Gap Year: Day One

It’s day one of a year that will change the lives of 13 young adults.

The fellows arrive at the Gap Year house. With hugs and kisses, some apprehension and sadness, they say their goodbyes to parents. They say goodbye to the life they knew before their gap year, and they say hello to something entirely new, not completely sure of what to expect. There is fear, there is joy. There is excitement buzzing in the air as fellows find other fellows to talk to, looking for friends in each other, each wondering what lies ahead on this first day of the next year of their lives.

Soon enough, it’s time for their first dinner at the Gap Year house. And everyone around the table, both staff and student, have to answer a question that stretches their minds, and perhaps their comfort zones: “What makes you a misfit?” Each person at the table fills the silence of eating with something about themselves, something that sets them apart. Again, a bit of fear weaves its way into their stomachs. But they know to embrace this thing that sets them apart. They know to fight against the fear inside them. Because they know no one here will hurt them. They are safe. And they speak, each in their turn, and say that wonderful thing that makes them different. Their badge of pride. That thing that makes them a misfit.

And they find they aren’t so different after all. They are all different, but similar in the fact that they are different. They find pride in that thing that sets them apart from the others. And the next morning, they wake with the memory still in their minds as they come to the table a second time, now for breakfast made by the staff. The fellows stayed up late meeting and getting to know each other, sharing their hopes and dreams for the year, and they don’t waste any time with silence as they talk all throughout breakfast.

At 10 am, they all head downstairs to learn the the schedule of the first three months of the year they are embarking upon. Here they learn what the expectations are for these three months as well as the simple truth that what they’re doing isn’t just a program, but a movement. And they are a part of that movement. They actively have a hand in shaping it. And this brings upon the fellows both a sense of responsibility and an electric excitement. After this, they are reminded of the importance of taking good care of themselves during the year, with emphasis on sleep, exercise, food and generally being healthy physically, mentally and emotionally.

After a break for lunch where the fellows get to go out of the house for the first time to check out the restaurants around the neighborhood, they arrive back for the rock-paper-scissors world championship. Here, the rules are that when some one get beaten by another player, they have to follow them around, cheering for them. One fellow who was a more shy and introverted person than most of the other fellows began to get a lot of support from the others by winning a lot of games. By the end, the whole room was chanting her name in unison when she became the rock-paper-scissors world champion. She experienced what it’s like to have a bunch of support behind her in what she was pursuing and to see how it affected her. Needless to say, she was smiling wide and knew she had just made some new friends.

After some fun improv games, things progressed to a bit more serious tone. Fellows were asked to complete the sentence “One thing you wouldn’t be able to tell by looking at me is…” fellows talked about everything from being very family-oriented to being self-critical or not being like other kids because they didn’t like to party. Then, they took a break where they spread out in the house, the park nearby or going on a short walk around the block and talked about their life stories on a one-on-one basis, getting to know each other better.

Then they returned to the community space in the house for a continuation of orientation. The room had a different feel this time when the question was asked. Complete the sentence “if you really knew me you would know…” There was anxiety in the air as people began to talk about their deeper selves and everyone got 2 minutes to talk uninterrupted. Honesty filled the air as the fellows allowed themselves to become vulnerable with one another, and the gentle caring of the fellows and staff in the room was palpable in the air. As they mustered their strength to show their true, raw selves, tears were shed and hugs were given. By the end, the fellows knew each other better than most friends know each other.

After a short break to collect themselves, the feel of the activities changed again. Again, there was a spark in the air. Excitement found itself in the back of the fellows’ minds. They started playing a game called elves-wizards-giants. Which is like rock-paper-scissors, but dividing people into two teams, miming silly fantasy characters and chasing people in an effort to tag them and recruit them to their team.

Jon, the main staff member in charge of orientation and one of UnCollege’s Program Specialists, has been getting people to open up and become closer in business and academic settings for about 10 years. His work is very intentional, and there is a purpose behind every activity in the orientation. When asked about why he gets people to open up to each other so early in the program, he had this to say:


“I’ve noticed, after doing this thousands of times, that when people get real with each other, they become comfortable with each other, and whenever you’re trying to create a culture or an ideal learning environment, people being comfortable with each other is an integral part of that.”


The day ended in a group meal. After a long day of teamwork games and brutally genuine moments, the fellows ate together as a family of deeply connected friends.

Posted by on September 20, 2014
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Unspend Your Student Loans

This fall, more than 3 million students are heading off to college for the first time. Many of them will take out student loans in order to afford it, and for a few, it’ll turn out to be a decision they wish they could have back.

For them, we’ve created a new program to pay back their student loans.

If you are a college freshman reconsidering your choices about college and student loans, think of this as a do-over.

