Leadership comes more naturally when you’re able to find alignment and flow between career and values.
Much of this comes down to how well you understand yourself and your own motivations.
What does your definition of success need to look like?
Is there a driving purpose and/or intrinsic motivation at the core of what you do?
Intrinsic motivation is doing an activity for its inherent satisfaction rather than for some separable consequence. In other words, doing something you love …
Being CTO is much easier (or at least less challenging) when working on something you love, rather than a motivation driven by less intrinsic factors, pressures or prestige.
Paul Graham wrote a wonderful essay How to Do What You Love including a passage about the “false friend of prestige” …
“What you should not do is worry about the opinion of anyone beyond your friends. You shouldn’t worry about prestige. Prestige is the opinion of the rest of the world. When you can ask the opinions of people whose judgement you respect, what does it add to consider the opinions of people you don’t even know?
This is easy advice to give. It’s hard to follow, especially when you’re young. Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.
That’s what leads people to try to write novels, for example. They like reading novels. They notice that people who write them win Nobel prizes. What could be more wonderful, they think, than to be a novelist? But liking the idea of being a novelist is not enough; you have to like the actual work of novel-writing if you’re going to be good at it; you have to like making up elaborate lies.
Prestige is especially dangerous to the ambitious. If you want to make ambitious people waste their time on errands, the way to do it is to bait the hook with prestige. That’s the recipe for getting people to give talks, write forewords, serve on committees, be department heads, and so on. It might be a good rule simply to avoid any prestigious task. If it didn’t suck, they wouldn’t have had to make it prestigious”
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