Pitfalls, Plans, and Prostates

"What is not started today is never finished tomorrow."

OBERLIN--Jacob Lamoureux's post-graduate decision became easier a month ago when he didn't make the College's roster of Watson semi-finalists. He wished, as usual, that he'd kept his plans and congenital confidence to himself. Lamoureux sought to study how public interest campaigns around the world effectively counteract harmful youth behavior.

Though he doesn't exactly regret the opportunity cost of applying, he has yet to officially fess up this failure to his exceedingly good-hearted recommenders, who were generous enough to take on the task at the very last minute.

The postmortem revealed that Lamourex's project proposal suffered from a condition to which all of Lamoureux's writing is susceptible: ambition untempered by reality. Also known as dumbassery.

So there ya have it, folks. Straight out of a made-up newspaper. Though it's not entirely true that my post-graduation plans have become easier: infinity minus one is still infinity...

In recent weeks, 30% of my thinking has been devoted to what I'm going to do next year. Professor Hirsch--whose words have stuck in my head even more vividly than the khaki shorts he'd wear to class--told us that, like it or not, what we do in the few years after graduating will have large influence over the rest of our lives. And so I keep adding new links and thoughts to an email thread I'm carrying on with myself, entitled "My Future." A folder named Life stares back at me from the middle of my desktop.

I prefer foot races to rat ones, and I know that I don't want my professional future to be characterized by a steady climb up the ladder in some organization. My dinghy anticipates optimal buoyancy from the whole forging-my-own-path thing, and I hope to combine my passions for entrepreneurship, education, and grooming into a start-up of some sort next year. At this point, it looks like I might have to groom on the side since it isn't fitting into the business plan. Oberlin hasn't prepared me much in the grooming department anyway, but as far as education and entrepreneurship go, it continues to give me plenty to chew on.

This past November 2nd: I ran (literally) from an Academic Amb event to Oberlin High School to meet with students about their college admissions essays (the most rewarding hour and a half of the week). The next day I ran (figuratively) from a workshop on classroom teaching to an Advisory Council dinner (less boringly known as a "Marvin Meal") and alumni networking event, where I hit the education table and a couple entrepreneurs in the room (a shout-out to Gene Carr and the uber-useful ten minutes I spent grilling him). The next day I had my first session of a module entrepreneurship course I'm taking to supplement two recently purchased books that will, of course, tell me everything I need to know to get a business going.

The next day I flew out to Seattle to work the 2011 elections with the consulting firm I interned at this past summer. When I got back to Oberlin four days later, I applied to take a practicum course that train students in consulting, and then applied to teach poetry in the D.C. public schools over Winter Term, a gig I was recently accepted for.

Hopefully, that's proof enough I care about education and entrepreneurship. Now that we've got the plot out of the way (and the less determined readers), we've got a whole lot of internal conflict to have fun with.

Ya see, I have an idea in the back pocket that excites me even more than the Watson world tour would have. But I've recently realized that this appealing alternative is threatened by the same lack of grounding that led my Watson app to an early execution (and by execution, I mean its death, not its doing).

This realization struck me gradually, swiftly, and repeatedly over the past month. I've failed to articulate this idea in conversations countless times over the past few months, so I might as well do it publically in print as well: The Back Pocket Idea (BPI) would involve touring poor high schools to providing training and establish enduring interests in extracurricular pursuits not offered by the school, in addition to (and this is where I lose everybody) recruiting elite students to join a national organization of young leaders dedicated to making the world suck less.

My Watson proposal involved working with about a dozen organizations. My current back pocket idea (BPI) would involve partnerships with, ideally, hundreds of high schools across America. That's all well and good, but it could be a sign I'm overdreaming and underplanning. I'm a career criminal as far as the first is concerned, especially when it's time to write a paper. Projects I've taken on have ranged from simply stupid (in freshman year after reading fourteen or fifteen books of African lit, I set out to write a paper spanning the evolution of the continent's literature) to interestingly stupid (in my junior year, I set out to write a textbook on creative writing pedagogy). (Come to think of it, both of those papers were done for classes taught by the same professor, who's also one of the two I asked for a Watson recommendation [I can tell you what kind of recommendation I'd write if I were him].) In such cases, the final product is usually less successful than a smaller-scale, narrowly focused paper would have been. "Zooming in" is advice I often give tutees after reading their papers, but I have trouble following this advice myself. I want to talk deeply about everything. Alas, one man's attempt at "comprehensive" is another man's [actually that same man's] "encompassing, ambitious but unfocused and ultimately unsatisfying take on a huge subject"--and it's all my infinitely unfinished business.