Stopping out of college is a big decision. We know. Four years ago, UnCollege was born out of Dale’s decision to choose his own educational path and stop out of college. He’s written about it a lot. He’s shared his very personal story. And he just published a new guide on the topic (which can be downloaded for free).

College can be a great choice, especially for students who are certain of their interests and career pursuits. But there are other choices, and fortunately there are more of them today than ever before. Real learning means actively choosing the experiences that have the most value to you. And the conventional college path doesn’t work for everyone.

So if you are a freshman choosing to stop out of college this winter to explore other possibilities, we want to help you get out from under the burden of your first-semester student loans so you can consider another option. The UnCollege Gap Year is an experience-based program that teaches young adults practical skills that they might miss in conventional classroom settings. Our participants, called fellows, are guided through a year-long course of self-directed learning marked by an overseas expedition, professional internship, personal coaching, and the launch of an individual project. It’s far beyond a traditional gap year. We leaned on decades of educational research to build this program, engineered it in Silicon Valley, and made it flexible enough that it can be taken as a supplement to a conventional college experience or as a stand-alone.

Here’s what you need to know about the Unspend Your Student Loans program:

Who is eligible?
•  students currently enrolled in their first semester of college
•  students with fewer than 18 completed semester units or 24 completed quarter units
•  students who have active Federal Direct Student Loans (subsidized and unsubsidized)
•  students applying for the UnCollege Gap Year program winter 2015 cohort only
•  students must be admitted for the winter 2015 cohort by November 15, 2014

How does it work?
•  UnCollege will select a total of two recipients by December 1
•  after the recipients exit college, a six month grace period goes into effect before the loan repayment period begins
•  before the grace period elapses, UnCollege will pay up to a maximum of $2750 each to satisfy the loans of the selected participants

We’re piloting this program with the hope of expanding it in the future, but for the Winter 2015 term we’re starting small with two participants. Obviously, inclusion in the Unspend initiative is competitive. Selections will be made based on a comprehensive review of the candidates’ application materials.

If you know a college freshman who might be interested in making a new choice, we’d love to pay back their first semester student loans and have them join our Gap Year program. It’s easy to get started. Grab Dale’s white paper “Should I Drop Out of College? A Dropout’s Perspective” and read the six crucial questions you need to be asking as you contemplate stopping out. You can always jump right in and apply to the program for the Winter 2015 term.

It takes courage for a student to step away from the conventional educational path when that paradigm is so entrenched. We hope this new program will help make it easier for students to take that step and join us for Gap Year.

Posted by on September 17, 2014
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Question Everything: A Gap Year Experience

By Jean Fan

Two years ago, I met Jean Fan. When a petite Asian woman sat down for coffee, I had no idea I was about to meet one of the most talented people I’ve ever met. I knew that she was smart and kind. I didn’t know that she was only sixteen or that she would become one of my closest friends. She told me she wanted to help UnCollege and ended up writing our newsletter. At the time, she was still in high school and planned to apply to elite universities. After two years working with UnCollege, she begins at Stanford next week.

- Dale Stephens

It’s a habit I picked up in high school, one that I can’t seem to shake. I’m (luckily) not referring to a secret smoking habit, but rather to my propensity to question everything.

Why am I doing this? Why are others acting this way? Why does the world work like this?

It can be a painful habit. Ask too many questions, and you start to notice that everything you thought you knew is fundamentally flawed.

Some days, I just want my brain to shut up. Most days, I’m grateful that it doesn’t.


The Benefits of Asking “Too Many” Questions

Despite the internal turmoil that it can cause, this questioning approach has done me a lot of good.

It’s led me to meet interesting people who share similar opinions. It’s allowed me to take advantage of opportunities that many people overlook. It helps me make decisions that are truly mine.

Questioning the cut-throat approach to college admissions helped me get into Stanford, and also have an enjoyable high school experience. Questioning the value of college led me to meet Dale, get a job at UnCollege, and decide to take a gap year.

During this year off from school, I’ve continued to ask myself many hard questions. By doing so, I was able to have an incredibly fulfilling gap year experience, and gain insight into what I want to do in the future.

In this piece, I want to share three questions that I thought a lot about during my gap year. Hopefully they’ll prompt you to continue your own lines of questioning as well.


The first question: Should I travel during my year off?

I didn’t want to travel, but I felt pressure to after realizing that it’s the thing you’re “supposed to do” on your gap year.

When I told people that I was just planning to stay in the Bay Area and work, I’d always feel a bit lame. In the beginning, I’d have to constantly remind myself that I didn’t have to do what others expected.

