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Interview by Ben Feuer.

Tell us a little bit about your professional background.

My first professional writing job was as a Paris correspondent. I did the city guide for USA Today and eventually graduated to covering a whole range of topics, including travel, restaurants, dating.  Anyway, I had always been interested in playwriting, and I had written a couple of plays in college, so I applied to to NYU’s Tisch School and I got in!

That’s the top playwriting program in the country!

It was a great experience!  Anyway, I was fortunate enough to get paid work as a playwright, book writer (for musicals … ed.) and speechwriter out of school, and I’ve done that kind of work ever since.  I have a play running in LA right now, and I had two shows last year in San Francisco.  I also have an upcoming one in New York, but that won’t be until 2017.

What do you like most about working as an essay coach?

For me it’s this fantastic combination of the work I did in journalism and playwriting!  I get to ask questions like a journalist, listen to the answers, and help candidates turn their responses into stories with arcs. I also love that you see the results immediately – it doesn’t take 5 to 10 years to do an essay with a candidate.  Finally, education is really important to me. I wasn’t starving in Africa growing up, but I did have to work 40 hours a week to help my Mom support our family.  I am where I am today because it was important to my Mom that I get an education.  Fortunately I grew up in an affluent community and therefore a lot of people helped me with my college essays and applications, among other things. This is something I will always do. I can’t imagine not doing it.

What have you learned from your candidates this year?

Aaron Sorkin gave a fantastic commencement speech at Syracuse – basically, he said that when you graduate with a degree in theater or communications, you often have to work jobs that have nothing to do with your major, at Starbucks or something like that.  And he just said that wherever you are, it’s important to bring your passion. If you make people coffee every day, make the best cup of coffee that they ever had.  Anyway, this candidate I had gave up music, which he really loved, to focus on his business career.  But just because he became a businessman, he didn’t suddenly stop being artistic.  He is better at his job now because he was once a musician.  It really taught me something about the value of being my whole self all the time.

What is the craziest thing a client has said to you this year?

I asked a girl why she was working in finance.  She told me that originally she wanted to be a doctor, but she decided that doctors were selfish because they only help their patients.  On the other hand, she could potentially make millions of dollars at a hedge fund and then help lots of people through charity.  I thought that was pretty insane.

I agree.

In her essay, she wrote about keeping hundred dollar bills on the corner of his desk and handing them out to people as she walked by.  That was her idea of charity!

What’s your favorite book on writing?

Other than The MBA Reality Check, you mean?  I make all my clients read that book before I’ll work with them.

Yes, other than that.

Stephen King’s On Writing.  That is one of the most useful books for writing essays because it doesn’t even attempt to teach someone how to write – as if that was even possible.  It just shows usable examples of how to pull disparate ideas together and create stories.  I prefer approaches that are not formulaic.

Take us through a typical hour with a candidate.

Sometimes I give them brainstorming homework.  I like journal entry things.  for instance, I might have a candidate fill an entire page of an MS Word document with one-sentence answers to the question, What Matters Most to me and Why?  Then I’ll go through the document with them on the call and highlight all the ones that are basically the same.  Usually it’s about 75 percent – which really tells us something about what is genuinely important to them.  I give lots of creative writing type assignments.  I also just like to chat -- ask them questions about where they went out on Saturday night, et cetera. Sometimes we get great stories that way – one guy told me about writing a political contribution check for the wrong candidate!  Then for about 20 minutes I give them an outline of what they’re going to write -- I outline each section with them. I try to save room for questions at the end.

Tell us a story from your childhood – the way you might ask a candidate to write an essay.

When I was thirteen, my best friend didn’t show up for school one day and I had no idea why.  It turned out her Dad had jumped off the Golden Gate Bridge.  It really disturbed me.  I remember asking my mom repeatedly on the way to their house to bring them some stupid casserole, “Why did he do it?”  And she just told me he must have felt really alone.   And I remember thinking that was so ridiculous, I could’ve told him he wasn’t.  It seemed so simple to me.  After that, it became very important to me to be there for people, especially when they fuck up. 

In high school I had an arch nemesis who hated me because I got the lead in the play over her.  She was very popular, I wasn’t – at least until she faked having a brain tumor.  She lost all of her friends. I remember I inviter her and her Dad over to my house for dinner one night after it happened.  It’s part of why stories became so important to me.  Everybody’s got one, you know?

What do you think is the hardest part of the admissions process for most candidates?

Constantly measuring themselves against the competition.  I get so many quant-heads obsessively analyzing the statistics, you know, just like they do in their job all day.  And it’s hard on them, because wherever they are they’re used to being one of the best and brightest, and all the sudden the whole pool of people they are competing with are special. So they obsess over how his GMAT is a little higher than mine, but I’m a little funnier than him.  What they don’t understand is that the process is more holistic.  They take individuals, people who are fully themselves, at these top schools.  This is especially true for interviews, I think.  You know they’re going to be good to go if they’re the kind of person who can just be themselves on a date.  I also I think it shows a lot of confidence to be able to joke about yourself.  Last year all of my HBS candidates got interviews, but one of them didn’t get in, and I think it was because she was just trying too hard and obsessing in the interview.

Any last words of wisdom?

I always tell people, especially for Harvard and Stanford, but really for all the top schools, that the essay they want to turn in is the one that, if they printed it out at work and accidentally left it there at night, there’s no world in which they would just leave it on the printer till the next day.  They would run back and try to break into that office to get a hold of it because they would be so afraid for someone from work to it.  To transcend the typical resume nonsense it’s got to be completely personal and pretty magical.

Thank you so much!

Thank you!

And if people want to work with you, or talk about their candidacy with you, what should they do?

Just contact our office and they can set up a call with me – I’m around!