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?


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.

Jul 28, 2010

15 comments · Add Yours

This is going to be an interesting series of posts. I can’t wait to hear what you have to say.


Sorry, I pressed submit too quickly didn’t press stop quickly enough, thus the double post. What I was going to add was —

I’ve noticed the same thing with reading. Out of everything I’ve read, even stuff that’s well-written, it’s amazing how much you forget if it’s not detailed. There’s books that I can’t remember the name of the protagonist, and yet others where I have no problem remembering not only the name of the protagonist but their relatives some of their backstory along with various hopes and dreams.

It’s like when you’re covernig a song — you have to do more than play the beats, you have to play them in your own way.

Details details details. As Chuck Palahniuk says — don’t aim to be liked, aim to be memorable.


Vewwwwwwy intewesting.

I’ll be very excited to see your follow up on this. What made Holden Caufield so interesting? Benicio Del Toro in the Usual Suspects? Why are people wildly interested in some characters/situations and not others?

You’re the perfect person to tackle this.


Thanks for this post. I’m sharing it with the high-school students I work with, as they all seem to wring their hands in despair over the precisely the traits that make them the most interesting. I’ve already been begging them to browse Cal Newport’s Study Hacks blog and rethink the way they’re experiencing their adolescence and high school experience (which, more often than not, is a blur of “extracurriculars”) Why waste the time in your life when you have the freshest eyes and, perhaps, the most wonder?

I was kicked out of high school the fall of my junior year for publishing an underground newspaper. I ended up at Brown University–no Harvard or, rather, Queen’s University:-)–but the perfect place for me. It’s clear they’re not alone in valuing intellectual passion and unquantifiable “interestingness” over pure numbers and levels of involvement. Now, whether or not a sixteen year old’s poor judgment qualifies as “interesting” or not is a topic for another time…


This is great! Just what I wanted to read.


As a soon-to-be high school senior, Cal Newport’s blog has helped me enormously in gaining the courage to turn down useless Student Council posts and cutting myself a little slack for that B in Chem (I’m not quite as spiky, anti-math/science as you, so this was somewhat tragic at the time). I’m glad to see that you’re tackling this issue as it relates specifically to writing, since I hope to make a way, one way or another, in the writing industry.

And hopefully, between you, Cal, and the lifestyle bloggers, high schoolers, college kids, and workaholics won’t feel so pressured to chase after time consuming, draining activities. Those activities don’t get you into college (most of the time), and they certainly don’t get you published.

I’m excited to see what else you have to say!


Brilliant. Thank you. I’m staying tuned.


Akin to your theme Justine is Cal’s excerpt from his new book, in Tim Ferris’ blog this week


Stimulating post and I would add that you are interesting because you are interested. Part of the general jumble of indistinguishable voices in print and online is the cacophony of people who are trying to be interesting but, mistaking popularity for interestingness, are not interested in much more than that. The people who are interesting get greater joy from learning than the grade; they do something because it fuels a passion, not simply because they earn a merit badge.

Second, minor point: I work at Harvard and I have to admit that there are days — usually after a glass of wine or two — when we sheepishly call ourselves the Queen’s College of the south:).


Love, love, love this post. What does make some people more interesting than others? Besides (sometimes) the circumstances of their birth, of course. (i.e., born to missionaries in Mongolia, movies stars, etc.) Look forward to reading the next post.


Easy Queen’s, not even the most prestigious in Ontario, but good school.


Ha. Spoken like an engineer at Waterloo. :)


so is that a picture of a suicide girl?

and also…

its sad to think that a student (or writer) can do everything “right” and still be considered white noise.

there are too many overachievers.


Interesting. Might be my new favorite word!


Hello from a fellow small-town Canadian girl. I was also bussed from the acreage to school.

I think interestingness is really what makes creative products (ex. screenplays, novels, even blogs) stand out because like you said there are so many out there and so many are well crafted.

Interestingness. I will have to keep this in mind.



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