One of the greatest challenges I’ve had in undertaking Reschool Yourself is explaining it. For me, it’s about so many things (personal development, the education system, pursuing even the craziest of dreams, etc.) that it’s almost impossible for me to condense the project into a couple sentences. In the nonprofit and business worlds, this is called an “elevator speech.” That is, if you had 30 seconds in an elevator with someone, how would you summarize the basics?

This week I’ve been working on my first retrospective article about the fall, and my 1,000-word piece quickly ballooned into a 2,400-word piece before I could even get to talking about middle school. I prayed to Ernest Hemingway, the master of brevity (and thus never a favorite of mine, given my love of nuance) to help me distill my writing.

Hemingway answered my prayers. Darren (a fan of all things manly and bleak, such as Mr. Hemingway) tipped me off to a writing contest through GoodReads.com, a social networking site based on book reviews, that asked for a story written within a 24-hour period purely in status update form. Each line could be only up to 140 characters. Coincidentally, this contest was a step toward realizing another dream of mine: to write status updates for a living.

I found the exercise helpful in getting to the core of the project without all the details that I love so much. If you ever need to summarize something, I highly recommend writing it in this form. The tone is spontaneous and simple, as if it were a child’s story. And everyone loves a good story.

Here’s the beginning of the Reschool Yourself story. I’ve edited the formatting and punctuation of the updates for easier reading.

The following is a true story about a transformation that is still underway. It’s about me, you, and the education system.

Last August, at the age of 28, I went back to kindergarten. I’d played the game of life like I’d been told to. I got the grades, went to college, and got a respectable job. But I still wasn’t happy.

As a kid, I’d used my imagination. I’d written stories, built forts, and drawn pictures. I’d had fun. But as an adult, I didn’t do things I enjoyed because I was always working, striving to achieve something impressive.

Workaholic. Perfectionist. Stress case. This wasn’t what was supposed to happen to me if I followed the rules. But it did happen to me, and I wanted to know why. I had a feeling that school had something to do with it.

School taught me that I had one shot to do things perfectly. I grew terrified of risking a mistake. In school, I’d learned that listening to others, especially authority, was more important than listening to myself.

By the time I graduated college, I felt more confused and unhappy than when I’d started school at five years old. At what point in school had I lost my way, and how? How could I become as joyful and creative an adult as I was as a child?

The only way to find out was to go back to where I started: Kindergarten. Then first grade, then second, and so on until college. In the fall, I would spend about a week in each grade at my old schools. My goal would be to go backward, to make peace with my past. In the spring, I would reeducate myself, the way I wanted to. My goal would be to move forward, into a future of my own design.

I would have the opportunity for something that almost everyone dreams of: a do-over.

The name of the project came to me: Reschool Yourself. A command to me, and to others, that transformation is possible at any age. The project was never just about me. It had three goals: help to transform myself, other people, and the education system.

I wanted to become like a kid again: joyful, imaginative, and learning all the time. I hoped to inspire other people do the same. I would also raise questions about an education system that often drains these natural qualities from kids instead of nurturing them.

To be clear, I never planned to tell the schools, “You screwed me up.” I wanted to keep the tone positive and hopeful throughout. Fortunately, it wasn’t hard to get permission. Sonoma, CA, is a small town, and teachers remembered me. They said, “We’d love to have you.”

I had the idea for Reschool Yourself in January, left my job in June, and started kindergarten on August 20, 2008. I’d been an educator myself for five years, running youth programs, and now I would get to experience school from the other side of the desk.

The story continues in Chapter 2.

It’s amazing how works of literature, like Pride & Prejudice and Hamlet, can be boiled down to status updates. Try it. It’s addictive.

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What do you relate to, if anything, in this story?

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