College Essay Lessons Learned



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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Harvard Admissions Essay: Lessons Learned

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Lessons Learned Are Lessons Lived


A few years ago, while helping my grandfather plant pecan trees in Tennessee, I realized something a bit disturbing. My grandfather never would live long enough to see those trees mature and produce pecans. Yet, there he was, toiling away with no possibility of personal benefit. When I asked him why he would plant trees knowing he would never enjoy the harvest, he just smiled and shook his head. Then he said, "Son, of all the pecans I've eaten in my life, someone else had planted the tree. They thought enough of me to plant trees, so I could have pecans. I'm just thinking of the next generation." In that moment, I realized that all people are takers, but only a few people become givers.


Being a taker comes naturally. From the moment a baby is born, it takes. It wants food and warmth and comfort. If no one fulfills the baby's desire, it screams until it gets whatever it wants. Becoming a giver in life takes time and instruction. We must be taught to share. We must learn to give. Unfortunately, most people never learn to really give. They give, but they expect something in return. They are still selfish. A selfish child becomes a selfish teenager who becomes a selfish adult. If a person has never developed a lifestyle of giving by their teen years, I doubt they ever will. A college degree or a high-paying job can change their income but not their heart.


Through my teen years, I volunteered at least two days a week at The Master's Outreach in my hometown. The Master's Outreach is a non-profit organization, which helps feed and clothe the needy. We even went to Central America once to take clothes, food, medicine, and other supplies. On other occasions, we sent supplies to help hurricane victims. Each one of these projects required a lot of time and effort by a few people willing to give.


By now, volunteer work has become part of my life. I intend to continue giving during my college career at Jones Community College and then, Mississippi State University where I will pursue a degree in architecture. With a college degree, I will have even more opportunities to serve my community. As an architect, I would like to become involved with Habitat for Humanity because they have such a good reputation and will be able to use my particular skills.

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"Harvard Admissions Essay: Lessons Learned." 11 Mar 2018

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I also like the idea of helping someone in my own community and Habitat for Humanity does that.


I do not intend to imply that this charity is the only way I intend to give back to my community. I just wanted to give an example. As opportunities arise, true givers toil away with no thought of personal benefit. My greatest desire is that my grandfather will live to see me mature and produce a harvest he can enjoy: a new generation willing to give.


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