I first encountered Jason Shah in an e-mail describing his web site, I Need a Pencil. I get lots of PR pitches about web products and I almost always ignore them. But something here caught me eye. First, Jason is a student; an undergraduate at Harvard, to be precise. Second, the service is free. And third, and most important, I Need a Pencil works in close conjunction with college access organizations around the world.

Put simply: Jason thinks that everyone should have access to SAT prep tools, especially those for whom access to college is neither expected nor guaranteed.

I concluded that Jason is someone that we had to meet. He agreed to sit through an interview to talk about his vision, life at Harvard, and what’s it’s like trying to run a company while a student.

Tell me the I Need a Pencil story.

I started INeedAPencil.com in March 2006 out of my frustration with limited options for students seeking quality test and college preparation tools without paying an arm and a leg. I was a junior in high school, and I was tutoring fellow students for the SAT when I realized how limited my reach was and how repetitive my job became.

Inspired by my family, especially my sister who had taught in charter schools, I decided to launch INeedAPencil.com as my attempt to extend college access to more people.

What specific events led you from Jason the high school student to Jason student with a company?

A pair of visits to my sister’s school where she taught in West Philadelphia. I still remember a sixth grader who asked me while he was working on his Thanksgiving essay how to spell the word ‘ball’ three separate times. It really struck me that there was such a gap in educational opportunities.

On a personal level, I changed high schools after my freshman year because my parents moved for my dad’s job. It made me rethink priorities when I had this ‘fresh start.’ I wanted something different out of Florida.

Funding was an issue. But I just got scrappy. I found web developers to do the initial work on the cheap while saving some features for after launch. I have used viral marketing techniques, rather than expensive mailing campaigns, such as friend referrals on my site and Facebook. Ultimately the initial costs were brought to less than $10,000 and I was fortunate enough to have the support of family and friends to raise that funding

What was your life like running the company as a high school student?

In three words: stressful but cool. When starting out, I wouldn’t go to bed until 3 or 4 and would be up by 6. Junior and senior year of high school are already stressful enough with college apps, clubs, community service, shows, exams…and classes [ed: unless you take a Zen approach and avoid the laundry-list trap].

I often did my homework during class whenever possible and would constantly be using my teacher’s in-class computers as my personal work stations during passing time when everyone was lingering in the halls.

A typical schedule: I would wake up and work for a couple hours on things that needed to be done by the web developers in India, so that it would get done before their workday was over. Then I’d go to school, come back, make calls, write reports and send emails until bed.

What’s life like now at Harvard?

I spend about 20 hours a week working on INeedAPencil.com.

The site fits in well with the other two stuff I do on campus. My main two activities are the Harvard College Entrepreneurship Forum and the Harvard South Asian Men’s Collective. The former focuses on empowering student entrepreneurs while the latter is a charitable and social organization dedicated to raising funds for charities improving the life of South Asians, in South Asia and the US.

Although these activities certainly put a greater strain on time than if I just did my classes and INAP, I find the experiences to be invaluable parts of college and way to learn lessons that entrepreneurship may not otherwise teach me.

On Study Hacks, we talk about The Law of Complementary Accomplishments, which says when you do one thing really well lots of other impressive accomplishments come along for free. Has this happened for you?

For starters, I think college admissions and scholarships were a lot easier with my experience and ability to talk about INeedAPencil.com. The McKelvey Foundation awarded me its prestigious Entrepreneurial Scholar award for $40,000 towards my college education; that with a couple other scholarships definitely were attributable to my work with INAP. Also, through the site I’ve come to meet some phenomenal people working in education; most recently this has included a series of professors at the Harvard University Graduate School of Education. I have also been offered a couple trips from Malaysia to North Carolina for a social entrepreneurship award and presentations. I have had phone calls with a lot of second degree connections to solicit advice and speaking with big CEOs and VPs has been really cool.

What advice would you have for a young student looking to make his or her mark.

For someone with the right idea, I’d strongly recommend to start looking at what frustrates you. Clearly it needs a solution. I get at least two or three business ideas a day just from seeing what annoys me or seems like it can be done better. Keep an eye for these things and train yourself because it’s all about the way you think, not what you think of.

As far as time and talent, that’s purely psychological. I have a million reasons to not ‘have the time’ but you can make time if an idea is worth pursuing. That either comes through sacrificing your time on Facebook or putting this new initiative as a higher priority than other things.

Update 10/8/08: I inexplicably reversed the names of Lance and Dana in the original version of the article. It has been fixed below.

9 AM

The world headquarters of Wiggio Inc. can be found on the first floor of a triplex, situated across from the fire station in a gentrifying North Cambridge neighborhood. At 9 AM, one Friday morning this past September, Dana Lampert arrived to start the new day. He had been at the office until 9 PM the night before. This was considered good. The two nights previous he had been there until 3 and 4:30 AM, respectively, coaxing along a tricky upload of their web site to new servers.

Dana is soon joined by Lance Polivy, his college friend and co-founder of the company. They begin their day by diving into the more than 100 product feedback messages that have gathered over the past 24 hours. The feedback concerns Wiggio’s flagship (and only) product: the wiggio.com website.

This site was launched by Lance and Dana the previous spring, while they were seniors at Cornell. The idea is simple: it makes organizing groups easier.

Here’s the pitch: with one web site, your group can setup shared calendars, construct polls, store files, and send mass text, e-mail, and even voice messages to members. Their primary market is student groups, though its potential audience is wider.

In this early start-up stage, Lance and Dana feel it’s important to respond personally to every piece of feedback. The process is tedious, but it helps keep the founders connected to the users. For a web start-up, users are everything. Without them, all you have is a fancy web site and a business plan.

10 AM

Dana retreats to his office for a conference call with another technology company. The firm wants to know more about Wiggio. These informational chats are typical for new companies: you never know what might shake loose.

