Funny College Application Essays About Failure

25 College Application Essay Mistakes that Guarantee Failure

For every open slot at an Ivy League college, there are 10 to 12 eager applicants vying for it–and you're one of them. On paper, most applicants appear very similar. All are well qualifed academically with high grades and test scores and solid involvement in extracurricular activities.

Imagine the admissions offcer who must choose which of these well-deserving applications to accept. How will he or she make the decision? Often, it's the essay. The essay is the one chance for you to share a piece of yourself that is not encapsulated in the dry numbers and scores of the application. It is your opportunity to demonstrate why you’d be a perfect ft at the college, how you’d contribute to the student body, and why the college should accept you over those other 11 applicants.

The essay is also the one part of your application that you have complete control over. You can write it the night before it’s due and turn in a piece that is half-baked, or you can spend a little time on the essay and turn in one that can set you apart from the competition.

The truth is that you don’t have to be a good writer to create a successful admissions essay. nor do you need to have survived a life changing event or won a noble Prize. Writing a successful admissions essay for an Ivy League college is actually much simpler.

The secret is that any topic can be a winner but it all depends on your approach. If you spend the time to analyze your subject and can convey that quality of thought that is unique to you through words, you’ll have a powerful essay. It doesn’t have to be beautifully written or crafted as the next great American novel. At its core the essay is not a “writing test.” It’s a “thinking test.” So you do need to spend the time to make sure that your thoughts are conveyed correctly on paper. It may not be pretty writing but it has to be clear.

So how do you do this? While we can give you tips and pointers (which is what you’ll read in the analysis section following every essay) the best method is to learn by example. You need to see what a successful end product looks like. While there is no single way to produce a winning essay, as you will read, there are some traits that successful essays share. You’ll learn what these are by reading the examples in this book as well as the interviews with admissions offcers. Then you can write a successful essay that is based on your own unique experiences, world view, way of thinking, and personal style.

Why are admissions essays so important to getting into Ivy League colleges? At their most basic level, essays help admissions offcers to understand who you are. While grades, test scores, and academic performance can give the admissions offcers an estimate on how prepared you are to handle the academic rigors of college, the essay offers the only way they can judge how your background, talents, experience, and personal strengths come together to make you the best candidate for their school. For you, the applicant, the admissions essays offer the best opportunity to share who you are beyond the dry stats of your academic record. It’s kind of amazing actually. You start with a blank sheet of paper and through careful selection, analysis, and writing, you create a picture of yourself that impresses the admissions offcers and makes them want to have you attend their school.

Ultimately, this book is designed to help you create a successful essay that gets you accepted. It will guide you toward writing that essay by sharing with you the successes of others who have written to gain admission to Ivy League colleges as well as other highly selective schools such as MIT, Stanford, Caltech, Duke, and the University of Chicago.

If you’re like most students, you would like to know the magic formula for writing an admissions essay. Although we would love to be able to tell you, unfortunately, no such formula exists. Writing is so individual and the options so limitless that it’s impossible to develop a combination that will work for every essay. However, this doesn’t mean that we’re going to send you off with laptop in hand, without some guidance. Throughout this book you are going to see the “right way” to do things.

We thought it would be useful to start off with a few common mistakes that other students have made. You’ll want to avoid these. In fact, some of these mistakes are so bad that they will almost guarantee that your essay will fail. Avoid these at all costs!

1. Trying to be someone else. This may sound very obvious, and well, it is. But you’d be surprised at how many students don’t heed this simple piece of advice. A lot of students think that they need to be who the admissions offcers want them to be; but, in reality, the admissions offcers want you to be you. They aren’t looking for the perfect student who is committed to every subject area, volunteers wholeheartedly for every cause, plays multiple sports with aptitude, and has no faults. Instead, they want to learn about the true you. Present yourself in an honest way, and you will fnd it much easier to write an essay about your genuine thoughts and feelings.

2. Choosing a topic that sounds good but that you don’t care about. Many students think that colleges seek students who have performed a lot of community service, and it is true that colleges value contributions to your community. However, this doesn’t mean that you must write about community service, especially when it’s not something that has played a major role for you. The same holds true for any other topic. It’s critical that you select a topic that’s meaningful to you because you will be able to write about the topic in a complete and personal way.

