The coaching process

Step by step

What to Expect

With 20 years of experience coaching writers of all abilities, college essay coach Anna Sharp will help you find the one-of-a-kind, give ’em goosebumps, knock it out of the park essay that is already in you, fully formed, yours for the taking. How will you get it out and onto the page?

As your college essay coach, I will walk you through the essay writing process step by step, providing simple and specific instructions and assignments tailored to your unique learning style, strengths, and schedule. Because cookie-cutter coaching can result in cookie-cutter essays, no two Naked Essay coaching experiences are alike. However, all students go through a similar pattern of brainstorming, free-writing, and revisions. Here are the basics of what you can expect from me as your college essay coach:

Step One, Choosing a Topic:

I am not going to let you waste another second wondering what to write about.

My tutoring is designed to eliminate the staring-at-the-screen part of the process. To zero in on your most promising material, we will use an amazingly effective technique called free-writing. I will give you specific questions and have you quickly scribble down your thoughts in a rambling, messy way. From this beautifully weedy, overgrown mess, we will find the acorn that will grow into a mighty oak.

Essays that get students into their dream schools are not skin-deep. The best topics are often emotional, difficult, or deeply personal. For example, free-writing helped recent students open up about the following: shyness and insecurity caused by a medical condition in childhood; OCD and anxiety; moving a lot/being the new kid and struggling with academic failure related to dyslexia; struggling with the role of “man of the house” following divorce and mom’s illness; being destroyed by the competition at Battlebots; taking a social risk and losing friends; and living apart from mom. (These writers are attending Cornell, Boston University, CU-Boulder, Hopkins, WPI, Stanford, and Columbia, respectively.)

First draft:

With simple, specific instructions and assignments that break the process into small, manageable steps, you will finish your first draft quickly.

I will show you how to let it all out, without stopping to rewrite, read what you have written, consult a thesaurus, or worry if you are doing it right or wrong or sounding pathetic or boring or weird. (Don’t worry, all your best qualities will shine in your final essay, but right now you just have to keep your fingers typing.) As your college essay coach, I will help you write without thinking too much because you are not writing from your head. You are writing from your heart—that is where your best story lives, in all its surprising, dramatic, vivid glory. Most teachers focus on rewriting and simply don’t have time to sift through rough first drafts, so this one of the biggest perks of working with a private college essay coach. Be silly, sappy, or clichéd. The best essays come from the worst first drafts. Let it all out.

Second draft:

As your college essay coach, I will help you make sure that your second draft starts with a hook, goes out with a bang, and everything in between keeps your reader riveted.

Is your first draft a hot mess? Good, then this part will be easy. Like Truman Capote, we will “believe more in the scissors than the pencil.” During this step, you’ll work with me as your essay coach to delete all the stuff that isn’t essential to your story. Then we can focus on fine-tuning any areas of your essay that need further development with a few final free-writing assignments.

Finally, deeply personal writing can involve many complicated themes and emotions: hope, regret, frustration, elation, embarrassment, pride. It can be hard for students new to narrative writing to strike the right tone. Before moving on to your third draft, we make sure the essay’s overall emphasis is upbeat and conveys a positive attitude, maturity, and resilience.

Third draft:

Only now do we start refining language, making sure that your essay sounds like the very best version of you.

We will make sure your cadence is conversational throughout and your transitions flow, giving your essay a final sentence-level edit without diminishing your unique, authentic voice.


This is the last step! I will proofread your essay and return it to you the same day. My method is to print a copy and go through it word by word three times to ensure your essay is 100% free of grammatical, punctuation, and spelling errors. You’re done—congratulations!


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