10:30 AM

Dana rejoins Lance They crawl the web, searching for the e-mail addresses of student leaders. The addresses are painstakingly entered into a spreadsheet, where they’ll later be merged into a mailing list used to spread the word about Wiggio.

As Dana notes, a surprising amount of his time is dedicated to “copying addresses and doing mail merges.”

“That’s the thing about a start-up that makes it different from a regular job. If you don’t do it, no one else will.”

12 PM

Attention is turned to hunting down a bug that was reported this morning. It concerns the site’s polling feature. Lance and Dana join Rob, one of the company’s developers.

Rob, along with his brother Derek, are the two programmers that built Wiggio. Their office, which is adjacent to the room shared by Lance and Dana, defines the programmer cliche. A line of six flat screen monitors spans a long desk. The side wall is decorated with a collection of programming handbooks that Dana describes as causing “visiting coders to drool.” An obligatory 24 pack of Coke Zero sits on a nearby filing cabinet.

Rob and Derek are the sons of Bob Doyle, a technology visionary and serial entrepreneur who owns the building Wiggio calls home. His office is next to his sons. The walls there are lined with an eccentric collection of books. Next to a three-volume series on classical physics sits a manuscript on ergodicity in probabilistic structures and a slim title improbably titled: Entropy and Art.

When I later visit, Lance points out a poster of a primitive looking 1980′s-era portable computer — a puffed-up, tan-plastic calculator-style contraption with a phone cord sticking off the side.

“That’s the first blackberry,” Lance explains. “Bob invented it.”

Bob, more than anyone else, was responsible for the transition of Wiggio the idea into Wiggio Inc.. He was the first major investor, back when Lance and Dana were still developing the idea at Cornell. He gave them the office space they use. He provided his sons to program the site.

This afternoon, Bob’s son Derek helps Lance and Dana hunt down the alleged bug. The process, it turns out, is messy. Fixing bugs is easy. It’s finding them that’s hard.

“This basically reduces to pounding away at the site trying to get it break,” explains Dana.

Pound they do, eyes transfixed on the screen.

1:30 PM

Dana makes a run to the UPS store. He’s shipping a box of promotional postcards to a contact at Yale.

He admits he spends a lot of time at the UPS store and dealing with shipping in general. Earlier this week he spent a late night unpacking the postcards from the large box they arrived in, and then repacking them into small boxes to be sent to individuals. The cardboard detritus of this missions still litter the conference room.

For a high-tech entrepreneur, Dana spends a lot of time with a box cutter.

2:00 PM

Dana begins hunting through the user statistics for the Wiggio web site, pulling out some trends that he and Lance like to follow. There’s probably some way to automate the reporting of these metrics, but that’s just one more non-urgent item on a crowded to-do list.

2:30 PM

An investor calls. He wants to discuss how the Wiggio team can deploy better analytics, and how this might produce real benefits. Dana spends a while brainstorming the different user behaviors that might be most important to monitor. They have to weigh the complexity of giving another task to Rob and Derek versus the insight it might provide.

This proves to be a core problem for start-up entrepreneurs. Everything is useful. Everything takes time. How do you decide what to do?

Imagine making those decisions two dozens time a day. Imagine that the wrong decisions could mean you’re broke and out of a job. Welcome to the world of Lance and Dana.

4 PM

I show up for a tour of the office. Chatting with Lance and Dana, I tease out the following origin story:

In the fall of 2007, Lance and Dana were taking an entrepreneurship class at the Cornell. Their final project was to pitch a business idea to a panel of venture capitalists and professors. Wiggio was what they came up with.

“We gave our pitch to the panel, and they said ‘you’d be crazy not to do this,’” recalls Lance “We had heard from the other teams in the class that the panel had been harsh, so this was a big deal.”

Not long after the presentation, Dana’s dad put the his son in touch with Bob Doyle. “Bob got excited,” Dana recalls. “He said that him and his team [i.e., Rob and Derek] could get this up and running in like six months.”

Development started in January. A prototype was launched in April. The next month, when graduation arrived, Lance and Dana committed to making the company their full time job.

Here’s what struck me about their story:

(1) Wiggio is very good idea. To test out the first prototype, last April, Lance and Dana sent the address to a group of their friends. By May they had 1200 users.

This is phenomenal growth. It turns out that student group software is incredibly viral. If you join a group that is using Wiggio and you like it — which most users seem to — you’re going to convince the other groups you’ve joined to do the same. The effect then spreads to these new members, who convert their other groups, and so on.

(2) Even though Wiggio is a very good idea, it was still very hard to get funding. After Bob’s initial investment — about a fourth of what they needed to fund their first year of operation — Lance and Dana thought the rest of the money would follow easily. Business professors loved the idea. Investors loved the idea. The site was built. It had been proven. Raising cash should be no problem.

But it was.

It took four months for the rest of the funding to come through. Lance and Dana moved to Massachussets in June, but it wasn’t until just recently — earlier in September — that they received their first paycheck. Practically speak this means three things:

1. They were living off of their savings accounts the entire summer with no guarantee that they would ever see any money for their efforts.
2. Dana had to commute from his parent’s home, a thirty minute drive, to save money.
3. As Lance puts it: “we ate lots of peanut butter sandwiches.” This sounds like a line, but they mean it. They were authentically pleased that now, with funding finally in hand, they could afford to eat lunch at the working class pizza joint down the street.

5 PM

Lance’s dad arrives from upstate New York for a visit. “I’m glad Lance is in a stable job, like a start-up, instead of going into something risky, like banking,” he jokes.

This premise, it turns out, is true. Both Dana and Lance had high-end job offers when they stumbled across the Wiggio idea. Lance turned his down. Dana’s management consulting gig, however, has just been deferred.

I ask why he’s holding onto his job offer if he’s committed to Wiggio? He says something official about the consulting firm being happy about the experience he is gaining.

Lance shifts uncomfortably.

