the importance of being interesting (and how you can develop your own interestingness), part one

I remember a pivotal conversation with my high school guidance counselor when I was 17. He called me to his office to inform me that my high school – a small Canadian school in the village of Lakefield, Ontario, population 1200 (or thereabouts), that bussed in farm kids from surrounding counties and native kids from a nearby reservation – was nominating me for a four-year scholarship to arguably the most prestigious university in the country (Queen’s University, which likes to think of itself as the Harvard of the North, and I know, I know, you probably just rolled your eyes. But bear with me).

I was dubious. My academic record was spotted with very high A’s in the subjects that interested me and very low C’s in the subjects that did not. It was also rife with absences, both legitimate and maybe not-so-much. My extracurricular activities amounted to a starring role in a high school production of The Sting and a year “studying” (I use the term loosely) abroad as a Rotary exchange student in Australia. I knew who the school stars were – the well-rounded kids who ran the student council and headed up the honor roll and spearheaded the academic teams and were involved in the community, etc., etc. I was not them, and they were not me. Throughout my entire high school career, I was, you might say, rather severely underscheduled.

So what the hell, I asked my counselor, albeit not in so many words, had he been smoking to even suggest this?

And he explained to me that high schools all over the country had lots and lots of well-rounded straight-A students with impressive extracurricular resumes who did all the things you were “supposed” to do to get into an excellent university.

What I did, on the other hand, was read novels. I read them obsessively.

I also wrote them.

I had a YA novel circulating through the Canadian publishing industry, I had met with editors and talked with agents, and I even had a mentor in the form of a Canadian novelist and sports reporter named Scott Young (father of Neil) who was the first person outside of parents and teachers to champion my fledgling fiction. I had won some writing competitions. My English teacher had taken one of my assignments – a humor essay – and, unbeknownst to me, submitted it to a local paper which published it (and he presented the newspaper to me with great fanfare in front of the rest of his students, an act which no doubt massively endeared me to all of them). Although I didn’t know it then, my high school was inventing a new award for graduation in order to recognize my creative writing.

So I wasn’t a candidate for Valedictorian, my counselor said. So I didn’t have the star-studded high school resume. What I had going for me was something else: I was unique. Which is why he predicted that I would stand out in the pile of applicants culled from high schools all across the country.

And here’s the amazing thing: he was right. Months later I got a call from Queen’s U saying that I was one of the students selected to receive the scholarship. When the principal announced the news at a student assembly, including the amount of money involved, an audible gasp rippled through the auditorium/gymnasium. And not long after that, through various feedback loops, I heard that some of the other students, and quite a few of the teachers and parents, were wondering just how and why it had happened: why I had gotten this big juicy prize and the Valedictorian candidates had not.

I could hardly blame them. I was wondering that myself.

Many years later, I had the opportunity to read scripts for a thriving young film production company called Room 9. The scripts had passed through some major filters. They were represented by legitimate agents with good reputations. Other readers at the same film company had liked them enough to pass them to me for another (and female) opinion. Room 9 was eager to make a movie and had the funds to do it; all they needed was that one magical screenplay that they could fall in love with.

So I read a lot of screenplays.

Sooooo many screenplays.

And before long, what I noticed was this: they were good. Every single one of them was an accomplished and well-crafted piece of work.

And they all kind of blurred into each other.

Of the countless screenplays I read, I remember exactly three. One was ultimately rejected because it targeted the “wrong demographic” (older women); another was rejected because Room 9 feared it would come off too dark and cynical (Kevin Spacey’s company ended up producing it); and the third was a little script called THANK YOU FOR SMOKING, based on the book by Christopher Buckley and adapted for the screen by a struggling young writer/director named Jason Reitman.

THANK YOU FOR SMOKING got made. It met with great popular acclaim at the Toronto Film Festival. Fox Searchlight and Paramount Classics competed for distribution rights. Jason went on to direct another little film called JUNO (you might have heard of it).

What SMOKING had going for it that the other scripts did not was this:

It was unique.

Yes, it was well-written, but so were all the others. Yes, it was smart, but so were all the others.

But SMOKING was interesting.

It had the quality of interestingness.

The excellent (and very interesting) Cal Newport has a new book out called How To Be A High School Superstar that is dedicated to the idea of interestingness. He provides case studies of students who, like me, coasted through high school with lots of free time, who kept themselves underscheduled and “relaxed”, and yet somehow managed to breeze into the nation’s top schools (one of these students spent exactly forty minutes writing her admissions essay). Because when everyone has straight A’s, when every screenplay is well-written and well-constructed and well-represented, when everyone and their Aunt Matilda has a blog and a Twitter account, when everyone is latching onto the idea of unmarketing and marketing with meaning and content marketing, when everyone can publish their novels and stories on the Internet, and some of those novels and stories are actually pretty good….what is going to separate the superstars from the rest of the pack?

Interestingness.

In my next few posts, I’m going to look at interestingness: what it is, why you need it, and how you can develop it.