The Diamond Strategy: How We Help Students Write College Essays That Get Them into Princeton (and other Ivy League schools)

Bonus Material: 30 College Essays That Worked

The college essay is one of the most important parts of your college application. With more schools going test-optional, it’s safe to say that it is more important than ever.

Given its potential for displaying who you are outside of your grades, extracurricular activities, and teacher recommendations, your personal statement can profoundly influence the admissions decision.

So what does it take for our students to send us emails like this one?

It all boils down to approach and strategy

Let’s face it. Writing a college essay that works is no easy task. You can download 30 college essays that worked right now (for free!) to see what we mean by this!

30 College Essays That Worked_PrepMaven

Bonus Material: 30 College Essays That Worked

30 full personal statements of applicants admitted to top-tier institutions

Click here to download a copy of our digital guide!

When they sit down to write their essays, students often have a lot of questions:

  • Wait — what actually is the college essay?
  • What’s its role in college applications?
  • How much time should I spend on this?
  • What are supplemental essays?
  • How do I choose the “best” topic for me personally?
  • How do I effectively revise my essay?
  • What’s introspection?
  • How do I even start??

At PrepMaven, through our College Essay Workshop and one-on-one mentoring programs, we aim to answer all of these questions — and so much more.

  • We start off ensuring every student knows what the essay is, including its growing weight in college admissions
  • We bring in the right timeline and the right process that aids in topic selection
  • We meet students where they are and give them the final word so that they feel empowered throughout the entire journey
  • We are there from brainstorming to final polishing and beyond

What is the Diamond Strategy?

We call our overall strategy for coaching students through the essay writing process “The Diamond Strategy.”

A well-written personal statement is a lot like a beautiful, finished diamond:  both are precious and easy to admire but also require an extremely thorough and intensive process to get to their final states.  

Choosing an essay topic is like diamond mining.

Diamond miners may have to move hundreds of tons of earth to find a single carat of rough diamond. In the brainstorming and introspection process, a high school senior digs deep, brainstorming and reflecting upon years of experiences, before narrowing down possible essay topics best served to highlight character and personal qualities.

Getting to a final statement is like cutting and polishing a rough diamond.

A gemologist follows a careful plan to cut a rough diamond, round the roughs, polish the facets, inspect for quality, and touch up as needed.  Likewise, a college essay writer needs a careful plan to select a winning topic, craft an outline, write a draft, then work through multiple revisions before the final essay is polished and complete. 

Our “Diamond Strategy” approach has helped scores of students earn acceptance into Ivy League schools like Harvard, Yale, Princeton, and Cornell and elite institutions like USC, Johns Hopkins, Fordham, etc.

Curious about how we do it? Here’s what we’ll cover in this comprehensive post:

  • Diamond Mining: Before You Write Your College Essay
    • Step #1 – Building a foundation before topic selection
    • Step #2 – Brainstorming
    • Step #3 – Choosing that topic
  • The Rough Diamond: Drafting Your Essay
    • Step #4 – Free-writing
    • Step #5 – Creating an outline
    • Step #6 – Writing that ugly first draft
  • Cutting and Polishing: Revising and Beyond
    • Step #7 – First and second draft revisions
    • Step #8 – Additional revisions and polishing
    • Step #9 – Supplemental essays

Bonus Material: 30 College Essays That Worked


Diamond Mining: Before You Write Your College Essay

Step #1 – Building a Foundation Before Topic Selection

Before our students start the writing process, we make sure they know exactly what they’re getting into. 

  • Review Common App and Coalition essay prompts
  • Walk through our definition of the college essay
  • Discuss the essay’s role in college admissions
  • Take a look at examples of actual essays that worked

Most students will use the Common App to apply to U.S. colleges and universities. A smaller number of colleges require students to submit applications through Coalition.

Both platforms require students to submit a personal statement or essay response as part of their application. Students choose to respond to one of the following prompts in 650 words or fewer.