5:30 PM

As I prepare to leave, I ask Dana what he would tell students who are interested in following a similar “glamorous” path, such as launching their own business.

“It’s not glamorous,” he replies. “I was up the other night until 4 AM trying to record a video, and the audio kept failing. That’s not glamorous.”

“There’s a lot of responsibility. More than a regular job. You have to push yourself.”

I ask him what makes this path worthwhile.

“It’s liberating to set your own schedule. To be your own boss.”

He then retires to his office to continue hunting down e-mail addresses for their student leader campaign. After that, a development meeting. Then, if all goes well, a short night’s sleep before a new day begins.

(The photo above contains, from left to right: Derek, Dana, Lance, and Rob.)

My friend Ben recently pitched an interesting idea for a blog post. He proposed that instead of a formal interview, we just have a conversation, drifting from topic to topic as we find things interesting. Ben’s a fascinating guy. His blog is well-trafficked, he commentates on NPR, he writes professionally, and is, relevantly enough, a college student. So I jumped at the chance.

Below are excerpts from our conversation. Check out Ben’s blog for his version of this post which will include different excerpts.

A Conversation Between Cal Newport and Ben Casnocha

Ben: So Cal, here we are on instant messenger. You have expressed concern about how email can be distracting. You don’t use Twitter because you say you don’t need yet another short-text distraction. Do you IM?

Cal: Not intentionally. Though people occasionally find me on gchat. I don’t like the slow pace and partial attention. Do you?

Ben: No. Same. Slow pace, partial attention. I wonder whether I will flip to other windows during this chat, or just watch the screen say “Cal Newport is typing…”

Do you adopt 4HWW habits with email?

Cal: Not really. I don’t do auto-responders, and I check more than twice a day. The big thing I’ve done with my e-mail was move from a single inbox to multiple “mono-typic pigeon holes.”

Ben: WTF is that?

Cal: This is sort of the height of unnecessary life hackerish geekdom, but I’ll explain: all of my mail gets filtered into one label or the other, so my “inbox” is always empty. Also, all of my mail automatically gets tagged as read, so there’s no difference between read and unread messages

Ben: Interesting. All marked as read. Why?

Cal: It prevents me from using my inbox as a big to-do list. Because I can’t really separate the new from the old, the easiest way to clean out a label (what I call a pigeonhole) is to actually have enough time to deal with everything and empty it out. If I read things quickly and then leave them in there, things get cluttered. It’s supposed to cut down on quick, attention-destroying glances at my inbox every 10 minutes.

Ben: A few weeks ago, I was interviewed for a documentary on lifehackers and the life hacking movement. Among other things I said that people who are big in life hacking tend to be a certain personality type.

Cal: What type did you describe for the documentary?

Ben: Super detail oriented. Neurotic. Oddly, sometimes also big procrastinators — setting up sophisticated life hack infrastructure IS their time wasting device. There was a book a few months ago that came out that said sometimes a messy office is the most efficient. I.e., don’t over-optimize.

Cal: I heard about that. The Perfect Mess, or something… I felt a little dirty, earlier, explaining my inbox setup. It’s something that was kind of useful — like buying a message pad for your phone — but I get uncomfortable focusing too much on those details. I wonder why this is…

Ben: Let’s turn to college for a moment. I’m interested in the idea that substitute experiences can signal as strongly as a formal credential. Some industries don’t require a formal credential.

Ben: Probably.

Cal: What industries?

Ben: Business and technology generally and writing / journalism. Unlike medicine or law, for example.

Cal: I’m assuming there is an implicit “start-up” behind business and technology?

Ben: Maybe. Probably. But even in non-start-up business realms, the formal credential is not required. As someone who will likely spend his life in academia, how do you respond to this? Academia being the credentializing institution of America?.

Cal: My thoughts lean toward the idea that college provides a reasonable and useful benefit behind the credential. However, the pricing and approach of students to the experience has drifted from optimal. In general, I find that a college graduate is a notably more sophisticated writer and critical thinker than a high school graduate.

Ben: Undeniably so. Here’s a question: how transferrable are the “study hacks” you blog about? That is, are you teaching skills students can use in the real world or are they unique to the formal schooling environment?

Cal: Both. A lot is applicable to the real world. Especially issues concerning time management and my essays on how to distinguish yourself or do something impressive. Tips on paper writing, for example, are less relevant to a 40 year-old.

Ben: Fair point. OK. One thing I’ve been thinking of recently is whether college students interested in journalism and politics, in order to stand out, must prematurely coalesce around a political party or established ideology, and hold certain to those beliefs, in order to get the appropriate internships at those publications.

This worries me because college is the time when you’re supposed to be uncertain and maybe proud of wishy-washiness — and yet uncertainty is often seen as counter to a sophisticated political understanding. Or even on the career front. Not knowing what you want to do in life is seen as bad, when in fact this is the one time when you ought to wander and be unsure. Thoughts?

Cal: This was on my mind when I received a recent e-mail from a Dartmouth student who just started his first semester as a freshman. He was worried that he had no specialized enough to be a computer science of physics major. In other words, to him, it was not just fixing on something right away at college, he had the impression that this decision had to be made much earlier…

It’s a challenging question. To do what I do — professional research — certainly requires specialization. I think the same probably holds for politics — intern over your summers! — or journalism — start working up the ranks at the school paper! And I often encourage students to focus, focus, focus…

Ben: Right.

Cal: But I can sense your hesitance…

Ben: Like, if you want to work for the National Review over the summer in college, you need to be bleed Red through and through. So any uncertainty or moderateness is beaten out of you. This is unfortunate.

Cal: Maybe not. If you want reward you need to be better at something than anyone you know. This requires focus. However, this is just one thing. For everything else in your life you can be open-minded. So, sure, the National Review guy is die hard conservative. But it’s probably healthy to have that voice in the conversation. For most other people, who are not focusing on writing for the National Review, they can be open-minded about politics.

