On Education

2021 marks 10 years since I dropped out of high school. It’s the kind of nice round-number anniversary which invites some introspection, and it feels like a good time to post some lessons learned.

First: nothing taught me to appreciate traditional institutions of learning more than dropping out.

Schools, universities, and other forms of organised learning have a bad rap. We’ve all heard the memes: they constrain the most creative students, they focus on testing memorisation of useless facts, they only teach for the test, and they’re rife with bullies. The most common comparaison is to child-sized prisons, which naturally evokes a yearning for escape back into freedom.

Escape isn’t all it’s cracked up to be, though. You lose access to important rituals and structures which help you find or build peer groups, you no longer have access to the labels which make you legible to the wider world while you figure out who you want to become, and worst of all, you largely lose access to a time and environment for low stakes exploration and experimentation.

For me, dropping out felt like treading water for years, made worse by suddenly being in an environment (namely, work) where getting ahead requires performing, and not just learning.

People don’t expect you to skip steps, so when you do they’ll assume you have skills which you didn’t give yourself time to learn. Patching up these deficiencies is a lesson in just how illegible most “skill trees” are, and just how much learning resources assume about your context. All except a tiny minority are (understandably) geared towards illuminating a shallow and narrow slice of knowledge for people on a guided and (relatively) linear learning path. The entry points into understanding and insight are few and far apart, and without help, finding them is a matter of luck and hard won judgement. This fact is never explicitly acknowledged though, and learning it is painful.

Dropping out and trying to go at it alone taught me just how social learning is. It was stumbling into a new set of concrete aspirations, and a community with good norms and a useful disdain for credentials which helped me find my way. The Culture that is Silicon Valley, with its emphasis on earnest effort, on curiosity, on ambition, and on optimism was an incredible blessing. Twitter, a few scattered startup meetups, and a couple of incredibly lucky interactions with people who gave me chances I didn’t quite deserve did more to get me out of the spiral I was at risk of falling into than any online lecture or ed-tech product.

But that’s not the future, that was just a lucky escape. My path isn’t reliably repeatable. Even though the escape routes have never been better, and there are more ambitious, accessible, and supportive communities of becoming than ever before, I don’t think they’re enough. The odds of finding them, and especially finding them at the right time feel too small. They by and large rely on you having already become a very particular kind of person (hard skills and all) by the time you encounter them. They’re in the business of growth, not of education. I’m more convinced than I’ve ever been that institutions of learning which are central to student’s lives for years, where they are guided towards competence and confidence, are an integral part of the future.

Second: despite the above, dropping out was, in fact, the right choice.

I mostly went to Swiss public schools. They were well resourced, and safe. I always had a pretty easy time with schoolwork, and I even like learning. But by the time I got to high school, I just couldn’t go on. I was absolutely lost. I was uninterested in the work, I felt disdain towards most of my teachers, I was completely unable to articulate what I was working towards, and I dreaded the future.

Most of my classmates were disengaged with learning at best. By the time we were 15, we had all been mechanically classified twice onto university bound tracks, and since all higher education institutions in Switzerland are available to all those who graduate high school, independent of grades, there wasn’t even that teleology to lean on anymore. A scary number drank or smoked weed during the day (some had started as early as 11 years old). A majority drank (yours truly included) on weekends and occasionally during the week, after class.

Because no one took school or our teachers seriously, it was high status to break the expectations of the institution by getting good or passing grades with the minimum amount of visible work possible. It felt like winning, which is embarrassing to look back on. Hard work and trying hard was seen as lame.

At the time, I was desperate for a teacher to explicitly acknowledge that my feelings were justified, that the hoops I was being asked to jump through were arbitrary, that they were pointless, but I understand why none ever did. The mediocre teachers couldn’t bear to acknowledge the possibility that it was all a charade, and the great teachers saw that the knowledge they were trying to share was, in fact, important and beautiful. I remember 3 of them (one econ teacher, one biology teacher, and one physics teacher), but they were too few and far between to overcome a general blasé culture.

Looking back, it is striking comparing my relationship with those 3 teachers and my relationship with other individuals which I’ve come to consider mentors: not only did the latter group invest more time getting to know the whole of me, they were also bought into my success in a way none of the adults in school ever could be. I engaged with all my teachers for a couple hours per week each, and they had many dozens of students. My success was a common good that no one felt responsible for, and I didn’t acquire the tools to take meaningful personal ownership of it until much later.

