July 8, 2026

The Essay Isn’t Hard. Knowing What to Say Is.

When a student tells me they are struggling with their college essay, the first assumption is usually that writing is the problem.

In most cases, it isn’t.

The students I work with in Brookfield, Oak Creek, Oconomowoc, and the surrounding areas can write. They have been doing it for years. They can put together a clear paragraph and tell a story that makes sense.

What slows them down is something else.

They are not sure what the essay is supposed to do, or what they want it to say.

By the time we get into July, a lot of students have opened a document, read through the prompts, and maybe started something. Then it stalls. Not because they can’t write, but because they don’t know if they are heading in the right direction.

I see it play out a few different ways.

Some students try to cover too much. They bring in multiple activities or experiences and try to fit everything into one essay. It feels like they are saying a lot, but it is not especially clear what they want the reader to take away.

Others pick a topic and describe it well, but stay pretty close to the surface. You understand what happened, but you don’t really get a sense of how they think or what changed for them.

And then there are students who just sit there at the beginning, because they know this matters and they don’t want to get it wrong.

All of that comes back to the same issue.

They are trying to write before they have decided what they are trying to communicate.

Admissions offices already have the transcript. They already have the activity list. The essay is one of the few places where a student can add context and help someone understand how they approach things.

That is not something most students have had to do before.

The students who move through this more smoothly usually take a step back before they start writing and ask a few simple questions.

What do I actually want someone to understand about me after they read this?
How does this connect to the rest of my application?
What does this show that is not already obvious?

Once they have some answers there, the writing part tends to go a lot better.

If those answers are not clear, the draft usually goes in circles.

If you have a rising senior in Waukesha, Watertown, Shorewood, or nearby communities and the essay is not moving forward, it is worth looking at it from that angle.

It is probably not a writing problem.

It is a clarity problem.

And this is the point in the summer where it is still easy to step back and fix that before everything else starts to compete for their time.

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