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What an Infamous Jail Break Tells Us About Teaching Persistence

By Steve Heisler — June 27, 2018 5 min read
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Several years ago, two convicted murderers escaped Clinton Correctional Facility, a maximum-security prison in Dannemora, N.Y. Hearing the news, I remember being amazed by their dedication and follow-through. It shouldn’t have been a shock—people with a strong moral compass don’t have a monopoly on perseverance. But still, I wondered: How could two people with the ability to persist through such challenges wind up in prison in the first place?

Over months, if not years, they surreptitiously cut holes in the walls of their cell with tools smuggled in by a prison guard. They snaked through tunnels and a steam pipe, and popped out of a manhole in the town.

I am not making light of their crimes: Their couple weeks of freedom ended in the death of one escapee, the wounding and recapture of the other, and the incarceration of the prison guard accomplice.

However, their escape does illuminate the power of persistence. The skills these men needed to escape are the same ones that students need to work through a challenging problem or finish one more rewrite of a paper. But while every school seems to recognize that persistence is necessary for academic success, many schools don’t recognize the importance of intentionally teaching it.

All Students Are Capable of Perseverance

One of the first shocks of my teaching career was the realization that some of the smartest kids in the room were sometimes the worst students. The most successful students seemed to be the ones most able to employ what I call critical success skills: habits including organization, self-regulation, and persistence. These traits are the hallmarks of successful people, and they certainly create the conditions for learning and growth to take place. Persistence is especially important.

Educators across the country have embraced the concept of grit, popularized by University of Pennsylvania psychology researcher Angela Duckworth. But even before Duckworth hit the TED stage with her research, educators and parents have encouraged students to apply persistence. Students see posters tacked to their classroom wall and hear teachers remind them every day to “Never ever give up!”

But knowing that persistence is integral to success isn’t the problem—making persistence a key learning objective is where schools often come up short.

All kids come to school capable of persistence, no matter how disengaged from academics they may seem. To see an excellent display of persistence with a child you think does not have any ‘stick-to-itiveness,’ I recommend getting into a power struggle with that kid. You’ll quickly see that the ability is there.

We first learn persistence in pursuit of fun: in play, sports, arts, or even the joy of learning shoe tying! All of us are amazingly persistent at those things that excite or amuse us. However, we can be stunningly lax at applying persistence when we’re feeling less motivated—that’s where teachers come in.

Teachers needs to focus on how we can help students shift that ability to persist toward a positive outcome rather than allowing persistence to drag that student toward an undefined, often negative outcome.

This process begins by working with a student to define a specific goal or vision.

Teachers Can Direct Motivation

On the first day of my classes, I always ask students to write down the grade they would like. In a small but important way, this makes academic success their stated personal goal rather than merely teacher or parent expectation.

So when one of my students was frustrated with essay revision, I reminded him of his own academic goal. I asked him to look at other times he was also frustrated but still able to succeed.

He referenced an athletic success and initially gave a general explanation of how he achieved it: “I don’t know,” he said, “I just kept going.” But when I asked him to examine those feelings more closely, he was able to define how he motivated himself. “It’s like an ‘inside voice.’ I just keep saying, ‘Come on, you can do this, just keep going!’”

There may not seem to be a big difference between those two statements, but the simple personalized specificity of that second response is really huge. No matter how many times we tell kids the importance of persistence, until they discover for themselves their own unique strategies and have a reason to apply them, it doesn’t seem to transfer.

Of course this student and I would have many more conversations, during which I would need to ask him to restate his goal and connect it to strategies he used to achieve previous successes. But every time we talked, it seemed to take less and less time for him to transfer the habit of joyful persistence he learned on the field to the habit of dogged persistence in the classroom.

You cannot “teach” persistence. However, you can certainly help students identify times persistence has already helped them succeed, both in and out of school, and help them reflect on their many large and small successes so they can reapply that skill anywhere as necessary. Helping students recognize the power already in them is where a good teacher or parent starts; helping students internalize that power as a habit is where great facilitative parents and teachers continue.

Persistence as Instructional Design

The men who escaped Dannemora exhibited these very qualities—the ones that teachers demand, expect, and regularly see in high-performing students. If we can separate distaste for criminal action from the person’s ability to successfully manage a crime, it’s clear that this well-executed escape was an astonishing success. The persistence and other critical success skills these two criminals displayed in organizing, planning, and breaking out were breathtaking.

The teacher in me wonders what might have happened if the enormous intelligence and powerful persistence displayed here could have been detected and better directed at an earlier time. What might have happened if they were taught how to apply these skills in more positive ways?

More broadly, the teacher in me wonders what could happen for all of our students if teaching persistence were part our instructional design, in every subject, and in our facilitative interactions. In writing instruction, for instance, typically revisions are often limited to a single draft and final copy. Yet real writers know (boy, do they know!) that the first couple of drafts just get you going.

I’ve seen amazing outcomes in writing instruction by allowing students to revise for higher grades as many times as they want (within limitations that keep this from becoming too onerous for the teacher). With a little facilitative coaching, most students will gladly seize the opportunity to succeed at their own speed.

Ultimately, what the teacher in me thinks is that if differently schooled, maybe these two cons would have been able to not only bust out of Dannemora, but to actually get away with it. Or better still, the teacher in me really thinks that maybe, just maybe, they could have effected a more successful life plan that might have helped them avoid going to prison to begin with.


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