.

I hear entrepreneurs putting brutal pressure on themselves because they believe they need to do everything right. This is the one company. The one shot. Every decision feels load-bearing.

Zoom out a layer and the picture changes.

Most entrepreneurs get many chances at building companies. Look at what a founder's career actually looks like over twenty or thirty years and it resembles an angel portfolio. Instead of investing money into 20 companies, you're investing time into maybe 7 ventures across a career.

A founder's portfolio is far more concentrated than an investor's, but the shape is the same. And that should take some pressure off. You can afford to play the risk-taker game here.

You don't have one shot. You have several. They don't all need to work. Statistically most of them won't. You need one to work really well.

Why does the wrong game hurt so much?

Because playing the wrong game makes you miserable and ineffective at the same time.

Perfectionists in risk-taker roles spread themselves across everything, do a competent job on all of it, and never produce the outlier result the role requires. The angel investor who avoids losses ends up with a portfolio of safe 2x outcomes and no fund returner. The founder optimizing to avoid failure builds something reasonable that nobody cares about.

Risk-takers in perfectionist roles cause damage. Nobody wants a surgeon who swings for the fences on nine patients hoping the tenth is spectacular.

The mismatch also shows up in how you feel about your own work. If you're beating yourself up over dropped balls in a role where only the big win counts, you're grading yourself with the wrong rubric.

So which game are you playing right now?

Run the question at three levels.

Your career. Over the next twenty years, do you need a consistent track record across many roles, or do you need one outsized outcome that makes the rest of it noise?

Your current job. Inside this role, is the reward for doing everything competently, or for getting one thing extraordinarily right?

Today's decision. The choice sitting in front of you this week has its own answer, and it may not match the other two.

Then act accordingly. If you're in a risk-taker game, stop apologizing for the things you're dropping and go make the one thing enormous. If you're in a perfectionist game, stop chasing the heroic swing and go tighten your process.

Most people never ask the question at all. They just import the rules they learned in school and wonder why the results feel off.

Until next time,

Dunky, the "risk loving" hippocorn

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