TEDxPrincetonU: How to Fail Successfully by Deborah Chang [Transcribed]

Please note: The video above has poor audio quality. As a result, I recommend that you watch it along-side the transcript below.

Hi! My name is Deborah Chang and I work in education entrepreneurship. I am also Princeton Class of 2010. When I was a senior at Princeton University, I applied to only one job, and that was Teach for America.

The reason I only applied for one job is because I thought life was something like this:


A series of steps, one that follows another. I thought this pretty much my entire life.

In high school, I only applied for one college, early decision at Princeton University. And in each year at Princeton I only applied to one program or summer internship. And so, my thought process in my senior year was: I will apply for Teach for America, I would do Teach for America for two years, I will continue teaching for two or three more years, then become an assistant principal for a school, and then ultimately start my own school.

I thought this was my life plan because I was passionate about education, I believed in making a difference in people’s lives through education, and my mentors in education, people I admired the most — this was the path that they followed.

This worked pretty well, until two years ago [in 2012], when I moved from teaching middle school science in Houston, TX, to teaching second grade all subjects in New York. And that’s where my life plan fell all apart because I was an awful second grade teacher, truly atrocious. And my students weren’t learning, my classroom was in a constant state of chaos.

It wasn’t because I wasn’t trying hard enough. I worked late nights, I worked weekends, I got into school really early, and I always asked my principal for advice and support. It just wasn’t the right role for me. And so, in December of that year, I made the really difficult decision that my students needed an education that was powerful and strong for them, but I wasn’t the teacher to give them that education, and I resigned. For the first time in my life, I had failed, and I didn’t know what to do.

Because for my entire life I was taught how to be successful, but I was not taught to fail. I think that’s probably true for a lot of people in this room right now. I mean, in elementary school, when I got 100 percents on quizzes and tests, my teacher would put a smiley face on it. I never had a teacher to say to me, “Wow, you got 100% on that test, it must have been too easy for you. Here, try something a little more complicated, I think you’re going to really struggle with it.” And then when we apply to colleges and we apply for jobs, we try to package ourselves in the best way possible. And even when I wrote about overcoming obstacles, it was in the context of overcoming and not the context of saying, “And this is what I have challenges with right now”.

But this problem of having your life plan fell apart it’s not unique to me. Here’s the statistic that is going to be really powerful about showing why we can’t really have life plans.


According to the US Department of Labor, of the children who are in school right now, 65% of them will be working in jobs that have not yet been created. This applies to us, too, because if you take a look at another study, 91% of millennials, people of my generation, plan to stay in their current jobs 3 years or less. There are whole industries shifting and changing beneath our feet. It seems that life will look more like this:


You go to a job, you find… “Hmmm it isn’t going to work for who I am or what I value.” Then you try something different. But then all of the sudden, it seems like overnight, things change, so you go in three different directions and you find two that don’t work and one that kind of does and you continue working on that. And so the only thing that’s certain about the future is that it’s uncertain. So failure is inevitable. And if failure is inevitable, we need to work that into our process of learning and growing.

I’m not saying that this is easy.

When I resigned from teaching I was lost for about a month. I had days when all I did was sit around in my pjs and watch TV. I just didn’t know what I was when I wasn’t a teacher because for so long my whole identity was about that, being a teacher.

Luckily for me, at the same time that I was going through this process of self-discovery, building up my self-confidence. I started rock climbing.

Rock climbing gave me the opportunity to learn how to be successful in something that I was a complete novice at. And as I continued to learning how to rock climb, I realized that rock climbing treats failure very differently. Unlike the “real world,” you are expected to fail. You’re expected to fail often and to fail publicly. In other words, you are expected to fall off the wall. And so, as I was going through this parallel process, I learned that rock climbing became this perfect analogy for how to fail successfully. And those are the lessons that I’m going to share with you.

rock climbing.JPG

Lesson #1, “There’s More than One Wall.”

