Episode 28 | The Essays Nobody Talks About Until It’s Too Late

Here is something that catches almost every family off guard.

They spend months focused on the personal statement. They feel prepared. And then August 1 arrives, the Common App opens, and the supplemental essays appear. Multiple prompts per school. Multiplied across ten, twelve, fifteen schools. Suddenly the writing workload is enormous and senior year has not even officially started.

This week on the podcast I am breaking down exactly what supplemental essays are, why they matter more than most families realize, and how to get ahead of them this summer — before the chaos of application season hits.

If you want to walk away with one thing, let it be this: the supplemental essays are where students have the most opportunity to stand out. They are also the most commonly underestimated part of the process.

Here is a quick overview of what we cover:

The Why This College essay is the most common supplement and the most misunderstood. Admissions readers are not looking for compliments about campus beauty or program rankings. They are looking for proof that your student actually chose this school specifically — which requires real research, specific details, and genuine connection between what the school offers and who your student is. Generic answers are visible from a mile away.

The Community and Identity essay gives students a chance to show something that does not appear anywhere else in the application. Not necessarily a dramatic identity story — just a genuine answer to what your student brings to a community and why.

The Intellectual Interest essay rewards students who have actual curiosity about something specific. Not a career goal. An intellectual thread. A problem they keep thinking about. A subject they would explore for free.

Short Answer questions are their own skill set entirely — punchy, specific, confident, under pressure. They take practice and they are worth taking seriously.

The good news is that while specific prompts change slightly year to year, the categories almost never do. A student who develops strong core answers to each category this summer and then customizes them for each school is in a completely different position than one who starts from scratch in October.

That is the whole strategy. Identify the categories. Develop the core content. Customize when the prompts drop.

Hit play for the full breakdown — including the practical five-step summer roadmap and what Josh and I are already mapping out as we build toward his senior year.

Here with you every step,

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Picture of LINDSAY PHILLIPS

LINDSAY PHILLIPS

High School Counselor and Independent College Counselor with over 10 years of experience. Self-proclaimed helicopter mom of two teen boys.

hi! I'm Lindsay!

High school counselor and self-proclaimed “helicopter mom” to two eye-rolling teenage boys. With over a decade of experience herding cats (ahem, working with students).

My mission? To transform the college admissions process from a stress-inducing nightmare into a family bonding adventure.

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