I have worked with many different people from all kinds of demographics. We all have a mind and we all have body. When the body changes though the mind is sometimes slow to catch up. Particularly if your image was not that great to begin with (what is truly defined as outer beauty is up to you, I'm purely going over why the there is the gap between change and realisation).
I wasn't poor as a kid, but times weren't great either. I remember when I started to work, make money for myself. Really make money at times. I remember buying a pair of designer sunglasses - when I put these things on, instant confidence, I felt like I was 'the man' and everything was perfect.
That was many years ago, the reality is they are just sunglasses, they always were. I own about 5 of a similar pairs right now, I could put a different pair on each day and I feel... about the same.
I've been relatively fit for at least the last 10 years, and well I've always been handsome (its a fact) So why did a pair of sunglasses make me feel so good about myself? But then years and experiences later I couldn't get the same feeling from multiple pairs. Its the same as the body, it doesn't matter if you look 'good' or not. Progress equals happiness - the sunglasses didn't change my appearance. They were just a symbol for me that I had 'made it', or at least done something relatively positive to go from wearing second hand shit as a kid.
The same way someone ridiculously over weight goes to the gym for the first time and afterwards feels like me putting on those sunglasses (more likely on the drive home from the gym then actually been at the gym) or the skinny kid does one weight session and goes home in mirror and flexes like Arnie.
It's got nothing to do with how you look, its about being proud of yourself, knowing you've done the work and knowing your moving towards you next goal.
Progress = Happiness.
Sure there are things easier for an attractive person - dating, job interviews, not wearing clothes. But all those things are just are not happiness, just things that can be enjoyable, maybe not the interview.
The same can be said for 1 million dollars (or a pair of sunglasses), many people say 'if I had more money I'd feel good', unlikely though, there's incredibly financial people that are still unhappy, stressed and even over weight or unhappy about how they look.
Which is what we are talking about, how you look. It comes down to self love, self awareness, self esteem. It's got nothing to do with the dollars in the bank or the numbers on the scale, NOT EVEN THE NUMBERS ON SOCIAL MEDIA.
Set goals, surround yourself with positive people, express gratitude everyday, learn to train for the enjoyment of the training (Crazy I know) instead of just doing it for the desired result.
Like anything it takes practise.
The same way you see the incredibly over weight guy in speedos strutting down the beach not giving a fuck. Or the guy at the red light driving the Ferrari staring at the guy in rusted out shit box with the pretty girlfriend next to him.
Having more does not silence that feeling of 'when I get x I will be happy'
'be happy with what you have, while you pursue everything you want'
There is no direct answer, but hopefully this stops you from forever chasing that next pair of sunglasses.