But I try anyway. Which results in me missing deadlines even more than I miss my awesome book collection back home, fully believing that the merit of writing such a pivotal paper in the field will excuse my finishing it a few hours late. But the papers turn out to be provocative and highly partial versions of the pivotal papers I have in mind. As was the case with my Watson project proposal. I had the big-picture idea, but didn't have the legwork in place. I built my "castle in the air" for sure, but it was so lofty I had no idea where to start on its foundations, or was too intimidated to start, which made the damn thing as unreachable as Kafka's. And now I'm working on the BPI castle and facing similar challenges.

I had to make a pitch last class in Business Model Innovation to a visiting entrepreneur who goes by the alias Saul Kaplan (that's also his name). I unleashed the same blathering that guest-starred in my interview for the Entrepreneurship Scholars Program (my one-minute pitch was two and half minutes long, so I'm pretty sure my prospects for that gig are grim as predictions about the coming Ohio winter) and drew some stuff on the board, which at least helped me understand what I was saying. Saul's critique: "I'm sure there's a good idea in there somewhere, but it's not coming across. Same problem with your first pitch--I would have given you a buck if you just said you were collecting money for prostate cancer, but all that other stuff just confused me."

Don't fret, faithful readers, my prostate is fine. Another 40% of my recent thinking has been devoted to a campaign the men's cross-country team is waging this November to fight prostate cancer, while our ladies are busy winning meets and racing at Nationals. Part of the deal is we make pitches to all our classes to recruit sponsors*, so I used 1/7 of my business model pitch time to give a spiel to the class about what we're doing, then passed a sock around for contributions to the cause. Apparently, I didn't convince Saul, and instead of a dollar, he gave me a pointer: Be crisper.

I thought the prostate pitch had actually been pretty good, but I tried to keep my indignation to a minimum since "the first principle is that you must not fool yourself, and you are the easiest person to fool" (Richard Feynman). So I revised my pitch to make it crisper, and got fifteen sponsors between the next two classes that heard it.

The Sexy XC Campaign, which culminates in a Beauty Pageant featuring me and eight teammates this Monday, is working, more or less. It's illuminating to compare our work on this to the planning that went into my Watson flop and my presently pie-in-the-sky post-grad entrepreneurial ambitions.

For the Sexy XC Campaign, our grand plans were made in the sphere of the real; ideas were weighed for actionability, not their hypothetical merit; there was no security of theory. In a cabal convened early this month in one of the campus War Rooms, Santino Alberto Merino, Joe "Joe" Dawson, Ty-Rex Diringer and I gathered to brainstorm ideas and lay out some strategy and timelines.

A goal, someone much smarter than I once said, is a dream with a deadline. Joe was determined not to leave that War Room without setting some deadlines, which we did, and we've hit most of 'em so far +/- 2 days. When something concrete needed to be done for the next day--our trading card designs or calendar pdf proof (don't ask)--Tino or Joe was up late that night, getting it done. None of it was abstract. If we didn't have a way to get it done, it wasn't on the table, and if we didn't get it done, we knew for sure it wasn't going to happen.

The sphere of the real includes not only making deadlines, but also contacts. We got the Sco booked for the event in plenty of time and organized over a dozen photo shoots (one of which entailed a third of the team getting out of bed at 7 a.m. on a chilly Saturday morning). Quinn buzzed us up some media with Fearless and Loathing, Derek got Denise the Lunch Lady to be on the judging panel (though she had to back out for family reasons--major blow #1 to the campaign), Ty called printing companies to (successfully) score discounts. I wrote a grant for seed money (which the Creativity & Leadership Project never even acknowledged receipt of, causing me to get mad at Oberlin for the first time since every morning when the vegan bagels get to the Science Center Cart late) and called the "Give a Spit" leukemia-fighting campaign to piggy-back at our Pageant.

Admittedly, plenty of mistakes were made along the way--and we even ended up cancelling a major part of the campaign for highly responsible reasons after putting in all the necessary work (at least 80 hours' worth, but that's a blog for another day). Nonetheless, it's chugging along. Dough is rolling in to help find a cure. Our coach caught wind of the hard work we were doing and was so excited about it, he called us in to talk with him.

In light of all the real world moving-and-shaking that needs to go into a month-long campaign to raise a few grand, it's laughable (not really) that I thought I could even be considered a serious Watson candidate without having secured solid commitments from the organizations I wanted to work with. Still, that would have been a more manageable mission if my project hadn't involved twelve orgs.