The wall that you see behind me in this picture is called a highball. There’s also one that looks more like a cave and one that’s at a steep incline of 45 degrees. Each wall requires a different sets of skills and each climber enjoys and likes climbing different walls. My mistake when was I was a senior in Princeton was thinking that I need to follow someone else’s path, that I need to do exactly what someone else did. Now that I’m into entrepreneurship, I realize that I make my own path and remember, there are paths that have not been created yet.

Lesson #2 is to “Fall on Purpose.”

The highball is the most difficult wall for me to climb and that’s because you’re okay like 2 feet of the ground, but when I am 8 feet off the ground, 10 feet off the ground, 12 feet off the ground, I am scared to death and at first I couldn’t even climb. The way I got over this was… I would climb to where I was just a little bit scared and then I would purposely do something I knew I would fail at and I would purposely fall. And the funny thing is, the more you do this, the more you purposely fall, the more you realize failure is inevitable. And then I was able to climb higher and higher and now, when I am at the very top of the highball I feel perfectly comfortable doing this.

In the same way when I first started looking for jobs after being a teacher, I was really scared about networking. My parents aren’t professionals and I just didn’t grow up in this environment where we asked people for coffee. But I did it anyway. And was I bad at it at first? Absolutely. I feel completely sorry for the people I met for those first coffees because I didn’t know how to ask the right questions. I didn’t know how to follow up. But like rock climbing, the more I took these meetings, the more I failed at it, the better I got. And so now I am really comfortable saying, “Hey, let’s talk, because we both have something unique to say.”

Lesson #3 is to “Land on a Crash Pad.”

That blue thing at the very bottom is actually about a meter high and very solid. It allows climbers to fall and to get up and get on the wall and try again. One of the best things I did building my career was to save money, because that was my financial crash pad. It was my ability to be able to survive resigning from my job. So while it was difficult for me personally, at least financially I knew that I could pay for food and I could pay my rent. And now that I’m in entrepreneurship, I’m also doing freelance consulting, because again that financial crash pad gives me the freedom and ability to do whatever I can with the rest of my time and allows me to take those big risks.

Next, “Find Good Partners.”

My friends in climbing are some of the best friends I’ve ever had, and that’s because they tell me where to go and why, they give me encouragement, and especially when I’m climbing outside, my life is literally in their hands. They’re there to catch me when I fall. In the same way, good mentors who are able to guide you, good friends who are able to encourage you and people who can pick you up when you fall, they can make the difference between staying down or being able to move on.

Lesson #5, “Choose ‘Just Right’ Problems.”

If you take a look at this picture, there are a lot of different colors on the wall. Each color stands for a different route or in rock climbing, for a different problem. And they range from easy problems that are graded a V0, to very difficult problems at about V15.

Currently, I’m a V3 climber. That means I’m not even going to touch V7s. If I try a V7 problem, it’s going to be too difficult for me. I won’t learn what I need to learn in order to be successful at it. At the same time I am not going to climb V2s the whole day because that’s in my comfort zone. It’s not going to stretch me, it’s not going to make me learn and grow, and so I do V3s, V4s. I choose just right problems.

One of the things I did really well in moving from the very structured world of teaching to the very unstructured world of working at startups is I took a halfway step. I decided to work in a school district first and at that school district I was able to learn skills of project management and working organizational politics. All the things that I was able to bring to my work in startups.

The final lesson is: “Take the Leap.”

At some point as a rock climber I’ve trained as hard as I could, I’ve gotten all the guidance that I needed, I made sure that if I fall, I’d fall on something that would let me get up again. So I just need to commit, I just need to take that leap for the top of the wall.

So now I no longer say that I have one job.


Instead I say that I am committed to solving big problems in education through entrepreneurship, and that the problem I am working to solve right now is how to bridge the gap between entrepreneurs and educators. This may be though a school, or through a startup. I am also learning how to code so I can eventually build products of my own. I no longer assume that my life is going to go according to plan. In fact I assume just the opposite so when I fail, and if I fail, I plan to fail successfully. Thank you!

If you’re interested, I’ve since reflected on this talk here

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