"Two years ago, I met Jean Fan. When we first 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 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 year off 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 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 time outside of the classroom, 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 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 year of alternative education 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.
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