To actually get stuff done, you have to tackle all kinds of practical to-dos that are often a little bit scary--like calling an organization or making a pitch to your class. I've been subconsciously wary of entering that territory as far as the BPI is concerned. I'm infatuated by ideas and most comfortable in the realm of brainstorming. But, honestly, who doesn't have a million-dollar idea? The only difference between a vision and a visionary is a lot of hard work and the suffix ary.

What I was doing was like trying to write a story by starting with the themes and deciding I'd worry about plot and characters later. That results in a bad story, as my first fiction teacher Chelsey Johnson told me three years ago; you need to start at the base of the pyramid, not the top; all that higher-level stuff emerges organically. This doesn't mean you can't have a big-picture goal and purpose--and that it's not a good idea to check in with it now and then--but it can also turn into a distraction from the grunt work you should be doing at the base of the pyramid 95% of the time, laying the castle's foundations (to mix metaphors). I keep obsessing over things like what I should name my organization, how I'd fund it past the grant-stage, and what celebrities I'd like to bring on board to build its cachet.

Meanwhile, other kids in my business class have launched ventures that are already profitable. They are definitely in the sphere of the real. (Man, if I keep employing that concept, I'm gonna have to come up with a pithier name for it.) I tease my friend Annika, founder of OSWAMP, that I'm determined not to let her steal my seed money from Oberlin's Entrepreneurship Fellows Program. She generously neglects to point out that, at the moment, I'm not much of a threat. Her program is up & running, the recipient of numerous grants. And it's already been featured for its coolness on Oberlin's website. Annika's in the Fo'Real Zone. (How's that?)

One evening shortly after Saul's critique, I hunkered down in my room with a heavy heart and a Post-It pad. How could I make the BPI as real as the Sexy XC campaign?

Saul said one other thing that stuck with me--that to test an idea, come up with the smallest version possible. Screw the hundred abstract high schools across America. We've got Oberlin High School half a mile away. Why not try a pilot program there? A basic brick of what'll eventually be a mansion. The cornerstone, as it were. As Paul Hawken writes, "Most successful businesses started from extremely humble origins... Kellogg's started as an offshoot of a sanitarium by selling wheat flakes. Coca-Cola was a rather quackish cure-all sold over the counter in an Atlanta pharmacy. Levi Strauss started when a German immigrant was overstocked with tent canvas during the California Gold Rush and turned the material into miners' pants."

I'm pissed that immigrant beat me to the miners' pants idea, but at least the Oberlin High School concept is focused enough to generate plenty of actionable elements. I need to contact college students who might be interested in teaching high schoolers a few classes on something for a week in the spring, maybe recruit instructors from interesting Excos. I need to contact the principal of the high school and get permission, then ask teachers to publicize the program and let me pitch it in classes. Along with Reuben Benzel, I'm set to be Oberlin Young Educators' High School Liaison for next semester, so that'll help. I need to write the curriculum I'd be teaching as part of the program. These are the fundamentals, the foundations--but it's easy to dismiss them as details when you're "thinking big."

But the Sexy XC campaign also works because of the top-notch squad of guys we've got running it; I dare you to find a more creative, charismatic, and committed clan anywhere. If you do, let me know because this is something I worry about all the time, getting the high-caliber people necessary for a business to thrive. I can only hope to have a similar team behind the BPI, which I'm sure would be a concept drastically revised for the better with a partner or two on board. Indeed, when I pitched an early version of this to my good friend Shira a month ago (a high school teacher in NYC), I got not only warm support, but lots of good feedback and advice as well.

During the aforementioned high school tutoring session (aforementioned like four chapters ago), I met with a sophomore named Jake who was already thinking about college applications. We talked about his move from Maine (where I used to live), homeschooling (of which we're both alumni), and our fascination with human behavior. It's not often you get to meet yourself, so I was pretty darn excited. We batted around the question of why kids smoke, an inquiry at the heart of my Watson project, and eventually got to discussing Malcolm Gladwell's Outliers, and the 10,000 hour rule mentioned therein. Jake has been tallying the considerable time he puts into practicing basketball (admittedly, this is where we diverge), which I found incredibly impressive. I drew for him the Merrill Covey Matrix that the ever-interesting Dean Doane showed me a few weeks ago, and we talked about how success happens by spending more time in that upper right zone.

I've got to spend more time in that upper right zone. I've got to give the BPI the time it needs. I've got to make the practical moves towards proving a local prototype, not only to a committee somewhere, but to myself. Only then will I be able to write a decent app that might win the fellowship funding that can make this all possible.