Cal: Last topic: advice for the college-aged. What would you tell an 18-year old arriving on campus about a college life well-lived?

Ben: First, read I Am Charlotte Simmons. Have you read it?

Cal: We own it. My wife read it. I haven’t.

Ben: You should. Especially given what you write about! My next piece of advice would be to focus on the “little things” — when and where you eat, meal plan, taking advantage of weather, having an ergonomic keyboard/chair, making sure your cell provider gets good reception in college campus, etc. Day in, day out, these little things make a big difference. Beyond that my advice becomes cliche — meet profs, have lots of sex, experiment outside your expected field of choice, etc.

Cal: What about the big question of “what should I do with my life?” As you know, my approach is sort of “there is no wrong answer, choose something and focus on it so you’ll start reaping rewards, you can always change later.”

Ben: Your approach is similar to that great Andy Grove quote, “Act on your temporary convictions as if they were real ones, and when you realize you are wrong, change course very quickly.” The problem with what you said is “…you can always change later” is very, very hard. People have problems with sunk costs and inertia. That’s why I’m not a fan of “focus on something and start reaping the rewards.”

Cal: Do you worry that on the other hand people get too hung up searching for some “right” path that doesn’t actually exist. Getting scared every time anything seems a little boring or annoying.

Ben: Maybe some search for the “right” path that doesn’t exist, sure. But the second thing you said, no. I think people tolerate waaaay too much boredom in their lives.

Cal: Final follow-up: what are the temporary convictions, if any, in your life right now that you are taking seriously.

Ben: One conviction right now that I’m taking seriously is that travel is underrated and harder to do as one gets older, so I’m trying to travel as much as I can.
You?

Cal: I’ve been a big believer in the 10,000 hour rule. Roughly, that being good at anything takes a long time. If you want to be good at something in your 20s, start in college. If you’re willing to wait until your 30s, you can start later. With this in mind, I’ve put my chips down on writing and solving interesting proofs.

Ben: Interesting. What’s the biggest problem in the world right now?

Cal: Unstable governments and massive inequity … which go hand in hand.

Ben: I would say ‘poverty’ more than massive inequity. Inequality is not inherently bad

Cal: We could put it this way: the low end of the scale is too low.

Ben: Do either of your two main tasks – writing and solving proofs – solve this problem? Or do you think about that at all, i.e., world usefulness of your work?

Cal: Neither solves this problem. My writing, I hope, helps the small segment it targets. In some sense, I feel like that leverages my particular abilities to their fullest extent.

Ben: With that, let’s call it a wrap!

Steve is a student at the University of South Florida, where he studies religion and international relations. He first came to my attention earlier this summer when he published a provocative blog post debating his post-graduation path. The two options he was juggling: going to law school or becoming an elite Special Forces operative. Steve, as it turns out, is an NCO in the US Army, recently returned from a tour of duty in Iraq. So when he says he’s interested in joining the Special Forces, this is not idle talk.

When I heard Steve’s story, I knew I had to get in touch with him. As you know, I’m fascinated by students follow unconventional paths, as their examples can help jolt us out of our own conventional wisdom-hardened ruts. When it comes to unconventional, I can’t think of anything more fitting than a student whose splitting his time on campus between studying and intense training to join the most elite group of warriors on the planet.

Steve was kind enough to answer my questions about how his military lifestyle affects his approach to college life. Excerpts from our discussion are below. You can find out much more about Steve at his fascinating blog: Educated Soldier.

Give me a sense of your daily schedule.

During my last semester, every Tuesday and Thursday, I had class from 12:30 p.m. until 4:00 p.m. I would wake at about 7 a.m. I would eat a quick, light breakfast and head to the campus library. There, I would drink my daily Americano from Starbucks (which I can say, by the way, is one of my rare addiction indulgences) and spend about an hour browsing the websites that I consider daily reading requirements. This was time spent totally free from concerns of studying or Special Forces requirements. Before leaving the library, I would make sure to do something school related. This usually meant working on a reading assignment, which I would typically spend about a half an hour doing.

I would then head immediately to the gym. My work out lasts from 9:45 a.m. until 11:00 a.m. I would then shower at the gym and eat on campus. It would then be 12:30 p.m., or close to it, and time for my class.

Following my class, I would come home and usually spend about an hour checking those same websites of interest again. Like my morning library routine, I would then dedicate about a half an hour or so to school work.

At about 6:00 p.m., I would go for a run. Now, you really have to understand that I enjoy running. It’s an addiction that I am quite proud of. That being the case, I can claim in all honesty that my daily runs would last from an hour to over two hours. And on Tuesdays and Thursdays, it was usually the latter.

After finishing my run, it was about time to clean up and go to bed. Before going to bed, I would tend to hang out with my roommates for a while, eat something light, and complete a little more homework. And, if needed, this is when I would do the bulk of my additional school work. Even if I only dedicated another half an hour to studying here, however, one can see that my schedule affords me a total of an hour and a half of studying daily without the studying ever seeming burdensome at any one time.

Also, I am a master of hip-pocket studying. That is to say that I always have a book on me and have learned the value of picking up a few pages here and there; for example, I ride the campus bus often and always complete some studying there.

How is this schedule different than what you followed before you began to seriously consider joining the Special Forces?

After joining the Special Forces training program, my daily routine at the university changed in two ways: First, my daily schedule wasn’t so regimented. While I did many of the same things as I do now, I didn’t necessarily plan to do them as well as I do now. Second, prior to joining the SF training program, each day I would either work out in the gym or run. Now I work out in the gym AND run daily.

Why has being ultra-disciplined not made your life less fun?

I definitely had more free time during my freshman year. Yet, I found that I haven’t had less fun on a more restricted schedule. What I have learned, however, is that fun has to be scheduled and a bit less spontaneous than it was that first year.