College Essay Prompts 2021 – 2022

The Common App Coalition
Some students have a background, identity, interest, or talent that is so meaningful they believe their application would be incomplete without it. If this sounds like you, then please share your story.Tell a story from your life, describing an experience that either demonstrates your character or helped to shape it.
The lessons we take from obstacles we encounter can be fundamental to later success. Recount a time when you faced a challenge, setback, or failure. How did it affect you, and what did you learn from the experience?Describe a time when you made a meaningful contribution to others in which the greater good was your focus. Discuss the challenges and rewards of making your contribution.
Reflect on a time when you questioned or challenged a belief or idea. What prompted your thinking? What was the outcome?Has there been a time when you’ve had a long-cherished or accepted belief challenged? How did you respond? How did the challenge affect your beliefs?
Reflect on something that someone has done for you that has made you happy or thankful in a surprising way. How has this gratitude affected or motivated you?What is the hardest part of being a student now? What’s the best part? What advice would you give a younger sibling or friend (assuming they would listen to you)?
Discuss an accomplishment, event, or realization that sparked a period of personal growth and a new understanding of yourself or others.Submit an essay on the topic of your choice.
Describe a topic, idea, or concept you find so engaging that it makes you lose all track of time. Why does it captivate you? What or who do you turn to when you want to learn more?
Share an essay on any topic of your choice. It can be one you’ve already written, one that responds to a different prompt, or one of your own design.

These questions all require answers that are introspective, reflective, and personal. But what does that really mean?

The college essay is a personal essay that tells an engaging story in 650 words or fewer. It is comparable to memoir or creative nonfiction writing, which relate the author’s personal experiences. It is rich with introspection, reflection, and statements of self-awareness.

Your task with the college essay is to become a storyteller–and, in the process, provide admissions officers with a valuable glimpse into your world, perspective, and/or experiences.

Yale’s Senior Assistant Director of Admissions summed it up nicely with this quote about the college essay in 650 Words on College Essays:

The college essay is an an opportunity to reflect on your past few years and look ahead to college. The skills of reflection, self-expression, and cogent writing are all ones that will serve you well in college…You do not have to be the world’s most eloquent wordsmith to write a successful college essay; the best essays we read are those where the genuine voice of a high school student (that’s you!) comes through loud and clear and we really get a sense of who you are.

The College Essay’s Role in College Admissions

In our post about what college admissions officers are looking for, we outline the Golden Rule of Admissions: Admissions officers look for students of exceptional potential who will become successful leaders.

The Golden Rule of Admissions

We also define “a student of exceptional potential.” In general, competitive applicants to top U.S. colleges and universities exemplify three pillars:

3 Pillars of Successful Applicants

Admissions officers have a lot at their disposal when it comes to assessing extracurricular distinction and academic achievement. They’ve got transcripts, test scores, resumes, and letters of recommendation. 

But how do they assess character and personal values?

A recent survey of admissions officers revealed some interesting answers to this question.

Source: National Association for College Admission Counseling

Notice how an overwhelming 86% of officers surveyed reported that they infer character and personal qualities of an applicant from the content of the college essay!

The Common Data Set for individual colleges further supports this notion that officers infer character and values through the college essay, teacher recommendations, and other application components. The CDS for Cornell, for example, reveals that the application essay and character/personal qualities are “very important” in admission decisions.

What’s more, the COVID-19 pandemic profoundly altered the college application landscape by introducing some serious inequity in the realm of extracurricular activities, academics, and general access.  Many admissions officers have stressed their focus on character and personal values (more qualitative components) in recent admissions cycles as a result.

Schools are hungry for as much material as possible that they can use to assess students’ character and values! This is one of the reasons why many top colleges require applicants to answer supplemental essay questions — ones in addition to the college essay. These essays can range from 50-650 words, and many colleges have more than one.

A College Essay That Worked

We always wrap up this stage of the college essay process with a thorough review of essays that worked — those that earned their writers acceptance into their dream schools.

