I feel for these kids. I was helping out at a college application bootcamp a couple of weeks ago at a great independent school—one that, in its very intimate setting, places a lot of emphasis on the personal development of its students—and I was making rounds as the seniors had designated time to work on starting their college essays. They’d discussed potential topics the day before, and went through some of the classic do’s and don’t’s of the process using a couple chapters from Harry’s Bauld’s book as a jumping-off point.

I am sitting with one student, asking question after question, trying to elicit any information about him that I could. He surfs, he goes to school, he has a younger sibling. He doesn’t know where he wants to go to school. He has lived in the same house all his life. He thinks his school is “pretty cool.” Nothing really traumatic has every happened in his family. He’s never been to a funeral, his parents are still together, they both work regular 9 – 5 sorts of jobs. “There’s nothing for me to say about myself,” he says. “I’m totally boring.”

I ask what his best friend would say about him. He starts giggling. Since it was the first display of emotion I saw from him, I pulled out my phone, set a timer for ten minutes, and told him that he needed to start writing—no deleting, no editing, no stopping, no censoring. If he can’t think of anything to say, write that phrase over and over until he gets unstuck.

All of the humor drains away as quickly as it had come on. From bit of a distance, I watch him strain to string a sentence together, and when I come back by to nudge him out of a long pause, he resorts to random, garbled clacking on the keys.

There is just nothing about high school (and perhaps even classroom learning on a broader scale) that can prepare us for that kind of writing. It’s as if every piece of direction or advice you give poses the threat of dragging the entire creative, self-expressive process to a grinding halt, because they’re just waiting to be told what to do. There’s so much pressure to produce, and produce something good and smart sounding, according to the things that other people have told you are officially smart, that there’s no space for anything that might be judged as trivial.

It’s the kids that judge themselves and their own thoughts, firstly, as trivial. There is no room for writing anything that is not good, so why write anything at all? That’s the core problem: not the mere fact that we have a lot of trivial thoughts, but that it’s not even okay to put those thoughts out into the world out of fear of judgment. How do we ever learn to express ourselves if we’re so quick to dismiss and shut down our own, individual thought process?

It’s unfortunate that this sort of process tends to get crammed into this one moment in time, when suddenly the pressure is on to present ourselves in all of our glorious peculiarities—because it’s suddenly what a higher power wants to see.

By Nick Soper