For example, I do not adhere to my regiment on weekends. I may go to the gym or run on any given Saturday or Sunday because I enjoy doing so. However, I have in no way made this a requirement for myself. I workout hard all week knowing that I going to have the weekends to do whatever it is that I choose. And this mindset has been beneficial in many ways.

Financially, saving my recreational activities for the weekend has been a boon. Like many college students, I like to drink and party. However, by establishing minor priorities, I have found it nearly never necessary to drink or party on a week day or night. Buying beer two nights a week (and usually less lately) is obviously cheaper than buying beer five or six nights a week.

Also, my physically demanding regiment has caused me to develop a much more physically in-shape body. While I can hardly claim to be a ladies man, being in shape does wonders in ways that people not in good physical shape rarely recognize. For example, each day that I work out especially hard, I tend to tackle everything else I do that day equally as hard. When I see tangible, positive physical changes in myself, my confidence is boosted. Doing anything — from taking a test to hanging with friends — is much more enjoyable with a high level of self esteem.

In addition to your personal training you’ve also joined a unit that’s dedicated to training soldiers to enter the Special Forces program. Give me a sense of what this is like.

This last weekend, for example, was dedicated to land navigation. We arrived to our drill location on Friday night for mandatory briefings. These lasted until midnight. We met next on Saturday morning around 6:30 a.m. for a Physical Fitness test that measured our maximum push-ups and sit-ups (both completed in separate two minute increments) and our time running two miles. Immediately after the test, we changed into uniform and packed our rucksacks for the day land navigation course.

The required weight for our rucks was 55 pounds. This was measured before we added food to last throughout the day and night and six quarts of water. My rucksack’s total weight after adding our needed items was 78 pounds. The day land navigation course lasted from 11:00 a.m. until 7:00 p.m.

This means that in temperatures that reached in excess of 100 degrees throughout the day, we were constantly searching through national forest terrain for points. The entire time we had rucks on our back, equipment vests on our chests, and a simulated rubber rifle in our hands. Our main navigational tools were simply maps, a compass, and a protractor.

The culmination of the day land navigation course only provided minor rest. A mere two hours later, we began the night course. This event ended at 4:00 a.m. With the same equipment on, and with no additional equipment to aid our night vision (besides a headlamp that was only useful when looking at the map), we had to traverse through the same hazardous terrain. One of members of the cadre sitting on a point that we had to locate encountered a bobcat. A peer candidate turned on his headlamp while crossing a stream only to have his light reflect off the two eyes of an alligator.

The total distance between points in the two courses exceeded 15 miles. This distance fails to reflect how far each of us candidates walked when sporadically lost or in our attempts to avoid particularly hazardous terrain.

While all the Special Forces cadre and candidates returned from the weekend safe but exhausted, I still wanted to share my adventures with you. What I did this past weekend was only a day and a half’s worth in a training effort that ultimately takes nearly two full years to complete. And only after Special Forces qualification and assignment to an Operational Detachment Alpha does the real training begin.

Most of my cadre and nearly all of my peer candidates are college graduates or on-going students. I just want to do my part to reassure the educated types that would frequent a site such as yours that in the Special Forces we maintain the company of highly trained, well-educated individuals.

I think I speak for all of use here at Study Hacks when I say your experiences make the standard student dramas of an all-nighter or busy exam period seem like a little girl’s tea party. Thanks again Steve!

My first encounter with graduate student and blogger Chris Guillebeau, was an article he wrote about running a marathon…on a cruise ship. He did this for no real reason; it just seemed interesting at the time. My next encounter was an essay posted on Zen Habits about arriving in a small Macedonian town, at 4 am, with nowhere to stay, and subsequently wandering into a all-night street party.

Then I noticed he has traveled to 83 countries and plans one day to visit all 198. He also maintains an excellent blog, The Art of Nonconformity, and he will be releasing on Tuesday a free PDF manifesto titled The Art of World Domination — something I’m eagerly waiting for.

With all this in mind I knew I had to meet Chris (pictured above, chatting with Archbishop Desmond Tutu). He was nice enough to answer some questions about his life philosophy and what it means to become a nonconformist student.

Can you talk about your experiences in college and then the unconventional path you followed afterwards?

“I started college when I was 16, and finished in about two and a half years. I wasn’t incredibly smart or anything; I just registered for lots of classes at multiple schools and then transferred everything at the end to graduate. I’m not sure I would recommend that method to others, since my focus was definitely on completing my degrees instead of learning, but it worked for me.”

“When I was 20 I went to graduate school and needed a way to make some money. I started selling random stuff on eBay (this was 1999, the early days of online auctions) and ended up building a small wholesale business that later expanded to consulting and design projects. I wish I could tell you it was strategic, but it was initially motivated by a strong desire to avoid working for someone else.”

“By far the most important life change I made was moving to West Africa in 2002 to volunteer as an aid worker. I spent four years working with government leaders and villagers in nine different countries there, and the experience affected me profoundly. I came back to the U.S. in 2006 to return to grad school, but I have spent every break since then traveling to as many places around the world as possible.”

What advice do you have for a college student who is wearied by the “traditional” options before him?

“My advice is pretty simple: you don’t have to live your life the way other people expect you to. This includes parents, professors, and even peers. If you’re wearied by the system, you have to decide exactly how wearied you are. Most people complain about the traditional paths but don’t bother trying to make their own. If it bothers you enough, you’ll probably find something else sooner or later.”

I’m interested in your notion of how to become “remarkable.” Could you describe your philosophy here?

“It begins with the observation that most people are what I call unremarkably average. It’s important to note that this doesn’t mean they are bad people; it’s just that they do what everyone expects them to and they kind of amble through life. A remarkable person is not innately special– rather, to become remarkable (or noticeable), we really have to find our own way somehow.”

