So, I'm perplexed with how to get him past the "I can't do it!" attitude. Over the past several months, I've seen a bunch of examples of things he's excited over, but then turn out to be "too much work", and he just goes back to reading a book (granted, a fairly advanced book, but still...).
Welcome to my life... and I know I am not alone.
My son -- just like yours, apparently -- has been conditioned to expect relatively easy mastery of everything he attempts. In my meetings with his school earlier this year, I would explain that we've got to do something now, because he's really getting used to rolling out of bed every morning and already knowing all the answers. That really was the extent of the effort required: Wake up, go to school, get A's. Lather-rinse-repeat.
And then came the litany of "it's too hard" when exploring a variety of extra-curricular interests -- same as your son. And at that point, any encouragement from me added fuel to the fire, because I was "making him do something hard." And then all the fun was gone.
Finally, through his piano practice, I was able to work with him and bring him through the "it's gonna be hard" process, finally with a modicum of success in recent months. He just finished his 3rd year of piano lessons, and most of the time he would lose his mind when a song didn't come instantly. "It's too hard... I hate this..."
So I required a short face-to-face pep talk at the beginning of each lesson as we worked on the more complicated piece(s). I really, really, REALLY stressed the fact that nobody expects him to play a song perfectly on the first try... or even in the first couple of weeks. Before he puts his fingers to the keys, we come to a solid agreement about our expectations for the practice. And I would set the bar at "Spectacularly Stinky!" for how I expected the song to sound at the end of practice number one. And with the next practice, we would shoot for "Slightly Less Stinky" and so forth -- keeping some humor in the descriptions and strongly emphasizing that we were not aiming for perfection, only incremental progress.
I kept up this strategy despite his occasional eye-rolling, but it did finally hit home. He began to ease up on himself and the frustration (for both of us) lessened dramatically. He was much more at peace with his sometimes hideous first attempts, and went through the step-by-step process of polishing one small section at a time. This was a HUGE leap for him, and he continues to improve.
I've recently had some success with him in other areas: he's learning the Rubik's cube, he's started the trumpet, and he's rediscovering his chemistry set. With each activity I revisit the initial goals, reminding him that he's not going to meet with success on the first try - or sometimes not even the first dozen... or more. And I'm also reminding him to celebrate the little successes along the way.
I think your instinct is spot on about needing to teach him how to follow-through with a challenging task or project.
I believe that allowing him to drop something at the slightest discomfort only reinforces the damage done by years of obtaining A's without any effort. And hopefully, after tasting the sweeter victory that often comes after overcoming a challenge, he'll become addicted to that instead!
