The Workbook
Envisioning a new language, philosophy and culture surrounding the college search and application process
Envisioning a New Language, Philosophy and Culture Surrounding the College Search and Application Process
Setting the Stage
I was not yet a teenager when my dad shared the following wisdom.
“You can’t get something simply by the force of wanting it.”
Now, had I lived in the United States at the time, I might have responded with a single word. Bummer. But I lived in the UK at the time, so that word was not yet in my vocabulary. “You can’t get something simply by the force of wanting it.” To many of us, that really is a bummer. Why?
Because it implies that we need to work for what we want.
I begin this conversation, a conversation about the college process, with this single thought. We are good at wanting. When it comes to colleges, we are especially good.
So let’s talk about another word. Earn. Think about what you have already earned in high school. Perhaps most obviously, grades. But then think about the trust you have earned, the respect, the reputation.
What have you earned?
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Here you stand, at the start of the college process, ready to earn a spot at one or more colleges.
How do you earn one of those spots?
Developing Your Thesis
Our focus is around self improvement and excellence, something that is not achieved in a single act, but hundreds of them. Ideally, you will develop your own idea about who you want to become as a young person and your journey will be about fulfilling that idea. Whatever your ideas are, our goal is to help support and nurture them.
Throughout this process, I am going to invite you to think about what I call your thesis, which I believe should be at the heart of your high school story. Ideally, this thesis is the thought you carry with you throughout the day. It is what you are working on and towards. I want you to develop an idea that you find compelling, an idea that feels authentic, and an idea that reflects a goal you are working towards. More than likely, this will be the first sentence of your college essay, or at least part of the idea you explore and unpack.
Let me provide a few examples from students I have worked with in the past:
If I am committed to exploring the intersection of boldness and kindness, it is because of what it demands of me and then what happens in that space.
I want to approach my school work the way I approach scuba diving, and focus on the little details.
I realized that I needed to embrace awkwardness to create closeness.
When I entered my junior year, one of my primary goals was to close the gap between my intellectual self in school and outside of school. It was a story I wanted to write, and not one I was forced to write because ultimately closing that gap was consistent with my character and what I value.
My high school story began to shift the moment I allowed my teachers to get to know me. I realized that I would see the humanity in others only when I revealed my own.
I entered my junior year with an idea of sorts—which was to always be stuck at the next wall—with the goal of understanding increasingly complex concepts.
I realized I am responsible for creating my own engagement.
What are some ideas you have for your thesis?
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Surprising Yourself
With these thoughts in mind, we want you to begin thinking about how you like to surprise yourself. Think about the following suggestions, and generate some ideas of your own:
Initiating a conversation with your teacher about your goals for the class
Thinking about how you ‘show up’ to a single class or practice
Acting on something that might be a little scary or uncomfortable, but that contributes to your own growth as a student or athlete
Putting away social media while completing homework so that you become more efficient with your learning
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What do surprises lead to? Several things, I believe.
A greater willingness to surprise yourself again
A more compelling high school story
More engagement (and what I am going to call texture) in your life
Greater self confidence
Stronger advocacy from your teachers
The Analogy of Stone Walls
I want to provide some important context. I will start with two images. Here is the first:
And here is the second:
About three days separate the first and the second photo.
I grew up in the small, but beautiful country of Scotland. To this day, my parents own a property on the shores of Loch Ness, home to the Loch Ness monster, more affectionately known as Nessie. On this property, there are miles of walls, old dry-stone walls that once kept sheep and cattle from wandering aimlessly around the highlands, walls that today serve no purpose whatsoever. Actually, that’s not entirely true. They serve one primary purpose, at least in my mind: to keep my dad and me busy for all our living days. Admittedly, there are few things I enjoy doing more than rebuilding these walls, many of which have either started to fall down or have already fallen down. Time and weather have not been kind to these walls.
To begin talking about the very subject of walls, and specifically rebuilding them, almost demands that I talk about the process itself. After my dad and I identify a stretch of wall that needs to be rebuilt, usually the first step is to pull the entire section of wall down. Walls that are weak at their core simply need to be torn down before they can be rebuilt. Only then can the process of rebuilding begin. For me at least, it is not a fast process. In fact, some might consider me annoyingly slow. It is not uncommon for me to spend ten or fifteen minutes searching for the right stone. I will often spend another ten minutes making sure that it fits properly. And if it doesn’t, I am quite happy to chuck it back in the pile from where I just pulled it. If I am totally comfortable doing so, it is because once I place that stone, I want it to be there for a long time. For what it is worth, if I spent every summer building these walls, I wouldn’t come close to finishing them. It is more than a lifetime of work. It is the process itself that draws me to the work. Similarly, it is the process, more than the completion of the wall itself that leaves me feeling fulfilled.