Ultimately, after thinking about why I wanted to take a gap year to begin with (to learn more about what I wanted to do in the future), I decided against traveling.* Instead, I had a very rewarding year working first at UnCollege, and later at Leverage Research.

It wasn’t as glamorous as spending the year abroad, and it’s not what many other people would want, but it’s what made me happy.

Do what you want, not what others expect: this is a lesson that I find myself having to learn over and over and over again.

*Towards the end of my gap year, I did end up running an experiment to test whether I’d regret not traveling. After 20 looong days in Peru, I can happily say that I won’t.


The second question I struggled with: Is education really the industry I want to be in?

I was a junior in high school when I started actively thinking about the education system. Now, a few years and internships later, my identify felt inextricably tied to this line of work.

Unfortunately, I was no longer happy. The more I learned, the more obvious it became to me that the deficiencies in education were symptoms of a much larger problem: we don’t understand humans nearly well enough.

For a while I felt very lost. It took me a few months before I was able to step away from what I was doing, and rethink one of my core beliefs.

But only because I pursued this line of questioning did I stumble upon something that was a better fit. For the second half of my gap year, I ended up getting hired for a research position that let me do exactly I wanted: study how people think, and think about how to improve it.

One of the features of my brain is that it constantly asks me, “Why are you doing what you’re doing?” If I can come up with a good answer, I continue. If I can’t, then I stop.

The benefit of questioning yourself like this is that it allows you to make very deliberate decisions. It makes you aware of when you’re doing things that sound good but don’t make any sense, and when you’re blindly following the crowd rather than thinking and choosing for yourself.


The third question I asked myself: Is college actually the thing I’m frustrated with?

Don’t get me wrong. After writing the UnCollege newsletter for two years, it’s obvious to me that there are problems in higher education.

I’ve spent a lot of time feeling frustrated with universities. During my gap year, I began to question whether that frustration was misdirected.

In the past few years, I’ve met a lot of wonderful people both in and out of school. It became obvious to me that my friends in college were often hacking their education just as avidly as the ones who weren’t.

What I see now is that I’m not frustrated by college. I’m frustrated by complacency. The thing I want is for all students to “take control of their education” — not for all students to drop out of college. In fact, I actually want to go to college.


The End of a Beginning

As I write this, I am finishing up my gap year. In one week, I will be a college freshman, and that is so so insane. I have to say that I’m excited.

After this year, I have much better picture of what I want to get out of school. I also know that if school doesn’t end up working out for me, I have the ability to get a great education on my own.

I wish I could say that I’m sad my gap year is coming to an end. But right now, all I can think about is how excited I am to begin the next phase of my education.

Posted by on September 10, 2014
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October 2014: Self-Directed Learning UnConference

The creators of the UnCollege Gap Year Program are bringing you the Self-Directed Learning UnConference this fall! This one day event will be a hybrid of keynotes, participant-led breakout sessions, and networking opportunities.

The Event

The summit will kick off with a keynote presentation by Dale Stephens, founder & CEO of UnCollege. He will speak about his experience as a self-directed learner, and how the tide in higher education is shifting towards self-directed learning. Participant-led Breakout Sessions will follow.

Whether you have taken control of your education, are an advocate for self-directed learning, or are just curious about how this movement is shaping the future, you won’t want to miss this event.

Get up close and personal with people who are leading this movement, and network with those who have found success outside of the traditional educational path. These are the movers and shakers!

Breakout Sessions

With an UnConference, breakout sessions are decided upon and signed up for at the beginning of the conference. Breakout sessions can be about anything from traveling to business plans to resume writing and more.

Anyone is invited to apply to lead a session! We welcome creative topics and session formats, as long as they add to the dialogue on self-directed education.

UnCollege Staff and Gap Year Fellows will be involved in contributing to Breakout Session dialogues, facilitating networking, and sharing their experience in self-directed learning.

If you would like to lead a session, apply here!

>>> Register for the Self-Directed Learning UnConference here.


Posted by on September 6, 2014
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The Truth About Your High School Experience

By Mohnish Soundararajan

A couple years ago, I almost died.

“Unlock the door you dick,” I said. Of course, I knew how these things went. It was the classic ‘lock-him-out-of-the-car-then-drive-off’ maneuver. It was late, there were girls in the vicinity, and the conditions were perfect: why not make a scene? So I jumped on top of the car. As I gripped the roof, I felt a jolt and then, the car started picking up speed.

He didn’t know I was on the roof.

The pace started to quicken. I yelled. No response, and the car started hitting twenty. Then thirty. Then — without thinking, I smacked the windshield. Crack. My friend slammed the breaks. I flew off and hit concrete.

Flash forward a few years.

