On Middle School and Entrepreneurship
“We wear the mask that grins and lies,
It hides our cheeks and shades our eyes,—
This debt we pay to human guile;
With torn and bleeding hearts we smile,
And mouth with myriad subtleties.“-Paul Laurence Dunbar, “We Wear the Mask”
Recently, I was talking to a friend about a new position that he’s taking – as a middle school teacher. *cue dramatic music*
Middle school gets such a bad rap. He shared that the topic is quite polarizing; people either love teaching middle school or positively hate it (and maybe even warn people away from it).
The thinking around hating middle school is that it’s such an awkward time of life. Puberty is a thing, adolescence is full of hormonal and developmental changes that are difficult to navigate, and being one of the adults around a group of children transitioning from childhood into young adulthood is difficult work. There’s really no other way to put it.
As we talked, I was reflecting on WHY we paint middle school as such a difficult, messy, and awkward period in our lives, which got me thinking about identity formation. For many young people, middle school is the time in our lives (perhaps the first time ever) where we consciously start to form our identities. Like Dunbar says in the poem above, “we wear the mask that grins and lies,” and I believe that is a learned process. For many of us, middle school is the first foray we make into the intentional choices that form us as people. To use Dunbar’s language, this is where we choose our masks, then wear them. The problem is, some of us never want to take those masks back off again. Ever.
It’s hard, yo! Identity formation is not an easy period of life. Thing is, it doesn’t end with middle school. I think so many people shy away from thinking or talking much this era of our lives because our experiences with identity formation can be so awkward. Telling ourselves and others stories about ourselves is part of the project of living life. Someone once said that repetition hardens a narrative, and I can’t think of anywhere that adage is more true than with identity formation. This follows us into one of the biggest projects of identity formation we face as adults: choosing a career.
When I was an entrepreneur, I struggled so much with telling (myself and others) a story that I didn’t truly feel aligned with my identity. Real talk, I’m honestly not sure if there’s another career path that gets so much simultaneous admiration and vilification. It’s either painted as a lazy way of avoiding having a “real job” (or understood as code for unemployment) OR it’s considered super cool and sexy and a little rebellious to be an entrepreneur. Given the stories we tell our youth and ourselves about rugged individualism and American exceptionalism, there is something that sounds right to our American ears about rejecting working for “the man” and having the boldness and courage to step out and do one’s own thing. Yet one of the reasons I ultimately rejected the label of entrepreneur (and am currently in the process of closing down my business) is because some of the stories I was repeating to myself started to lose meaning to me after awhile. People would constantly say, ‘Good for you! It’s so good to see that you’re doing what you’re passionate about.’ The only problem is… I wasn’t. It may sound like a subtle distinction, but I built a company that I thought would be financially viable and profitable, not one that I was necessarily passionate about. Yet even when I hit both of those markers of conventional “success” in entrepreneurship, it bothered me deeply that that the story that sprung up around WHY I was an entrepreneur frequently didn’t match my lived reality.
I’m not sure if there’s anything more powerful in life than the stories we tell ourselves, what we (choose to) reinforce and why. The conversation with my friend was free-ranging, and as we philosophized about education in America, it got me thinking about what it says about American society that we hate on middle school (and let’s be real, often middle schoolers) so much. As someone deeply involved in youth ministry and a former educator myself, I consider myself a firm ally of children and youth, all the weird smells and awkward glory of middle school notwithstanding. I think that what we’re really afraid of when we dismiss middle school is the deep fear that identity formation engendered in many of us, fears that, for some of us, stick with us to this day. I don’t know why we tell ourselves as a society that we reach adulthood at 21; I really don’t. We spend the entirety of our lifespans growing up. It’s not something that is completed within any particular decade, and in the grand scheme of life, as a twenty-something myself, I am probably in the life equivalent of like, 3rd grade. I haven’t even reached my own “middle school” yet, and I know that my own process of identity formation will span so far beyond. I find that exciting, and I look forward to the growth and development.
We as humans tend to be quite uncomfortable with ambiguity, change, and transition, and that’s okay. As we seek to become even more fully the people we already are, resistance is pretty much guaranteed. No matter along which axis we seek to more fully develop into our identities, we have to keep in mind that there are power structures, individuals, and obstacles in place designed to keep us back from full flourishing. Today, though, I’m grateful for the adults who choose to walk with youth through these messy seasons on life. I’m also grateful for the lessons of middle school and for the time in life that first awakens many of us into the messy realities of owning our identities. It’ll be a lifelong project.