A question that often comes up, sometimes a bit quietly:
“Are we already behind?”
In almost every case, the answer is no.
But it’s easy to feel that way, especially given the tendency most of us have to compare ourselves to others. Should my child be at batting practice every evening? Should we be insisting on math enrichment? Should my child be learning a second, or even third, language by now? Is it too early to begin test prep? Is it okay to send my child to summer camp instead of summer school?
Parents are not wrong to ask these questions. We want what is best for our children, and we want them to have open doors to their futures. And the last thing we want is to fail them when early preparation might have made a difference.
Curiosity Over Accomplishment
The good news is that there is no perfect path and no perfect future. There is not a formula for high school or college preparation or college admissions. What matters most in middle school is that we expose our children to a variety of opportunities that might just create enough of a spark to kindle curiosity. And, at this age, curiosity matters more than accomplishment.
But middle school and high school move fast. (Remember that old adage about parenting? Long days, short years.) It won’t feel like long before your middle schooler has morphed into an uneasy teen about to apply to college. Suddenly, your child is asked to craft a narrative that weaves together their high school experiences, their academic path, their choice of extracurricular pursuits, their commitment to community. For many students, the questions on college applications force them to piece together a whole from disparate pieces. Perhaps nothing creates more unnecessary stress for parents and students than the realization that their high school choices could have been more intentional, more aligned.
Intentional, Not Urgent: A Different Kind of Plan
Imagine instead, a thoughtful plan that provides direction and perspective beginning long before the word ‘college’ lands on the family dinner table. A plan that is not urgent, but intentional.
If that kind of clarity would be helpful, Kate is glad to talk it through with you.
Beginning With the End in Mind
When I think of counseling students at younger ages, I am reminded of the work of Grant Wiggins and Jay McTighe, who first introduced the idea of “backward design” in their 1998 book about curriculum and instructional planning, Understanding by Design. As a longtime educator, I place great value on the idea of beginning with the end in mind. Applied to college planning, this approach, starting with a goal and then planning activities that support it, ensures that each decision a student makes is aligned with a desired outcome.
What Backward Design Looks Like in Practice
Consider, for example, a student who loves to write and dreams of attending a selective college, perhaps to study literature, perhaps to pursue a different humanities discipline. It’s too soon to tell. But that student knows enough about her interests to be able to make some thoughtful decisions with an outcome in mind. With intentionality, she might consider summer programs that align specifically with that interest or explore adjacent ones. She might decide to write for the school newspaper, form a book club in her local area, found a club at school. Maybe she chooses to submit something she is writing, a research paper for class, a short story, to a contest or a magazine. Perhaps the debate team begins to interest her, or mock trial, two other activities that require her to write and think critically. Now, when college applications ask her to articulate her interests, she has a narrative, one that she built authentically and with a goal in mind. That is backward design.
Careful planning leads to clarity and confidence. Starting early can make a difference.
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She began her career at Kent School as an English teacher, coach, dormitory faculty member, and assistant athletic director, developing a deep understanding of students both inside and outside the classroom. After earning her master’s degree from Northwestern University, she joined Westminster School, where she ultimately served as Director of College Counseling, guiding students and families through academic planning and highly selective admissions.
Kate later held senior leadership roles at Pomfret School and for 12 years at The Winsor School, where she oversaw grades 5–12 academics, supervised college counseling, conducted mock interviews, and helped shape institutional strategy.
Having worked as a teacher, advisor, college counselor, academic dean, and associate head of school, Kate understands how admissions decisions are made — and how to position students thoughtfully and authentically. Today, she focuses on what she values most: partnering one-on-one with young people to help them tell their stories with confidence and purpose.
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- The One Habit That Matters Before High School - April 22, 2026
