What We Didn’t Learn in School: How to Change the System

Last week, Bari Weiss ran a series in The Free Press titled, “What We Didn’t Learn in School.” She asked six writers to share lessons learned outside of the traditional academic environment. Their stories are well worth reading, but this one in particular, “How Perfectionism Can Destroy You,” by Hadley Freeman cut deep.

Her story felt eerily familiar. Like Freeman, perfectionism has often been a stumbling block in my creative, freethinking journey as an adult. Maybe that’s why this essay has sat in draft form since I began it…nine months ago. But, inspired by Freeman’s piece and the broader series, I’ve decided to liberate it from my Google Drive archive.

Here’s my take on the prompt: “What We Didn’t Learn in School” – How to Change the System.

When I was 13, I aimed to be the paragon of perfection in a strict middle school where rules reigned supreme. You know the type—no shorts, fingertip-length skirts, no hall walking without a pass. Despite this rigidity, I got a 110% in sixth-grade science and spent late nights taking school assignments way too far, like creating a life-sized Egyptian coffin made from cardboard, complete with a cast of my own face.

One particularly frustrating rule was that lunch seating was assigned by the alphabetical order. Nobody liked it. (Let’s be real – we were 13, all we wanted was to hang out with our friends and drink each other’s Capri Suns.)

But one night, I saw a news clip on TV about a boy who challenged his school’s rules with something called a “petition.” He gathered support, the rules changed, and he even got on local TV. It sounded exciting—so instead of reading or journaling about my academic goals that night, I stayed up writing my own petition: a proposal to let students choose their lunchroom seating.

I saved everything I ever wrote as a kid, so I still have the exact wording of that petition. Here it is:

The next day, with my heart racing, I handed out copies of the petition at each table in the lunchroom. I felt a mix of exhilaration and fear as I watched papers shuffle, pens pass hands, and signatures appear. The room buzzed with activity, and I could hardly breathe. Holy shit, I thought. This is actually working.

Change is funny—unpredictable and non-linear. Something inside me pushed against my goody-two-shoes tendencies, nudging me to take a chance on grassroots democracy. That decision shaped my life trajectory. And I have the school administration to thank.

Because what happened next was this: The most powerful teacher in the school collected all the petitions, marched over to my table, and publicly reprimanded me for defying authority. She told all the other teachers I lacked “good character” and ensured I was permanently banned from joining the National Junior Honor Society, the most prestigious academic club.

That single moment crushed my creative spirit, bending it back into compliance mode for years to come.

Like Freeman, my experience made me question the very purpose of school—is it to enforce compliance, or to foster creativity and independent thinking? One prevailing narrative is that the purpose of school is to prepare us for the world of work. The more education you receive, the better your chances of achieving career success in the job market. 

While I bought into this idea early on, the moment I graduated college with a journalism degree—in the midst of the 2008-2009 recession with no jobs in my field—I began to see things differently. In fact, I sometimes felt over-educated. Too caught up, perhaps, in the structured memorization of grammar rules and the comfort of knowing exactly what to expect on every test. So much so that, when I was launched into the unpredictable world of tech startups, venture capitalists, and entrepreneurs, I found myself having to unlearn many of those so-called "straight-A fundamentals" to succeed.

I’m not alone in feeling ill-prepared for the world of work. According to a 2023 Pew Research Center survey, only one of four adults say it’s extremely or very important to have a four-year college degree in order to get a well-paying job in today’s economy. This represents a significant shift in public perception, as nearly half of Americans (49%) now believe a college degree is less important today than it was 20 years ago. Additionally, only 22% think the cost of a four-year degree is worth it if loans are required.

This broader skepticism toward the effectiveness of our educational system in preparing us for the real world mirrors the doubts that first hit me in the 7th grade. Let’s set aside for a moment the obvious issue of how much of my self-worth hinged on getting accepted into a middle school honors program and instead focus on a more foundational question: What might an incident like that signal to a kid like me about the way life is going to go?

Maybe my teacher’s perspective was, “This kid needs to learn that the world doesn’t revolve around her.” Fair enough. From where I sit today, I can see she probably just wanted to diffuse the situation and get through another day of managing over-eager kids like me. For her, it was just another sacrificed lunch break of her own to keep a bunch of kids in line. She’d go home, have a glass of wine, and move on.

But from my perspective—as a sheltered kid with a Hermione Granger complex and no clue how to handle conflict—my takeaway was: “I just got punished for coloring outside the lines.” And also: “I guess what kids want doesn’t matter here.”

Unfortunately, this experience catalyzed long-term doubt about what I could say and who I could trust. For years, I struggled to decouple my relentless drive to make positive change from my crippling fear of getting in trouble. Even now, when I’m caught in the thrill of a bold or impulsive idea, I instinctively glance over my shoulder. I’m still waiting for the teacher in the lunchroom to come yell at me.

I’ve spent much of my adult life trying to rewire that discordant feeling.

One reason why I suspect that adults today—from the writers of The Free Press narratives to those surveyed in the Pew Research study—feel more dubious about degrees is because the real world looks a lot different from traditional academic environments. There is no assigned homework, no structured learning path, no grades, and certainly no “right answer.” When we are finally set free from academia, we don’t feel empowered. We feel scared. Unprepared. 

The pace of technological change is outstripping the ability of school curriculums to keep up. While completing formal education by age 18 or 22 might have sufficed in the past, it’s no longer the case that learning stops there. Don’t forget: Our education system was designed when most people worked in agriculture or industry, long before digital technologies transformed our economy and workforce. 

