We are a commune of inquiring, skeptical, politically centrist, capitalist, anglophile, traditionalist New England Yankee humans, humanoids, and animals with many interests beyond and above politics. Each of us has had a high-school education (or GED), but all had ADD so didn't pay attention very well, especially the dogs. Each one of us does "try my best to be just like I am," and none of us enjoys working for others, including for Maggie, from whom we receive neither a nickel nor a dime. Freedom from nags, cranks, government, do-gooders, control-freaks and idiots is all that we ask for.
We and others have written about the topic of self-esteem and self-respect ad nauseum. There is healthy narcissism and unhealthy narcissism; there is healthy self-hatred and unhealthy self-hatred. Pride is a mortal sin, but pride in a difficult accomplishment seems like a good reward.
We generally consider self-respect as something which must earned against some inner or outer obstacles, struggles against fear, temptation, or external resistances and challenges. We generally think of self-esteem as similar to self-administered mother's love or God's love. That is, unearned and undeserved. A modest dose of that never hurts and few of us are thoroughly evil or worthless. A good dose of humility never hurts either. We all have plenty of reasons for self-contempt and self-disappointment, and those deserve our attention however unpleasant that may be. I do not trust people who are not open to doing that job on themselves.
Are you sure that you don't have the descriptions of self-esteem and self-respect reversed? It seems to me that esteem is something to be earned and respect something innate. Esteem comes from accomplishing something to be proud of, respect is a simple courtesy afforded everybody simply by virtue of their existence. If I worked hard to become an accomplished musician, I might interchangeably be considered an esteemed musician or a respected musician, but it seems to me esteem would come from recognition of my hard work moreso than respect which would be more a recognition that I'm a good musician without getting into whether it was a result of my hard work or just my luck at being born with an innate talent. Which brings up my concern with various "pride" movements - how can you be proud of something you had nothing to do with? Proud to be Irish or gay or left-handed? Why? It's not like you had a choice. Proud of my chili recipe or my baseball card collection or knife-throwing skills? Sure - because I worked hard at those things. Self-esteem can come from knowing you're better than most people at some particular skill, self-respect comes from knowing that just because you're not as good as others at a particular thing it doesn't make you less of a person.
And as far as a good dose of humility goes - if you're doing it right, the more you learn the more you learn how much there is you don't know. A truly ignorant man is only ignorant of one thing, and that's how much he doesn't know. A wiser man knows he's ignorant of an infinite number of things.
That you get wiser with age is true in general. But now that I've gotten a healthy dose of the age thing I wonder if it's just that the world has had more time to beat you about the head and shoulders.
After WWII, there was a study about self esteem. It concluded that high self esteem was more often associated with evil - after all who had more self esteem than the SS? - and that lower self esteem was more highly correlated to charitable deeds - those who think they are not good enough are motivated to do good to prove they really are valuable.
I don't think anybody would say that high self esteem in and of itself is toxic, or that lower self esteem necessarily makes a better person, but the fetish about raising the self esteem of kids is at best a waste of time and at worst, damaging.
I believe one of the important functions of Christianity in Western Civilization is that it teaches humility. If you (and your life) is no more valuable than that of another, you are much less likely to mistreat or kill another.
The self-esteem movement in the US was a back asswards catastrophe. Rather than kids naturally feeling good about themselves because they had actually accomplished something significant, the LEFTISTS decided that if a kid felt good about himself, he would accomplish great things.
The problem was, they tried to make kids feel good about themselves by rewarding kids for doing nothing, e.g. participation trophies, accolades for crappy work, etc.
I used to coach high school wrestling. When I started, there was ONE state champion for each weight class. Now, there's a Class 1A champ, a 2A champ, 3A champ and 4A champ.
Football's even worse with so many classes that it's common for 3 (wins) & 7 (losses) teams to make it to the playoffs.
The kids get the inflated notion that they're "great" - until they graduate, enter the big world and find out that they really suck. It's not that they didn't have the potential to be great.
It's that they had little incentive to do the work that would have transformed their potential into actual greatness because they were given the message that they had already achieved greatness.