Benjamin Caldarelli, M.A. '04, Coaches the College Bound
By Lia Kizilbash Gillet 

Benjamin Caldarelli, M.A. '04, guides students through the college application process and takes them on a journey of self-discovery. (Photo by: Monica Khana)

Calm. Organized. Confident.

Ask any high school student in the midst of the college admissions process and it's unlikely they will use words like these to describe their experience.

As an independent educational strategist and college admissions coach, Benjamin Caldarelli, M.A. '04, helps his clients feel all this and more. Caldarelli, founder and chief counselor of Benjamin College Consulting, works with students during their high school years and as they face the daunting tasks associated with college applications and, more significantly, self-discovery.

Now based in New York City, Caldarelli started his practice in 2009 while he was also teaching English at Arizona State University.

"I enjoyed the classroom, but it was often individual writing conferences where I could really get to know students and inspire them to do their best work," Caldarelli said. "Not just for a grade, but for themselves."

While his counseling practice initially focused on coaching Phoenix area high school seniors through their numerous application essays, Caldarelli quickly realized how many students could benefit from more comprehensive college guidance and decided to take the plunge into full-time counseling. Today, he works with high schoolers throughout the country and international students from around the globe via Zoom. 

"The national statistic is one school counselor for every 400 students," Caldarelli said. "On average, they receive a total of 38 minutes to plan their future. That's simply not enough."

Caldarelli says that while some students come to him with clear ambitions, many have a more vague sense of their hopes and dreams. When students come to him for advanced planning much earlier in high school, Caldarelli is able to help them develop a personalized roadmap to explore their interests in greater depth. He helps break big ideas into manageable and actionable pieces, and students gain foundational knowledge and skills to take their learning well beyond the classroom. Regardless of when they start, Caldarelli helps students develop a strategic approach to the entire college preparation and admissions process.

Caldarelli considers himself akin to a modern-day Socrates.

"Through mentorship and coaching, essentially continual questioning, I can highlight the relationship between their academic achievement and the intellectual vitality colleges are looking for," Caldarelli said. "I try to nurture their curiosity, creativity and philosophical reflection."

After high school in Chicago's western suburbs, Caldarelli attended the University of Illinois Urbana-Champaign, where he received a bachelor's degree in political science and English. 

"It's an excellent university, but given what I know today, I see how easy it was to overlook other advantageous options," he said. "It's part of what drives me to help students find schools that are the best academic, personal and financial fit for them. I visit an average of 20 to 30 campuses annually so I can advise students and their families based on first-hand knowledge." 

NIU, however, was well-suited for Caldarelli, where he pursued a master's degree in literature. He arrived on campus committed to a career in education and excited to join a community that cared about books as much as he did.

"There was something very special going on inside Reavis Hall," he said. "I was reading night and day to keep up with three graduate seminars and trying to figure out how to teach the two sections of freshman English I was assigned. Professors David Gorman and Brian May were exceptional. The books we read and our conversations 20 years ago have stayed with me. Many books from their courses with my notes scribbled in the margins sit on the shelf next to my desk today. Most of all, they challenged me to not only think deeply, but to write with clarity and arrive at insight."
 

When asked what books he recommends as a "must read" for the college application process, Caldarelli says there are many but offers Who Gets In and Why, by Jeffrey Selingo, for a behind-the-scenes view into the workings of an admissions office and Man’s Search for Meaning, by Victor E. Frankl, for inspiration and understanding how the pursuit of higher education can develop from a larger purpose. Caldarelli is also authoring his own book, The Citizen Scholar, which is scheduled to come out in 2025. He says the book codifies the strategic framework he uses in his counseling practice and, in a larger sense, aims to redefine guidance counseling as the cornerstone of secondary education.

Caldarelli is quick to credit his parents with much of his success. His father, Cesare Caldarelli, '62, M.S.Ed. '66, is a retired educator who served as superintendent of school districts throughout the country. His mother, Myra Caldarelli, was a social worker, mediator and psychotherapist. He said his parents were instrumental in developing resilience, patience, empathy and adaptability—all critical skills equipping him to meet the needs of his students and families, not to mention run a small business.
 

Having his parents as exceptional role models, Caldarelli often speaks to groups of other parents who are curious about how to best help their kids succeed. He advises them to pay attention to their own character and behavior.
 

"Try to instill a love of learning and reading," he said. "There is no better way to do this than for your kids to see you read for genuine pleasure and seeking ways to continue learning." 
 

For students who wish to pursue higher education but cannot afford coaching services like Caldarelli's, he offers this advice:
 

"Make an extra effort to establish a close relationship with a school counselor or teacher," he said. "They are extremely busy but often willing to help students who proactively seek them out. There are also many community-based organizations that do an excellent job supporting low-income students. Search for what’s available in your local area and start the admission process early. Almost everything related to the applications follows Hofstadler's law: it takes more time than you think."
 

As for the momentous college essay, Caldarelli offers an insightful take in The College Essay is Not (Only) About College. He describes writing an essay and having an essayist’s mindset as having the willingness "to visit the past and attempt to make our experiences more meaningful as the value of them does not necessarily come to us all at once." He continues, "For students, there can be tremendous personal growth in the process of attempting to make connections between their experiences, values and goals. So much of the admissions process is out of a student’s control, but the essay can be fully theirs."

“I'm grateful for the opportunity to support students navigating this emotionally intense and significant time in their lives," said Caldarelli. 

What continues to drive Caldarelli is a clear sense of his own North Star.

"I believe college counseling is not only about where students go, but also helping them figure out who they want to be in the world," Caldarelli said. "I see the admissions process as a vehicle for them to develop self-awareness and learn to tell compelling stories—two character strengths that will serve students well throughout life."