Jeff Interview, Part II: U. Chicago, The Labyrinth of Learning, and a Famous Final 'Yes'

In Part I of my interview with Jeff, the focus was on his experience growing up globally before settling in to Charleston, SC and the great magnet high school there. Part II picks up with his decision to apply to and then enroll at the University of Chicago.

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How did you decide to apply to and then enroll at the University of Chicago?

I decided to apply to the University of Chicago because in 2007 Chicago was a highly ranked school with an acceptance rate near 40%. So I thought what the hell and sent an application. At that time (when Ted O'Neill was the admissions dean), you could submit your application before the deadline as long as it was before 11:59 pm anywhere in the world. I believe the westernmost place on this side of the International Date Line is Baker Island (wherever that is), so before midnight Baker Island time was the real deadline. Which really saved me because I think I submitted mine at 4 am Eastern Time. My favorite subjects in high school were math, history, and English, but critical reading and critical thinking weren't really central to who I was until much later, after I'd been exposed to the University's "life of the mind" culture.

University of Chicago, South Campus

 Is the atmosphere as intense there as some seem to think it is? Why do the students like to wear shirts that say ‘where fun comes to die?’

I think the weather's more intense than the schoolwork. Of course the schoolwork can become overwhelming, but if you're a chronic procrastinator like I am waking up in the morning can be overwhelming. Nothing's as seductive as just five more minutes.

I think the intellectual culture at Chicago is real but definitely not oppressive. These kids want to be there. Of course you'll see shirts like "where the squirrels are cuter than the girls and more aggressive than the guys" or "where the only thing that'll go down on you is your GPA" or "if I wanted an A I'd have gone to Harvard," but these are definitely tongue-in-cheek. 

U. Chicago known for having the most innovative admission essay questions of any school in the world.  Which question did you choose to answer?

Okay here is the topic I chose:

"Modern improvisational comedy had its start with the Compass Players, a group of University of Chicago students who later formed the Second City comedy troupe. Here is a chance to play along. Improvise a story, essay, or script that meets all of the following requirements:

• It must include the line “And yes I said yes I will Yes” (Ulysses, by James Joyce).
• Its characters may not have superpowers.
• Your work has to mention the University of Chicago, but please, no accounts of a high school student applying to the University—this is fiction, not autobiography.
• Your work must include at least four of the following elements: a paper airplane, a transformation, a shoe, the invisible hand, two doors, pointillism, a fanciful explanation of the Pythagorean Theorem, a ventriloquist or ventriloquism, the periodic table of the elements, the concept of jeong, number two pencils."

University of Chicago campus

 Are there a few classes or professors you would highlight?

 I studied math, which was totally different from high school math, and they were some of the hardest courses I took. I didn't do exceptionally well, but it definitely opened my mind up to new ways of thinking. My favorite classes were in history and French. One professor of the ancient Near East, Andrea Seri, really introduced me to the relation between history and literature and the concepts of history as narrative as opposed to history as truth, history "as it really was." Two notable French professors were Marie Berg and Daniel Desormeaux, the former having really taught me how to speak and the latter having taught me how to read--and I mean that for any language, not just French. I've found, at least in my case, you don't really know your own language until you learn another.

What kinds of things did you do outside of the classroom?

What a strange question for a UChicago student! No, but in seriousness I went to the gym, hung out at the local coffee shop, went to concerts and museums and art exhibits, the usual (nerdy) stuff.

Did you take advantage of the huge number of events and opportunities in Chicago itself?

Not as much as I would have liked to. Mostly food trips to Chinatown or going downtown for cultural activities. I actually went to Grant Park to hear President-elect Obama's victory speech in November 2008; that was really awesome! And he gave another speech, I believe in support of someone running for state office, at the Midway, which intersects the campus. He lives in the neighborhood, so it's always a novelty to point out to visitors the street that's cordoned off by police and Secret Service: "That's where the President lives!"

But you can get kind of stuck in the People's Republic of Hyde Park. Chicago had a really awesome public transport, but it was goddamn hard to motivate myself to go outside for extended periods of time during the winter in Chicago.

Michelangelo: Delphic Oracle

How do you think your education has changed you?

I used to be (and really still am) afraid of so many things--failure, death, uncertainty. In large part we're prisoners of our fears, and education is a key that unchains us from these bonds. Some may ask, "Does God exist?" Not having an answer is terrible; it can paralyze people or turn them toward mania. Education tells us that not having an answer is okay. We have no Delphic Oracle to deliver truths, but I think even if we did she would tell us sometimes wisdom consists of knowing we know nothing.

In my conversations with you give great thought to many big issues. Have you always been this way?

 No, I think you have to start the process of getting over yourself before you can think of big issues in a neutral way. I'm not sure (in fact I'm quite certain) I haven't gotten over myself. I'm definitely less self-conscious than I was four years ago. In a way this is a very natural progression; I think most people ask big questions as they age. It would be weird for a ten year old to be pondering whether world history has any logical progression or why evil exists if God is good and omnipotent or why so much social misery still exists and how best to resolve these ills. I mean this kid would certainly be really precocious but I'm not sure she would have had a great childhood.