It was me and my best friend, in high school Econ, ripping up a quiz in front of our entire class during the last semester of our senior year. The reaction we got was nothing short of hysterically beautiful.

And it was worth 10 points.

There was no denying how great it was to graduate, college acceptance and denial letters in hand. It was a time where everyone felt like they could look forward to the future without the burden of the past, while also pretending that the college they were going to was their dream school.

Yet, after a barrage of quizzes, notes, tests, study packets, folders, textbooks, and frantically shared finals study guides, high school had both given and taketh away.

It had taken a toll I couldn’t quite put my finger on. And after we left, none of us could. There are stories that we tell ourselves and then, there‘s the truth. When I was in high school, I — as well as everyone else — had our stories wrong.

The Work

I remember one of my classmates asking the teacher:

“Why is this important? When will I ever in my life need this?”

Our science teacher made jokes that were raunchy enough to get a laugh but didn’t push the envelope enough to be arrested for sexual harassment. Here, though, he looked visibly pained when she asked, like she had just told him some awful knock knock joke and he just had to sit there and take it. For a moment, I really thought he was at a loss for words.

“You just need to know this stuff to get into college. It’s good for you”

And that was that. In my four years, I realized that no one had a good answer to this question. Because after it was all over, most of the work we did in high school was pointless, unusable, and forgotten.

The truth is that we knew back then that all the work we did was simply practice for a future so far off we couldn’t even conceptualize what it would look like. No one was excited to learn and build their future. Talk to any high schooler and they’ll tell you, first hour on a Monday is like being physically assaulted by the devil.

The problem is that adults, policy makers, and nearly anyone east of the west coast believe that being uninspired for 8 hours a day was a rite of passage, a mark of tradition, not something that could be improved, changed, even solved — even though in history, especially the Renaissance, teenagers looked up to adults because they had the expertise, the wisdom, and the well-grown beards they themselves wanted to inherit. Their teachers truly inspired them.

Now, teachers don’t play that role.

Instead, it’s a “love-hate-mostly-hate” relationship with teachers. They aren’t judged by how much they taught you, a useful metric, but by how often they let shit slide. The best teachers, we thought, were always athletic coaches.

Every break we got, we took. I remember a stretch of three days with no homework and thinking: I’m so glad I don’t have to learn today.

And that was when I kind of sensed that high school was starting to lean me away from wanting to work hard, from wanting to crack open a book, and exploring what I was capable of. It wasn’t anybody’s fault, especially not the teachers. But it felt like it was mine.

We tuned in to teachers the day before the test, not because we wanted too, but because we had too. I like to say the difference between an author researching American Literature and a student studying it, is that the student is probably trying to find a window to jump out of.

The People

When you’re in it, there is no life outside the school hallways. You seem to know everyone yet, at the same time, you don’t know everyone. As far as your 15 year old self was concerned, high school was the world and that was all there was to it.

And you care — more than you’d like to admit — what other people think. I remember walking into the school restroom and about 3 guys checking, wetting, and matting their hair. It was like walking into the early moments of some bizarre beauty pageant nightmare but with dudes.

For most people, high school is awkward and frustrating. And outside of high school, there was truly nothing to do. If you felt like your town was empty, sterile, and fake, well, that’s because it was. A precondition of being a good parent is moving to the suburbs, where ironically, giant nursing homes are erected for students and seniors alike. It was scribbling away at home work, glowing phones, hanging out in basements, discovering alcohol, and trying our best to accrue new experiences in a place where new experiences were in short supply.

Those new experiences get stunted when we realize there’s only so many people in this small, small town. You’re forced to be friends with the same people regardless of whether or not they’re the types of people you love being around or if they’re even a good fit. I was lucky to have great friends in high school, but I was also painfully aware of the people that didn’t — not because they were insane or weird, but just for the fact that they were an island of one, end of discussion.

There is nothing you will miss more than having a locker, walking in the hallway, chatting with friends, giving out ridiculous handshakes like it was free candy, wondering who will say “hi” to you in the hallway (and who won’t), and of course, truly understanding the silent anxiety of picking a lunch table.

With nostalgic-tinted glasses, I tell people I enjoyed high school. But I also recognized the bullshit that was so classically emblematic of it.

When you’re older, you get to choose who you’re tight with, who you fit in with, and what you want to do. Yet high school, more than yourself, dictates the terms and conditions — for better or worse.

Like many smart adults have told me, finding out who you are is a long, arduous process that takes years. But it’s incredibly noticeable during your high school ones, a time where you’re making fake and real friends and you’re picking up good and bad social skills and you’re learning a lot more quickly about yourself than you ever have in your entire life.

Because even if you feel lost, that’s fine — the long con is that most people in high school are.

