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Obama’s CTO Gives Advice On How Learning Works In Kio Stark’s New Book, Don’t Go Back To School

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The following is an excerpt from my new book Don’t Go Back to School: a handbook for learning anything.

To someone who has never tried, it’s not obvious how to learn the things you want to learn outside of school. I’m on a mission to show you how. To do that, I became obsessed with how other people learn best, and how they do it without going to school.

My research based on interviews with 100 independent learners revealed four facts shared by almost every successful form of learning outside of school:

  • It isn’t done alone.
  • For many professions, credentials aren’t necessary, and the processes for getting credentials are changing.
  • The most effective, satisfying learning is learning that which is more likely to happen outside of school.
  • People who are happiest with their learning process and most effective at learning new things — in any educational environment — are people who are learning for the right reasons and who reflect on their own way of learning to figure out which processes and methods work best for them.

This interview with Harper Reed is a great example of how independent learning works. Reed served as the Chief Technology Officer for Obama for America during the 2012 election; before that, he was CTO at Threadless. He is an engineer who builds paradigm-shifting technology and leads others to do the same.


I love computers and I’ve always been around computers. I can’t really talk about education without talking about computers. I went to high school and I actually really loved it. I took all the classes I could, I was prom king, student council president. I did everything I could to be more involved in high school and that is obviously not the normal path you’d expect for a computer geek.

But, along with that, I was constantly getting into trouble with computers. Never with the cops, but I was always getting banned from all the computers in the school district. Then, they would let me back in, and I would mess up again for whatever reason. It happened over and over. I was caught in this dichotomy of trying to be involved, but whenever I was trying to get involved with computers, I messed it up because I was curious and experimenting outside what was allowed. After that, I went to a small liberal arts college. I studied history along with computer science, because I knew ultimately I was going to work with computers and I wanted to learn something else, too. I studied Catholic history and the history of science, which overlap a lot. I’m not Catholic. I’m not a religious person at all, but it was really fascinating to learn all of the idiosyncrasies of Galileo and Bruno and all these different weird scientists who got burned at the stake for their discoveries.

I realized about probably three-quarters of the way through my education that in terms of computers, I actually wasn’t learning anything I needed to learn to get a job later on. I did learn some coding concepts in college, but more importantly I figured out that I’m an experiential learner. I need to put my hands on things and really see them, and really chew on them. It was better to do it in a real context, where it mattered if I did it right. Like where there was money at stake. So, I did an internship in Iowa City, IA. I worked for a real company that was trying to make a profit. The company built ecommerce apps. As an intern I started learning web apps to build web pages. Given my way of learning, it was fascinating to see how the management dealt with me. I was a child. I asked questions like a child does. “Why is the sky blue?” They just said, “It’s just blue. Go with that.” I said, “No! Tell me why we’re doing it this way. What is this?” It was client services, so we were just doing it because the client wanted it done, with no thought behind it. But all the questions I asked gave me this opportunity to see how things worked and the value of asking things that seemed obvious to everyone else. It gave me a lot of hope. It really kicked off the career that I have now.

The methods I used to learn technology don’t work for everything. I’m struggling with learning Japanese. My wife is Japanese and I want to learn the language, but I don’t know how. I take classes, I fail, it doesn’t work out. I have to figure that out. With technology, I immediately find a problem I want to solve. It’s usually about learning a new programming language or learning a new technology. If it’s a real problem, I want to get to where I can actually picture the solution and be able to see it through from the beginning to the end. For me, I can’t learn from videos. That just doesn’t do it for me, although there’s a lot of video learning right now. I find it very frustrating. So usually what I do is I just go through a tutorial of some sort and then really start iterating, doing it over and over. I start trying to be creative on top of that, and say okay, now that I can figure out how to do this, how would I use it? So I set a new goal pretty close in difficulty, and when I achieve that, I do that again, until suddenly I’ve learned something. When you’re in that process, it can also be the best time to teach someone else. A tech writer named Mark Pilgrim, who writes manuals for learning coding languages including Dive into Python, and Dive into HTML5 said, “The best time to write a book about something is while you’re learning it yourself.” So you know what’s hard to learn and can talk in an excited, confident, honest way about how you got to the place where it’s not hard anymore.

For me this whole process is really collaborative. I treat everything like I’m the CEO of my life. CEOs have boards of directors and boards of advisors and these are groups of people who they’re using to really rely on for help and advice to be successful. I think every person should treat their life like that. So, if I’m stuck, I know I can reach out to a buddy, or I can reach out to my brother. I know I can reach out to these people who are experts in whatever I’m trying to do. I try to surround myself with incredibly smart people who are often, if not always, smarter than me. Because other people are so important to learning, I also think one of the most significant things about the internet is democratization of access. Anyone can email you about self-learning and you’re probably going to respond. Probably. I think it’s about how you phrase it. We are all very busy, but we’re probably going to respond if you approach it efficiently.

You can learn a lot about this from a really good book called Team Geek by Brian W. Fitzpatrick. It’s actually about project managing software development geeks, but it applies to most things with communication. It should really be called “Interacting with People,” because all it is, is just little tricks on how to interact with people, how to make those interactions better. There’s a section called “Interacting with an Executive,” and that part should be called “Interacting with Busy People.” It says if you want to connect with someone who is very busy, tell them three bullets and then a call to action.

So if someone wanted help from me, it might go like this: “Harper, I’m interested in what you’re doing with the campaign. I’m going to be doing technology for a campaign in the coming election. Do you have a hint for product management or project management software that you guys use?” I can answer that quickly. It’s very simple. Then all of a sudden there’s this person who probably wouldn’t have had an opportunity to talk with me, and I can help them out. I love what that kind of efficient communication does for you.

Kio Stark is a writer, researcher, teacher, and passionate activist for independent learning. She teaches at NYU’s Interactive Telecommunications Program. She is also the author of the novel Follow Me Down. You can find out more about her work at KioStark.com.