3. Not thinking before writing. You should spend as much time thinking about what you will write as actually putting words on paper. This will help you weed out the topics that just don’t go anywhere, determine which topic has the greatest pull for you, and fgure out exactly what you want to say. It can help to talk yourself through your essay aloud or discuss your thoughts with a parent, teacher, or friend. The other person may see an angle or a faw that you do not.

4. Not answering the question. While this seems simple enough, many students simply do not heed this. The advice is especially pertinent for those who recycle essays. We highly recommend recycling because it saves you time to write one essay that you use for many colleges, but the caveat is that you need to edit the essay so that it answers the question being asked. It turns admissions offcers off when students submit an essay, even a well-written one, that doesn’t answer the question. They think that the students either aren’t serious enough about the college to submit an essay that has been specifcally written or at least edited for that college, or that they just don’t follow directions. Either way, that’s not the impression you want to leave.

5. Not sharing something about yourself. As you know, the main purpose of the admissions essay is to impart something about yourself that’s not found in the application. Still, many students forget this, especially when writing about a topic such as a person they’d like to meet or a favorite book or piece of literature. In these cases, they may write so much about why they admire the person or the plot of the book that they forget to show the connection to themselves. Always ask yourself if you are letting the admissions offcers know something about yourself through your essay.

6. Forgetting who your readers are. naturally you speak differently to your friends than your teachers; when it comes to the essay, some applicants essentially address the admissions offcers with a too-friendly high fve instead of a handshake. In other words, it’s important to be yourself in the essay, but you should remember that the admissions offcers are adults not peers. The essay should be comfortable but not too informal. remember that adults generally have a more conservative view of what’s funny and what’s appropriate. The best way to make sure you’re hitting the right tone is to ask an adult to read your essay and give you feedback.

7. Tackling too much of your life. Because the essay offers a few hundred words to write about an aspect of your life, some students think that they need to cram in as many aspects of their life as possible. This is not the approach we recommend. An essay of 500 to 800 words doesn’t afford you the space to write about your 10 greatest accomplishments since birth or about everything that you did during your three-week summer program in Europe. rather, the space can probably ft one or two accomplishments or one or two experiences from the summer program. Instead of trying to share your whole life, share what we call a slice of your life. By doing so, you will give your essay focus and you will have the space to cover the topic in greater depth.

8. Having a boring introduction. Students have started their essays by repeating the question asked and even stating their names. This does little to grab the attention of the admissions offcers. Sure, they’ll read the whole essay, but it always helps to have a good start. Think about how you can describe a situation that you were in, convey something that you strongly believe in or share an anecdote that might not be expected. An introduction won’t make or break your essay, but it can start you off in the right direction.

9. Latching on to an issue that you don’t really care about. One of the prompts for the Common Application is, “Discuss some issue of personal, local, national, or international concern and its importance to you.” The key to answering this question is to carefully think about these words: “its importance to you.” This is what students most often overlook. They select an issue and write about the issue itself, but they don’t really explain why it is important to them or how they see themselves making an impact. If you write about an issue, be sure to pick one that is truly meaningful to you and that you know something about. You’ll probably score extra kudos if you can describe how you have done something related to the issue.

10. Resorting to gimmicks. Applicants have been known to enclose a shoe with their essays along with a note that reads, “now I have one foot in the door.” They have also printed their essays in different fonts and colors, sent gifts or food and even included mood music that’s meant to set the mood while the admissions offcer reads the essay. A few students have even sent cash! While gimmicks like this may grab some attention, they don’t do much to further the applicants, especially those few who’ve sent money, a defnite no-no. It’s true that you want your essay to stand out but not in a way in which the admissions offcer thinks that you are inappropriate or just plain silly. If you have an idea for something creative, run it by a teacher or counselor to see what he or she thinks frst.

11. Trying to make too many points. It’s better to have a single, well thought-out message in your essay than many incomplete ones. Focusing allows you to go into depth into a specifc topic and make a strong case for your position. Write persuasively. You can use examples to illustrate your point.

12. Not being specifc. If you think about some of the best stories you’ve been told, the ones that you remember the most are probably flled with details. The storyteller may have conveyed what he or she thought, felt, heard, or saw. From the information imparted, you may have felt like you were there or you may have developed a mental image of the situation. This is precisely the experience that you would like the admissions offcers to have when reading your essay. The key to being memorable is providing as many details as possible. What thoughts were going through your mind? What did you see or hear? What were you feeling during the time? Details help bring the admissions offcers into your mind to feel your story.

