Two insights from an undergraduate accounting course completed in the late Pliocene: 1) I was not destined to be an accountant and 2) sometimes a product can be used for that which it was not intended originally. A warehouse full of football helmets were determined to be unsafe. The helmets had a defect and could not be marketed as helmets. But maybe the company won’t have to write off the entire cost of their factory full of imperfect football helmets. Because it’s possible that the helmets could be used for some other purpose—as flower pots, for example. Selling the discounted and dysfunctional helmets as flower pots would be better than tossing the helmets in the trash because I could never quite wrap my head around how to write off the entire cost of a “product” or possibly a “liability.” Or was it an “equity” or an “income”? Again, I did not and do not have an accounting brain. But I did learn that extending consideration beyond preconceptions can be worthwhile. Apparently there is a whole world that exists beyond the end of my nose. My understanding of my trip to Rock Point School in Vermont was straightforward: I would lecture on my book, Get Your Kid into the Right College. Get the Right College into your Kid. I felt confident about my ability to give this talk because I have been discussing this topic for some 30 years now with anyone who will listen. Coleridge’s Ancient Mariner has nothing on me. Wake me up at 2:00 am and I’ll start mumbling about how John Glenn—US senator all all around successful hero-type guy—went to Muskigum College rather than Harvard. So I thought the talk went pretty well. Rock Point parents and members of the Burlington community seemed eager to consider my suggestions. Their questions were on point and thoughtful. It was also empowering to hang out with the Rock Point folks: their head of school is a visionary educator; their admissions department is brilliant and thorough; their teachers are endlessly patient and dedicated. I enjoyed a campus of like-minded educators. Some schools I visit shut down at 3:01 in the afternoon. At Rock Point, the staff never goes home. Most employees live within a hundred yards of campus. The residential educators interact with students around the clock. Shared purpose and great campus food. What could be better? Here’s where my brain went off the rails: I was pleased to sit in on a faculty meeting where a roomful of compassion educators discussed how to best support students without enabling them. I had little to add to the conversation so let me summarize—“steal” is such an unpleasant word—the consensus: to distinguish between supporting and enabling, “follow the child” as Montessori suggested some years ago. A student who shows up for extra help, acknowledges her deficits, embraces her learning differences, and wants to succeed is entitled to every support and scaffold. Tutoring, extra help, support for her executive functioning issues—all are appropriate. On the other hand, there are students who refuse gentle guidance of any kind and subvert the integrity of every positive suggestion on their behalf. “Ben” declined to attend class at his small, nurturing college. He did not show up for tutoring or therapy, preferring violent video games, Internet pornography, and Cheetos. Nor did Ben attend mandatory meetings with the dean of students to discuss repeated disciplinary infractions. Harassing women, public drunkenness, false accusations against professors, and—proving *everything* is available on the Internet—sending elephant shit to his roommate. “Hey, he pissed me off,” Ben explained. The dean was unimpressed with Ben’s rationale and insisted that Ben.enroll for subsequent semesters. Ben’s mother, rather than getting Ben the help he needed, hired attorneys, unethical educational consultants, and a public relations firm to help Ben be reinstated to the college. Ben’s mother argued that the college had not understood or the nature of Ben’s learning differences. “What is it about elephant shit that we did not understand?” asked the dean. Ben’s mother is the poster child for enabling rather that supporting. I was grateful to the wonderful faculty and staff at Rock Point School for helping me make this distinction. We want to help our children in every way we can, but there comes a point where helping is hurting. Not everyone deserves a seventeenth chance. Football helmet might be flowerpots, but Ben does not yet deserve to be a student anymore than I deserve to be an accountant.