See Parts I , II , III ,and IV in my series revealing where I’ll be going to college.

In the time between January 1 and April 1, when you hear back from schools, I reflected on what I’d want out of four years of college. Some things that came to mind included: a) study topics I can’t study anywhere else, b) form close relationships with brilliant teachers, c) form close relationships with students who can be friends for life, and maybe business partners, and d) increase my exposure to randomness.

On April 1st I got a handful of thick envelopes, and some thin ones too. The responses were all over the map, as predicted. Neither my counselor nor I knew what to expect, given my unique file. It all depended on how much the school appreciated what I did with my time the first two years of high school.

I was thrilled to receive acceptances at colleges which excited me, and in mid April took a trip to visit three schools: one in east Chicago, upstate New York, and east Los Angeles county. After returning from my three visits, I returned to San Francisco with a smile.

When I told my Jon, my counselor, where I’d decided to go, he answered with a grin, "Listen Ben, I don’t tell anyone this, but I’m going to tell you. Usually I say there’s no such thing as a perfect fit, but in this case I’m wrong. This is a perfect fit for you."

All around me my friends were hearing good news and bad news. Some people got screwed, some people got lucky, some people got what they deserved. Some people treated it as a pivotal turning point in their life; others, like me, treated it as another meaningful event nestled in a mosaic of cool, interesting twists and turns.

Since I had decided to attend a college that intrigued me, I now had to decide about deferral. The notion of Real Life University always intrigued me – especially the travel component – so I decided to defer my admission for one year so I could travel, work, and publish my book.

Tomorrow: Where I’m going and why

See Parts I and II and III in my series revealing where I’ll be going to college.

I tried to improve my grades. The fall of my senior year I earned a 3.97 GPA, bumping my cumulative GPA to a 2.99.

Heartened by my improvement, I visited a range of colleges. I visited liberal arts colleges. These kinds of schools are the gem of United States higher ed. Private liberal arts colleges only serve undergraduates, are committed to a broad base of learning, and boast a high student to faculty ratio. My whole family has been educated in liberal arts colleges (Smith, Claremont, Amherst, and Middlebury) and all had tremendous experiences. I also visited large research universities. In a large university there are more resources, more people, more organizations, and more happening, but less face time with professors, a less personal atmosphere, and sometimes overwhelming living situations.

I did not look at undergraduate business programs. I have many real world business experiences and, besides accounting, classroom work wouldn’t enrich it much I think.

I did consider the overall entrepreneurial culture of a college campus. I want to be around kids who dream big and aren’t ashamed of to say it. I considered how passionately students took to the "life of the mind". I talked to professors, studied their programs, and pondered their probable availability for one-on-one dinners and their ability to awaken a classroom. I considered the location and weather of the college. Having lived in San Francisco my whole life, I haven’t seen snow for more than a few days at a time. I like moderate-to-warm weather. Finally, I considered the college’s alumni network – its vibrancy and distribution of careers.

In my application I had 500 words to tell the college about myself. My personal "character" is where I had to shine, given my poor grades. I wrote an essay about "life entrepreneurship," using a Joan Didion quote as a jumping off point. I had immense difficulty crafting an essay that would communicate my four crazy years of high school / Silicon Valley. My (private) attitude was, "Some college admissions people will get it, some won’t, and that’s how it goes."

Some schools, especially small colleges, still do personal interviews. At every school but one where I interviewed, I got in. Given my experience a) interviewing candidates at my own company, b) interacting with adults, c) communicating a sales pitch, I always kicked butt in my interviews.

Throughout all this I talked to adult friends and school peers. I learned early on that books and articles about higher education were fairly useful while the random anecdote by an bachelor-toting adult was usually not. This, of course, is the fascinating influence: everyone who’s gone to college (about 27% of America) seems to have an opinion about colleges and admissions. The problem is the world’s changed. Also, as time passes, cognitive dissonance does wonders. College grads think about those four, long, incredibly expensive years in a way that’s kind on the brain. Sometimes they repeat nice-sounding catch phrases like, "College is all about learning how to think" or "It’s not about the college you go to, it’s about what you get out of it." (There’s some truth in both.) But – but! – all this being said, several adult friends really illuminated this time in my life with characteristic wit, hindsight, and humor, and I appreciate that.

On January 1st I submitted my applications online to a dozen schools and hoped for the best!

See Parts I and II in my series revealing where I’ll be going to college.

