I went the other way. When I first started out in my career, making more money than I ever dreamed of (low expectations, not huge pay), I still felt poor. Because I thought making $50K, or $80K, or especially $180K after I married, was SO MUCH MONEY that I could have everything I wanted as a kid -- big pot of savings, big house, nice car, makeup from the mall, etc. Basically, financial security + a wealthy lifestyle. But no matter how much I made, I always felt poor, because it still wasn't enough to fund all of that. And worse: at each income level, I was exposed to more and nicer things that I never even realized "normal people" bought when I was a poor kid. I mean, when you're on food stamps, you're not exactly surrounded by people driving BMWs and owning second homes, you know? But plop me down in a law firm, and damn, my lifestyle was much more constrained than everyone else's. I remember shortly after I got married getting Conde Nast Traveler, and reading about all these $400+/night hotels as if that was just nothing, and thinking, man, we make $180K, and I'm not even close to being able to afford that, so who are these people who talk about it like it's just a normal part of life?* I ended up canceling the subscription because it made me feel worse, not better.
OTOH, the MMM philosophy -- and years of experience -- have taught me that chasing stuff willy-nilly will never bring contentment or a feeling of wealth, because there is always something more/better/different. And the more I focus on what I have (which is pretty fucking awesome), the wealthier I feel. Honestly, the day that I realized I never had to work again if I didn't want to was one of the most amazing days of my life. Every day I am conscious of having the privilege of deciding if I want to keep going in to work or not, and there is really no higher privilege than that.
But I am also older than you. So I think it is natural when you are building your assets to focus on what you are giving up; it's hard to constantly turn things down, even when you are doing it for all the right reasons and are overall happy with your lifestyle and choices. But let me tell you, when you're on the other side of the mountain and looking at that nice fat pot o' cash**, that completely goes away. Now, if I want to buy something stupid that I can't afford, I need to give up something -- my freedom -- to get it. And in almost every case, the "thing" just doesn't feel worth the mental weight of knowing I "need" a job again, so I can happily go on my way without feeling deprived at all.
*Also note that my version of normal assumed about a 20%-25% savings rate; at the time, I had not yet realized how unusual that was.
** And by "cash," I mean "VTSAX."