School told me it was preparing me for my future, but it felt unwilling and unable to help me figure out what that future looked like. I don’t recall any single conversation about it, in fact, beyond some platitudes. There was a distinct lack of inspiration and aspiration.

For a long time, I thought I was the problem. Leaving felt necessary, but it also felt like failure, like running away. Others complained, sure, but they seemed mostly able to just get on with it. A few even thrived! Why couldn’t I?

After 10 years of feedback from the real world, I’m inclined to be kinder to my past self. Looking back, the way I felt seems largely justified. It was a bad environment to be in, and I wasn’t learning. I was heading nowhere in particular. I ended up in a good place thanks to skills and direction I acquired after leaving school, and I struggle to come up with ways I might have acquired them had I not left.

But — to get back to my first point — it’s also true that many of the things I found most frustrating with my schooling — the curriculum, the teachers, the strong peer culture (in this case, a bad culture), the schedule (which made anything other than school nothing but a side show) — are all things which I know I missed after I’d left.

This, then, is my third lesson learned: the problem wasn’t in the abstract, it was in the specific. The problem with education, in other words, is not with school as a concept, it is with particular circumstances at particular schools.

This is in many ways frustrating. It makes the life of the idealist complicated, because it means you have to carefully consider what to change and what to keep, and it means having to exercise judgement about the specific form of what you keep. It points towards implementing many small improvements, instead of any one large revolutionary intervention.

I’m doubtful, for example, that better in-classroom tech, no matter how smart, would have done much on its own to address the general growing nihilism of me and my peers. The teachers were also relatively well trained, and it’s clear that many (maybe even a majority) cared, but they were generally hamstrung and most were unable or unwilling to cope with the enormity of a task which was not strictly their problem.

The solution also wasn’t about making the environment less structured, or worse, giving the keys over to the students in the naive hope that we’d have lead ourselves to achievement. That would only have made things worse. I spent most of my free time and a good chunk of the money I earned flipping burgers during the first year of my newly found freedom after leaving school on all sorts of escapism, some more destructive than others.

The most negative elements of my experience with schooling are hard to quantify, which means they’re incredibly hard to systematically fix. And the fix is likely messy and fragile. It requires hiring great teachers, giving them great training, and giving them an environment where they themselves can thrive, and you need to help them set and maintain strong values.

And that’s not enough! You need to also provide great curriculum, a great, safe, physical environment, some great software tools, you need to find ways to deal with crises, you need to deal with bullying or general misbehaviour, and you probably need to feed everyone, too.

And that’s not it! You need to find ways to pay for this, without locking most people out. You need to figure out how to keep your schools well stocked, without breaking the bank. You need to have strong convictions about what ought to be taught, and what doesn’t make the cut, and you need to find a way to handle those who disagree. You need to keep the state happy that you’re doing a good job, and you need to make sure your students still do well on standardised tests, too.

And if you’re serious about it, you need to do this (and keep doing all of it) at thousands of schools, and for millions or tens of millions of students.

It’s an almost silly problem to try and tackle. It’s why everyone who’s ever tried to fix education has focused on magic bullets. But the truth is there’s no alternative. Solving education requires embracing all the messiness, and all the difficulty. Reading about the history of education reform means accepting that we’ve been having the same debates for at least a hundred years. We aren’t idea constrained, we’re constrained by the fact that high quality education requires sustained excellence in all areas of execution, even the unsexy parts.

That’s what led me to Higher Ground, which I joined in April. I think it’s likely the most important company around today. It’s got the ambition, the pedagogical depth, and most important of all, the willingness to confront the messiness involved in building and opperating schools. In fact, over the past 5 years, Higher Ground has built 84 schools (serving all ages up to high school), and is set to open another 20 to 30 schools this year. We train our own teachers, we’ve built a pretty incredible modernised Montessori curriculum, and we’re building the tech we need to keep expanding. The company as a whole is idealistic, but everywhere I’ve looked I’ve found colleagues who care about the nitty gritty and the concrete. The road ahead isn’t straightforward, but I’ll be damned if it isn’t exciting.

If this sounds exciting to you too, reach out. We’re hiring across product, engineering, operations, and pedagogy.