“By the way, I’m not interested in telling people how to live their lives. What I’m interested in is showing that there are alternatives out there and you don’t have to be like everyone else.”

What’s the one misconception, commonly held by college students, that you would most like to dispel?

“I just finished a master’s degree at the University of Washington, and during that time I got the chance to hang out with a lot of other students, both graduate and undergraduates. I would never say this is universal, but I did notice that a number of students tend to think that the school has a responsibility to find them the job of their dreams after graduation. There is inevitably a lot of disappointment when this doesn’t work out, and I think it’s far better to take personal responsibility for your own plans from the beginning.”

What are some specific things a college student could do right now to transform their life from conformist to nonconformist?

“Well, the fact is that most people are conformists, and I don’t necessarily think everyone should change. But for those who want to do something else, I think it starts with clearly understanding what it is you really want and how you can cause that to happen. Then, you have to think as well about how you can help improve the lives of others, because most people are not ultimately satisfied with a life focused only on themselves.”

“Once someone knows what they want and how they can help others, the plan of attack is to start taking it step by step. One thing that helped me in college, both undergrad and the grad program, was always asking the question, “Is there another way to do this?” If your advisor is sending you in a direction you are uncomfortable with, I’d push back a little, or suggest an alternative, or just get a new advisor. There are usually multiple ways of accomplishing any goal, including academic goals, and it has greatly helped me to think a lot about the alternatives instead of just doing things they way everyone else does.”

Interesting Posts from The Art of Non-Conformity

• The decision to be remarkable.
  
• The plan of attack.
• Follow your passion?

David Masters, a student, self-described “part-time peace activist,” and blogger, has an appealing worldview: life should be creative and playful. Here’s where it gets interesting: David doesn’t let students off the hook. He argues on his thoughtful blog, Be Playful, that undergrads should enjoy their academic efforts. Indeed, studying should even be, dare I say it: “fun.”

After hearing this claim I knew I had to interview David. There is something downright Zen about his take on student life, so, considering our recent conversations, I thought we should poke around a bit and see if we can’t figure out what makes this fun-loving student tick.

First things first: the major. What’s your advice here?

Choose a subject that you love and that you’re passionate about rather than focusing on what gives you the best career prospects. I chose a combined major of Theology and Social Sciences for two reasons: I love searching for meaning, and I’m passionate about social justice and making the world a better place. [ed. Daniel Pink would agree.]

What does it mean to connect your classes to everyday life?

Making your studies meaningful to you means that they become a part of who you are; it also makes studying a joyful experience rather than a slow drudge, because you can see how what you are studying makes an impact on you (or the world) right now.

For example, in my Political Theology class we’ve been learning about how the state maintains its power through violence. It’s interesting to apply this idea to news about different countries, like how China has been treating pro-Tibet protesters, and how America shows off its power through the war on terror.

I’ve heard you mention an interesting trick regarding the bibliography for a paper…

When choosing books to read for a writing assignment I try to make sure that the majority of books in my bibliography aren’t on the course reading list. Choosing books that aren’t on the reading list makes your paper stand out to the professor; it will be different from the pack and will read as more independent and creative.

You claim you can make studying more like play. Let’s say it’s a typical day for David. What does it look like?

This may initially sound like a contradiction, but the key ways in which my studying is playful is that it is structured and focused. Sports and games, though playful, are very structured, and it is this structure that allows for great feats and achievements.

I know the best time for me to study is in the morning, so I study then. I read the assignments, and I work on the paper. I prefer working at the desk in my room, so my notes are handy to compare different ideas; if I’m in the library, I’ll find a quiet corner desk near to the shelf I’m researching. I like to be done by 4pm to have time and space to socialize and relax.

I guess what is different is the way in which I engage with my studies. When I read through the assignments, the most important thing I am looking for is new concepts, or old concepts seen in a new way, and connections to other things that I have read, and I’ll mark up these. [ed. Scott Young would agree.]

What’s the biggest mistake you see your fellow students make in how they approach their academic lives?

Failing to be organized and to structure their study. I guess many students see this as freedom, but in my mind, they’re a slave to deadlines. Having a structure means that you can work at your own, relaxed pace, and you don’t feel guilty or worried about unknown looming deadlines, because you know exactly what’s coming up.

Any final unexpected nuggets to share with us?

I think one of the best things that students can do is to contribute to the world in some way. It’s best to choose just one thing to give your time to, so you don’t end up over-scheduling yourself.

I loved the Study Hacks story of Tyler and how he applies what he learned in his past studies to make a different to the world doing cancer research.

If you don’t know Daniel Pink, you should. His bestselling books, Free Agent Nation (2001) and A Whole New Mind (2005), heralded the arrival of the conceptual age. Dan has also written on issues of business and technology for The New York Times, Harvard Business Review, Fast Company, and Wired.

His full biography reads like a Zen Valedictorian, post-grad adventure tale. He attends Yale Law School then never practices a day of law, deciding, instead, to bum a ride out to Washington. Soon he’s a vice-presidential speech writer. He leaves that job to write two of the most important business books of the last decade. He then wins a fellowship to move to Japan and study the Manga industry.

Enter Johnny Bunko

Perhaps most exciting for Study Hacks readers, however, is his latest project, the new book: The Adventures of Johnny Bunko: The Last Career Guide You’ll Ever Need (illustrated by Manga hotshot Rob Ten Pas). In Bunko, which tells the story of a young graduate receiving workplace lessons, Dan lays out six core pieces of advice for making it happen in the real world. As someone who works and writes a lot about these issues, I can say with conviction: this is some of the most dead-on, effective young career advice that I have ever read. (Don’t take my word for it, you can preview the rules here and read the first chapter here.) The Miami Herald, perhaps, puts it best: “[Johnny Bunko] blows away all the rest with its clarity, simplicity, and intelligence.”

As you can imagine, I was quick to get in touch with Dan. I asked him what advice he had for a current college student looking to jumpstart a Pink-esque career after graduation. He was kind enough to respond.

