How Did You Learn to Take Risks?

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Last week in Inside Higher Education, Matt Reed, who writes a column called “Confessions of a Community College Dean” wrote a column about risk and reward that raises an important question for which I have no answer.* It’s still one worth grappling with.

A former student came to him for help asking to change some grades. She had taken dual-enrollment courses in high school and those grades pulled her GPA below what was necessary to be considered by top-tier law schools. Setting aside for another time the issues raised by the drive to be in the top-tier of schools, law firms, or anything else, Reed found himself dealing yet again with the choices students face between ranging widely through a curriculum and trying something challenging and taking courses that ensure a ‘good’ GPA. And that choice appears early in life, doesn’t it? High school students start doing the equation regarding Honors courses and which activities to join. Some decide which sports to play based not on enjoyment and talent, but on some equation about risk and reward.

It’s all very well for me to say to a student, it’s worth the risk of taking a course that will be difficult for you. But the costs, literal dollar costs and opportunity costs, are very real and very different than they were when I was making those decisions about my course of study. Reed states the tradeoffs this way:

“When rewards are allocated according to competitive GPAs, then academic risk taking can seem like unilateral disarmament. If I take a flier on, oh, let’s say Russian, and it turns out to be my academic Waterloo, then I lose real opportunities to a more cautious classmate who never took a risk.

Is that kind of caution what we want to reward?

Deep learning requires some level of trial and error. We don’t always allow for that, and sometimes even punish it.”

When I developed the Leadership Yoga workshop, one of the principles on which it was based comes from Lorraine Matuszak’s book Finding Your Voice: Learning to Lead Anywhere You Want to Make a Difference. “Risk-taking is definitely something that can be learned…. In fact the process is quite simple. Try new things. Be creative. Put yourself in situations that are slightly uncomfortable – stretch.” It’s something I encourage participants to try. It’s something I work at practicing. It’s something, I try to help others try for themselves.

But before we can help others learn about taking risks, we have to find our own risky path, don’t we? It may be applying for that next job or starting that graduate program a bit later than planned. It might be proposing a new program or attempting something you always thought would be fun. And of course, for each of us, what is risky varies. For some, jumping out of an airplane is unacceptable risk, but for others the risk of looking silly can be very powerful. Part of imposter syndrome is the experience of feeling out of place. It also comes from being new in a place. Either way it’s risky.

One of the advantages of having more years of experience, is more experience with risk. It’s learning that feeling silly isn’t the end of the world. It’s learning how to recover from failure. It’s redefining one’s own definitions of risk, failure, and of success. How do we learn about risk? Unfortunately, there’s only one way, just as Dr. Matuszak said, we have to put ourselves in uncomfortable positions, we have to practice, we have to stretch ourselves. When we do this work, we can help others do the work, too. We can help them find their own way through risk to reward, through challenge to deep learning. It’s our work as educators. It’s also our work as leaders. How did you learn to take a risk? How do you help others learn?

Take care,


*Here’s a link to the article by Matt Reed:

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