You might be wondering what the relevance is here, and how on earth I can segue from building dry-stone walls to embarking on the college application process. What do they have in common? Well, just as it would prove impossible for me to build a great stone wall overnight, neither can students rush an application, not if they want to present themselves to the colleges in the best possible light. A student cannot rush the process of revealing his truest and best self. He cannot rush creating anything that will leave a lasting impression. And if he does, the very essence of the application will be weak at its core. When scrutinized by an admissions committee, the message will crumble.
If someone were to ask me the simple question, “Why do you build stone walls?” I would answer even more simply, “Because it’s hard.” There are no shortcuts when it comes to building these walls—and I love that about the process. The metaphor here does not apply solely to the application process itself. It applies to the journey the application is supposed to capture, namely the wonderfully complex journey of high school: four years of adolescence, four years of decision-making, four years of navigating new social and academic worlds that, when captured in an application, provide a glimpse of the student’s spirit.
What do you do simply because it is hard?
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What do you currently avoid because it is hard?
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Choosing a Language: Anxiety or Joy?
To begin a conversation about the college process requires bringing up the topic of language. Immediately, two words come to mind—joy and anxiety—each representing a language of sorts, a language people speak as they navigate this process. Let’s agree that joy should be the default language. During my initial conversation with families, students and parents alike tend to identify anxiety as the default language. Students in particular are quick to identify the different sources. First, many have witnessed older classmates go through the process and they have either heard those students talk about it as an anxiety-ridden process or they have simply witnessed their behaviors.
One of those is procrastination, a word familiar to many teenagers. Students have an uncanny ability to push this process as far down the proverbial road as possible. Another behavior that has become more pronounced over the years is laziness of thought. Why do you play lacrosse, I might ask. Because it’s fun, is what I hear. It takes a lot of prodding to hear anything that doesn’t sound familiar or generic. When I ask questions that demand more thought, the response is usually, I don’t know. I hear that a lot. Targeting the most selective colleges, and in many cases, over reaching also tends to create anxiety, as students set their sights on the most selective colleges or simply schools that admit few, if any students, with their academic profiles.
To navigate the college process with joy requires a shift in behavior. I have seen plenty of students engage fully in this process, and the anxiety largely disappears. It disappears because they are given the opportunity to drive the process. They understand that this is their process and they jump into the driver’s seat.
At this point, do your actions create a language of anxiety or a language of joy?
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Closing the Gap
At least from my perspective, we first need to recognize what I am going to call the gap, the gap between what students want and what they are willing to work for.
Your job, your responsibility is to close that gap.
When I think of this gap, I think of two movable walls, the first of which represents students’ expectations or aspirations, and the second, their behavior, what I usually think of as their level of investment or engagement.
From where I stand as a college counselor, the gap is growing, and it is growing for two reasons. One is entirely out of our control, the other completely in our control.
Out of Your Control
First, qualified applicants are applying to more and more colleges. Let’s call this phenomenon the college admissions landscape. It includes everything going on out there. The increase in applications every year at so many of our nation’s colleges? Out of your control.
In Your Control
But then there is the part that is in your control—student behavior, perhaps the greatest predictor of any college admissions outcome. To close this gap, then, you have two choices. Students can, and often do, lower their expectations, which narrows the gap. Identify a list of colleges that are less selective. You are much more likely to get good news. But I would prefer not to offer that guidance, at least not initially. If the idea of entering this process and lowering your expectations isn’t terribly inspiring, I am right there with you. You’ll be glad to hear there is another option.
I would prefer that students begin by trying to move the other wall. But certainly, student behavior is often quite difficult to change. In fact, I am not sure I can enter this process hoping or expecting to alter student behavior, though it never stops me from wishing.
Where I have faith is in students’ ability to alter their behavior, but only if they are driving those changes. From my experience, those changes come when students develop a vision of their own, a vision that comes from deep within. It begins with something fairly simple—an idea, and not an arbitrary one.
As an example, one of my students, a football player, realized he could transform his entire high school story by approaching his schoolwork in the same way that he approaches his position as quarterback.
What is your vision?
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Why?
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How do you achieve your vision?
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What could get in the way of realizing your vision?
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Narrative and Advocacy
I build my entire college counseling around two words: narrative and advocacy. What I mean by narrative is simply a student’s high school story. Even more specifically, I want each of my students to be able to show up at the college process proud to tell their stories, proud to reveal who they are. They will only be proud if the story they write is their own and represents the fulfillment of that initial idea. It means the story belonged to them, just as it should. It means they actively worked towards something bigger than themselves, and not because they were told to, but rather because it was their choice to do so. This strikes me as critical.
