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CHAPTER 03 OF 12 · 8 MIN READ · 8:10 VIDEO

Attitude Is a Choice

The single biggest advantage you have in your career, and the exercise that changes it.

The coach was not there yet. First practice of ninth-grade JV soccer, everyone sitting around on the grass, and on that field I was maybe the fortieth-percentile player. We all knew what a practice was supposed to start with. I said, "We should run laps." Everybody said yeah. We ran two laps, finished, and I said, "We should stretch." So we stretched.

The coach finally turned up a week or two into the season. When it came time to vote for captains, everybody looked at the kid who had said the obvious thing twice.

I want to be clear that I was not a good soccer player. The vote had nothing to do with skill, and it took embarrassingly little: do the obvious thing, be of even minor service to the people around you, give credit away, notice good work without letting it offend you. Pure leadership is gentle. What it took instead of talent was a willingness to open my mouth in a group of kids who could all outplay me, and willingness turns out to be the whole game.

WHERE SKILLS COME FROM

I say some version of this to younger colleagues constantly: the single biggest advantage you have in your career is your attitude. Not your intellect, and not your stack of skills. Run the chain backward and you can see why. Where did the skills come from? Learning. Where did the learning come from? Experience. And where did the experience come from?

A willingness.

"Hey, you wanna try this today?" "Yes." "I think I have a way of thinking about this. Do you wanna hear it?" "Absolutely." Compound twenty years of those small yeses and you get a person with rare skills, and the yeses were the attitude. The willing person gets handed the strange project, sits in the room they were not quite senior enough for, ships the thing nobody owned. The skills are downstream. Everyone hiring and promoting can feel this even when they can't name it, and it is why the fortieth-percentile kid gets the armband.

THE PART YOU CONTROL

In a meeting, a one-on-one, a hiring decision, an outage, a customer ticket, a finance review, the way you act in the moment is barely under your control. Something happens, your brain fires, and you react. There is no time in a live conversation to weigh seven candidate sentences and select the statesmanlike one. Maybe a little of that arrives with age. Mostly, the reaction that comes out of you was decided before you walked in, by whatever attitude you carried through the door. So the leverage is all in the carrying.

Two practical notes on the reacting itself. First: sometimes keep your mouth shut. Sleep on it. The number of situations improved by a fast response is smaller than the number improved by a slow one.

Second: let people think. My resting expression reads as upset, so when a colleague riffs out a big idea and I go quiet and stare at the middle distance, they conclude I hated it. I didn't hate it. You said a lot; I'm still absorbing it; I am, in that moment, a loading spinner. The best working relationships I've had made room for that. In the remote years, a newer teammate once joined a huddle where nobody was talking, apologized, and started to back out, sure they had walked in on something private. We were thinking. Another swore they must be on mute. We heard them fine; we were considering what they'd said. Daphne and I would sometimes mute a mic and not notice for a while, because twenty-five silent minutes on a call was normal between us: one of us had said "hmm," pulled up the problem, and gone into it. Engineers do this to each other all day without ceremony.

One caution before you import the habit. In most companies, everyone in the room is waiting for you to finish so they can talk, and silence gets read as verdict. If you're going to think, say so ("that's a big idea, I'm still absorbing it") and then let the spinner run.

LIST ALL OF THEM

When something is coming that you dread, or that matters, ask yourself: what is my attitude about it? The first time, the answer is usually "I haven't thought about it." Good. Now list the options. All of them, every way a person could possibly feel about this thing. I am dead set about the word all.

I run this with my kids. One of them had gymnastics practice, Tuesdays at four, and things were going well. What's your attitude about practice? "They didn't put me on the team I wanted, so I'm stuck practicing with kids I'm better than." That is a possible attitude, and it's the one that shows up on its own. Keep listing. A few entries later: "I believe not selecting me was a mistake, and every Tuesday at four I get an hour to show the coaches they made it." Same kid, same gym, same facts. The first attitude produces a sulk in a leotard. The second produces the best training hour of the week.