The Afterwards

After I flew off the car, nothing really changed. I loved telling the story like it had life-changing implications and that I saw every moment of my life before I hit the ground — me at 10, me at 30, me marrying Kate Upton — not because it did, but because it should have. It was nearly the most exciting thing to ever happen to me at the time and like every high schooler attracted to the dramatic, I wore the moment with a badge of honor. It wasn’t that I was too risky or reckless or that my friend was in the wrong or anything. Nobody got hurt, we got ice cream afterwards, it was fine.

No, the thing about that is, it just happened. Sort of like how high school just happens. You start it, you do it, you’re done, and you look back, and you’re like, whoa, what just happened? What did it all mean? What did I just do?

And no one is giving answers because, like a science teacher, most of the time, all they have is an empty gesture — a nod, a wink, a smile, maybe a pat on the ass if they’re creepy, and then? You’re on your way.

During Prom, I remember the moment when the Sophomore escorts and I arrived in suits, freshly pressed. Prom was new to the us. And when we arrived we were (how do I put this delicately…) ready to get some ass. After it happened, we traded hilarious stories, somehow wrecked a hotel room, and realized we had just gone through something Lifetime movies were made of. Prom, the big deal. And at 16, it was the biggest of deals, on top of flying off a car or getting shot in a parking lot. At the time, it was nice knowing that. But afterwards, the next Monday?

We went straight to class. And just like that, it was over. And all we had left was nostalgia.

Mohnish Soundararajan works for bestselling authors and startups. If you dig this and want more, subscribe via email here and check out

Posted by on August 30, 2014
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Nominate a Future Fellow

We are excited to announce the creation of a future fellow nomination process to allow parents, counselors, and those in the UnCollege community to identify motivated individuals who would be great for the Gap Year program.

Over the last few admissions cycles we have realized that some of our best and most passionate applicants have come from referrals from an UnCollege fellow, parent, mentor, or friend. That’s awesome! In an effort to support the continued referral of potential fellows by those within the community we are launching the Nominate a Future Fellow Campaign.

Think you know someone who would excel in the Gap Year Program? Nominate them! We’ll reach out to them and they could receive a tuition discount as a Nominated Fellow.

Here’s how it works:

1. Use this form to nominate as many awesome, motivated people as you would like
2. We’ll reach out to them to let them know they have been nominated
3. If they complete their application and are admitted to the program they will receive a $1,000 discount on their tuition as a Nominated Fellow.

If you have any questions about the program feel free to get in touch with the Director of Admissions, Zack Martin at 415-347-9715 or via email at [email protected]

Posted by on August 28, 2014
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Hacking your First Year of College

By Jon Gordon

Many of us look at college as a time to play. I did. The grand plan was to meet people, take some classes, party, and make some friends. Maybe there would be a few romantic connections along the way. If all went well, I would get a degree while doing as little work as possible. I figured once I graduated, I would get hooked up (perhaps with one of the friends I made) and start working in the “real world” in some fantastic job that recognizes my potential and puts me on the fast track to wealth and happiness while also doing some good for the world.

I was shocked when it didn’t work out.

I am writing this in my 30’s, as someone who is leading a good life. My path to here has meandered, and I’ve sometimes doubled back to where I started. I wish that someone had told me a few things when I was going to college, but the truth is I probably wouldn’t have listened anyway. However, what I’m about to share would have helped me and therefore I offer them to you, just in case you decide to listen.

Each time I read the statistics around college, I shake my head. Student loan stats are staggering: over a trillion dollars owed, the average being around $30,000. The unemployment statistics are depressing: just over half of recent college graduates are underemployed or unemployed.

The bright spot is that this time in our lives there are more and more alternative forms of education and programs designed to sidestep this flaw in our system. Do a quick search on some of the programs – I dare ya – the future is out there.

Yet, the dream of a college education still remains the avenue most of us are taking. So if you’re not planning on going all Robert Frost on us then you’d better take advantage of your time in university.

Here are the essential six tips to successfully Hack your First Year of College.

1. Be proactive.
Insert your favorite cliche here about seizing opportunity. Colleges have so many resources designed to help their students and yet a small fraction of students use them. Go to things! Stop by your career center or counseling center or student life center. Whatever, go some place and poke around. Show up to events. You’d be surprised how many things there are that you may be interested in. Utilize the resources they have.

