Category Archives: Career

The Case Against My Own Education

Bryan Caplan just released a new book: The Case Against Education: Why the Education System is a Waste of Time and Money.

Instead of a doing a regular review of Bryan’s book, I thought I’d do a little introspection. Bryan’s argument is that education is a major waste of time and money.

Does this hold true for parts of my own education? If so, which parts?

Pre-K: Not wasteful!

My formal education started at a Montessori pre-k. It’s a little difficult to use introspection to determine whether this was a waste of time and money, as I don’t remember much about pre-k. I do have a vague memory of being confused most of the time. I didn’t understand what I was supposed to do there. But perhaps this is the point of Montessori. I don’t know.

But I don’t view this as a waste of time (what else was I supposed to do at the age of 3?) or a waste of money (the pre-k was not that fancy so I assume it was priced just a bit above the cost of babysitting). So seems like a decent use of mine and my parent’s resources. It allowed me to be confused in a safe environment and it allowed my parents to work.

Elementary School: Not wasteful!

At Parkview Elementary, I learned to read and write and do math, which have all been very useful in my life. Me being at school also allowed my parents to work, which provided our family with a home, food, and the comforts of a middle class lifestyle, which made for a happy childhood. If I had not been at school, I can’t really think of many productive uses of my time, so I don’t see many trade-offs in having attended Parkview Elementary. The combination of the school teaching me the basics and providing cost-effective babysitting (Indiana is not an extravagant spender on elementary schools) seem well worth the time and money.

Middle School: Not wasteful! 

At Ben Franklin Middle School, I honed my basic writing and math skills, as well as picked up some basic science and social studies, which probably helped ground me in the modern / liberal world order (science, democracy, etc.). I also was put in an orderly environment which helped prepare me for a society that values conscientiousness, agreeableness, and the maintenance of civilized social coalitions. If I had not been a school, I suppose I could have worked in nearby farms (labor laws permitting), which would have also reinforced conscientiousness, but probably have been lacking in math, writing, and more advanced form of social coalition building. I don’t think I was prepared to work at the types of firms that would have developed my professional skills, nor do I think that most firms would have found it cost effective to teach me math and writing, which would have been hard to teach myself.

Early High School: Not sure 

9th and 10th grade at Valparaiso High School were also good educational  years: I learned Algebra (which I still use) and further practiced writing, with an additional emphasis on research (which I still use).

However, at this age there were some real trade-offs in going to school. By the age of 14, I could have started contributing to companies at a rate that would have been worth paying me a minimum wage (if not more!) for roles that would have both helped the company and helped me build a lot skills. This is probably true at free market rates, and definitely true if the government took some of the money they were spending on me in education and used it subsidize employers paying my wages.

On average, I think you learn more about how to succeed in skilled jobs rather than in school, so I imagine I would have picked up a lot of useful soft and hard skills (goal setting, data analysis, project management, giving and receiving feedback, etc.) that I didn’t really pick up at school. And while I doubt most employers would have taught me Algebra, I imagine I could have taught myself in the future if the job required it.

So this feels like a toss up: I was learning things in schools that have helped me, but I also could have learned a lot by working at interesting jobs.

Late High School: Waste of time and money!

Most subjects I learned in high school (advanced math, science, literature, etc.) have been of very little use to me in life. Of course, I didn’t know what I would end up doing for a career at the time, but taking a bunch of advanced coursework seems like a pretty inefficient way to keep doors open for a wide breadth of future careers. For the most part, given my strong foundation in reading and math, I could have learned many subjects down the road if my chosen career had required it.

Probably 90% of what I learned in late high school I’ve forgotten and don’t really use.

I do think going straight to the work force would have been a much better education than school, but I worry a bit about making career decisions at such a young age. But a bunch of 3-12 months internships / travel experiences / short-term jobs likely would have been much better than learning Calculus, both terms of intellectual and social development.

Had I been working, I would have become a better person (in all senses of the word) faster.

College: Complete waste of money!

I was an English major at Tulane. I learned very little. Writing papers about novels is not a very transferable skill; the courses weren’t that rigorous; and most of the good novels I read I probably would have read eventually throughout my lifetime. I would have learned so much more (and been happier) had I been working at a few great companies over this time.

People also always argue that college is a time for intellectual exploration, but I don’t buy that. Life is a time for intellectual exploration, and you either enjoy being curious or you don’t. Even if I had been working, I would have still read a ton and had a bunch of great conversations, which probably would have allowed me to explore more topics at deeper levels than I did at Tulane.

1st Year of Law School: Not wasteful!

The first year at Yale Law School is basically a one year bootcamp in a mental model (how lawyers think) and logic (outline the arguments of legal cases). Even though I don’t practice law, both of these things have been helpful to me. I’m a big believer that mastering professional mindsets (lawyer, entrepreneur, teacher, VC, etc.) helps you solve a diverse set of problems as you move up in your career, and I do think that logically ordering arguments is a generalizable skill in the modern day workforce.

I sometimes wonder if schooling from ages 16 to 20 should alternate between internships and 3-6 months of curriculum from a variety of graduate degrees that provide useful mental frameworks. This would also be a great way to meet a lot of interesting people.

