In the end it's all relative to your expectations. For example let's take 2 different people; "A" and "B".
"A" has rich parents (few hundred million). "A" has rich friends. "A" enjoys expensive past-times. "A" currently lives off around $1,000,000 per year (mortgage, food, entertainment, etc.). Most of "A"'s associates have a similar lifestyle. If "A" loses all of his money and is forced to take a job at $150,000 a year then he'll be absolutely miserable. He'll feel poor because all his friends and associates have so much more, and because he's become accustomed to a way of life he can no longer afford.
Now person "B" has a blue collar job, no savings, and makes $50,000 per year. "B"'s parents are not rich, but were always able to put food on the table. "B"'s friends and associates all live fairly similar lifestyles. If "B" is suddenly handed a magical supervisor role that pays $150,000 a year he'll feel absolutely rich. He'll have more money than any of his current associates. He has more money than he even knows what to do with.
Both "A" and "B" now make the same amount of money, but "B" is happier than "A" and it has everything to do with expectations, and since they have the same amount of money, then money must not be a direct factor.
You can keep taking this further until you hit a point where there's not enough money to cover bare necessities. This means that every single $ you make above the bare minimum to live a healthy life is unnecessary if you manage your expectations. For many of us it's easier to make more money than manage our expectations though. If you're barely scraping by on a $100,000 salary, maybe it's time to step back and examine your expectations and priorities.
+1, I think all of this is true and wise, but I will offer a contrasting perspective. I think it is good to have high expectations, not so much financially but in general.
I was working a stable, dull job, had a quiet social life, and was reasonably happy and content. But I decided that I could be living much more. I quit my job, moved cross country, started and finished a Ph.D. program, got an academic job, and also got much more adventurous in my social life. Across the board, my life was characterized by a lot more hardship, failure, and painful exposure to things which I wanted but were out of reach.
My life has been much, much better as a result. I am actually making much less money than I would be if I had kept on at my old job, but I raised my expectations relative to the life I was living, and this made all the difference.
It's in our nature that achievement makes us happy. I think it has something to do with Dopamine being released into our brains.
What I've found to be the secret for myself is that I only appreciate something as much as the effort it took to get it. It doesn't really matter what it is I'm trying to get, how much I enjoy the result seems to depend entirely on how much effort it took to achieve. If I work my ass off for $100, then it might feel like the best $100 I ever made. If someone hands me $1,000,000, I won't turn it down, but I won't care about it nearly as much as that hard-earned $100.
So setting realistic but challenging goals keeps us happy. If the bar's too low we don't appreciate the gains. Too high and we can lose our motivation.
Money can be part of those goals but it doesn't have to be.
It really starts to blow your mind when you start applying this principle to everything in life (I'm not running a cult or anything, ymmv).
How do you know this? You didn't live the other life, so you seem just to be speculating about how the other life may have turned out. You know know that the life you chose really is better.
This question is, in my experience, the crux of many people's depression.
I realize that may seem to be hyperbole but consider that it is a question that cannot be reasonably answered. Even when it seems like it can, for example a friend of mine was stressing over the fact that they did not take a job offered to them by a startup, the startup was acquired and the person who did take the job did quite well. They felt like they had been 'stupid' to not taking the job, but everyone knows a company is the sum of its people. With the different mix the outcome could have been different.
I sometimes joke about knowing that I never invent time travel, because if I had I would have gone back to the summer of 2000 and told myself to cash out of equities. My wife said, but what if doing that prevents you from having the set of experiences that lead to you inventing time travel? Or maybe future-you sees the value of the path you took vs 'other' road you did not take.
Fundamentally you have to decide, move on, and accept. As a parent it is especially hard to do since you not only don't have any sort of manual on what the right thing to do is, everyone's child is different and so the 'right' thing is really impossible to know apriori.
So perhaps its not so much knowing that your life has been better because of your previous decisions, its more about understanding that the quality of your life, its 'betterness' if you will, is a combination of variables and that you've always decided to be true to your principals. So having solid principals for making those decisions you can be satisfied with your part in how your life has turned out.
I am comparing my life now to my life eight years ago, and also to some extent the life of my friends who are still living in the same town and working at the same company.
As far as how my other life may have "turned out"... I guess I'm not really sure what that means. I think the one comparison I can really make is if I had not made a lot of changes. Of course it is possible that I could have changed my life in some totally different direction, maybe without leaving town, and life would have been even better than my life now. That, of course, I can't guess.
But I feel conviction in my bones that I did right.
If you hadn't made any changes your life would have been exactly the same. And if you had made changes at a later point hen it would have been similar to ones your making now.
I think people underestimate how much work/effort/time it takes to change ones perspective.
"A" has rich parents (few hundred million). "A" has rich friends. "A" enjoys expensive past-times. "A" currently lives off around $1,000,000 per year (mortgage, food, entertainment, etc.). Most of "A"'s associates have a similar lifestyle. If "A" loses all of his money and is forced to take a job at $150,000 a year then he'll be absolutely miserable. He'll feel poor because all his friends and associates have so much more, and because he's become accustomed to a way of life he can no longer afford.
Now person "B" has a blue collar job, no savings, and makes $50,000 per year. "B"'s parents are not rich, but were always able to put food on the table. "B"'s friends and associates all live fairly similar lifestyles. If "B" is suddenly handed a magical supervisor role that pays $150,000 a year he'll feel absolutely rich. He'll have more money than any of his current associates. He has more money than he even knows what to do with.
Both "A" and "B" now make the same amount of money, but "B" is happier than "A" and it has everything to do with expectations, and since they have the same amount of money, then money must not be a direct factor.
You can keep taking this further until you hit a point where there's not enough money to cover bare necessities. This means that every single $ you make above the bare minimum to live a healthy life is unnecessary if you manage your expectations. For many of us it's easier to make more money than manage our expectations though. If you're barely scraping by on a $100,000 salary, maybe it's time to step back and examine your expectations and priorities.