Talking with your kid about college when he’s a freshman in high school—or even at the end of eighth grade—may seem premature. All that stuff will work itself out in a couple years, right? Think again. The financial aid and college admissions process will be stressful no matter what, but waiting will only make it worse. By not talking about your kid’s college possibilities and your own expectations now, you could end up disappointing him (and let’s face it, yourself) down the road if he’s thinking one thing and you’re envisioning another.