13. Crossing the line. Some students take to heart the advice to share something about themselves, but they end up sharing too much. They think that they must be so revealing that they use their essay to admit to something that they would never have confessed otherwise. There have been students who have writ-ten about getting drunk, feeling suicidal, or pulling pranks on their teachers. It’s possible that in the right context, these topics might work. For example, if the pranks were lighthearted and their teachers had a good sense of humor about them, that’s acceptable. But for the most part, these kinds of topics are highly risky. The best way to determine if you’ve crossed the line is to share your idea with a couple of adults and get their reactions.

14. Repeating what’s in the application form. The essay is not the application form, and it is not a resume. In other words, the essay is the best opportunity that you’ll have to either delve into something you wrote in the application form or to expound on something new that doesn’t really ft on the application form. It doesn’t help you to regurgitate what’s already on the application form.

15. Not having a connection with the application form. While you don’t want to repeat information from the application form verbatim in your essay, it’s usually a good idea to have some continuity between the form and your essay. If you write an essay about how your greatest passion in life is playing the piano and how you spend 10 hours a week practicing, this hobby should be mentioned in the application form along with any performances you’ve given or awards you’ve won. It doesn’t make sense to write about how you love an activity in the essay and then to have no mention of it in the application form. remember that the admissions offcers are looking at your application in its entirety, and they should have a complete and cohesive image of you through all the pieces, which include the application form, essay, transcript, recommendations, and interview.

16. Not going deep enough. One of the best pieces of advice that we give students is to keep asking, “Why?” As an example, let’s say that you are writing an essay on organizing a canned food drive. Ask yourself why you wanted to do this. Your answer is that you wanted to help the homeless. Ask yourself why this was important to you. Your answer is that you imagined your family in this situation. You would greatly appreciate if others showed compassion and helped you. Why else? Because you wanted to gain hands-on experience as a leader. The point of this exercise is to realize that it’s not enough to just state the facts or tell what happened, that you organized a canned food drive. What makes an essay truly compelling is explaining the “why.” You want the readers of your essay to understand your motivation. Keep asking yourself why until you have analyzed the situation as fully as possible. The answers you come up with are what will make your essay stronger.

17. Not getting any feedback. Practically every article that you read in a magazine, book, or newspaper or on the Internet has been edited. The reason is that writing should not be an isolated experience. You may know exactly what you want to convey in your own mind, but when you put it on paper, it may not come out as clearly as it was in your mind. It helps to get feedback. Ask parents, teachers, or even friends to read and comment on your essay. They can help you identify what can be edited out, what needs to be explained better, or how you can improve your work.

18. Getting too much feedback. Asking one or two people for feedback on your essay is probably enough. If you ask more than that, you may lose the focus of your writing. Having too many editors dilutes your work because everyone has a different opinion. If you try to incorporate all of the opinions, your essay will no longer sound like you.

19. Trying to be extraordinarily different. There are some people who are extraordinarily different, but the truth is that most of us aren’t. What’s more important than conveying yourself as the most unique person at your school is that you demonstrate selfanalysis, growth, or insight.

20. Ruling out common topics. There are topics that admissions offcers see over and over again such as your identity, your relationship with your family, extracurricular activities, and the Big game. While these topics are very common, it doesn’t mean that you shouldn’t write about them. Your topic is not as important as what you say about it. For example, many students choose to write about their moms or dads. A parent can be one of the most infuential persons in a student’s life, and it makes sense that this would be the topic of many students’ essays. So don’t rule out mom or dad, but do rule out writing about mom or dad in the way that every other person will write. Explain how your dad made banana pancakes every morning and what that taught you about family, or how your mom almost got into a fght with another mom who made a racist comment. Make a common topic uncommon by personalizing it.

21. Forcing humor. You’ve probably seen at least one sitcom on Tv or one monologue by Conan O’Brien or David Letterman with a joke that fell fat. Maybe you groaned at the Tv or gave it an un-amused expression. Keep in mind that the jokes on Tv are written by professional writers who earn large salaries to be funny. now, remember that the great majority of us are not headed down this career path. What this means is that you shouldn’t force humor into your essay. If you’re a funny writer, then by all means, inject some humor. Just be sure to ask an adult or two to read the essay to see if they agree with you that it is funny. If you’re not humorous, then it’s okay. You don’t need to force it.

