I didn't read this as him wanting people to feel sorry for him. He repeatedly says if it's challenging for high earners to deal with student loans, then what about people in lower earning fields? The point was education costs are getting beyond ridiculous for everyone and we need to try to put the brakes on that.
We can all criticize the apparent choices people have made, but that doesn't change the fact that education costs are insane right now. It doesn't take into account the reasons people make some of those choices. Some people choose locations because they want to be close to help care for aging parents, or near family with their kids, or spouse is still in training there, or not moonlight across the country because of kids, or be paying for elder care, etc. It's not always the ego and the Benz holding people back.
I just took a huge financial hit to move back and care for my grandma. This meant I made $15,000 less in a higher cost of living area. I just get by now, break even. My choice? Yes. Poor choice? Yes. Would I make it again? Yup. Does the fact that this was my choice mean I can't be frustrated with the state of higher education costs and vent that frustration? Nope. Tuition costs are ridiculous regardless.
We could all probably make better financial choices, but I'm fine with this piece and someone pointing out "I'm a high earner and I'm having a hard time with this, so imagine what regular folks are going through."