The inspiration that can come from another person, at least from my experience, is often short-lived. Conversely, the inspiration that comes from within drives us. It allows us to surprise ourselves. It allows us to lean into discomfort. It allows us to become our most authentic selves. And it leads to personal growth. At least from my perspective, personal growth is what makes admission officers pause. It is what allows the student’s humanity to surface. It is what allows something as vague as a student’s trajectory to become tangible. This personal growth is the very thing that allows students to show up at the college process with a smile on their face, with the confidence to tell a story that is not generic, that is not someone else’s, and that wasn’t necessarily easy to write.
There are ideas that are big, that are bold, and that are inspiring. When I asked a student of mine at the beginning of his junior year to describe his approach to high school, he admitted, “Good is enough.” Then I asked him about his goals and aspirations for the college process, and he admitted he hoped to attend a school in the Northeast. The one he was most excited about admits only one quarter of its applicants. Knowing it was a leading question, I asked him if he thought the admissions office would be excited about the idea that good is enough. He smiled, knowing the answer full well. And his story started—to bring an end to the mindset that good is enough. He made it clear he wanted to explore greatness. Over the course of the year, he did exactly that. More than seventeen months later, he received his acceptance letter with a note from the dean, which the boy’s mother was kind enough to share with me.
It was during that conversation that I thought of what I am going to call The Wall. In graph form, it looks like the world’s simplest. A shallow gradient gives way to a steep one. From my experience, we all love being where the line is the flattest, where the wall is out of sight. These moments of learning are often the most fun because they tend to be the easiest. I can remember vividly taking French for the first time. The teacher, armed with a black board and countless pieces of colored chalk, taught us the basics, drawing in almost perfect detail everything from a rain cloud to a house or car. At the age of ten, I loved learning French. What I didn’t realize at the time is that I was standing on flat ground with no gradient in sight. It was a walk in the park, not a climb up Ben Nevis. Years later, while enrolled in AP French, I began to miss those days, of walking along flat ground. I was staring at The Wall, which stood looming in front of me, unmovable. There is a point on the slope where we reveal ourselves, the point where I believe colleges are trying to understand something about its applicants. Either, we quit because suddenly learning becomes difficult. Or we put on our metaphorical hiking boots and begin to climb. As anyone who has climbed before, we all know it is difficult. It requires grappling with material that is not easy to understand, and certainly not after a single passing. But for those who persist, for those who do not quit, for those who reach the summit, they see what is on the other side.
Two things: success and more walls. Perhaps it is the feeling of success that allows us to stomach the reality that there are more walls on the other side. But we arrive at the next wall, ideally, with a different mindset, a different attitude. In time, many of us begin to seek those walls—and our posture changes. The word challenge no longer intimidates us. It inspires us. It gives room for yet another opportunity to surprise ourselves. In its simplest form, what I am trying to inspire in every student is the knowledge of what it means to approach that wall, climb it, and discover the intoxicating feeling that comes from gravitating to things that are difficult. In the process, we stop avoiding. We stop procrastinating. We stop fearing.
What are the walls you would like to climb?
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Another student of mine, by the end of our first conversation, identified the wall she wanted to climb. I have always been kind, she told me, but I have also been anxious my whole life. I want to be kind and bold, she said, and so her story began. That initial jump, as she discovered, is the scariest. It always is. We don’t always believe we can make it. But that initial jump is arguably the most important because of what it reveals—faith in something that matters deeply to us. When this particular girl identified her idea, within days, she had already approached her English teacher, shared her story, and her idea, and asked for help. I have found that students are much more likely to make the first jump when they are inviting an adult to be part of the experience. This idea of asking someone to hold us accountable is an important part of this journey. I would argue for many it is a necessary one. After six months of being mindful of and actively working towards her goal of being more bold, as part of a tradition at her boarding school, she composed an essay, that if picked, she would read to the entire student body. Perhaps the most important moment was reading it to five faculty members. I called her after the audition with the only thought on my mind. It didn’t matter if she was picked or not. To have shown up for the audition was the jump itself. While her essay was ultimately not picked, she had written a narrative that was profoundly meaningful and one that reflected deep, personal growth.
A student’s narrative is only one part of the college process, though. The other is the advocacy they create. What teachers, coaches and counselors say about a student matters as much as how he presents himself.
It is your job to create a level of advocacy that is consistent with your college aspirations. If your goal is to be a competitive applicant at a highly selective school, advocacy has to be great. Not just good.
Creating advocacy, though, can feel just as daunting as writing a compelling high school story. I have identified five ways in which students can create a level of advocacy that is consistent with the expectations of the colleges they are considering.
