For purposes of this post, the student’s name has been changed and I use they/them pronouns to further assure anonymity. They’ve consented for me to share their essay and our experience working together.
Writing an essay that reads effortlessly can take quite a bit of work. Sure, we all have moments where an idea comes and the words flow. When it happens for me, it’s dizzying and electrifying. And it’s admittedly rare.
The Common App essay is a student’s opportunity to explain themselves uninterrupted to someone offering their undivided attention. I like it to read easy and conversational. Many students have a difficult time trading longer phrasing and an academic tone for more natural language with a polished finish. It’s no sweat for me to edit drafts with these characteristics—my students see what should be deleted and receive a detailed comment about other ways to convey the same idea.
But what about the student who knows what they want to say yet freezes at a blank Doc and blinking cursor?
Enter Taylor.
Taylor came to our first meeting as excited as they were anxious, ready to dive in to applications but knowing they needed a plan and schedule. They also brought three potential Common App essay topics. Taylor animatedly discussed them and the direction they envisioned for each. I liked them all, but I knew without a doubt which one would stand out.
Taylor did the New York Times crossword everyday. They were dedicated to the puzzle in much the same manner that many of us Wordle’ed our way through those early months of 2022. The difference was their obsession began when they were 15! For Taylor, the crossword was a daily conquest that he had mastered over years. I haven’t remembered to do the Wordle in weeks.
During our meeting, I heard them talk with such excitement about the puzzle that I knew a beautiful essay could potentially come quickly. I expressed as much, told Taylor to type the same stream of consciousness they had just spoken to me, and sent them off with a rough draft deadline.
But two weeks went by. Reminders went ignored. So we met again and revisited the other potential sources of inspiration for their essay. I reassured Taylor that the crossword was the best topic.
September passed with a blank Google Doc despite additional meetings.
When we met again in early October I shared with Taylor that I type really fast. For my first job out of college, I worked for three attorneys who recorded voice memos of pleadings, letters, deposition questions—you name it—for me to transcribe. Eventually, I barely had to pause or rewind.
I told Taylor to put away all their materials—no notes, no computer—and said, “tell me about you and the New York Times crossword.” Taylor expressed with passion, honesty, and vulnerability. Their voice came naturally through the piece because they literally spoke it. I typed nonstop. I won’t pretend it wasn’t full of mistakes, but the story was out. What Taylor couldn’t write was suddenly 1,752 words. I edited it to something manageable, cutting swaths of text students tend to see as indispensable that I know are unnecessary. And with a topic and story as good as this one, I knew there wasn’t much room for fluff.
We worked back and forth together, debating how to keep ideas but cut words. I’d suggest to Taylor where I envisioned another sentence to connect or develop thoughts and encouraged them to speak it out loud if the cursor caused their mind to once again go blank.
What follows is Taylor’s essay that, in my opinion, reads so fluidly that I imagine some admissions officers read it twice—it’s that enjoyable. Completing the NYT crossword puzzle is a fete that academics respect and an ability others envy, but Taylor doesn’t come across conceited. It demonstrates their curiosity, commitment, dedication to self-improvement, and ambition without explicitly naming any of these important values within the text. A 650-word essay typically takes 4-5 minutes to read, but this one goes by in a flash. I hope you enjoy it as much as I enjoyed helping Taylor craft it.
I did my first New York Times crossword puzzle in a doctor’s waiting room on a Monday morning. With the help of my mom and Google, I managed to complete it. That was two years ago. Now I finish Mondays before breakfast.
This isn’t too impressive, considering they’re the easiest. The puzzles grow in difficulty throughout the week. Sundays are the most difficult and double the size of the other puzzles. I usually finish by lunch.
After a few months, I started to recognize common clues and redundant themes. I began to lose interest. In fact, I’d likely have given them up altogether if not for Thursdays.
Thursday puzzles are the most frustrating which is exactly why they’re my favorite. I know Mondays are simple, Tuesdays are themed, Wednesdays are a little harder, Fridays have longer clues, Saturdays lean esoteric, and Sundays are big and confusing. But Thursdays? They are always a surprise and always contain a trick. I live for the Thursdays.
My appreciation for Thursday’s crossword doesn’t come as a surprise. I’ve always been fascinated by the why and the how rather than the what. I’m more interested in the tiny gears that rhythmically tick the second hand on a watch than the time it displays. I had the same connection with Thursday’s puzzles.
I can’t solve Thursdays with the same process I use for other days. For starters, I solve the puzzle backwards. I find the trick first then move on to the solving clues, which typically hint to the puzzle’s theme. The more clues that seem to fit my hunch, the more excited I get that my theory may prove correct. Finding that one special answer, from which I can derive so many more, exhilarates and challenges me like nothing else.
I don’t believe in having answers handed to me. I enjoy using what I know to find what I don’t. For me, an answer is only meaningful if it’s a product of my own efforts, if it’s something I earned.
My interest in Thursday puzzles led me deep into the crossword-making rabbit hole. After weeks of brainstorming, months of constructing, and a few days of editing, I submitted my first original Thursday crossword to the NYT for publication. Their 90-day waiting period felt like years. Finally, I received an email from the Crossword Editing Team: “Dear Taylor, We regret to inform you…” I was heartbroken. But my disappointment turned to excitement as I continued reading. Rather than a generic rejection, they provided personalized feedback for my puzzle, helpful comments, and well wishes for my next try.
I took their message to heart and submitted a new puzzle a few months later…then another one, and then two more. Over two years, I created and submitted 6 crosswords to the Times. With each one their commentary was more positive and constructive. I measure my progress by the NYT’s response to puzzle number 6. Again, that dreaded “unfortunately…” But as I scanned the message, I saw little criticism. The Team wrote that they loved my puzzle, and it had even made it to their final three contenders. While mine didn’t win, they specifically noted my word play, humor, and inspiration and stated they’d keep an eye out for more of my puzzles.
We all start life as blank crosswords. There will always be those who look to others to fill theirs in. But not me. I want to find the answers for myself. Surely I won’t be able to complete them immediately; but the harder I search, the more I’ll find. With each new answer, the intersecting clues become a little bit easier to solve. I may never complete my puzzle, but the answers I enter will be worth more because I will have found them myself.