But even if I do get that decent application together, there's still the question of whether I should even try to launch so soon. Since many individual project grants restrict their applicant pool to college seniors, there's a strong temptation to go into it right out of Oberlin--but that would mean I'd be leading the charge as an educational "outsider" in many ways, without the full-time classroom experience that might familiarize me with the system and help me avoid costly mistakes. A stint with TFA or the MATCH Corps would allow me to polish my skills interacting with high schoolers, start an after-school club for young leaders, learn what works, meet some possible partners, and build from there. With no funding...

A joint M.Ed/MBA at Stanford (my ideal post-graduate degree) would be a pretty awesome booster shot against project failure--but you don't get into Stanford without doing some pretty impressive stuff first. Chicken-and-egg dilemma.

And that's not the only prob I'm facing. It's gonna be hard to get into Stanford if my GPA (still recovering from a freshman year poetry course taught by a prof with different ideas about poetry than I) limbos any lower than a hippie on April 20th. And it's facing its gravest threats yet this semester. The only test I've ever absolutely bombed in my life was this past Tuesday, a computer science doozy that felt like one of those pre-tests meant to determine what level you're at before releasing the verdict on whether or not you should be allowed to take the course. Wonderful as it was to get back with the consulting team I might be working with after graduating (a complication I haven't yet mentioned; in a nutshell, 2012 elections on the horizon + a job offer = even tougher post-grad decision), those four days in Seattle were like a bomb expertly dropped to produce maximize damage to my academic life. And the Sexy XC campaign was another stick of dynamite (pun intended).

And as a senior, I'm facing another problem I haven't encountered in my first three years here. For instance, I enjoy the comparative literature course I'm taking right now, but I sometimes wonder if at this point I should be focusing on mastering InDesign or HTML instead of reading An Artist of the Floating World...

The answer to that is no. I am, after all, someone whose life plans are in part based on the belief that reading and writing literature is a valuable enterprise. You can be an expert on everything and still exemplify Sartre's point that "everything has been figured out, except how to live." Literature, well-written and well-read, helps with that latter endeavor. As K. Burke put it, stories are "equipment for living." Though not directly relevant to the practical process of launching a venture, a lot of what you get in various humanities courses at Oberlin can affect the core beliefs and values that undergird life decisions.

I recently finished a paper (due at midnight and turned in three hours late [though not according to Pacific Coast Time, which is the time I was going by]) exploring the cross-cultural theme of people pursuing the wrong goal in hopes of attaining society's esteem. Specifically, it focused on how misplaced ambition is portrayed as the primary adversity to love in story after story (even well-placed ambition has a tenuous relationship with love--ever try to read Hobbes when thinking about a gurl?). This essay was a useful reminder to me that, unless you do the right stuff for the right reasons, you're pretty much doomed to an unhappy life. But that's a whole 'nuther blog.

Speaking of which, this post is well on its way to becoming the type of omni-encompassing essay I've historically regretted writing. Such essays, I'm afraid, are emblematic of my existence. Like them, I try to take on too much--and at what expense? I do a lot of stuff on campus, but none of it as well as I could if I had more time to devote to each. Isn't college supposed to be about prioritizing and specializing? There's a theory of governing that states power is best directed towards aiming to do One Big Thing. With so many demands on my time, delivering quality is hard, but quality in a world of crap is the only thing that's worthwhile. Focus is how you turn into a superstar. Where are my 10,000 hours going? Hey, where are your 10,000 hours going?

Well, too many of mine have gone into this blog post, so it's time to wrap it up. All this anxious agonizing, I'm sure, is in vain. Mom says she knows things will work out.

Mom, I can't help recalling, also had an "instinct" back in the day that I'd get into Amherst College, which I didn't (Amherst Waitlist '12). So that lost her some prophecy cred. But I think she's right in this case. Naïve as it may sound (and as deus ex machina an ending to this post), I've lived too long to believe the Big Guy doesn't have some sort of plan for me, even though I haven't worked it out yet. Oberlin is way better than Amherst, after all.

And so, to infinity--and beyond! I just gotta survive this beauty pageant first. There are a lot of (actionable) sit-ups to do before then.

If he ends up getting crowned Mr. Oberlin (which he plans to), you will win three times your money back at the event. And either way, you'll be fighting prostate cancer and thanked with a first-edition, collectible Jacob Lamoureux trading card, which will be worth a lot of money after he becomes president (which he plans to).