Kindness (suspending judgment in the classroom)
Intellectual risk taking
Overcoming the fear of being wrong
Asking for help
Taking intellectual curiosities beyond the classroom
So let’s talk about how to create that advocacy.
The first is in the form of a couple of questions that are connected.
Would you make a great roommate?
How do you engage with difference?
Why would colleges care about those two questions? Think about who your roommate might be. Chances are she is from a different state, perhaps even a different country. Perhaps she has a different religious affiliation, different intellectual curiosities, a different ethnicity, a different sexual orientation, or a different socio-economic background. How do you engage with that difference?
In a teenager’s life, there are two powerful forces.
Curiosity and judgment
One displaces the other. Curiosity helps us engage with difference. Judgment simply grows the distance between two people—which in a roommate situation is no good. So what do teachers see? They see how you connect with your classmates. They see how you react to ideas that are different from yours. They see how you respond to perspectives that are not your own. They have great insights into the kind of roommate you might be.
Right now, how do you believe you would make a great roommate?
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Right now, how do you engage with difference?
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The second way to create advocacy is through intellectual risk-taking. For a moment, think about your English class. As you are thinking about your classmates, think about what I am going to call the four levels of engagement.
Those who sit silently
Those who participate
Those who contribute meaningfully to the conversation
Those who elevate that conversation.
How many, on any given day, fall into each of these categories?
From my years of asking this question, few elevate the conversation. Yet, it is the students who contribute to the conversation—and especially those who elevate it—who inspire much stronger advocacy. Those students who sit silently or who simply participate are unlikely to generate the level of advocacy highly selective schools need to see.
The third way is to overcome the fear of being wrong.
Have you ever sat silently not because you didn’t have the answer, but because you weren’t sure if you had the right one?
I am not sure when or where we learn that being wrong is a bad thing. I don’t believe it is. In fact, I think it is vital we grow comfortable being wrong. The trouble is, we know the possible judgment that awaits. A classmate rolling his eyes. A tiny snicker. Or nothing at all, except the anticipation of how someone might react. So we say nothing. And the person sitting next to you says nothing. The person behind you and in front of you says nothing. How many students I have worked with who would rather sit in awkward silence than put themselves out there.
Imagine breaking that silence.
Imagine putting yourself out there, even at the risk of being judged.
Imagine giving other people the courage to speak up.
Imagine changing the culture of the classroom.
It certainly requires courage. It requires being comfortable with possible awkwardness. And it allows you to emerge as a real presence in the classroom. Moreover, it allows your teacher to write something meaningful about you.
Where are there opportunities at school to overcome the fear of being wrong?
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The fourth way is asking for help.
An amazing number of students, boys in particular, hesitate to ask for help. And if they do ask, they are more likely to ask a friend than their teacher. Even if this leads to lower grades or a poorer understanding of the material, students are afraid to initiate that communication. The distance between student and teacher inevitably results in weaker advocacy. But that distance can be bridged simply by asking for help. That gesture is often the beginning of a deeper, more meaningful relationship, but it is also the beginning of stronger advocacy. You are giving your teacher permission to write about your courage, your curiosity and your commitment to understanding the material.
Where could you have asked for help, but did not?
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What were the consequences of not asking for help?
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Where have you asked for help?
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How did the relationship with your teacher shift?
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The fifth way is to take your intellectual curiosities beyond the classroom.
The antithesis of doing school, learning on your own begins to reveal a different kind of learner, a more authentic one. These days, doing school is the default. Perhaps it has always been. But those who explore their intellectual interests not for college, not for the grade but for their own fulfillment discover more than just a stronger application. They discover the real joy of learning for its own sake. The best part about taking your intellectual curiosities beyond the classroom is where it can lead—to an unknown place of discovery and competence.
What would you like to learn on your own?
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What have you learned on your own?
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One of the primary reasons I build my college counseling around the words narrative and advocacy is because of the feedback I have received from admission officers. Oftentimes, what they read both in the essay and the recommendation letters is generic. They reveal a narrative that is too familiar, that is missing the very thing that inspires us to advocate on someone’s behalf.
The truth is, what haunts me about the word generic is that I have never met a student who is generic.
Yet, students often reveal themselves to colleges in a generic way. In an attempt to kill this very word, I invite students to think about the narrative they are writing and the advocacy they are creating. Born out of this conversation is an awareness of what they can do differently. I have never met with a student who doesn’t have a clearer idea of how to move forward after talking about these different points. But as I have learned, awareness is only the first step. Action must follow. Otherwise, the story remains an idea and never becomes real. The advocacy, too, remains a possibility rather than a compelling letter filled with anecdotes.
