tl;dr: Challenge for its own sake *is* probably pointless; but challenge for the sake of getting better at meeting challenges is good, because life is challenging.
I just read Carol Dweck's "MindSet"... in all the books I've reading during this self-help kick, I think its identification of Fixed Mindsets vs Growth Mindsets is the most useful concept.
Precocious kids are prone to developed a Fixed Mindset, feeling that their intelligence and abilities are intrinsic, critical to why they are special, maybe even why they are loved. While that's not a sure recipe for unaccomplished lives, the tendency to seek only those activities that will validate their self-image, and also to lash out with anger at the external "causes" of their failures, is painful and ultimately self-limiting.
Describing the core of the Growth Mindset is trickier... and I don't think that's just because it's not my native outlook (for most things, anyway) -- its a more nuanced belief. It holds that the value of life is in the process, that abilities and intelligence are plastic and that constant growth and striving are the hallmarks of a life well-lived. In some ways, it's the opposite of a "goal-oriented" outlook; rather than apply a cost/benefit ratio like I always do, favoring low-hanging fruit, a person with a good Growth Mindset will reject things that are too easy as unworthy of their time and attention; much better to get a good challenge that can teach, even if the "good" results are less assured.
(One of the implications of a Growth Mindset is that maybe a bit of masochism is a good thing! And I can certainly see traces of my own Fixed Mindset in stuff like exercise... huffing and puffing during an activity that someone more fit would find easy is humiliating, and that's what I would focus on, rather than believing in a capacity for physical development.)
For a long time, I thought Challenge for Its Own Sake was borderline psychotic. But now I can see that challenge for the sake of being better at rising up to meet future challenges is probably crucial, because LIFE IS CHALLENGING. No matter where we are with intrinsic or developed abilities, whatever accomplishments dot our portfolios, the world can provide interesting challenges that we shouldn't shirk from for the sake of our precious egos.
So, changing my mindset is going to be... a challenge, Meta-ly enough. But I might be well placed; I've always disliked "trusting my gut instinct", and learning that my gut-instinct fear of having my ego bruised is masquerading behind an intellectual mask of "cost/benefit ratio" is empowering.
It's also a mindset I'd like to help instill in the brains of my friends' kids. Most of my friends are pretty smart, and their kids have lots of potential, and are probably already ahead of their peers in a lot of ways. Instilling the love of the struggle is tough; it isn't as easy to admire a struggle as it is to just say "you're smart!" and "you're so talented!" but I think the end result would be worth it.
Why I make Terrible Decisions; or, Poverty Thoughts Simply and clearly written and eye-opening. (Cracked.com actually has some similar pieces, thoughtful but in a more juvenile style: http://bit.ly/1cHLl0U ) I've got friends going through the muck of this and I don't know how to help them find an exit.
'Embarrassment is ignorance leaving your body.'