22. Writing the essay the night before it’s due. Almost every stu-dent has done it—waited until the last minute to write a paper or do a project. Sometimes it comes out all right, but sometimes not so much. It is not wise to procrastinate when it comes to writing a college admissions essay. It takes time. Even if you are able to write an essay the night before it’s due, it’s still better not to. The best essays marinate. Their authors write, take some time away from it and then return to it later with a fresh mind.

23. Failing the thumb test. As you are writing your essay, place your thumb over your name. Could you put another name at the top because it could be an essay written by many other students? Or is the essay personal to you so that basically yours is the only name that could be at the top? If you fail the thumb test, it’s time to rethink the topic or your approach to it. You want your essay to be unique to you.

24. Forgetting to proofread. Some students put the wrong college name in their essays, a mistake that could easily be avoided by proofreading. Many more students have spelling, grammatical, or punctuation errors. While these types of errors usually aren’t completely detrimental, they can be distracting at best and be signs to the admissions offcers that you’re careless and not serious about their college at worst. Avoid this by not only using your computer’s spell check but by asking someone else to help proofread your essay. Twice is better.

25. Not writing to the specifc college. In addition to learning about you, admissions offcers also hope to learn how you would ft in at their college. Be as specifc as possible about a college, especially if you are writing an essay about why you’d like to attend that particular college. Explain one or two things about the school that make it the best one for you. Make sure that what you are writing is not so general that it could be said of any other college. In other words, it’s good to describe how you visited the campus and had a conversation about Marx with a sociology student. It’s not as good to state that you want to go to Harvard because it offers a high quality education.

26. Not spending time on the rest of your application. Remember that the essay is one piece of the application. It can certainly help your chances of being accepted, but you need to have everything else in place as well. Sure, it takes time to work on the application form, recommendation letters, and interviews, but you are taking actions now that will affect the next four years of your life and beyond. It’s worth the effort.

More Information



The lessons we take from failure can be fundamental to later success. Recount an incident or time when you experienced failure. How did it affect you, and what did you learn from the experience?

Phew. Read it again.

Okay. This isn’t so hard, right? Throughout this process, if you ever feel overwhelmed or stressed just repeat that to yourself. This is not impossible. The point of the personal essay is not to trip you up or trick you. Instead, it is the Common Application  giving you a golden opportunity to share your voice, personality, and a snapshot of your experiences with the colleges to which you’re applying. Be honest and genuine, and you’ll do just fine. That, and follow this guide!

The Question: What is it asking? Should I answer it?

Before we launch into explaining the prompt, let us begin with this: if the personal statement prompts seem vague and slightly similar to each other, you’ve caught on. They are. These prompts are designed to encourage students to talk about themselves, to show adcoms personality and style through writing, and to allow high schoolers to exhibit their wide array of personalities and experiences comfortably and adequately. Thus, they are not designed to elicit specific responses, but rather a broad range of creative pieces.

For this reason, choosing which question you’ll answer is much less important that deciding how you will answer it. Nonetheless, if you’re unsure of whether or not this is the question you should be answering, read on for an analysis of what it’s loosely asking of you.

Of course, if there is a particular story about yourself that you wish to share that involves what you consider to be a major, life-defining failure that you think has played an important part in forming you as you are today, this is the perfect opportunity to talk about it. In such a scenario, the prompt becomes similar in nature to the first personal essay prompt on the Common App. This is okay. Like we said, the lines differentiating all of the personal essay prompts from each other blur a bit.

More broadly, though, this prompt is asking you to reflect on times in your life when things did not go as planned and to show that you learned something from those incidents. Thus, it positions you well to show humility and maturity by not only admitting that you are less than perfect (as we all are) but also reflecting on your mistakes and rendering them learning opportunities.

In this vein, many students will write about “failures” that were not so grave or may not seem particularly life-changing—like failing to wish your best friend a happy birthday one year or forgetting to take out the trash after being asked to do so by your father. Even in these instances, the potential lessons to be learned are endless if you are willing to think creatively and imbue a little bit of cheeky humor in your personal statement. If you think of yourself as someone who is particularly reflective or able to derive lessons from various life experiences, this is certainly a prompt you would be good at writing.