2nd and 3rd Years of Law School: Wasteful

I just got deeper and deeper into a knowledge base that I never use.

In Sum

My personal experience has been that school was really valuable until about 10th grade, and then, save for the first year of law school, was pretty wasteful relative to what I could have learned in a bunch of internships and jobs.

Of course, what is true for me might not be true for others.

One last point: from a policy perspective, I do think that grades K-10 are very important for both individuals and society, and I’m grateful to be working at a job that is trying to make that experience more pleasant and productive for millions of children.

Advice for Ambitious 19 Year Olds Who Want to Work in Education

I just read Sam Altman’s blog post on career advice for the start-up industry. I enjoyed his post.

Here’s my version for the education sector. Of course, the world (thankfully) is not so ordered that you can plot your way to changing the world. But you can (and should) put yourself in situations that increase the probability that you can change the world (if that is your ambition, which it need not be).

Lastly, I know some folks think posts like this are obnoxious. But I wish adults had been honest and open with me about this stuff when I was nineteen. No one was. This caused me to make some early mistakes that I regret in that they decreased meaning, happiness, and purpose.


1. Go to a College that Offers Rigorous Coursework and Great Classmates – and Don’t Solely Major in Education 

If you want to impact education, it’s best that you go to college, as education is a fairly regulated industry that often requires a degree of some sort, especially to teach. Unfortunately, in too many schools education coursework is not rigorous. So you should major in something rigorous that ideally aligns to your emerging strengths and includes some quantitative coursework; good matchings include: policy and systems strength (economics); quantitative and logic strengths (engineering, computer science); writing strength (philosophy, history). While in college, you should find ways to get real world experience in leadership and working in teams. You should get to know a lot of awesome people; maybe even do some drugs. For all of these reasons, you should go to a college where you are confident you can get rigorous coursework and meet great people. Such schools come in all shapes, sizes, and prices.

2. Teach or Become a High Dosage Tutor at a High-Performing School 

You don’t have to have worked in a classroom to affect education; however, not teaching will limit your opportunities down the road and will risk creating instructional blindspots that can be difficult to overcome. If you simply aren’t built for teaching a full classroom of students, do full-time high dosage tutoring. Either way, join up with a high-performing school. It might feel good to be a martyr at a terrible school, but you will not change much and you will have lost two years where you could have been building the skills that would allow you to really help children over the long-haul. At minimum, teach for as long as it takes you to become pretty good (most likely at least three years) or as long as it takes to realize you will never be good at it (most likely at least two years).

3. Start Taking Small Bets and Learn From Them 

On your way to becoming a good teacher (probably in year two or three) start taking small bets that align with your passions and emerging strengths. Grab some coworkers and create an education app. Volunteer at a think tank. Create a new class at your school. Spend the summer working in a developing nation. Start a blog. Work on a political campaign. While you are making these small bets, make sure you’re listening to the feedback. What do you enjoy? What are you better at than other people? In the future, what might you be better at than most people? In the future, what might you be better at than 99% of people? What might actually help kids? What might not?

4. Then Take a Big Bet with a Great Team Where You Will Grow 100x

At some point, take a big bet. This could be in teaching: you could attempt to team up with some great math educators create the world’s best high school Geometry curriculum. It could be in entrepreneurship and leadership: you could join the founding team of a very innovative or high-growth charter school. It could be in ed tech: you could join a start-up or early stage company. It could be in a union: you could partner with likeminded educators and launch a new union. Ideally, you’ll want to join a smallish team that is led by a few amazing people who can challenge you immensely and from whom you can learn a ton. If you launch something yourself, you’ll likely be trading deep mentorship for ownership, so make sure you get some great informal or formal advisors. Also, whatever you choose to do should have an incredibly high upside – if it works, does it have a chance to change the game for kids?

In most cases, don’t set your eyes on trying to move up in a larger organization. While you can do a lot of good by contributing to a large organization, in most cases you won’t get the experiences you need to grow 100x. Starting new entrepreneurial ventures within a large organization (if they let you) might be an exception (but probably not).

5. Continue Doubling Down on High Upside Opportunities that Align with Your Strengths

At some point you should figure out what you’re really good at it (you generally have to be really good at something if you want to change the game for kids). Then keep taking opportunities that utilize these strengths and have high upsides for kids. If you get in a rut, go to grad school. If you’re not in a rut, don’t go to grad school.


Just some thoughts. Again, life is not so easily planned, but the above are things to consider.

As for me:

I did (1) poorly: I majored in English at Tulane which turned out not be rigorous. It wasn’t until law school that I was pushed to be a more rigorous thinker.

I did (2) poorly: I did not teach, which I regret.

I did (3) well: While in law school I worked and lived in Sierra Leone; worked in India; wrote a novel; led a legal team on an education lawsuit; volunteered in New Orleans after Katrina. I made a lot of small bets.

I did (4) well: I teamed up with Sarah Usdin and Matt Candler to launch New Schools for New Orleans. I grew 100x and eventually became CEO. I think we did a lot of good for kids.

Time will tell if I get (5) right.


Good luck. Kids are waiting for you.