"If you could find a way to get Billy in as a pitcher," the e-mail from one of my player's fathers says, "it would really make his day."

It's a simple appeal to boost a nine-year-old's happiness. This is, after all, just little league.

Yet, we're into our sixth game and most of the other boys are invested in our so-far poor results. One mother relates that her son was teased at school and wants to know what we can do about it. "Play harder and get better," I say.

Billy is a likeable boy. He is also one of the reasons we're losing. He doesn't play hard or get better. He doesn't make it to every practice or game. In the outfield he looks in the wrong direction. "Billy, game's this way!" In the infield, he kicks dirt at his feet. "Billy, ready position!" If he is paying any attention he makes a perfunctory twitch indicating that he's ready, but one or two pitches later Billy snaps back to a state of unreadiness. He looks startled when balls come toward him, and on the occasion he gets a hold of one, his shoulder and elbow somehow move in opposite directions. It has to be an optical illusion. The throw itself often sets in motion miscues that end with the other team celebrating.

And now I hear his happiness depends on being a pitcher.

I groan, anticipating that once on the mound--what choice do I have?--he'll hear the opposing bench's cheers and his teammates' quietness as they witness him walk batter after batter. "Come on, Billy!" someone will shout from the bleachers. "You can do it, Billy!" Which, let's be frank, is what you say when no one, least of all Billy, believes you can. The attempt to "make Billy's day" will ruin his and everyone else's. You hope no one mocks him at school the next day.

Little league to middle age

That Billy doesn't see it is one thing. Billy, after all, is nine. But why doesn't his father? "Son," he needs to say, "you're not ready to pitch. Let's practice and maybe you'll get there."

If little league is innocuous enough--or not, given the way competition among boys determines status off the field, too--the situation of people who do not see where they stand, their abilities and limitations, comes up quite frequently well into adulthood. Unrealistic self-evaluations and false encouragement from people who should be candid or know better bring to mind the phrase that the path to hell is paved with good intentions. We're all big on dreams and destiny and vision, and we grasp onto stories about people who, through persistence and determination, proved a naysayer wrong. We like late-bloomers almost as much as prodigies. The message is not to give up. Believe in yourself. Do not let others put you off of your dreams. We are buoyed up by cliches, which begin to obscure the fact that gloom-to-glory tales are exceptions.

When eventually we do accept our own limitations, we pass down our hopes to children, and nurture them to believe they can do anything they set their minds to--a nice idea that's often a set-up to the disappointment that will eventually come to pass.

A professor I know lamented the phenomenon among his masters students. They are educated people by any reasonable standard, and that they're in a humanities-related field shows they are ambitious about knowledge rather than just money. But the leap from masters to doctoral candidates is like single-A minor league ball to the majors, and only a small minority will make it.

"The number of students who don't see that they're not up to it is astonishing," my friend says. "It's not just that they're applying to doctoral programs when they shouldn't be. They're even applying to top-tier schools. You just wonder what they're thinking that they could overrate themselves so badly."

They don't care for being told where they stand, either. A few months ago one of his mediocre students asked him for a recommendation for her application. He recommended that she take stock of her strengths and weaknesses. "I don't know why he hates me," she told another student. It had to be intensely painful to have slogged that far only to realize she wasn't going further. Yet, to the extent that the evaluation was right, it's a pain that was unavoidable.

"I'm a really good writer," a woman tells me. She may be, but in my experience "really good writers" tend not to make bold declarations about their talent. If anything, they seem to carry an excessive load of self-doubt. Invariably it's the untalented who declaim, who assume that success is all about who you know or getting big breaks, who don't understand, even at an advanced age, that if you want to grab the ball and take the mound, you should have an idea of whether you can get the ball over the plate.

Middle age to the beginning of wisdom

In the case of my nine-year-old pitcher, you could argue that there is something worthwhile, maybe even noble, in trying. As the poet Robert Browning put it, "Ah, but a man's grasp should exceed his reach, or what's a heaven for?"

Well, okay. But grasping when you aren't even close, least of all when you haven't really put the time in, when you haven't merited even a noble failure, is just being wishful, if not delusional. A person who keeps chasing an unrealistic dream may feel as if he just can't catch a break. If you realize your vision is a mirage, do you not change course? Where does encouraging someone, either because they're not ready or because they're just not good enough, cross into irresponsible counsel? When is just not trying--in other words, not engaging in futile effort--the better choice?

I suspect that often enough, somewhere in there, the mind and body know, even if they're willing to be deceived. At some point, even if you can't figure it out, colleagues, customers, teammates, boards of directors, profit and loss statements, will enlighten you. Disappointment is a grim reaper.

If all of this seems terribly negative, there is something to be said for striving for what is attainable. It's less stressful.

At my local coffee shop, I run into a man who has always seemed to me comfortable having made reasonable accomplishments, a man who had the wisdom to reach for the attainable and live in good humor.

"How do you feel?" I ask.

"Old, fat, and ugly."

"And otherwise?"

"Otherwise I'm all right, thanks for asking."

He doctors up his coffee with milk and sugar and walks out through the door, his silhouette framed by the white light of a sunny morning.

I wonder if 60 years ago or so, he had hoped to get a chance to pitch.

Todd Pitock, a long-time Juggle contributor, daydreams in Villanova, PA.