pride

I do not believe pride and self-respect to be synonomous

not to get into a discussion on semantics
but,
the dictionary defines respect as "a feeling of appreciative, often deferential regard; esteem; Willingness to show consideration or appreciation"
and there are many definitions of pride, ranging from "respecr for oneself", to "the correct level of respect for the importance and value of your personal character, life, efforts, or achievements" to "a haughty attitude shown by somebody who believes, often unjustifiably, that he or she is better than others, or deserves more"
so let me be clear when I say that I don't believe them synomous, I have to clarify that I think the search for one's own correct level of of respect for their importance is needlessly internalized and an impossible circular journey. One apt to lead to too much ego and and too little humility. It seems to me that it should simply be enough to know that you are of unique value and and importance to yourself, and as such you should treat yourself well: choose a life that can make you happy, and people who can recognize the value in you, and the richness your effort and character brings to their life. Anything more is ego,and apt to lead to that final definition of pride, and anything less self-defeating and demoralizing.

And so, as I get older, I find increasing circumstance that leads me to believe these qualities to be at odds, often mutually exclusive to eachother
Self-respect if about making choices about how you wish to live, love and communicate your needs. It's about prioritizing what makes you feel fulfilled and happy, and finding ways to meet your needs in an ongoing fashion. It's about seeing yourself for who you are and what you want, in order to get that, and to give to those around you who can share in mutual fulfillment.
it's about accepting the inevitability of compromise, but seeking that which is most essential to your own happiness.
Respect, it seems to me, is a continuum,and if you see yourselves as any part of the world around you and the environment you create then you need to foster respect in those around you to build it in yourself, you need to believe in others abilities to make valuable choices for themselves, you need to show regard and consideration for their needs, and you need to believe in their fundamental desire to the same for you if you can expect to build this confluence of esteem.
Self-respect is implicitly pragmatic.
Pride is about that face the world sees. It's about the ego and the need. About self-protection, about ourselves in our most isolated and defensive posture.
And yes, sometimes you need to have a little pride in order to achieve some self-respect.
But I've found that often pride rears it's ugly head when one employs the least introspection, and respect, both in it's shared and inwardly directed form, requires a certain seperation from our ego to see how other's needs and desires intermingle with our own.
You can't demand respect any more than you can force another to have hold you in high regard. It's a self-defeating prophecy.
But ideally, with the right amount of mutual consideration, you can earn it, you can inspire it, and you can find a way to do without ostentatious odes to your value and power, when you understand that those around you really do care about you, really do perceive you as a person of consequence.
And it's funny to me how people are most likely to call upon the great deity of respect when their pride is injured and their ego bruised. In these moments pride employs the all the naiivette of optimism and the self-defeating blindness of pessisim, and the pragmatic spirit of respect flees out the back door.