You seem to think that I am making a negative judgment here. His lifestyle is fine with me and I assume he is a great person. He clearly has made many smart decisions around things like building lasting wealth through real estate and keeping good relationships with his family. He also clearly values his flexibility and his lifestyle, looking for 100% remote jobs almost exclusively. He talks quite a bit about the tax code and his three houses and how he wants to renovate them and use them to make money. However, if you look at the time spent on these things, it pretty strongly suggests that he prefers these things to programming/engineering.
I don't judge him as a person for this. In fact, he's probably better as a friend than many of us who did sacrifice a lot of this stuff for a career. Unfortunately, many careers in knowledge work are "up or out," and if you don't choose "up," "out" will be chosen for you.
Fair enough, but I don't think you realize how the original comment comes off. There's a lot of wiggle room in the terms "interested", "engineering", and "unremarkable", but the way I take it is: if one hasn't become a legend in their field by age 40, not only do they not deserve a job, they don't deserve to be here (since they're clearly not interested in engineering).
You're right on many of these points and I probably take it personally because I'm coming up on 20 years and am unremarkable. You never know what people went through to get where they are.
I went to a cheap state school, didn't major in CS despite wanting to desperately because my family convinced me it was a bad move, graduated into the GFC, got pigeonholed into QA for a while, spent years getting my masters in CS, wasted energy on side projects for many years, cared for sick family members for many years, struggled with major impostor syndrome and insecurity.
I've done things I'm proud of and I made it to FAANG after all that, but am unremarkable. It's kind of offensive to then hear that I'm not interested in engineering because I'm not a Distinguished Engineer or whatever.
If you made it to a FAANG without going to a top 20 college, there's a near 0 chance you are unremarkable. The rest of the story more than confirms that you aren't coasting.