The interview follows…

Your own post-college path seems serendipitous. How did you stumble onto this path. And once on it, how did you keep moving in such an interesting direction?

You’ve got it right. There was a lot of stumbling and serendipity. Since I knew I wasn’t going to practice law, I decided to go into what I then found most interesting: politics. I worked on a number of political campaigns as a policy and communications person — and then, yes, stumbled into speechwriting. What happened is that I wrote a few speeches. They weren’t awful. Then they asked me to write a few more and before I knew it, I was a speechwriter. I got reasonably good at it, did it for awhile, but then got sick of the b.s. of politics. At that point in my life, I was becoming deeply interested in business and technology — so I decided to go out on my own and write about those topics.

All of the books and most of the articles I’ve written since then have really emerged from pursuing the things I was curious about. That’s a key. Curiosity. I tried to follow my curiosity and see where it took me. Also — and this is important — I decided that since so many people could outsmart me, nobody would outwork me. As you know, I’m a big believer that persistence trumps talent.

What’s the biggest myth about the post-graduation search for a job that you would like to dispel?

That you need to have a carefully articulated plan. Too many people make career decisions for instrumental reasons — because they think what they’re doing will lead to something else. Not enough people make decisions for fundamental reasons — because of the value of the activity itself.

The dirty little secret is that instrumental reasons don’t work. It’s way too tumultuous out there. The people who really flourish are those who make decisions for fundamental reasons. They have to live with a certain amount of ambiguity about not knowing what’s going to happen next. But that keeps them alert to unexpected opportunities and the serendipity you talked about earlier.

What lessons would you give to Johnny Bunko’s little brother who is, let’s say, a rising college sophomore?

1. Begin the process of discovering what you love to do and what you’re great at — what, in some sense, you are on this planet to do. You won’t necessarily find the answer in college. But asking that question will put you on a promising trajectory.

2. Pick the professor, not the course. In the hands of a good teacher, every topic can fascinating.

3. If you’re in the arts, take a laboratory science course. If you’re in science, take a studio art course.

4. Exercise. Seriously. Exercise is one of the few things in life that is uniformly, unequivocally good for you.

Thank you so much for your time!

How to Become Good

Marty Nemko is good at becoming good. As he outlined in a recent blog post, when he set his sights on becoming a career coach he eventually logged over 2800 clients. When he decided to parlay this expertise into writing, he landed a career columnist gig first for the San Francisco Chronicle, then the Los Angeles Times, then transformed this into a contributing editor slot at U.S. News & World Report. He wanted to learn the art of rose hybridizing, now three of his varieties are sold nationwide. He wanted to try playwriting and won the “Roar of the Crowd” award for the best Bay Area entertainment of the week. His first screenplay caused a stir. He has a radio show.

And the list continues…

To use Study Hacks parlance, Marty is a finisher. He doesn’t just tackle projects that pique his interest, but he also manages that rarest of the rare skills: to consistently push them into the elite strata of noteworthy accomplishment. Fascinated by his approach, I asked Marty to share some of his famously unconventional advice on how to become good at becoming good.

What do most people get wrong when they set out to become good?

The average person isn’t smart enough to tackle lots of things, yet they try and thus become dilettantes. They need focus, unrelenting focus — until the world has provided sufficient signs that it is interested or not interested in that person’s focus.

What’s the role of talent versus strategy in becoming good?

Strategy is absolutely necessary….but insufficient. Talent and drive (or luck — damn those lucky people) are required.

Many people who focus on something for a long time can get pretty skilled, but have a hard time making that transition to the big-time. How does one make that final push from amateur to expert?

Become an amazing and relentless marketer. That skills is usually orthogonal to (the less accurate term is “incompatible with”) becoming expert at something, yet it is critical, alas, especially in this society where the stupid public responds to marketing hype more than to excellence. Why else would dishonest idiots like Oprah be more beloved than, for example, Christopher Hitchens on the Left or Larry Kudlow on the right..

What advice would you give a young college student looking to make a name for himself in something?

Forget passion unless it’s a rare one. Too many other people will be passionate about it, eviscerating your chances of “making a name for yourself.” Don’t be a lemming. Make a name for yourself in some pursuit that top people rarely pursue: Be the most amazing undertaker, industrial acid broker, advocate for the most under-served and worthy kids (in my opinion: intellectually gifted boys in elementary school.) Even if the field seems mundane, you will feel more rewarded and better about your life being a vanguard in a dull field than a soldier in a “cool” one.

[For more on Marty, check out his popular website, which includes, among other content, his new blog and a collection of his most popular articles on life, goals, work and achievement.]

Every January, during MIT’s Independent Activities Period, Computer Science Professor Patrick Henry Winston gives a famed lecture titled: How to Speak. During this perennially popular event, Professor Winston walks his audience through a series of tips and strategies, developed and honed over decades, for mastering the art of speaking. I attended his lecture for the first time this year, and was not disappointed.

The crowd was literally at capacity. Every seat filled. Every step filled. The ground surrounding the podium filled. And a crowd spilling out into the hallway straining to hear. Having arrived early, I was able to snag a desk an thus take copious notes. In this post, I draw from these notes to present to you, in detail, the secrets behind the Patrick Winston Method.

The Formula

I = f(K,P,T)

Your Impact is a function of your Knowledge about speaking, Practice, and Talent — in decreasing order of importance. Winston’s advice focuses on your knowledge about speaking. This is the easiest way to gain the biggest increases in your impact.

How to Start

Some advice for starting your talk.

1. Don’t start with a joke. The audience is not accustomed to you or your speaking style yet. Humor will be difficult at this point.
2. Do start with a menu. Tell them exactly what you’ll be speaking about and in what order.
3. Do provide an empowerment promise. Explain why your audience will come away from the talk better than when they entered.

