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By Anastasia Mills Healey

Artwork by Justin Negard

We all know overachievers. A National Merit Scholar who pitches for the state champion baseball team while also starring in the school musical, working in the office of an elected official, and discovering an enzyme critical to understanding a disease. This type of multi-talented student is what Lisa Bleich, the author of “Surviving the College Admission Process,” says colleges used to look for, but now, they’re interested in students who are more “angular” instead of “well-rounded.”  This way, when applicants with a variety of different focuses are admitted, the student body is well-rounded.

According to Stephanie McCaine, an independent college admissions advisor and founder of Hamlet Education Group in Katonah (who previously worked in admissions at colleges and a private high school), this could look like “having an in-depth experience that covers different aspects of the one thing that you really enjoy—it could be working in a lab but also volunteering for an organization or tutoring younger students.” But she advises, “If you aren’t clear on a passion, don’t do things just to check a box. Everybody knows when you’re doing things to check a box. It’s very obvious.”

Application stats

  • Colleges receive 12 million applications annually.
  • 1/5 of students apply to 10+ colleges.
  • In the last five years, Common App submissions to selective colleges have increased by 30 percent.
  • Between the classes of 2026 and 2041, the number of high school graduates will decline by 13 percent in what’s called the “demographic cliff,” but applications are not expected to decrease.

Source: Jeff Selingo, author of several books about college acceptance, including “Dream School,” released this September.

“We’re not counting up the number of involvements applicants have,” says Jennifer Gayles, director of admission & inclusive outreach at Sarah Lawrence College. “We really just want to see what excites them and what they have been committed to. We’re a small school; we’re building a campus, a class each year that brings students from all different backgrounds and experiences. So, the application really helps us not only assess that they’re prepared for the work they’re going to do here but also that they’re going to be an engaged member of the campus community.”

This certainly doesn’t mean that there’s no place for multifaceted applicants. Gayles says some students with disparate interests, like history and music, are drawn to schools like Sarah Lawrence for their open curriculum. “We often talk about our students being hyphenates,” she says.

Caitlin Read, dean of enrollment management at Purchase College, SUNY, says the same types of interdisciplinary studies are possible there. “We had a student last year who was interested in both chemistry and visual arts, and her senior project was developing organic paints.” Read thinks the trend around “well-rounded” students stems from applicants trying to impress Ivy League institutions “when things were shifting from being difficult to get into to impossible” and from a lack of clarity around admissions without standardized tests. “As schools have gone test-optional, who gets in and who doesn’t becomes more opaque,” she explains.

Tips from Jennifer Gayles, Sarah Lawrencc

  • Be authentic
  • Don’t pad your activities on your résumé.
  • Organization is key.
  • Be aware of differences in colleges’ application criteria.
  • Keep notes, especially about what you see and learn on tours.
  • Ask someone you don’t know well to read your essay.
  • Show demonstrated interest in different ways.

Control the narrative

Read says her office encounters “well-rounded” applicants, as “a lot of students are figuring out what they’re interested in. And what we would like to see is, if students have been involved in a million different things, how are they understanding their journey? For these students, control the narrative and provide some context. So, it’s not like, ‘Well, I tried things, and I didn’t stick with them.’ The narrative may actually be that they’ve learned a lot about themselves and their interests from those experiences. They’ve made friends. They may even have found out what they’re not interested in and see it as positive that they put themselves out there, that they tried things, even if it didn’t ultimately end up being a direction they wanted to take.”

Tips from Caitlin Read, Purchase College, SUNY

  • Do the supplemental essay(s).
  • Think outside of the 10 schools everyone applies to.
  • Listen to your school counselor.
  • Use tools like Naviance and BigFuture to develop your list.
  • Control the narrative.
  • Parents must let kids drive the application process.
  • Visit campuses in person whenever possible.

McCaine explains that colleges examine student activities outside the classroom for several reasons, and understanding this can help frame the narrative. They care about “your time management skills, your ability to work with others, your ability to express and communicate your ideas…How do you tolerate challenges? How do you challenge yourself? What do you do when you hit a roadblock? Because all those things happen in high school. Maybe you’re taking your AP courses, or you’re balancing your sports and your social life and academics. And that’s why colleges want to see what else you’re doing. It’s not just strictly about whether or not you are engaged in your community. It’s about how you manage the different aspects of who you are and your life, because that’s what you’re going to need to do independently, ideally, when you go to college.”

Approach college applications strategically

Instead of adding the pressure of a plethora of activities to pad an application, our panel advises students to pursue what interests them and take the time to research a wide range of colleges because “there’s a lid for every pot—there are well over 3,000 colleges in the United States,” McCaine says. And instead of “trying to mold kids to schools,” she says we “need to start doing a little less reverse engineering and identify where your kid is going to thrive. Where are they going to grow? You shouldn’t have to be someone else to fit some other school’s vision of what a student should be.”

Tips from Stephanie McCaine, Hamlet

  • Education Group
  • Understand the baseline of student expectations for each college.
  • Be authentic.
  • Don’t be swayed by trends.
  • Deeply research your top choices.
  • Clean up your social media.
  • Don’t set unrealistic expectations.
  • Not every student needs to take the SAT.
  • Don’t reverse engineer a fit.
  • Be aware that admissions and incentives can come after May 1. Colleges that aren’t reaches might provide incentives.

Read says students should try to find a good fit by “thinking about what kinds of disciplines they are interested in, what kinds of careers might be of interest, and the activities available. Also, do they feel comfortable in a big school or a small school? Do they want to be close or far from home? And then, once you have a few schools, you can also find similar schools.” McCaine reminds parents that the college landscape has changed and to remove unrealistic expectations. “Try to remember that you would not even get into the school you attended, so why are you asking your kid to go to a school that has a single-digit percentage admission rate?”

Once students have a list, Gayles advises they show interest by visiting, attending virtual events, meeting a representative at a college fair, and submitting any supplemental essays, as “the fact they’ve taken the extra step to answer a question that is more specific to the institution” shows engagement.

Above all, McCaine wants to remind families to frame the college application process in a positive way. “What we put kids through these days is crazy,” she says. “This should be a really exciting time. When I was in high school, I loved looking at the brochures and dreaming of sitting under the tree on a blanket with my friends. It was totally romanticized; it was exciting. There’s a whole world of possibilities.

This article was published in the September/October 2025 edition of Connect to Northern Westchester.

Anastasia Mills
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A former editor at Condé Nast Traveler, Fodor’s, and Travel Agent, Anastasia Mills Healy is a Greenwich-based writer and editor who writes for Time Out, Lonely Planet and others, and is the author of “100 Things to Do in Connecticut Before You Die” and “Secret Connecticut.” 

Creative Director at Connect to Northern Westchester |  + posts

Justin is an award-winning designer and photographer. He was the owner and creative director at Future Boy Design, producing work for clients such as National Parks Service, Vintage Cinemas, The Tarrytown Music Hall, and others. His work has appeared in Bloomberg TV, South by Southwest (SXSW), Edible Magazine, Westchester Magazine, Refinery 29, the Art Directors Club, AIGA and more.

Justin is a two-time winner of the International Design Awards, American Photography and Latin America Fotografia. Vice News has called Justin Negard as “one of the best artists working today.”

He is the author of two books, On Design, which discusses principles and the business of design, and Bogotà which is a photographic journey through the Colombian capital.

Additionally, Justin has served as Creative Director at CityMouse Inc., an NYC-based design firm which provides accessible design for people with disabilities, and has been awarded by the City of New York, MIT Media Lab and South By Southwest.

He lives in Katonah with his wonderfully patient wife, son and daughter.