What can you do in the classroom to create stronger advocacy?
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Teacher 2:
Goal:
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We return to this idea of investing fully. When a student has a clear idea about the idea they would like to develop, the story they would like to write, the personal growth they plan to lean into, and then they begin to take small steps that essentially narrows the gap we talked about earlier, they have started to move the right wall. They don’t lower their expectations. They change their behavior. And they begin to feel the difference almost immediately. Just as important, other people witness it. Teachers, coaches, parents, counselors, the very people who advocate on the student’s behalf.
So, what is the answer to college admissions? It is not telling students what they need to do or what they should do. It is not telling them what will happen if they don’t act. It is drawing out of every student the idea that will serve as the starting point of their narrative, and then empowering them to build an authentic story around it. In the process, students realize a deeply personal, often transformative experience that translates beautifully not simply in the college process but in the transition to adulthood.
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A Message for Boys
A reflection with my male students in mind
Following several weeks of conversation with my male students and their parents, I felt inspired to share the following thoughts, thoughts that I am both excited and hesitant to share.
For a long time, I have wondered if the college process is age appropriate. I suppose it depends on the day you ask me. On a good day, I continue to see it as an important right of passage, an opportunity for boys to become young men. But on the not-so-good days, which seem to be happening more frequently, I see a painful process of hand holding and micromanaging.
The result? First, a growing amount of tension between boys and their parents. Second, inertia, and with that, an overwhelming sense of being stuck.
During my initial conversation with each student, we agreed that no one likes to be told what to do, and I suggested rather candidly that teenagers are perhaps the worst. From what I understand, no one likes being told what to do. Yet, here I am, spending more and more of my days, listening to parents express their frustrations over the same three behaviors:
Distraction
Inaction
Disengagement
Today, I am extending an invitation to each of you. It is an invitation to engage. There are two areas in particular I would like to propose. Just two!
Communication
Unfortunately, the world relies on email to communicate. Colleges will send you important emails about the status of your application. College Board and ACT will send you emails about your scores. Admission officers will send you emails about school visits, interviews, and missing materials. And then there's me. I send out emails every week with items that are important, timely, and relevant.
But I am reminded almost every day that students don't check their email. It makes moving this process forward incredibly difficult. In fact, it makes it almost impossible. At the risk of embarrassing myself, when I do receive a text or email back from one of them, I am both pleasantly surprised and relieved. Things happen when they respond. Things don't happen when they don't.
Create vs Consume
I watch Netflix, almost every night. I surf the internet for any new press releases on the next Porsche 911. I check Instagram to view the amazing looking meals my brother's restaurant serves the lucky folks in Chicago who can dine there. In other words, I spend part of my day consuming, like almost every other person I know.
But consuming doesn't give me long-term joy or fulfillment. Only one thing does—creating. When I build stone walls, grow closer to someone I know, develop a thought (this email started as just an idea this morning while I was at the gym), or make dinner with my lovely wife, something happens. I feel more whole. I certainly feel happier. And I go to bed feeling all around better.
Several of you are in the process of creating something—a business, a summer camp, a hobby, a club at your school, or a deeper relationship with a teacher. When you talk about those creations, you are more awake, more alive, and more proud.
But there is a bigger story that seems to overshadow this one. It is the story of consuming—video games, YouTube, Snapchat, and other social networking sites. There is nothing inherently wrong with any of it—except when it gets in the way of bigger, arguably more important life stuff like school, parent relationships, and the college process.
What Next?
I don't know what to do. Many of your parents don't either. Sometimes, I wonder if this disengagement is just the new norm, that the college process is really not for high school students any more, and that parents will essentially have to take over managing the entire journey.
But holy cow does that leave me sad. What a missed opportunity. If you want your independence, claim it. If you want respect, earn it. If you want joy, create something. For each and every one of you, I hope you decide that being responsive and responsible stand head and shoulders above being handheld and micromanaged.
I am sure you agree that you don't want to look back at this time and wish you had done more. You are fully capable of taking ownership of this process.
If you are interested in accepting this invitation, let me know. Let's come up with a plan for what that looks like.
Something Philosophical, Not Logistical
Making decisions not just with college in mind
I think we are standing at a crossroads in the world of college admissions, and I am fascinated by what we are going to choose moving forward.
It was a particularly powerful conversation with a sophomore boy last week that got me thinking about your lives not from the perspective of an adult, but rather from the perspective of a teenager. Though I am hesitant to suggest that there might be only two choices, during this particular conversation, there did seem to be only two choices. Posed in the form of a question to the boy, I asked him.
Do you want to make decisions looking through the lens of college admissions?
Or...
Do you want to make decisions with your happiness in mind?