Words of Caution

Before we go any further, we need to address some common pitfalls you should avoid while brainstorming. The first major mistake you can make is forgetting the prompt, which is easier to do than it sounds.

Somewhere between drafting your personal statement and pressing the ‘submit” button on, it is easy to lose sight of the text of the prompt you are answering. This is understandable, since once you become embroiled in writing a 650-word incisive description of yourself, details can fall to the wayside. That said, it’s extremely important to remember the first sentence of Prompt #2: “The lessons we take from failure can be fundamental to later success.”

This lesson is stated in no uncertain terms. And thus, if you decide that it is true, the insight that you draw from your “failure story” must go beyond the story itself and delve into further analysis. In other words, the moral of your essay cannot simply be that your failure was fundamental to a later success—this will impress no one. Your insight must go beyond this, focusing—as the prompt suggests—on a lesson you learned from your mistake.

If you choose, you can take issue with the opening statement itself, perhaps using the lesson you learned to emend it. If you come to a conclusion by the end of your essay that a supposed failure was actually a success in and of itself, and you want to argue that there is no such thing as a failure at all, that is acceptable.

On the other hand, we caution you from feeling pressured to discuss a failure that has led to a “future success” that you have already achieved. If making mistakes is part of the journey to ultimate success, it is perfectly reasonable for you to still be in the process of reaching your goal, and speak about the process you’ve made towards your goal instead of a final result.

The Process

Now that you’ve mustered the courage to choose a personal essay prompt, and you know what this specific prompt is asking you to do, it’s time to get down to business and start writing.

Step 1: Brainstorm

The first step to writing any good personal essay is to put some serious thought into what you will write, and the best way to do this is to force yourself to come up with a handful of possible essay topics. Brainstorming is a great way to ease into starting an essay, because it can be as casual as you want. Sit down with a fresh notepad (or new Word document) and start jotting down some notes. These don’t need to sound good, nor do they need to be in full sentences, nor do they even need to be chronological. The point here is to simply get yourself thinking—save the nuances of language and niceties of commas for steps 4 and 5.

Still just a bit daunted? Let’s start brainstorming together, shall we? Let’s pretend you were in a meeting with one of our essay specialists. The first thing we’d do is start you thinking about the various levels of failure and achievement you have experienced and/or achieved in your life. Since we obviously cannot do that verbally with you here, we’ll do the next best thing: provide you with the brainstorming prompts we would give you in a consultation. Below, you’ll find these—try to come up with at least some response to each one.

  1. Can you think of any “failures” (major or minor) that you have experienced in your life? Hint: the word “failure” is in quotes here because it is open to interpretation. For some, major, dictionary-definition “failures”—big mistakes or missteps—may come to mind easily. Regardless of if this is true for you or not, it can be helpful to take notes on the minor failures in your life too, as well as incidences when you considered yourself a failure but others didn’t (or vice versa). This is all to say that you have license here to interpret the word “failure” as you wish. It should also serve as a reminder that you are allowed—and even encouraged—to take a creative approach to answering this question and any other on the Common App. For each “failure” you enumerate, list the lesson(s) you learned from it.
  2. Alternatively, can you think of any successes that you are particularly proud of? Why do you consider them successes, and why are you proud of them? What failures can you think of that led up to this particular success? Did those failures hamper or aid you in reaching your ultimate achievement? For each “failure” you enumerate, list the lesson(s) you learned from it.
  3. Do you have any as-yet-unrealized goals or successes? What are they, and why do you strive for these things? What failures have you encountered thus far in trying to achieve those successes? What failures (if any) do you anticipate as you continue to pursue these goals? For each “failure” you enumerate, list the lesson(s) you learned from it.
  4. Is there anything about yourself or your character that you feel must make it into your personal statement—in other words, something integral to your identity that the adcom will not hear about if you do not include it here?

Step 2: Determine Your Story Arc

At some point, you’re going to have to commit to a topic of discussion for your personal essay, and sooner is better than later—so you’re going to do it now, in Step 2. Fear not! If you are not completely sure that you have chosen the right topic, you’re not alone. Choosing the topic for your personal essay can feel like a huge decision with a lot riding on it, but the fact is that this decision is not as final as it feels in this moment. Your essay is going to change so much in the interim between your first draft and final revision. We promise that by the end, it will communicate everything you want it to.