2. Don’t be stupid about being stupid.
Some could argue that doing stupid things is one of the best things about college. Hear me out. I’m all for stupidity, but in moderation. Sleep and exercise have been proven to be two of the biggest factors in learning. Throw in healthy eating and you’ve got the tripod of setting yourself up for success. Sleep is when we incorporate our short term memory, aka learning. So staying up till 4 every night is probably a bad choice. Same with eating. Late night burritos are amazing, and please enjoy them, just don’t be stupid all the time. Your college will have a workout facility. Probably. Use it. Exercise helps to improve our brain cognition, lowers stress, increases endorphins, in short it is a good thing. And it can help make up for your lack of sleep and all the burritos. Freshman 15 is a real thing. Believe it.

3.Talk to your professors.
Go to office hours. Speak up in class. Get to know them. They are here to help teach you. Plus, when it comes to internships, opportunities, recommendations or anything else cool that they know about or you will need them for it helps if they know your name. Plus if there is a subject that you are interested in and want to know more about…they are literally experts in the field. Nothing bad comes from developing a relationship with your professors.

4. Have original & creative thoughts.
Much of our education system growing up is you repeating what you have heard. While this has it’s uses in the workplace it’s far more important and fun to offer new ideas. Be aware of this as you are going through your experience. Don’t choose classes because your friends are taking them. Or you can get the notes. Don’t sit silently in your classes. Being able to articulate and then defend an idea is one of the greatest life skills there is. Don’t just listen to your professors and accept what they say. Question everything. Yourself. Those around you. Everything. Find out what you really think.

5. “Stay on target.” – Porkins, Star Wars
Once you have an idea of what you like and want to do then start doing it. Move towards that goal. Stay focused. Work towards creating experience in the field. What classes or knowledge from other disciplines would be helpful? What can I do to make this more efficient? Are there meetup groups? Online courses? In short…what can you do to get ahead while still having fun and enjoying yourself.

6. Take Breaks
Enjoy your time. Enjoy the people that you are meeting. Have less all night study sessions and more all night conversations. You actually learn more taking a break in the middle of a couple 25 min sessions then going straight through for an hour. Work hard. Work smart. Chill. Hang out. Repeat.

We support all forms of learning, and if you’re going to take the time and spend the money to go to college, please make the most of your experience. You’re young, and despite the feeling that you have too many choices to make, I implore you to start learning. You’ll make mistakes, and that’s part of the journey.

Posted by on August 26, 2014
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Do You Have to Choose Between Challenging Work and Seeing the World?

By Casey Rosengren

Six months ago I decided to forsake the traditional career path to spend an extended period freelancing and working on side projects while traveling around the world.

In retrospect, it was a great decision. As a result, I’ve met many interesting people and come across many great opportunities. However, at the time, it was a difficult choice to make. The uncertainty drove me crazy – I wasn’t sure what the future would bring.

I made plans to embark on my journey in July, starting in Central America, and then moving onto Southeast Asia and Japan. I was excited to be preparing to travel, but as I was laying the groundwork for my trip, something felt bittersweet. I was also sad to be leaving the thriving startup communities I’d found in Philadelphia and New York City.

Extended travel is an experience that is hard to put into words. It changes a person, leading one to challenge one’s assumptions about what is important, consider life from another cultural perspective, and learn deep and hidden truths about oneself. It can even impact one’s effectiveness down the line, as recent research seems to suggest that people who have spent three or more months abroad are more flexible, creative, and complex thinkers.

However, living in an environment like New York City or San Francisco also has a lot of value. These cities are filled with passionate, intelligent people, and are places where ideas fly back and forth and collaborations spring out of serendipitous conversations.

While living in a major tech hub, it’s easy to take the community for granted. There are always hackathons and events going on, and people are generally interested in technology. It’s not uncommon to hear that hot new app discussed over Sunday brunch in the context of business, philosophy or gender theory.

As I was mulling this over one day, I thought, “What if we could create that kind of community abroad?”

Inspired by the success of non-traditional organizations like Hacker School and Unschooling, I decided to create Hacker Paradise, a self-directed co-working & programming retreat in Costa Rica, where participants come together for twelve weeks to work on side projects, learn new frameworks, and have an amazing, international experience.

One could argue that there are advantages to locating a retreat like this in a major city. Hacker School and Hackership have picked New York and Berlin, respectively – each cities with thriving tech communities. However, we chose to hold our retreat in Costa Rica for several reasons:

  1.     Rent is affordable.
  2.     It allows participants to get away from the hustle and bustle of daily life and focus on building things.
  3.     It’s relatively rare in a career to spend 3 months learning and working on side projects, so you might as well do it in paradise.

We’re not the only organization taking advantage of this trend.

For example, an organization called Phileas and Fogg flies a select team of designers and developers to remote locations for 3-month periods to build new products. They offer their employees a chance to step outside the San Francisco bubble and gain a new and exciting life experience. As a result, they have been able to attract top talent at a lower cost than they’d be able to if they were just another run-of-the-mill startup based in Silicon Valley.