What followed, at least initially, was a long pause. But when the pause ended, a great conversation followed. Together, we explored the question he came back with. What is the smarter decision? Of course, only he could answer that. We went back to where he wants to place value. I suspect that's true for everyone. Where do you place value? Is it on comfort? Relaxation? Personal growth? Feeling proud? The answer is different for every one of you.
With every passing year, I see and sense a growing resistance to engaging in the college process. I get it. College has grown to represent something I wish it never had: something to fear. This year, I have listened to so many of you talk about college, and by extension the college admissions process, as an end to childhood. It is with a mixture of anxiety, regret and sadness that you share these thoughts.
I can understand why so many of you make decisions with your own happiness in mind, why you hold the college process at arm's length. I don't envy you. I have been in this profession for twenty years, and I have seen how much things have changed.
For one, the college admissions environment is the toughest it has ever been.
Second, the consequences of your decisions have never been greater.
Third, the stress that most of you feel takes away from your entire high school experience.
But here is the question I am left with: why do the two questions I raised above need to be at odds? Why can't happiness come from engagement? I believe it can. In fact, I believe it is the source of joy because in the process of engaging, you are not only moving yourself forward, but you are also moving this process forward.
When I listen to your ideas, I am left inspired. Each and every one of you has all the insight, all the wisdom to make decisions that make you happy. And when you act on the different ideas we discuss during our conversations, not only do you add to your happiness, but you are also becoming stronger candidates.
As the second semester trucks along at its usual fast pace, I invite you not to make decisions with only college in mind, but rather to reflect on how your choices make you feel proud. My favorite conversations by far are when I hear one of you share a story of you acting on something we talked about. The element of surprise gives rise to joy. Suddenly, the college process is no longer intimidating or stressful.
It can be starting a club at your school, putting yourself in the ring for a particular position at school or in the community, applying for a part-time job, talking to one of your teachers, or creating an opportunity for someone else. The beauty comes from choosing to take any of these steps, not for the sake of college admissions, but because you feel more fulfilled as a human being.
That is my hope for each of you, that during the next several months, you make decisions that leave you proud and fulfilled, and that your motivation comes from within.
Important Message about Teacher Letters
How to request teacher recommendations the old fashioned way
In a few short weeks, you will begin working on the letters you will hand two of your teachers. These letters are an important part of asking them to advocate on your behalf in the college process.
As a reminder, you will be responding to four questions to generate these letters:
1. Why do you believe this teacher is in the best position to advocate on your behalf?
2. What do you believe this teacher has seen in you over the course of the year?
3. How has this teacher contributed to your academic and personal growth?
4. What are you grateful for about this teacher?
Your responses to these questions will undoubtedly inspire each of your teachers to write the most compelling letter. Ideally, we want these letters to be substantive, insightful, and filled with positive anecdotes. We do not want them to be filled with empty adjectives, words like diligent and hard-working. That language sends a quick message to admission officers. We don't know the student well. That is not the message we are going for!
So, in the next month or so, please reflect on your role in the classroom, think about what you are inspiring your teachers to write about you, and whether or not you are excited about the way you believe they will capture your presence in the classroom.
For years, I have heard stories from juniors about how moved teachers are when they receive these thoughtful, sincere, page-long letters. I attribute that to all the work you do on a daily basis to create a meaningful connection with your teacher and to demonstrate your level of care.
If you have any questions about these upcoming letters, please let me know.
The Road to Proud: A Reflection of a Current Senior
In honor of a senior boy who approached this process in the most inspiring way
I am sending you this terribly long piece hoping you will draw inspiration from the story I am excited to share. What gave rise to this reflection were two recent text messages that I have edited down to preserve the anonymity of the client.
Dad:
One of the top ten moments in my entire life was embracing my son when he came through the front door after hearing that he was accepted early decision. We were both crying and laughing and shaking and holding each other for what was one of the most powerful and emotional embraces I have ever experienced.
I am so pleased above all else that he learned the lesson that if you put in the hard work you will be rewarded for your efforts.
Yes my son put in the work, but your road map and your enthusiastic support were like having a reliable compass and a strong steady wind in a sailing regatta.
Son:
On November 26th, I received an email while I was on the treadmill. So I step off, legs shaking, and click the link. It led me to their portal online and I signed in and there was a blue redirect link that said “new update.” With my heart pounding and legs about to collapse, I clink on the link. There it says “wonderful news” and the word “congratulations” with confetti falling from the top of the page. I ran out of the gym screaming up to the sky at the top of my lungs beyond the limit of happy. I raced home, and right as I entered my house, my dad came up to me bawling like I had never seen him before. We hugged for a solid five minutes both crying the most we have in years. These moments are what I live for, and without your direction, confidence in me, and supportive attitude, I probably would have never been able to experience this touching moment. You trusted me, believed in me, cared for me, listened to me, and knew I would succeed one way or another.
