Can someone be ambitious and also remain humble?

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Harvard Business Review goes and poses a good question: “If humility is seemingly so important, then why are leaders often so arrogant?” It’s a good question. If you were trapped on a desert island with a browser that could somehow only access Forbes and Inc and Fast Company, you’d assume humility is the norm in so many organizations, and is constantly being discussed and practiced. Most of business journalism is drivel, and a big reason why it’s drivel is because it talks about shit that’s not happening at all like it’s happening at scale, then every article mentions the same four companies, all of whom are always in Silicon Valley. I digress.

The HBR article then answers the question in the headline with this section:

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There are a few important things to pull out there:

  • “Without hesitation, it means I can tell others what to do.”
  • “Many of us believe that if you’re not winning, you are losing”
  • “Life is fundamentally and always a competition”

I think the thing most people miss is this. It takes a very specific type of person to want to run a big company. It’s almost like being President in a way. By the time you’ve convinced yourself that you should run for President, you are already very ambitious and you probably have a degree of ego.

There are 100 Senators and 400+ Congressmen, 50 Governors, countless State Reps and Mayors and City Councilmen/women. Only 1 person every four years becomes a Governor again, or the President, or some high-ranking role. All the others slide away or keep doing what they’re doing.

It’s similar in companies.

As much as we don’t discuss this, any place over 50 employees has 5–7 people with all the decision-making ability and authority. The rest of the people are doing task work, “making trains run,” or moving projects along. They’re hitting boxes.

They might go up a level here or there, but by and large the top will remain similar for years — barring scandal, revenue losses, etc.

The mentality of those people — still predominantly men — who want to get to the top is so so so so so so much different than the mentality of the people who are down there doing the task work.

That’s the dichotomy of work.

It’s not so much “I am humble doing my task work” vs. “I am ambitious trying to get the corner office” as it is that everything else is different:

  • How you put yourself on the cross
  • How you dress
  • How late you stay on projects
  • The vocabulary you use
  • The situations you try to get yourself invited to
  • What you’ll sacrifice
  • Your worldview

The last one might be the most important. A lot of executive world-beaters do think in the ways you see in that image above. “Life is a competition,” i.e. “I must crush my rivals for market share.” Or “I can tell people what to do,” i.e. “I am protected by hierarchy even if I have no idea what I’m doing.” Same: “If you’re not winning, you’re losing,” i.e. “All I do is win, win, win…”

That’s where work falls apart for a lot of people. It’s that the gap in sheer thinking between those with decision-making ability and those without is so wide. It’s almost like speaking a different language, or speaking to people from a different time. How can I relate to someone who would yell at a MIT professor that he wants to “tell people what to do” when that’s never been something I’ve cared about? How can I believe in “cross-functional collaboration” when some guy who’s telling me to believe that also thinks “life is fundamentally a competition?”

The dichotomy is the essential flaw of work, and no Inc article or robot revolution is going to save that just yet.

Blogging, largely about work and how to improve it. How I make (some) money:

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