Similarly, MindValley an online education company, relocated from the U.S. to Malaysia, where they are able to attract workers from all over the world who seek something different than the traditional 9-to-5. They pay their employees a comfortable wage for Malaysia, and are able to operate a modern SAAS company at a fraction of the cost.

The Digital Nomad movement is another great example of this trend. As more and more work can be done from anywhere in the world, freelancers and remote workers have set up shop in places like Thailand and Cambodia, where living is cheap and every day is an adventure.

Peoples’ values have changed over the past decade. Now, fewer people are willing to sacrifice an interesting lifestyle for stability and a good salary.

Why spend your time working on side projects in your tiny, expensive studio apartment when you could be building things in Costa Rica?

Life is short – you shouldn’t have to choose between challenging work and seeing the world.


Posted by on August 9, 2014
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The Hidden Benefits of Learning Lots of Different Skills

By Connor Grooms

Connor Grooms writes about how to learn any skill in one month at his blog, One Month Master.

For the past year, I’ve dedicated myself to learning many skills across different fields. I’ve learned to rock climb, design iOS apps, DJ, write sales copy, and hip-hop dance.

Along the way, I discovered several unexpected benefits of learning lots of different skills.

Whether you are just getting started in self education or want to eventually become a specialist, there is a lot of value in spending a few months to a year to learn many different skills.

You have a better idea of what you want to do with your life.

There’s an expectation built into the education system that we should know what we want to do with our lives by 18 or 19. But really, there are many 45 year olds with no idea what they want.

For those of us who haven’t stumbled across our life’s mission, the way to figure it out is by trying many different things — except most 18 and 19 year olds haven’t had the time to gain that many experiences.

This is a goal that college ostensibly fills, but fails at. The problem is, learning about a job is not the same as actually doing it. Only by trying a new skill or job can we really know if we will enjoy it or now. Because as Dan Gilbert showed in his book, Stumbling on Happiness we are terrible predictors of what will make us happy.

By trying many different things, you find out a lot about yourself. This gives you confidence once you begin to focus on one thing.

You can relate to more people.

Relationships form the bedrock of all success. To build relationships, you need to be able to relate to people — that is, have something in common with them.

The more fields you understand, the greater your chances of being able to relate to someone. Often, you’ll connect with someone over something unrelated to how you end up getting value out of that relationship. For instance, I connected with a friend of mine over DJing and a love for travel, and now we do business together.

Not only will being able to relate to more people make you more friends and connections, but it will also help you become more persuasive. Empathy is the core of copywriting and successful marketing. And whether you are in business or not, we’re all selling something, whether it’s convincing your parents that dropping out of college is a good idea, diffusing a fight with a friend, or getting a date.

You become a connector.

Upon arriving in Saigon, I met a fellow entrepreneur named Jeremy who also happened to be a local musician. He made a few valuable introductions and now I have some DJing opportunities lined up.

What just happened there? By having a foot in two different communities, Jeremy was able to make several valuable introductions for me.

The more communities you are tapped into, the more often you can provide this type of value to people. Learning new skills lets you relate to more people, which lets you have friendships in more communities.

So not only do you get to learn a cool new skill and meet other interesting people involved in that skill, you also have the chance to connect these interesting people to each other.

You become a fascinating person.

Here’s a secret about spending time with successful people: you don’t have to be successful yourself. You just have to be interesting.

After spending a few months learning in different areas, you’ll be fascinating. Not many people can switch from talking about trading Bitcoin to surfing in Indonesia to the science of smart drugs to what makes a good sales page. Your skills will be different, but that’s how you’ll be unique.

It’s a cliche for a reason: you are the average of the five people you spend the most time with. Being interesting helps ensure those five people are successful.

You become better at learning.

Learning quickly and effectively is a skill. And like any other skill, you get better at it the more you do it.

You probably already know that constant learning is key to success. But what if you could learn just 50% faster? How much of an impact would that make on your life?

There are principles about learning that you pick up when learning each skill that can be applied to other topics in the future.

For instance, I learned to row by watching hundreds of Olympic races and internalizing the technique of world-class rowers. I learned to design by diving in and through trial and error, comparing what I had designed to websites I knew were good.

When I learned to DJ,  I combined these techniques, spending plenty of time ‘figuring it out’ through trial and error, but also time imitating the sets and techniques that were successful before.

Knowledge compounds. If you’ve ever tried to learn a new language, you might find yourself saying, “oh, this is just like ____ in English!”. The more your branches of knowledge you have to build off of, the more frequently you make these sorts of connections.

You can see the Matrix.

This is the biggest reason that specialists should spend time branching out.