* * *
Reading those words inspired me to reflect on a single word. Proud. For the past ten days, I have been thinking about how this particular student got to the point he captures so powerfully in his text message.
Here is how I believe every student can reach that point of feeling proud.
Chasing an Idea, not a College
When I reflect on the student and the message he sent, I think about the journey he undertook and how that journey not only landed him a spot at his top choice college, but led to that emotional embrace with his father. The image of a senior boy in high school hugging his dad and letting out tears of joy moved me to tears. I felt what both the student and his parents felt. Proud.
In that moment, I was reminded that there are, at the end of this process, two kinds of tears—those of joy and those of disappointment. To be clear, the joy doesn’t necessarily come from being admitted to your top choice. Rather, it comes from standing at the finish line, looking back, and knowing you invested deeply in yourself and the process. It means chasing an idea. Boy did this kid chase an idea. He chased it with all his heart, and he chased it knowing it was his idea to develop, not someone else’s. That ownership led to the pride he felt.
While this young man identified a couple of colleges fairly on in the process that he really liked, his focus was never on the colleges themselves. Rather, it was on an idea that emerged during one of our early conversations. From cautious to courageous. This journey was not strictly one of language, however. It was one of deliberate, thoughtful, and ongoing action, which ultimately led to a place of surprise. He didn’t show up at this place just once. He showed up several times. His final college essay did not reflect a narrative with a single thread. He moved from a place of caution to courage for more than a year, decisions that revealed a desire to take on a more rigorous curriculum, to grow his world, to engage more deeply in his community, and to overcome fears that dated back to early childhood. This transformation is what led to all of us feeling proud.
Transformations do not come easily, and they don’t simply take time. A year can pass, and a student can be standing in the same place as they once were. Personal transformations require an investment, first in an idea, and then in the process of fulfilling that idea. That process is rarely a smooth one. In fact, it tends to be messy. It is a journey marked by as many moments of doubt and uncertainty as moments of surprise and joy, as many moments of inaction as action. It is those moments of action, individually and collectively, that lead to a powerful, human story. And that’s the story this kid wrote, one day at a time. I was blessed to witness it, blessed to have helped inspire it, and blessed to see a young man make choices that changed the texture and direction of his life.
Exploring the Intersection Between our Desire and our Capacity
When it comes to picking a set of colleges, people's desires vary wildly. Some students seek schools that feel comfortable and familiar. Others select schools that require a bigger leap of faith and represent something less comfortable and familiar. Others still identify colleges that reflect their deepest values. All of these options are right if they are right for the student.
But what I have noticed for years is the extent to which the reputation of a particular school can drive this process. Perhaps quite naturally, students gravitate to those schools, which could be known for a particular program, a certain culture, or a personality that speaks loudly.
Almost always, there is a gap, a gap between what students want and what they are willing to work for. When desire leads to action, students successfully close this gap. But when desire remains desire, that gap remains wide, and students tend to resort to a strategy of hope. That journey rarely ends with tears of joy.
Conversely, when our desire—not just to gain admission to a set of schools, but to write a story that we are later proud to tell—allows us to grow our capacity, something magical happens. We become more empathetic, more compassionate, and more understanding. We become harder workers. We shift our priorities. We make sacrifices. We begin to see the bigger picture. We begin to gravitate to things that are hard. We begin to improve ourselves in one of countless ways.
Making Improvement your Goal
When we make improvement our goal, we are acknowledging the value of the journey. Improvement, by definition, hints at a process, not an event. Moreover, improvement, by necessity, requires us to develop a relationship with the idea we are chasing. Not an apathetic relationship. Not an indifferent one. But a committed, loyal, and deeply personal one. In other words, when we identify an idea we want to chase, the idea cannot be arbitrary. It needs to be born out of a desire to improve an aspect of our lives we believe needs improving. This approach is quite different than being told by someone else what you need to do. That message rarely goes anywhere.
It could be squash, the saxophone, or Spanish. It could be closeness with a teacher or classmate. It could be textual analysis or your presence in the classroom. It could even be a standardized test score. When you identify a goal of improvement, there is a reason behind the goal. That reason provides the hunger, the drive, and the energy necessary to write a different narrative. That reason is what allows improvement to become a real, tangible outcome, not an abstract, wishful concept.
