getting rid of the ish

Hi kryptokabbage, welcome to the forum. Your question seems to involve what difference there is between humility and self-deprecation, between pride and hubris, between self-esteem and a superiority complex.

We know that people can make themselves feel better by putting others down or holding them in contempt, but this does not mean feeling good about yourself must always come at the expense of another. Some people see this obvious problem but  strive for equality by cutting themselves down to the lowest common denominator and refusing to acknowledge anything about themselves that is above average, thereby not offending anyone with an inferiority complex. But this is self-deprecation, definitely not the solution.

One thing to consider is that you can make improvements to yourself and feel good without letting the ego inflate beyond proportion. For instance, you can try seeing an improvement as giving you increased ability and responsibility to wisely help others improve themselves similarly, if they ask. These are primarily increases in power. Some use power to increase the divide between themselves and others by kicking them down and propping themselves up, and  some use power to increase the unity between themselves and others by lending them a hand. It's the difference between a bully and a friend.

As far as practical advice goes, feeling from the heart and thinking lofty thoughts - getting yourself into a clearer vibrational mode and higher frequency - for a couple minutes automatically puts the ego in its place without suppression. Try feeling good about yourself while simultaneously focusing on feelings of compassion for the less fortunate, respect for those more powerful than yourself, and acceptance that in the end all is well. It can be done, and avoids the problems of self-deprecation, hubris, and snide superiority. Just some suggestions....

I'm sure no one here will be surprised that I'm recommending The Four Agreements.  It just covers everything, imho.

http://www.miguelruiz.com/teachings/fouragreements.html

Very excellent.

I would like to post them here if you don't mind.

1. Be Impeccable With Your Word
Speak with integrity. Say only what you mean. Avoid using the word to speak against yourself or to gossip about others. Use the power of your word in the direction of truth and love.

2. Don't Take Anything Personally
Nothing others do is because of you. What others say and do is a projection of their own reality, their own dream. When you are immune to the opinions and actions of others, you won ­t be the victim of needless suffering.

3. Don't Make Assumptions
Find the courage to ask questions and to express what you really want. Communicate with others as clearly as you can to avoid misunderstandings, sadness and drama. With just this one agreement, you can completely transform your life.

4. Always Do Your Best
Your best is going to change from moment to moment; it will be different when you are healthy as opposed to sick. Under any circumstance, simply do your best, and you will avoid self-judgment, self-abuse and regret.

That's advice we can all take!