The Big Four

A collection of four heuristics that make a talk work.

1. Cycling. Deliver ideas first in brief, then in detail, then in summary. To use the lingo of artificial intelligence: let your audience load the schema, then fill in the details, then let them know what’s worth indexing for future reference.
   
2. Verbal Punctuation. Provide a mechanism to help people who “fogged out” to easily rejoin the talk. For example: “We have just finished talking about the first heuristic, cycling, I am now going to talk about the second heuristic for helping to make your talks more interesting…”
3. Near Miss. When explaining an idea, also describe other ideas that are close but not quite the same. This will help people understand what the important points are that define your idea.
4. Ask Rhetorical Questions. Don’t make them too easy. Don’t make them too hard. Wait 6 seconds for an answer.

The Tools

Four tools that can make or break your presentation.

1. Time and Place. If it’s in your control: mid-morning is the best time. Choose a location that will look full with your expected audience size. Make sure it is well-lit. Don’t let them turn down the lights. (“It’s easier to see slides in a light room then to seem them through closed eyelids.”)
2. The Board. A blackboard lets you draw natural graphics that highlight your points. It also paces you. The speed of writing matches the speed with which people process information. Use a logo that captures the main point and that you can return to. (“I once saw a Sloan professor lecture for a whole hour about a triangle; it was amazing!”) It also provides a target. The best thing to do with your hands? Point at things on the board.
3. Slides. Don’t use anything less than 24-point type. If you can’t fit the information at this font size then you have too much. Follow these four rules:
   1. Don’t read the slides! “A special circle in hell for those who…”
      
   2. Don’t stand far away from the screen. This requires divided attention from your audience.
   3. Have one meaningful picture per slide. If it’s found in Microsoft’s clip art gallery, it’s not meaningful.
   4. No pointers. Laser or otherwise. These are distractions. You’ll play with them. They’re annoying. Stand by the screen and point with your hand or refer to visual anchors on the slide.
4. Props. When possible, use a prop to illustrate an idea.

Special Cases

Three specific types of talks. (Notice, the first two are specific to academia, but the advice is none-the-less generalizable to other arenas).

1. Oral Exams. Some strategies:
   1. Show your hand early on. Within five minutes have explained what you did and why it’s important.
   2. Situate your results in time, space, and field. That is, explain the trajectory over time of your area of concentration, where else people are working on the same problem, and the consequence of your result for the field.
   3. Practice. Ask your friends to listen to your talk. Tell them to try to make you cry.
2. Job Talk. Here is what they want to see in a candidate:
   1. Has a vision.
   2. Has done something about that vision.
   3. Don’t finish with a conclusion slide. Instead have a contributions slides. Something that spells out clearly what you did.
3. Getting Famous. If you want to become a world class speaker, try to deploy Winston’s Star. A five-point checklist of things to make your talk extra memorable:
   1. Symbol. Some icon that makes your ideas easy to hold on to.
   2. Slogan. A simple linguistic handle for your ideas.
   3. Surprise. Make people say: “did you see that talk…”
   4. Salient. Have an idea that really sticks out.
   5. Story. Tell stories that engage the audience.

How to Stop

Some things to keep in mind about concluding a talk:

1. Deliver on your promise made at the beginning. Remind them what it was and summarize how you satisfied it.
2. Tell a joke. They know you now. And if they leave happy they will assume the entire talk made them happy.
3. Call for questions.
4. Don’t thank the audience. It makes it seem like they did you a favor by listening to your boring babble.
5. End with a salute. Compliment without thanking. (i.e., “You’ve been a great audience, I hope you learned a lot about how to give a great talk.”)

The Randomness Factor

In early May, 2007, Ben Casnocha, a college student, entrepreneur, author, and all-around big thinker, posted a blog article titled: Expose yourself to bulk, positive randomness. The idea, which was later developed in more detail in his book, My Start-up Life, proposed a simple change: If you want interesting, grand things to happen in your life, stop trying to plan out every last detail. Instead, go out of your way to expose yourself to randomness. Lots of it. And then put in an effort to follow-up.

This pro-randomness philosophy runs counter to the cult of systematization that pervades much of the productivity blogosphere — which is why it intrigues me. So I asked Ben to walk us through the concept…

What is your randomness philosophy?

The philosophy is based on the difficulty of predicting which projects will ultimately be most successful. Sometimes it’s the random projects that turn out to be most important. To wit, we ought to “expose ourselves to randomness.” We should proactively generate opportunities that might seem random…but who knows?

“Randomness” includes, among other examples, conferences no one else is going to, obscure books, and the odd person you met who you’re not quite sure is interesting.

What are some examples from your own life where randomness paid off?

Some of the most interesting things that have happened to me — experiencing exotic situations abroad or getting my book published — have in part resulted from seeking out randomness. Without an overarching career goal in life, I can follow these various threads of randomness to their end. Once I was at a funeral, and met someone, and followed up, stayed in touch, and the person became one of my most important business mentors. This counts as randomness because I didn’t meet him at a business networking function. It was at a funeral.

What can a fellow college student do to live this philosophy?<

Take classes you might not otherwise take; go on that trip you’ve been putting off; make unusual choices; go to as many visiting speakers as possible. Try to build the most rich and diverse “input stream” as possible.

What are the pitfalls?

If you take a meeting with some random e-mailer, there’s a chance he turns out to be uninteresting and a dud [ed: or a serial killer]. There’s also a chance he could go on and be your future co-founder. So you need to apply some filter. The key is to use a different filter than everyone else to pick up on people and ideas that others might miss.

Of course every day can’t be an experiment in randomness. Every day shouldn’t be random meetings, random web surfing, and random walks through the park. Allocate certain time to pursuing unusual paths — but it shouldn’t be your whole day.

Let’s do the Michael Pollan thing: summarize your philosophy in seven words or less.

Be open to random opportunities. Who knows?