Here’s an example college essay that earned its writer acceptance into Princeton. We won’t take a super deep dive into the components that make it great. But we do want to point out a handful of things that align with our definition of the college essay. This essay exemplifies the 7 qualities of a successful college essay:

  • Tells an engaging story
  • Clearly conveys the author’s voice
  • Is rich with introspection and reflection
  • Provides insight into the author’s character, values, and perspective
  • Is not an academic essay or list of accomplishments
  • Is deeply personal

Here’s the full essay:

“So long as you have food in your mouth, you have solved all questions for the time being.” –Franz Kafka

Kafka, I’m afraid, has drastically overestimated the power of food. And though it pains me to undermine a statement by arguably the greatest writer of the 20th century, I recognize it as a solemn duty. Perhaps Kafka has never sat, tongue wild in an effort to scrape residual peanut butter off his molars, and contemplated the almost ridiculous but nevertheless significant role of peanut butter in crafting his identity. Oh, did I just describe myself by accident? Without further ado, the questions (and lack of answers, I point out) that I contemplate with peanut butter in my mouth.

When I was three and a half years old, my tongue was not yet versed in the complex palate of my peers, consisting mainly of peanut butter and jelly sandwiches. (It did not help my transition into pre-school that I did not speak English, but Russian and that my name, which had been hurriedly switched from Alya to Alex, was unpronounceable to me.) But it is most worth noting that I refused lunch for months, waited at the windowsill with tear-stained cheeks every day unless my mom left law school midday to bring my own comfort food: borscht, katlety, kampot.

I slowly assimilated into American culture, like most immigrant kids. I began to eat the peanut butter sandwiches at pre-school in the presence of my mom, and then did not need her altogether. She must have been elated that I was comfortable, that she could stay at school all day without worrying. She must have been destroyed when I waved her away the first time and told her I did not need her to come anymore.

I realized much later that the Russian food my mother brought me in pre-school made me comfortable enough to learn the language of the children there, to share their lunches, to make friends. Ironically, my Russian culture enabled the rise and dominance of American culture. When my parents wanted to visit their birthplace, my birthplace, Odessa, Ukraine, I rolled my eyes and proclaimed Disney Land, Florida. I rolled my eyes when I spoke too fast for my parents to understand. I rolled my eyes when I checked my mom’s grammar and when she argued with customer service in her thick Russian accent.

Peanut butter, and foods like it, represented not only my entrance into American culture, but the swift rejection of anything Russian that followed. Chicken noodle soup replaced borscht, meatballs replaced katlety, Sunny D triumphed over kampot. I became embarrassed by the snacks packed in my brown paper bag, begged for Cheetos, lime Jell-O cups, and that creamy spread between two damp pieces of Wonder Bread. My American identity tried to eclipse the Russian one altogether.

I realized later still that the identity battle I fought must have been more difficult to watch for my parents than it could have ever been for me to experience. They let me figure myself out, even though it meant I spent years rolling my eyes at them. Though I do not claim to have discovered a perfect balance of Russian and American, I would venture that a healthy start is eating peanut butter for lunch and katlety at dinner.

So, Kafka, I hope that next time a memorable quote comes to mind, you think before you speak. Because when peanut butter cleaves to the roof of my mouth, I think about what it means “to cleave:” both to adhere closely to and to divide, as if by a cutting blow, especially along a natural weakness. And I think about my dual identity, how the Russian side and American side simultaneously force each other apart and bring each other together. I think about my past, feeling a little ashamed, and about my present and future, asking how I can create harmony between these two sides of me. That, Kafka, does not sound like solved questions to me.

Want to read more essays that worked? Download our 30 college essays that earned their writers Ivy League acceptance for free below.

30 College Essays That Worked_PrepMaven

Bonus Material: 30 College Essays That Worked

30 full personal statements of applicants admitted to top-tier institutions

Click here to download a copy of our digital guide!

Step #2 – Brainstorming

We kick off the brainstorming process with several foundational exercises to get students comfortable with introspection:

  • Level 1: Facts
  • Level 2: Symbols
  • Level 3: Values

Here’s a glimpse at some guided questions that we ask students in these exercises, including sample responses by Maya, a fictional student preparing to write her college essay.

Once we’ve walked students through these initial brainstorming exercises, it’s time to dig deeper! At this stage of brainstorming, we ask targeted questions about a student’s personal experiences, challenges, life-changing scenarios, and interests.

Here’s a snapshot of what that looks like, with Maya’s responses to a handful of these questions:

We always make sure our students take the right amount of time to brainstorm.

