I've followed Ryan's writing over the years, especially since our careers were on a parallel path throughout most of his time as CEO. I've led a company that had a difficult time in achieving a PFM and as such everything else was painful. And I was also blessed to have a perfect PFM in another company. I think I've seen enough of the spectrum to be able to say that Ryan's writing is not reflective of the job itself, but more of his perception of it, which I am not even going to try to analyze. This is not meant as an attack at Ryan, but more as a data point for anyone else who is considering becoming a CEO and is feeling discouraged from reading too much of Ryan's stuff.

The job has its downsides, and the worst thing that can happen to you is 1) be a first-time CEO, 2) have no PFM, and 3) have no safety net. If you hit that trifecta, it's not going to be easy. But here's the deal - you'll get through it, and you'll come out on the other side with a much improved mental model that will allow you to be more successful in your next go around. You may or may not ever achieve market-level compensation, and you may even end up in debt. But it will get easier each time you try, it will come the closest to being your own boss, you will learn more than doing anything else, and most importantly, you won't turn 70 and think of yourself as having not taking enough chances in your life.