When raising a child, is it most important to stress the practical aspects of life, and the reasonable limits of expectations in life, based on the life experience of the parent, or to stress the possibilities for life, and to encourage following ones heart, or dreams?
Balance is always a prudent goal, though I’d err on the practical (read: realistic; or in your own words: reasonable) side.
In another sense: Is most important for a child to see the world as it is, or for what it could be?
As it is. Truth trumps mere possibility; the actual is superior to the potential. Plus, one’s ideals for the future are only feasible after due regard for the facts of the present. And a lot of them border the Utopian and are in fact less realizable than many a naive Romantic [read: liberal] dreams. An idealist is inevitably a cynic; and cynicism breeds pessimism along with a bitterly hardened heart that often isn’t very open to the Holy Spirit.
The world isn’t so cruel a place when one considers that success within it has very little to do with material comfort, power, feelings of content, or lack of suffering. In fact, as a parent I’d focus my child less on a future within this world than I would on one in another. As a husband and father, and thus as protector of the family spiritually prior to even resoursefully and physically, a man’s chief duty is to help secure a spot in Heaven for those over whom he has natural authority. (Generic truth; not necessarily assuming you’re a husband, parent, or even male.)
For example: Is it just as important to dream of being President one day, as it is to plan for college?
Since the child will not be President, but will most likely go to college, no. Further, I wouldn’t worry about a child’s acquaintance with self-esteem boosters, or even a borderline narcissistic faith in his own individual efficacy, considering public school and Hollywood still exist. (If I’m not mistaken, the “self-esteem” movement is still alive and strong in elementary schools; and happily-ever-after movies will always bank more.) The trouble with building too much hope in a kid, it seems to me, is that when he’s able to think on his own and expose certain comforting lies, he’ll suddenly suspect
everything you told him of bearing a similar false character and heart-warming function. That’s probably why a lot of folks “outgrow” God.
Lastly, I
suppose I ought to disclaim that I’m pretty young and that my only real experience with kids comes from a period of my life roughly between the ages of three and twelve. Anyway, your question made me think of one side of Kierkegaard’s (false) Either/Or:
*[T]he aesthete uses artifice, arbitrariness, irony, and wilful imagination
to recreate the world in his own image. The prime motivation for the aesthete is the transformation of the boring into the interesting.
This type of aestheticism is criticized from the point of view of ethics. It is seen to be emptily self-serving and escapist. It is a despairing means of avoiding commitment and responsibility. It fails to acknowledge one’s social debt and communal existence. And it is self-deceiving insofar as it substitutes fantasies for actual states of affairs.*
Source: Stanford Encyclopedia of Philosophy, entry on SK]
But at least they’ll have the optional viewpoint. Many peoples dreams are frustrated in this life by factors outside their control-disease, place of birth, etc. And, if we do become satisfied with anything this world has to offer, we’d be settling for something far less than what we’re made for.
Where did you find such a wide brush to paint such a broad brushstroke? 
