I think about this a lot, both in IT and civil infrastructure. It looks so trivial to “fix” from the outside. In fact, it is incredibly draining to do the entirely crushing work of real policy changes internally. It’s harder than drafting a blank page of how the world should be.

I’m at a sort of career crisis point. In my job before, three people could contain the entire complexity of a nation-wide company’s IT infrastructure in their head.

Once you move above that mark, it becomes exponentially, far and away beyond anything I dreamed, more difficult.
And I look at candidates and know-everything’s who think it’s all so easy. Or, people who think we could burn it down with no losses and start over.

God I wish I lived in that world of triviality. In moments, I find myself regretting leaving that place of self-directed autonomy.
For ten years I knew I could build something and see results that same day. Now I’m adjusting to building something in my mind in one day, and it taking a year to do the due-diligence and edge cases and documentation and familiarization and roll-out.
That’s the hard work. It’s not technical. It’s not becoming a rockstar to peers.
These people look at me and just see another self-important idiot in Security who thinks they understand the system others live. Who thinks “bad” designs were made for no reason.
Who wasn’t there.
And somehow I think this is the mental unburdening conceit of Authoritarians.

Everything is possible, tomorrow, when you don’t care about endemic complexity of real-world problems and the humans already architected to try to solve them.

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I’ve always felt that the luckiest people I know had a talent for recognizing circumstances, not of their own making, that were conducive to a favorable outcome and their ability to quickly take advantage of them.

In other words, dumb luck was just that, it required no awareness on the person’s part, whereas “smart” luck involved awareness followed by action before the circumstances changed.

So, was I “lucky” to be born when I was—nothing I had any control over—and that I came of age just as huge databases and computers were advancing to the point where I could use those tools to write “What Works on Wall Street?” Absolutely.

Was I lucky to start my stock market investments near the peak of interest rates which allowed me to spend the majority of my adult life in a falling rate environment? Yup.