The key here is to make use of your brainstorming notes—the more notes you have, the easier this step will be. So that they stand out, highlight all of the “failures” you enumerated over the course of the first three prompts, paying special attention to the listed lessons you were able to pull from each one. Ultimately, you should try to choose to write about a failure based more on the lessons you learned from it than the failure itself.

If that is confusing, think about it this way. Suppose you are deciding between two topics. The first is the story of how you were late to ballet class (and thus allows you to discuss your most substantial extracurricular activity), but it doesn’t provide much of a platform for discussing a major life lesson (you learned how important it is to be punctual, and that’s about it). The second is harder to discuss because you’re ashamed about it: you weren’t there for a friend when they needed you, and consequently, you ruined a friendship.

As you are deciding which failure to discuss, look for overlap in your notes. If you are choosing between telling two stories—one recounting how you learned to be responsible and the other recounts that plus something else—go for the second one, the one that allows you to cover more ground and tell more about yourself. In the end, that’s the point of the personal essay.

Once you’ve decided on the failure you want to talk about, create an outline that includes three parts: 1) an introduction that sets up a tension or problem you need to solve (likely, the failure you will be discussing), 2) a climax (perhaps the moment when you learned from your failure or its ramifications affected you), and 3) a conclusion (this can be an insight that you are able to have in hindsight or a connection to some larger theme in your life).

Step 3: Draft

To execute this step correctly, you have to really commit. In the drafting phase of the personal essay, your job is to simply get words on the page.They do not need to be polished. They do not need to sound smart. They simply need to exist.

Try to get down your whole story, start to finish, replete with details about the failure and what you learned from it. When you feel stumped or lost, return to the prompt. If you feel yourself drifting off topic, reread the question to remind yourself what you need to be answering. Do whatever it takes to say what you need to say. Then, close your computer and walk away.

Step 4: Rewrite, rewrite, rewrite. Edit. Rewrite some more.

At least 24 hours after completing Step 3, Phase 4 can officially begin.  In this phase you will be shaping and re-working what you’ve already done. Luckily, since you already have words on the page to work with, this need not be so daunting.

The first order of  business is to make sure that you have touched on everything you wanted to discuss—the failure you experienced, the lesson(s) you learned from it, and your responses to the fourth brainstorming prompt (important details about yourself that you strongly believe should make an appearance in your personal statement).

Once you can ensure that all the content you want to include in your essay has been written down, you can play around with structure, style, and voice a bit. Work on your lead-in—perhaps you want to start with a dramatic one-liner, a quote, or a funny anecdote. Maybe you want to shock your reader by explaining your failure in the very first sentence. Or even, perhaps, you want to start your essay in the middle of a story, and circle back to the beginning at a later point.

Meanwhile, the less creative approaches to editing your essay are just as important. It should be a given that you need to edit for correct grammar and spelling, and you should likewise carefully consider your word choice here. Show off your vocabulary, but maintain your voice (adcoms know the difference between a person who has an impressive vocabulary and a person who has a thesaurus).

Step 5: Edit for word count, keeping the piece at 650 words or less.

This should be your last step, because your limited space should not be a factor in your decision to include or exclude important aspects of your story or explanations about yourself. Our essay specialists encourage their students to use their words efficiently so that they can say as much as possible in their personal statement, and we’re giving the same advice to you.

So write your essay with every vital detail intact, and then go back with a red pen once all of your thoughts are written down. This way, you’ll have written down everything you want to say, and all that will remain for you to do is say it in fewer words.


Hopefully armed with this guide, you’ll be on your way to writing an effective response to the Common Application’s second prompt that will demonstrate your abilities, experience, and personality to colleges in a compelling way. If you’re looking for further guidance on your college essays, check out our submit an essay, essay editing, and elite applications mentorship programs.


Happy writing!


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Lily Calcagnini

Lily is a History and Literature concentrator at Harvard University who is doing her darnedest to write a thesis about all of her favorite things at once: fashion, contemporary culture, art journalism, and Europe. A passionate learner, she cares deeply about helping high school students navigate the process of college admissions, whether it be through private essay tutoring or sharing advice on the CollegeVine blog.

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