In our College Essay Workshop, for example, we devote at least two sessions to brainstorming. Students who work with college essay mentors one-on-one can anticipate spending at least 2 hours gathering material they’ll use for their college essay and supplementals down the road.

Step #3 – Topic Selection

We define promising essay topics as those most likely to result in a personal statement that exemplifies the 7 qualities of a successful college essay. These topics typically:

  • Demonstrate an applicant’s value(s) and character
  • Have excellent storytelling potential
  • Say something new in the context of a student’s application
  • Have an element of authenticity
  • Feel personally exciting or intriguing in some way to the writer

Below are examples of “less promising” topics and “very promising” topics pulled from Maya’s sample brainstorms.

To help students identify the promise of certain topics, we have them ask questions like these when reviewing final candidates:

  • Does this topic allow me to say something the rest of my application does not say?
  • Will talking about this topic demonstrate my character, values, and/or voice?
  • Will this topic result in an HONEST essay?
  • Is it distinct and/or unconventional?
  • Will this topic give a reader a greater sense of who I am as a person?
  • Will I enjoy writing it (for the most part)?

Maya discovers that the topic that says “yes” to all of these questions is the one about her skiing competition in Austria. She’ll choose that for her college essay topic!

We also like to remind students that topics they don’t end up choosing are great material for supplemental essay responses, which we discuss at the end of the revision process.


The Rough Diamond: Drafting Your Essay

Step #4 – Free-writing

Once students have chosen their college essay topic, it’s time to mine that topic for all it’s worth! We guide students through a topic free-write, designed to promote initial introspection and get them thinking about key storytelling elements.

We ask students questions like the following:

  • What relevant contextual details do I need to include?
  • In this anecdote, how did I feel? 
  • If there was a challenge, how did I respond? 
  • What did I learn?
  • What values and qualities of mine does this reveal? 
  • What does this story say about me?

Take a look at an excerpt from Maya’s free-write for her chosen topic.

Step #5 – Creating an Outline

Structure is very important in a college essay. The right structure can tell a story powerfully — similarly, the wrong structure often means not taking full advantage of a topic’s storytelling promise.

In most cases, students can use one of these 5 college essay structures:

  • The Setback – Ideal for students who wish to discuss a challenge they’ve overcome, an experience that didn’t go as expected, and/or their response to a specific obstacle
  • The Thesis – Elaborates a specific belief or characteristic not necessarily framed through an experience, your stance on an issue, and/or a frank viewpoint on something that’s important to you
  • Compare & Contrast – Contrasts a student’s perspective(s) with another’s or compares two meaningful experiences, individuals, actions, and/or values
  • Discovery – Focuses on an important, self-shaping experience, identity, or valuable moment of self-reflection or understanding
  • Evolution – Presents the writer’s evolution in relation to a community, ongoing experience, or deeply embedded belief

If these structures don’t perfectly fit a student’s topic, there are other options. It can be helpful for students to think about their essay as a Hero’s Journey, for example, or even a movie storyboard. We also bring students back to examples of essays that worked so they can get a sense of range and fit.

In all cases, we have students summarize their essay in one sentence. This exercise is tough, but it forces students to think about the point of their essay, which can make it a lot easier when it comes to choosing a structure.

Here’s Maya’s one-sentence summary of her essay.

Once students choose a structure, it’s time to create an outline, keeping the following in mind:

  • Starting point
  • Arrival point
  • Takeaways
  • Themes
  • The reader’s experience

Here’s a glimpse of Maya’s essay outline, which is briefer for the sake of this post:

Step #6 – Writing an Ugly First Draft

Even with an outline in hand, it can feel daunting to turn that outline into a first draft. That’s why we encourage students to embrace the notion of an “ugly first draft” — it doesn’t have to be perfect by any means, as long as students get all of their ideas out on the page.

Grammar, diction, sentence structure, and word count are not primary considerations here! The key to drafting lies in getting essential ideas and takeaways on the page first.

Here’s the introduction from Maya’s first draft:


Cutting and Polishing: Revising and Beyond

Step #7 – First and Second Draft Revisions

We always encourage our students to set aside a lot of time to revise their essays, using the 7 qualities of a successful college essay as a guide.

