Plan to Fail

Lots of students make bad decisions. Josh Wymore recounts his own -- and argues for giving them second chances.

February 26, 2015

With tears in his eyes, Michael looked at me from across the table and asked for a second chance. I had hired him only a few weeks before, and he had just gotten busted for bringing alcohol on campus -- a significant offense at this Christian college. I wasn’t sure what to do with him.

Our director of discipline gave me the freedom to decide whether or not to fire him but recommended that I let him go. Michael's hall director vouched for his remorse, but she was unsure of his character. I too wanted to give him a second chance, but I didn’t know him well and wasn’t sure I could trust him.

After several conversations with my colleagues and some honest talks with Michael, I decided to give him a second chance -- but only one more. I told him, “Michael, I believe you’re better than this; I don’t think this is who you truly are. I’d like to give you a chance to prove yourself. But I can only give you one more shot. If anything else comes up, you’ll be done.” He was incredibly grateful and assured me that he would indeed live up to the challenge.

I could relate to Michael. Because of my big risk, big reward type of personality, I was very familiar with the experience of public failure in my undergraduate days. Many a conversation with my mentors began, “So, Josh... why did you think that was funny?”

Some of these failures were humorous and harmless, but others were more damning. Announcing in chapel that the president was accepting applications to date his daughters? Admittedly, not my finest moment -- but probably not that big of a deal. But talking my way into a coed’s apartment so that I could steal all her undergarments? Yeah, that was a really bad decision.

What’s more remarkable than my litany of faux pas is that seemingly intelligent people continued to entrust me with leadership positions. What’s more, they gave me real, meaningful responsibility -- enough that I could continue to fail with increased consequences. Rather than ignoring my deficiencies or allowing them to define me, they chose to trust me in spite of them.

Something about that choice -- that decision to empower me, to believe in me -- was effective in a sort of reverse psychology way. Instead of using my elevated platform to create more campus commotion, I took it pretty seriously. I spent a lot of time planning staff training, creating meeting agendas and following up with each of my coleaders. I continued to fail along the way, but I did it while wholly applying myself to serious work. And that experience changed me.

Years later, I would get my master’s degree in higher education and go into student affairs. My experiences left me with a soft spot for similarly well-intentioned students who failed dramatically. One such student asked to meet with me after I rejected his inappropriate video submission for our campus’s film festival.

I began our visit with, “John, you have no idea how ironic it is that I am about to have this conversation with you. I bet you’re thinking, ‘Why is everyone so uptight? Can’t they just chill out? I’m not trying to offend anyone.’” John was amazed at my ability to read his mind, and eventually he understood why assaulting handicapped people with dodge balls might be over the line for our film festival. I challenged him to elevate his standards of humor, and he did just that. Before graduating, he competed in two more of our events and gained respect as one of the best student filmmakers on campus.

And of course, there’s Michael. He did keep his word to me after all. In fact, he turned out to be one of my best staff members that year. A few months later, he swung by my office to say hello, and he asked, “Josh, do you remember that conversation we had?”

With tear-filled eyes he spoke of how he’d been phoning it in for so many years, content to be a follower when he should have been a leader. But something about that unflinching challenge to be a man, a real leader, struck a chord with him. And he’s never been the same since.

One of the most formative things we can do for students is to provide them with the opportunity to fail. But most importantly, we have to give them responsibility after they fail. Calling out our students to take ownership of their foibles and flaws says two critically important things that all students need to hear: life has consequences, but those consequences do not have to define you. Choosing to believe in students -- especially amid their failures -- can be transformative for them.

Had someone not taken a chance on me -- or rather multiple chances on me -- I would not be where I am today. My wife recently asked me why anyone who knew me as an undergrad would seriously consider hiring me now, and that’s a good question.

My only answer is that those saints have a worldview that understands failure to be a necessary part of growth. College is one of the safest places for students to fail, dust themselves off and jump back into the fracas. Let’s not fail our students by robbing them of the opportunity to do so themselves.


Josh Wymore is a research assistant in the Center for the Study of Higher Education at Pennsylvania State University.


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