There’s a lot of books written by CEOs that are filled with advice about what to do, but not many talk about what it’s really like mentally and emotionally to be a CEO, especially the profound sense of loneliness that comes with the job. Ben Horowitz’s The Hard Thing About Hard Things was the first business book I read after becoming a CEO that realistically described what it’s like (especially for someone doing it for the first time):
This means that you will face a broad set of things that you don’t know how to do that require skills you don’t have. Nevertheless, everybody will expect you to know how to do them, because, well, you are the CEO.
Much of the book is an extended pep talk for founder CEOs struggling with the demands of a high-growth startup environment, where each day can bring a new existential threat to a still-fragile firm:
If there is one skill that stands out, it’s the ability to focus and make the best move when there are no good moves. It’s the moments where you feel most like hiding or dying that you can make the biggest difference as a CEO. In the rest of this chapter, I offer some lessons on how to make it through the struggle without quitting or throwing up too much.
And having weathered quite a few such existential crises as a CEO himself, Horowitz’s pep talks rise above just rah-rah motivation and read more like a cold splash of water on the face:
There are always a thousand things that can go wrong and sink the ship. If you focus too much on them, you will drive yourself nuts and likely crash your company. Focus on where you are going rather than on what you hope to avoid.
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Great companies don’t hire skilled people and motivate them, they hire already motivated people and inspire them.
— Simon Sinek
I spent much of my career at O’Reilly Media, where, as happens at many companies, there are quarterly “all-hands” meetings. My favorite thing about those—especially early on when I was still pretty low on the proverbial totem pole—was hearing Tim O’Reilly talk about what the plans were for the months and years ahead. There aren’t many people out there who get more excited talking about the future than Tim O’Reilly, and I usually left those meetings incredibly inspired and feeling like I was part of something that really was helping to change the world.
At one of those meetings, Tim shared a story that I remembered quite vividly, so much so that I smiled when I saw it show up in Simon Sinek’s book “Start with Why”:
Consider the story of two stonemasons. You walk up to the first stonemason and ask, “Do you like your job?” He looks up at you and replies, “I’ve been building this wall for as long as I can remember. The work is monotonous. I work in the scorching hot sun all day. The stones are heavy and lifting them day after day can be backbreaking. I’m not even sure if this project will be completed in my lifetime. But it’s a job. It pays the bills.” You thank him for his time and walk on. About thirty feet away, you walk up to a second stonemason. You ask him the same question, “Do you like your job?” He looks up and replies, “I love my job. I’m building a cathedral. Sure, I’ve been working on this wall for as long as I can remember, and yes, the work is sometimes monotonous. I work in the scorching hot sun all day. The stones are heavy and lifting them day after day can be backbreaking. I’m not even sure if this project will be completed in my lifetime. But I’m building a cathedral.”
While I’m sure some of it was natural talent, Tim has become a master at showing people those cathedrals, and convincing them to bring their tools and get to work. But for the rest of us who could use some help in the Inspiration department, Sinek’s book is a must-read.
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