Because when I moved to America at 16 and had nothing, and was homeless so I could pay for college, I didn't give care about how I looked relative to others. And if I spent my money impulsively or even worse cared about impressing anyone other than myself, I'd likely be in crushing debt right now just like most people who appear to be "living the life". Last I checked, hard work is not privilege.
Nobody likes to talk about how the "self made people who need their privelege checked" did before they were well off. Not the pitfalls, not the multiple years of 90 hour work weeks.