I just started reading Benjamin Franklin's Autobiography. This paragraph surprised me:
And lastly (I may as well confess it, since my denial of it will be believed by nobody), perhaps I shall a good deal gratify my own vanity [by writing this]. Indeed, I scarce ever heard or saw the introductory words, "Without vanity I may say," but some vain thing immediately followed. Most people dislike vanity in others, whatever share they have of it themselves; but I give it fair quarter wherever I meet with it, being persuaded that it is often productive of good to the possessor, and to others that are within his sphere of action; and therefore, in many cases, it would not be altogether absurd if a man were to thank God for his vanity among the other comforts of his life.
Fascinating! Thank God for vanity? Wow...
But you know, it makes some sense. It seems to me that modesty is good when it helps you achieve what you set out to achieve, and modesty is bad when it stops you from achieving what you set out to achieve. Whether modesty is effective or not depends on the situation. Some situations call for it. Some don't.
It seems to me that there's a certain kind of pragmatic humility that'd always be good to have. Knowing what you don't know, knowing that there's a lot of skills you don't have, understanding that even your best reasoned judgment of a situation might be overlooking some details...
That's good. But it seems like being modest (and not vain) would work for you in some situations, and against you in others. Sure, the excessively modest person will rarely be criticized, but he might also miss an opportunity to share valuable work he did, to connect with good people as a result of that work, and so on.
I've felt this way for a while, but I couldn't find a way to put it before reading the above. "Most people dislike vanity in others even if they're vain themselves, but vanity has some benefits to the man that has it and others within his sphere of action."
Third parties outside your sphere of action will usually react in a unfavorably to any vanity they see. Especially people that dislike you anyways. But when it's appropriate, a little vanity can go a long way towards promoting important things you're doing and lighting the path you've walked for people who want to follow later.