It depends on how one describes 'bragging.' There's a very fine line between being confident in one's abilities and being boastful, and what looks like confidence to one person may seem boastful to another. So this is something to take into consideration.
If someone can *actually* do the things they're bragging about, sure, let them brag. If they can't they're just going to look like an ass and Lord knows there are plenty of those out there. On the whole, though, I don't think it's helpful as it encourages people to be content with the progress they've made and then stop. Be content, enjoy the fruits of your labours, but then realise there's a time to move on, too.
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As the water grinds the stone, We rise and fall As our ashes turn to dust, We shine like stars... --Covenant, "Bullet"
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