Nice piece, as usual. According to this I've retired quite a few times.

I was very lucky when I first went self employed, and earned a shitton of money for many years in a row. I was very unlucky, that I was together with someone very transactional and manipulative (and I was unaware of how easy it was to manipulate me) and no matter how much money I made, I was still living at (and often above) my means.

It took a hard wake-up call from a couple of good friends to get me to back to living well under my means (one of my retirements). It was very sobering to look back at how much money I had basically burned over many years for no increase in long term happiness (or even mid-term in many cases).

I think it was Jim Carrey who said (I paraphrase) he wished everyone could become a moviestar millionaire so that they could realize they don't need it. I never wanted fame. Fortune is very relevant.

"Happiness is not having what you want, it is wanting what you have" is something I never forget.