The reason for all is that the first two or three entries on the list are the attitudes you already hold; they are why you needed the exercise. The one you'd choose on purpose is usually sitting somewhere past number five, and you only reach it by refusing to stop early.

RUNNING IT ON MYSELF

I don't much like industry networking events, historically. When one lands on my calendar, the list starts with the attitudes I actually hold: this is a waste of an evening; these people work in a part of the industry that isn't relevant to me; I could be at the gym, or playing tennis, or with my kids; this is boozy noise nobody will remember. All of it feels true, and none of it helps me do the thing I have apparently agreed to do.

So I keep listing, and somewhere down the page I hit: someone at that event has a story that would fascinate me, delight me, and teach me something, and my goal tonight is to find out who it is.

That one changes my behavior before I leave the house. I don't stand in the corner. Every introduction becomes an audition: are you the one? At a dinner recently I met a young founder who had done a dual degree between Harvard and Berkeley. I didn't know that program existed (it's like the Brown-RISD arrangement), and I decided on the spot that this was probably the story. Tell me everything. We ended up deep in a conversation about practicing an instrument as you get older and how the purpose of practicing changes, and I got a real education out of my own evening. From her side of the table, a middle-aged man accounting for his banjo hours is a modest return on the same conversation. I'll take my end of that trade.

THE PREREQUISITE

Every chapter from here forward asks you to walk toward a group of people whose language you may not speak and whose motives you may distrust: sales, customer success, the CEO. Each one starts with an attitude adjustment and only then gets to machinery, because the machinery operated under the wrong attitude just automates your contempt. This course is attitudes and information, in that order, and the attitude half cannot be assigned to you. It is chosen, not installed, and you now have the procedure for choosing it.

THE EXERCISE

  1. Pick the next recurring thing at work you dread: a standing meeting, a review, a person.
  2. From memory, write down every attitude you could hold about it. The ones you already hold go first, in your own words, ugly ones included. Keep going until you have ten.
  3. Run the prompt with your list pasted in, and leave with one attitude you picked on purpose.
  4. Walk in carrying it. Afterward, write three lines: what changed in you, what changed in them, what changed in the outcome.

THE PROMPT

Paste this into whatever AI you work in, ideally one connected to your company's material: Claude Code in a company-brain folder, Cowork, Codex, or similar. Write your list first; the AI does its best work with your own list to check.

There's a recurring situation at work I dread, and I want to walk into the next one with an attitude I chose on purpose, picked from a full list of the attitudes I could hold about it.
The situation: [one or two lines: what it is, who's there, how often]
My list, written from memory before asking you:
[paste your list]
1.Find what you can about this situation in the material you can reach: calendar entries, meeting notes or transcripts, Slack threads, email, docs. Tell me what usually happens there and how I tend to show up, citing what you read. If there's little to go on, interview me, one question at a time.
2.Compare that record with my list. Which attitude does my behavior there show? Which did I leave off? Add to the list until it has at least ten, including a few I wouldn't have come up with.
3.Help me pick one. If I pick something noble that I won't keep up past the next occurrence, say so.
Hand back a short note I can reread before the next one: the attitude in one sentence, what I'll say and do in the first five minutes, and one thing someone in the room could see that would show I'm carrying it.

OR RUN IT AS A SKILL

WHO THIS HITS HARDEST

The earlier in your career you get this, the more it compounds. The senior readers have the harder version of the same assignment: many of your default attitudes were chosen years ago, by a version of you that no longer exists, and they are still walking into rooms ahead of you.

Next: your second boss. Everyone in product works for the CEO, whether or not the org chart says so, and almost nobody acts like it.

NEXT · CHAPTER 04

Your Second BossEveryone in product reports to the CEO, whether the org chart says so or not. The two-sip answer, and the careers it makes.