Maybe that’s why many mid-career professionals I speak with, including top-level executives with proven success, admit that fear of uncertainty often holds them back from making a job change. Despite their success, the rapidly changing landscape makes new challenges feel impossible, underscoring how outdated educational models leave us unprepared for lifelong learning.

In my own tech career, I’ve constantly had to level up my skills in job after job, year after year, just to keep up. When I couldn’t get hired as a journalist, I pivoted into consulting. To shift into tech startups, I learned sales, then marketing, then how investors think and how businesses operate on a macro level. Eventually, I applied those skills in emerging industries like blockchain and AI. Success no longer plateaus with a single job or a single path. The learning never stops.

Today, we’re on the cusp of transformation in nearly every industry, driven by globalization, technology, and hyper-connectivity. But if we’re conditioned to strive for perfectionism, as Hadley Freeman experienced, or punished for pushing boundaries—like with a petition in the lunchroom—how can we acculturate the next generation to embrace transformational thinking? How do we ever expect system-wide change to take root?

I’m struck by our deep understanding of this paradox, yet continual struggle to break free from it. Rewiring systemic inertia of outdated educational models requires rethinking not just what we teach, but how we approach learning itself.

Last summer, I observed David Noah, founding principal and executive director of Comp Sci High, guide a group of high school principals through an exercise to reimagine school. He posed a simple yet profound question: “If you could start a school from scratch, what are the 10 most important things kids today need to learn? These can be hard skills like algebra but they can also be things like public speaking.”

The principals in the room, school leaders from all five boroughs in New York City, quickly got to work. After ten minutes, they shared their lists. I noticed a lot of overlap in broad, universal skills:

What are some broad, universal skills that kids today need to learn?

• Communication

• Problem solving

• Collaboration

• Creativity

• Personal finance

• Computational thinking

Then the exercise got harder. “Look at your list,” instructed David. “And now turn that into a school day. You can choose 5 classes to teach all of these skills. What are those classes?”

And in just 30 minutes, I watched years’ worth of systematic pressure dissipate immediately from the room. Inevitably, a few staple courses made it on the boards: Reading. Math. But then some funkier stuff, too – a computer science class, a focus on physics, political science instead of world history. Notably, not a single group chose to recreate the standard subjects we teach every day.

Nobody said, “What we are doing at my school is the best it can be.”

When I asked David about the exercise several months later, he confirmed that, in all his years of running these exercises with educational leaders, there is never consensus on a single, standardized set of classes that we all need to succeed. He noted:

“It’s really more about learning how to learn. People generally agree that we all need to learn how to read, and maybe learn some fundamental math skills. Beyond that, it’s about getting kids motivated to pursue specific knowledge that is exciting to them.”

Sounds so simple, right? And yet…

Even after all this time, I haven’t been able to extinguish my instinct for network activations (through grassroots petitions or otherwise) from my approach to problem solving. So, drawing from these insights and feedback from many other educational professional I've interacted with over the years, here are a few actionable ideas that might help bridge the gap between the way we learn and the way we work:

1. Invite students to shape their education. They’re smarter than we give them credit for; student voices could guide their own learning experiences through project-based learning that encourages them to stoke their inherent curiosities. If they want to sit in the lunchroom with their friends, and all the other kids agree, maybe give them the win. If they want to use AI in their homework assignments and it terrifies you that it might be “cheating,” maybe instead invite them to define the policies and boundaries alongside you. Maybe.

2. Integrate real-world skills, including technology, across all subjects. Learning new technology feels as fundamental as learning a language. (I’m not kidding when I tell you that I dreamt in AI prompts a few weeks ago.) We might reframe technology adoption as a mindset, as opposed to a singular tool or all-purpose certification. Things like project-based learning, based on prompts that mirror real-world problems in an increasingly project-based world, could likely help drive home subject matter expertise in nearly every subject. AI tools make this extreme customization more possible than ever before.

3. Reconnect schools with their communities. I’ve seen first-hand the impact that just one positive interaction with an outside industry expert can have on the trajectory and aspirations of a high schooler. By inviting professionals to engage with students directly at schools, we could foster real-world connections and create opportunities for students to tackle community-based problems. Not to mention that exposure to a wider range of socio-economic backgrounds is one of the biggest drivers of economic mobility among under-resourced populations.

4. Inspire teachers with creative opportunities beyond the classroom. I don’t know how I would have successfully pivoted into so many different jobs and industries without real world experience. And I don’t know how teachers can keep up with the ever-changing industry outside of school environments without a little help. By encouraging teachers to interact with industry professionals, we might reignite a passion for teaching through real-world experiences. Oh and also, it might help us remember to have a little fun on our learning journeys, too.

5. Promote critical thinking and lifelong learning. In a rapidly changing world, equipping students with a modular set of versatile skills will better prepare the next generation for inevitable career pivots and path changes. There is no such thing as one dream job anymore, or even a single career path. The best thing we can do is encourage an acute awareness of our individual learning strengths, and get really good at converting those into transferable skills to apply anywhere.

To prepare the next generation for an uncertain future, maybe it’s time we encourage a little less compliance and a little more chaos. After all, our learning journey might start in the classroom (or, in my case, the lunchroom), but it’s certainly not where it ends.

Speaking of endings, if you made it to the end of this essay, get yourself a treat from the vending machine in your cafeteria of choice today. I really wish I could have written this in fewer words. (Trust me, I tried.) But this is the best it’s going to get. And you know what? At least for today, that’s good enough.