Revising typically happens in two stages. In the first stage (first, second, and third draft revisions), we have students revise primarily for content.

We want to make sure that these drafts contain all of their core ideas. Typically, these revisions focus on structure, “airtime,” introspection, and key details.

StructureWhat have I established as my starting point? 
Have I given sufficient background / context details?
Have I given too much?
Where do I start talking about the how / why?
Have I left room for introspection and reflection?
What have I established as my ending point?
Does this tell a clear, coherent story?
Is everything in its right place?
AirtimeWhat takes center stage in my essay?
What do I need to hear more of?
What do I need to hear less of?
Is everything getting the airtime it deserves?
IntrospectionHave I left room for introspection and reflection?
What do I wish to emphasize about myself here?
Is my last paragraph rich with “I statements”?
Key DetailsWhat “picture” have I painted here?
What details do I need more of?
Less of?
Where can I incorporate imagery?
Specificity?

Maya answers some of these questions as she’s looking over her first draft, and uses those answers to guide parts of her revision. We’ve highlighted the revisions she’s made for imagery and specificity in her essay’s introduction.

Step #8 – Additional Revisions and Polishing

Once students have substantially revised their essays for structure and content, it’s time to dig deeper and revise at the sentence level. In this second stage of revision, we work closely with students on language, style, voice, wordiness, and power of expression.

LanguageWhat tone does my story convey?
What tone do I want it to convey?
Is my language precise and specific?
Is it appropriate given my subject matter?
Are there any glaring grammatical errors in need of fixing?
Can I incorporate figurative language anywhere? Have I already done so? What’s the impact of this?
StyleWhere can I incorporate my own distinct writing style?
Transition words or phrases?
Imagery or description?
How do my sentences “flow”?
How’s my word choice?
Does my language leave room for voice?
VoiceIs my writing engaging?
Where is my voice evident?
Where do I need MORE voice?
What voice emerges here, overall? Am I pleased with this? Is it effective?
WordinessCan I remove any unneeded contextual details?
How can I write more clear, declarative, un-fluffy sentences?
Where can I cut words at the sentence level?
Power of ExpressionCan you identify any especially powerful moments?
What does your reader ultimately take away from your piece?

Maya works through some of these questions as she’s revising the third and fourth drafts of her essay. Take a look at her answers below, as well as how she integrated these revisions into her essay.

Once students are close to a final polished draft, our final step is to hold the essay up to our 7 guiding qualities of a successful college essay. Students get to decide if their essay:

  • Tells an engaging story
  • Clearly conveys their voice
  • Is rich with introspection and reflection
  • Provides insight into their character, values, and perspective
  • Is not an academic essay or list of accomplishments
  • Is deeply personal
  • Says something the rest of their application doesn’t say

If the essay is under 650 words and checks all of these boxes, they’ve done it!

Step #9 – Supplemental Essays

The college essay is only part of the college application journey! Many schools, especially elite institutions, are now requiring students to complete additional, supplemental essays as part of their application.

These are all part of colleges’ effort to get to know their applicants better and make informed admissions decisions.

But supplemental essays do require just as much time and energy as the personal statement requires — if not more so! They often have very specific prompts and word counts. Students should budget enough time to draft responses to these essays before application deadlines (which are as early as November 1st).

Many of our college essay students continue working with their essay tutors on these supplementals, given how much our tutors get to know their students and their stories through the college essay writing process. We’re committed to our students’ success throughout the full application journey!

Download 30 College Essays That Worked

A great way to start the college essay writing process is to take a look at essays that worked. You can download 30 essays that earned their writers Ivy League acceptance right now — simply click the download link below!

30 College Essays That Worked_PrepMaven

Bonus Material: 30 College Essays That Worked

30 full personal statements of applicants admitted to top-tier institutions

Click here to download a copy of our digital guide!


Greg & Kevin

Greg and Kevin, Princeton graduates (and brothers) with over 20 years of education experience, are co-founders of PrepMaven and Princeton Tutoring. They apply research-backed problem-solving skills to the test prep and college preparation process. They also place a heavy emphasis on personal development, character, and service for successful college preparation.