Amidst the onslaught of documents is a particularly important one: your transcript to-date. For students at UHS, my high school, this can always been a damning moment. UHS is a hard school. Most of the courses are upper level college classes. The students are bright and hard-working. Formerly stand-out students become simply average after enrolling at UHS.

My college counselor, Jon, showed me my cumulative GPA through my fall semester junior year: 2.67 out of 4.0. It wasn’t pretty, even considering the usual bump up most colleges give to students from UHS in consideration of the academic rigor. My PSAT scores – a predicator of SAT results – were good not great.

Jon and I spoke about the process and my prospects. We talked about my entrepreneurship but more important, my intellectual interests and activities. Jon, a former professor and associate director of admissions at Stanford, was a smart and funny guy, and we had to work hard to stay focused on college stuff, given our propensity to meander off-topic. Finally, he cut to the chase:

"Ben, I want you to know something. A lot of schools like to talk about wanting kids who show intellectual drive, who are well-balanced, to have passion for the activities they pursue. Unfortunately, a lot of this is window dressing. I’m going to be blunt. Your numbers will hurt the averages of these schools and hurt their rankings. They really need to be convinced that you’re special, and it’s hard to articulate what you’ve done in such short space and to people not versed in business, blogging, whatever. What you’ve done the past few years seems mighty impressive, but much harder to boil down than fantastic artwork or an amazing piano recording. And your numbers, frankly put, show an inability to master academic work. So I want you to know that you’re facing an uphill battle."

I responded: "I understand. I’ve made choices and they have consequences."

He smiled, relieved I wasn’t going to be one of those students who would only apply to a handful of name-brand colleges, or who’d self-righteously assume his talents were delivered from heaven and self-evident.

Even though I was kind of disappointed my real world entrepreneurial experiences wouldn’t have as much mileage in my college admissions as they could have, I still had a huge advantage over most applicants: I attended a private high school, I had the resources to apply and personally visit a dozen schools, and had college educated parents who would support me emotionally and financially.

•••

When I think about my academic struggles, I don’t feel sorry for myself (ok – sometimes I do, when I’m forced to slave through multiple choice tests, which I undoubtedly bomb). Let’s face it: I got my ass kicked. But. I’m still happy, and I’m still dreaming, and who knows…maybe I’ll move a mountain someday.

See this old New Yorker article which I blogged:

"In 1981, two professors…began following the lives of eighty-one high-school valedictorians…According to Arnold’s 1995 book “Lives of Promise: What Becomes of High School Valedictorians,” these students continued to distinguish themselves academically in college; a little less than sixty per cent pursued graduate studies. By their early thirties, most were “working in high-level, prestigious, secure professions”—they were lawyers, accountants, professors, doctors, engineers. Arnold totted up fifteen Ph.D.s, six law degrees, three medical degrees, and twenty-two master’s degrees in her group. The valedictorians got divorced at a lower rate than did the population at large, were less likely to use alcohol and drugs, and tended to be active in their communities.

At the same time, Arnold, who stays in touch with her cohort, has found that few of the valedictorians seem destined for intellectual eminence or for creative work outside of familiar career paths. Dedicated to the well-rounded ideal—to be a valedictorian, after all, you must excel in classes that don’t interest you or are poorly taught—the valedictorians had “used their strong work ethic to pursue multiple academic and extracurricular interests. None was obsessed with a single talent area to which he or she subordinated school and social involvement.” This marks a difference, Arnold said, from what we know about many eminent achievers, who tend to evince an early passion for a particular field. For these people, Arnold writes, a “powerful early interest evolves into lifelong, intensive, even obsessive involvement in the talent area.” She goes on, “Exceptional adult achievers often recall formal schooling as a disliked distraction.” Valedictorians, by contrast, conformed to the expectations of school and carefully chose careers that were likely to be socially and financially secure: “As a rule, valedictorians relegated their early interests to hobbies, second majors, or regretted dead ends. The serious athletes among the valedictorians never pursued sports occupations. Most of the high school musicians hung up their instruments during college."

Chris Yeh goes on to say:

In other words, while valedictorians do well, most of those who are most successful in life were definitely not valedictorians. Let me emphasize one line from the quote above: Exceptional adult achievers often recall formal schooling as a disliked distraction.

School isn’t like real life. In fact, it’s about as far from real life as can be imagined. The lessons that let you be successful in school (follow the rules, work hard, know the right answers) are completely the opposite of those that help you become a successful entrepreneur (change the rules, work smart, know the right questions).