I think he lost touch with real life along the way. He is Rich and writes to HENRY’s. He doesn’t seem to understand why middle class folks get to FI with much lower expenses and it feels like he dismisses us as the ones with rose colored glasses. And he doesn’t understand why we react to him badly.
He successfully FIREd, but then in his words he got “bored.” He wrote about how he just couldn’t stomach how much money he was leaving on the table by not working during his highest earning years. His is a textbook case of someone who struggles with the concept of “enough” and of how retirement should not be the end-goal, but a means to an end. IN other words, he saved enough to be FI and then retired with no real plan for post-FIRE life.
What bugs me is he doesn’t seem to recognize that pitfall. His experience with ER was miserable even though his financials were solid. Ironically, since then he’s argued that the financials (e.g. the ‘4% WR’) are not to be relied upon, yet he hasn’t recognized that his ‘failure’ was due to having a solid financial plan but a very ambiguous life plan.
He could have just said “hey, I learned FIRE isn’t for everyone and I find great meaning in my work, and here’s my latest financial models” and he would have continued to resonate and be relevant (see Michael Kitces). Instead he decided to shit all over the FIRE community because it wasn’t for him, and to write a long series of intentionally outrageous click-bait articles filled with massive errors all to drive traffic (and revenue) to his site. He likes money more than his integrity.