After Labor Day, everything accelerates. Teachers begin covering substantive material. Tests and papers appear on the calendar. Students must manage multiple deadlines. Fall sports consume afternoons and evenings. Seniors face college applications, while juniors begin the most important academic year of high school. The habits students establish during September can shape their entire school year. […]

Every September I watch the same dynamic play out with families across the shoreline: there’s a strange compression to it. Summer stretches long and unstructured, and then, almost overnight, school starts and the full weight of the academic year — homework, activities, testing timelines, college deadlines for older kids — arrives all at once. Families […]

Junior Year Is When College Counseling Actually Starts to Matter Sophomore year, when I mention college counseling, most families wave it off — plenty of time. By junior year, that changes fast. This is the year the process stops being theoretical and starts requiring actual decisions, and the families who start engaging now, rather than […]

Twenty-five years in, I’ve learned the biggest risk for most seniors isn’t a weak transcript. It’s drift — good students who lose the fall semester to disorganization, missed deadlines, and essays that sound like everyone else’s because nobody pushed them to write something true. Building the List: Fit Before Fame A lot of families walk […]

Every October, I have some version of the same conversation with a junior in our office — recently a student from Madison, sharp kid, solid student — who shrugs when I bring up the PSAT. “It doesn’t count, right? It’s just practice.” Technically, true. Colleges never see a PSAT score. But I’ve spent over two […]

Every fall, I sit across from a senior — sometimes at our office in Old Saybrook, sometimes over Zoom with a family in Guilford or Madison — who says some version of the same thing: “I thought I was done with this.” For most students, they’re right. By October of senior year, the testing chapter […]

My inbox this morning is flooded with thank-you notes from students who just received their August SAT scores. For some, this means admission chances have skyrocketed to their first choice.  For others, the chance of merit aid has dramatically increased.  For all… the pressure is off. For many high school seniors, the October SAT represents […]

Relevant excerpt – published in The Hill: According to a 2025 report by faculty at the University of California, San Diego, a math placement exam for freshmen found that a quarter of those who tested below middle-school level had perfect 4.0 GPAs in their high school math classes. Inflated grades are worse than useless — they lie. Colleges do […]

When I started this work in the early 2000s, I was grateful that my own educational background had prepared me for it. I’d graduated from Georgetown, then Penn Law, and earned a master’s at Penn’s Fels School of Government — years spent immersed in high-stakes higher education as a student myself, before I ever tried […]

A few years ago, I was working with Joe, a sophomore at East Lyme High School in Connecticut. He told me that his teachers, at least two of them, really didn’t like him, and that he understood why. Teens change quickly, and boys in particular seem to do it in fits and starts. They can […]