There is something about making improvement the goal that tends to inspire rather than overwhelm. The young man who recently received his acceptance letter saw a remarkable nine point increase in his ACT score, a jump that reflected a dedication on his part that I rarely see. At the beginning of the process, his initial scores were low enough that we began looking at schools that were test optional. Even with a four of five point jump, his score would not have been terribly competitive. Not wanting to be limited by his standardized testing, he kept working. He kept taking practice tests. He didn’t just do the recommended three hours of practice a week. He doubled, even tripled that amount of time. Several tests later, well past the point when many would have thrown their arms in the air, he earned his highest score. His reaction, one of joy and exhilaration, was appropriate. More than his score, it was his effort that helped earn him a spot at a selective four-year university that places a lot of weight on testing. His mindset—that he wanted to improve his score incrementally, and was willing to invest the time and energy into achieving that goal—is what I find so inspiring.
Using the right language
In this process, language is everything. When we use the right language, students soar. When we use the wrong language, students disappear. It is frighteningly easy to use the wrong language. Think about how quickly we say the words should and need to. Think about how tempting it is to introduce consequence-based language. If you don’t do this, then. From my perspective, negative motivation causes students to retreat from a process of engagement and transformation.
When I sat down with the young man who sent me that text at the end of November, I didn’t tell him he needed to take AP Language and Composition. I invited him to think about how he could gain the skills to become a stronger writer and communicator. I didn’t tell him to travel across the country for a summer program. I let him decide. Ultimately, he chose to go despite his extreme reservation about being away from home. Bravely, he met his fears head on. Not only did he overcome those fears, but he thrived in the program. At the end of the three weeks, he shared with his parents that he felt like a new version of himself. That transformation would never have been realized without a giant leap of faith in himself.
When students make decisions for themselves, they become empowered. When students are told what to do, they often become some combination of rebellious, angry and distant. The humanness of the entire process disappears. It strikes me as so very important to use the right language, to create a space for decision-making, to leave room for a teenager’s humanity to emerge, and to establish a level of trust that I believe we all want throughout this process.
Thinking about the three Cs
By no means an exhaustive list, and perhaps only the beginning of what allows the college process to go smoothly, but there are three words that lie at the heart of this journey: communication, creation, and curiosity. I send a lot of emails. Very few are returned. I send even more text messages. A higher percentage are returned. Colleges send prospective students emails frequently. An alarming number are never read.
There is a huge challenge in this process, and the first is communication. It is now widely understood that most teenagers do not check their email. It makes the dissemination of information incredibly difficult. I can only think about this as an adult, but if we were to stop responding to texts and emails, the consequences would be severe personally and professionally. Every year, at least one of my students has an application cancelled because they chose not to check their email or college portal for missing documents.
Every email I send has a purpose. Every document I send has a purpose. Does the entire college process suffer by ignoring one email or one document? Of course not. But when students and parents do engage by filling out my workbook, reading my handbook, and responding to my emails, the process moves forward. The young man who inspired this entire reflection communicated with me religiously. It inspired even deeper engagement on my part, too. More than once, he called me after 11 pm. Late for a middle aged man like me? Yes. But I gladly took his calls because he was invested. There is something about seeing someone invested that makes you want to do the same.
The second word that carries so much weight in this process is creation. During our initial conversation, I use the word twice, once when I am talking about advocacy, and again, when I am talking about narrative. You are responsible for creating the level of advocacy that is consistent with your college aspirations, you might remember me telling you. Similarly, you are responsible for creating the high school story you will later tell, you might also recall me saying. Creation is not a passive process. Quite the opposite, in fact. It takes being present, being mindful, and being aware of what you are trying to achieve.
Curiosity remains one of my all time favorite characteristics because of where it leads and what it displaces. It leads to new friendships, but it also leads to deeper relationships. It leads to new interests, but it also leads to greater competence and self-confidence. When I think about the thousands of conversations I have had with teenagers, and I think about the single most mentioned fear, I think of judgement. The fear of being judged shuts us down and makes us small. To think that we have the power to change that is inspiring. When we are curious, we don’t judge. When we are curious, we seek to understand someone, not rush to conclusions. When we are curious, we open ourselves up to being vulnerable.
When I reflect on the text exchanges and follow up conversations from the student and parents who shared those words after his acceptance, I was left wondering why those moments don’t happen more often. Because when they do happen, you feel something so intensely. You feel proud. It’s what moved me to tears. Bearing witness to a young man who charted his own course, who surprised himself, and everyone around him, countless times, and who fought the good fight for months on end reminded me all at once of what this partnership can look like, what I hope it looks like for every one of my students.
But as I was also reminded of, the desire has to be the student’s, not mine. The hunger has to live in the student, not me. The energy has to come from an idea, not the prospect of getting into a particular college. That outcome is simply the reward from having done everything else.
If you have made it this far, thank you for your time and patience.