CEOs are not always normal people. What are some of the more extreme, intriguing habits or practices of CEOs you have worked with or encountered?

CEOs often start off as normal people, but then the job after maybe 18 months … rewires your brain.

What changes:

  • Your mind thinks about work 24x7x365 — in some fashion. This does not mean being in the office constantly, or not taking vacations. It does mean your mind is constantly thinking of new ideas, how to fix problems, how to recruit new team members, how to update your product, etc.
  • You become obsessive-compulsive about your product, at least up to $50m+ in ARR. Being there from Day 0, you know all the issues and gaps. Having visited 100+ customers, you know what they need. You’ll see every pixel that is off, even part of the app that is slow, everything.
  • Imposter Syndrome grows, rather than shrinks, over time. The better you do, in fact, often the more insecure you feel. DropBox or Slack or Zoom or whoever is always growing even faster than you. This is odd and not expected.
  • Your family stops understanding (as much). It is too much for the family to deal with all the startup near-death experiences, the dramas, the founder conflict, etc. for more than the first 6–12 months. It’s too much. You can’t drag them into everything forever. As part of that, they start to not understand as much what you are going through.
  • You get much more efficient and effective. You gain a superpower. You know how it all works together. Often, you can do amazing things in 5–10 minutes that it would take others days to do. More importantly, as time goes on, you’ll be able to see things in the future and the present that others may need months to see. You have to channel this, and be careful how often you burden others with this superpower, however. Otherwise, you can quickly overwhelm the team here.

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Published on December 18, 2018

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