I really only stopped caring what people thought after I got divorced (I was 43 at the time). Before that, it was 'the big house', 'the bmw', 'running the cool business'.. ostensibly, showing off to everyone else how impressive I could be (I wasn't). I felt like a fraud because I hated what I was doing. Others still had more money, a bigger house, and a cooler car. It was an arms race and I was losing. But when all of that was stripped away after the divorce, it was again, just me.. along with my three young kids in my two bedroom apartment. I realized that all of that was stupid, and really didn't contribute anything to who I really was. I was forced to do only what was absolutely necessary.. to stop being selfish and focus on my kids and rebuilding my life. Although I was struggling, it was liberating. Now I could regain what I lost: money, sure..I was always pretty good at my job, but mostly my humility. I didn't come from much, which I used to wear as a badge of honor when I was younger. Losing a lot of 'stuff' made stop caring about where I lived, or what I drove. I could just simply 'focus' on what I personally felt was important, not someone else's arbitrary standard. Now I drive around my neighborhood (in my 12 year old honda) looking at all the late 30-40 year olds racing inexorably towards their collective mid-life crises, doing their home improvements, driving their Teslas that they can't afford, berating their kids because they're not impeccably perfect in every way and I think to myself : 'yeah, I know.. it's coming for you too'..