Written this morning to a mom on a message board whose 6yo son is unwilling to try anything new:
Some kids tend to learn internally, and they love being able to surprise people by learning with almost no apparent effort. For whatever reason, they're under the impression that they're loved and valued for what they can do, rather than for who they are; their self-worth is tied to achievement. Because of that, they find it frightening to risk failure as they begin to work their way gradually up a learning curve. They'd rather not be a bike-rider than be seen to have tried and (at least temporarily) failed.
There are a lot of things that can be helpful with kids like this (I've got two of them, 13 and 10, so I've been in your shoes), but none of them are going to be quick solutions. It takes years to gradually shift things.
There's a good article here on this type of child, and the praise that may be contributing to his unwillingness -- or at least not helping the situation. It points out the importance of shifting the focus of praise from achievement to specific feedback about good effort, and I think this is crucial.
It's important for parents to model mistake-making. Taking up something that's difficult for you, and working away at it on a near-daily basis in front of your child, humiliating mistakes and all, helps show him that mistakes are all part of the game.
Play games with mistakes. Guessing games are good. "Guess My Number" is a good one, because each wrong guess ("Is it twenty?" "Too big." "Ten?" "Too small.") becomes a clue. This is a great metaphor for trying to learn a new skill like reading... mistakes are our friends, they help us get closer to the right answer.
Consider enrolling your son is a hobby or interest that (a) is individually paced (b) requires regular practice (c) involves the sequential and parallel accumulation of multiple component skills that are built upon each other. Swimming lessons, tae kwon do or some other martial art, piano lessons, gymnastics, flute or violin might fit the bill. As a parent you'll need to put lots of effort into supporting him as he continues to learn, but that successful long-term learning will serve as a touchpoint for him in other areas of his life. You'll be able to say "Remember when your tennis serve almost never went over the net? But by practicing every week, it got better and better and by your second year, you had a real serve!" And he'll sigh and realize that he just needs to keep plugging away at memorizing his three-timestables.
Document, document, document. Find ways to show your son that even at the earliest stages he is making progress. He probably has his eyes on the peak of the mountain he's trying to climb, and so any progress he makes is probably going un-noticed. Point out to him that he's making good progress in the more immediate scale of things, encourage him to notice the work he's doing as he follows his learning path, and he may feel more satisfied. Direct his gaze to more immediate things, rather than that far-off mountain-top. For reading, you might start a Reading Dictionary with him, a booklet of alphabetized words he can read. Use a Hilroy exercise booklet, and put a letter of the alphabet on each 2-page spread. As you notice that he is able to read words, write them in. In the beginning a child might have two or three words only -- his own name, stop and no. In another few days, there might be six words ... and no, he's not a fluent reader of novels, but it's clear that there has been progress. The form your documentation takes will vary depending on the task. Sometimes it might just help to have a chart that you colour in showing the amount of work that's been put into a task (say, for bike-riding ... how many 5-minute sessions has he put in?), or photographs showing the progress of a project like a garden, or camcorder documentation of something like piano playing.
Be clear and conservative with your stated expectations. Don't say "come on, I'll bet if you really tried to ride your bike you could get it down this weekend -- you're so close!" This sort of 'encouragement' increases fear of failure, because it makes it clear that you expect his success fairly quickly and suggests that you will be disappointed if he doesn't achieve this. Instead say something like "If you can do a five-minute try on your bike with me 5 times a week, I think that by daddy's birthday in September, you will be able to ride. And you might learn sooner than that, who knows?" Prepare him for the fact that it's not going to come quickly, that you do not expect his success to come quickly, but that you know it will come in good time.