The greatest breakthroughs of the last century have primarily happened at the cross section of several fields, where knowledge and ideas from one field were used to make a breakthrough in another. Much of Apple’s success could be attributed to their focus on design. But had Jobs not become interested in calligraphy, he may have never push design as a core value of the company.

Ken Wilber took this to the extreme, taking wisdom from dozens of fields, from Taoism to Physics to Politics, to create his Theory of Everything.

Seeing the big pictures makes you aware of the changes and shifts. This is where the opportunities are.

Read more about Connor here.


Posted by on August 2, 2014
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To Ivy or Not to Ivy: We’re Missing the Point

By Jean Fan

I first read William Deresiewicz’s “The Disadvantages of an Elite Education” when I was a junior in high school. It resonated so deeply with me, a 15-year-old entrenched in the race to get into college.

Because of this essay (and the raw emotions it provoked), I spent my last two years in high school questioning everything around me. Because of this essay (and the line of questioning it led me to), I started working at UnCollege. Because of this essay (and the person it prompted me to become), I got into Stanford.

Now, six years after that essay was published, Deresiewicz has written a similar piece, “Don’t Send Your Kid to the Ivy League,” to precede the launch of his book later this summer. This essay about elite education is just as controversial as his last.

Time, in that sense, is unchanged. But I’ve changed, and it’s disconcerting to me how much of Deresiewicz’s thinking I now disagree with.

In his latest essay, Deresiewicz makes a number of arguments to back up his claim that we should stop sending our kids to Ivy League universities and their equivalent. His main concern: “Our system of elite education manufactures young people who are smart and talented and driven, yes, but also anxious, timid, and lost, with little intellectual curiosity and a stunted sense of purpose: trapped in a bubble of privilege, heading meekly in the same direction, great at what they’re doing but with no idea why they’re doing it.”

There are three basic problems here. The first is the notion that young people being “lost” and having “a stunted sense of purpose” is a result of their attendance at an elite university.

Last weekend I was at a party in Silicon Valley. From the Ivy Leaguers who were spending their summer doing internships to the hackademics who had left to pursue their own education, there was one thing everyone there had in common: we don’t know what’s ahead.

Of course undergraduates attending elite universities are on the whole “anxious” and “timid.” They are in the early stages of their adult lives, and they are still trying to figure things out — like all of the other young people out there. The kinds of people that Deresiewicz describes with disdain are not unique to Ivy League universities. They are everywhere, and they are the result of being young and being human.

The second problem is the idea that elite universities are not selecting for young people who are genuinely intellectually curious.

When I reflect on my high school experience, I’ve found this to not be the case at all. The five people from my graduating class who got into Stanford, Harvard, and MIT all stood out from the rest of the student body because of their extraordinary desire to learn. The people at school who were clearly overachieving only to get into college were also the people who failed to get into their top choices.

In particular, my own admission into an Ivy League equivalent is proof that they’re not selecting for the people who are “content to only color within the lines.” I mean, I put UnCollege on my college applications.

The third and most important problem, however, is the idea that making such generalized pronouncements — especially about the deeply personal decision of how to learn — is actually helpful.

This entire debate leads me to believe that people are completely missing the point.

The right question is not: Should I or should I not go to an Ivy League university?

Instead, students everyone should ask: What do I value, and what path will most effectively get me there?

What William Deresiewicz values is that young people learn how to think and how to “build a self.” This certainly sounds like something worth striving for.

So let’s assume for a moment that Deresiewicz is correct when he claims that an Ivy League education will not get you this. But what if you’re okay with that? What if this isn’t what you wanted to get from college, anyways?

If you take Deresiewicz’s advice, you are also implicitly taking into account what he values, possibly abandoning the things that you want in the process.

The thing is: if you value prestige, if you value guaranteed success, if you value having four years to learn whatever you want… then attending an Ivy League University might be right for you. On the other hand, if you value getting a first-class education as cheaply as possible, if you value learning how to learn, if you value mastering a skill… then not going to college might be right for you.

It’s true that lots of young people are like sheep, blindly following the herd. It’s ridiculous, however, to think that telling students what not to do will help them become any more independent minded.

We can’t be prescriptive about decision making without understanding what the individual values, and we can’t know what every individual values. Therefore, broadcasting our own opinions about what young people should do doesn’t actually help them. On the contrary, it can lead them astray, just in a different direction.

Certainly there are systematic problems in education that need to be solved. But they aren’t going to be solved by convincing students to go to public schools rather than Ivy League universities (as if thousands of other kids won’t immediately replace them?).

It’s going to be solved by helping students understand what their educational options are and what those options mean… and then encouraging them to (based on what they value) decide for themselves.


Posted by on July 26, 2014
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