I first met you when you were reading Umberto Eco’s Prague Cemetery. Very few people I know read Eco and even fewer who are in a tech career. Why do you search out great books and writers? Do you have a favorite author and if so why this one?

 It's fun. Reading is terribly fun for me, though I'm a terrible reader. I usually passionately dive into a great novel and lose interest after an intensely good first 100 pages. Then I move on to another one, and the same thing happens. Then I move on to a third. Then maybe I finish one of them, because by now I've probably realized that at this rate I'll never have the satisfaction of having finished any of these three, and put the other two off for a few more weeks or months. I don't know why I lose interest, since if I go on to finish the book I'll have found that it was very pleasant. I think it's because the other books are tantalizing and distract me because they are just as interesting. I procrastinate.

A while back I mentioned that education really helps quell our fears. I think reading is a major, if not the major, part of education, and in addition to being fun it helps reduce our fears by giving our lives structure and meaning. Borges once said, "I am not sure that I exist, actually. I am all the writers that I have read, all the people that I have met, all the women that I have loved; all the cities that I have visited, all my ancestors." One can never overstate the power of narrative in shaping who we are because we are the stories we tell ourselves. If I'm feeling angry, I'm Achilles, if I'm in existential angst, I am Hamlet, if I need redemptive action, I'm Jean Valjean. So there's both an aesthetic and practical aspect, but really one could say these two are the same things. It's pleasing not to be bored, or anxious, or nervous, or confused. As Keats said, Truth is beauty, and beauty truth.

Shakespeare is my favorite author. It's an obvious choice, but I can't help it. Hamlet's soliloquy sums up, in infinitely prettier language, most of what I've been saying. The ultimate question with no answer: To be or not to be?

You are now out in the world applying your learning to analytics and data. Can you describe what it is you do?

I work at a digital marketing firm. Basically, what we do is connect online shoppers to online retailers. Say someone wants to buy a digital camera. That person might type "digital camera" into the Google search. Our job is to use Google's online advertising service, AdWords, to create a text ad that would be most likely to entice the user to click the link in the ad and be redirected to the retailer's product page. Every time a user clicks one of the ads, the retailer pays Google a certain amount:  that's how Google makes a lot of its revenue. That's the general idea, but there are many intricacies involved. For example, because so many different retailers sell digital cameras, we have to adjust the ad copy to attract users or bid higher for a certain ad so that it will show up in a higher position on the search engine page.

How do you think all the data that is now being collected and analyzed will change the way we live in the future?  Some people paint a portrait of endless possibilities and others that this is just another example of hype that will not change things much. Which side are you on?

I'm on the side of whoever's monitoring my Gmail account as I type this! No but all joking aside all this data makes me think we're increasingly "distracted from distraction by distraction." We have so much data and information, which is great because it makes the world so much more connected. Social media has, like the printing press of ages past, helped in the incredible dissemination of information and really decreased the distance between people. At the same time, has instantaneous access to bits and pieces ruined our ability to filter the necessary from the frivolous, to keep prolonged attention on a given topic? I don't know, we'll have to see, but I'm hopeful that this influx of technology changes things for the better.

Where do you see yourself say 5 years from now?

To be honest I want to go to medical school. But I'm not going to make any predictions just yet. Let's see if I make it through this week all right.

 Do you have advice for students who are thinking about majors in college?

I say follow your dreams. Though that may be terrible advice because your dreams might not be marketable. I've never been good at choosing practical things to study, so I'll give you some great advice handed down to me by my old CEO: it's best to mix your passions with your strengths with what's marketable. I think that's really good advice, though I have no idea how to do it. I'm starting on that journey myself.

But no matter the major or intended career path, go talk to your professors! They're starved for the attention of bright young people, and you'll meet some really cool minds. I sure wish I had gone to office hours a lot more, as it really helps with your schoolwork as well. Also, get involved in extracurricular activities, because there are so many in college. Do an internship and try to go abroad; these experiences open your mind.

 Do you have advice for parents and students as they begin the stressful journey of applying to highly selective schools?

It's only as stressful as you make it. Remember that this is a beginning and not an end. So much emphasis is placed on prestige and getting there and not on how well the student will fit into the school's environment once he or she is there. Go on campus tours and visits, get to know the place, and don't get hung up on name brand recognition. And of course, keep your eye out for good financial aid packages and/or scholarships/work-study because you won't want to be buried in student debt after graduation.

What are you reading right now and would you recommend it?

The Brothers Karamazov. And yes I said yes I will Yes!!!

                                                        Joyce: Molly Bloom's "Yes"

The number of books, blogs, and columns on the college process numbers in the millions. Some are great (RIP the New York Times free site, The Choice, which closed up shop last week), some are good, and some mislead either consciously or unconsciously.

Jeff’s words are among the most honest, witty, and wise I have come across on the ways in which education matters and, to put it punningly, minds us and re-minds us into who we are, and were, are and will, and will become. I am lucky to know him and to have him give freely of his time to share his words and the words of those who have shaped him into the person he is.

At least for this entry, I think all that is left to add are words from Jeff’s favorite author: “The rest is silence.”