Category Archives: Advice

Meditating Away Education Reform

I am at my best when:

  1. I work out at least 45 min 6 days a week.
  2. I have 0-1 drinks five days a week and 2-3 drinks on at most two days a week.
  3. 90% of my calories come from whole grains, fruit, vegetables, and seafood.
  4. I meditate at least 10 minutes a day.

I do not believe in diets or 90 day exercise regimes or anything like that, so my effort is spent trying to tweak my life to make the above livable long-term habits.

I am improving but have a long way to go.

As for meditation, I started meditating in law school and even lived in McLeod Ganj for a few months, where I worked with the Tibetan Government In Exile.

But I find it very hard to meditate daily, especially when so much of my life is structured around quick and / or deep mental bursts.


Recently, a friend recommended the app Headspace, which I have started using.

So far, the meditation techniques are fairly basic (I’ve only done the first four), but, despite (or perhaps due to) their simplicity, I find the mental barrier to begin meditating is lower with the app.

I hope this continues and my practice improves.


A common meditation technique is to let your thoughts float by as if they were clouds; to treat thoughts as separate from consciousness; to understand them as passing sensations.

This week, as I was meditating, education reform was on my mind, and as the app instructed, I let the thought of education reform float away.

It felt very good and, for an instant, fully dissociated me from the education reform tribe.

My guess is that this is an important habit to cultivate, that emotional separation is as important as intellectual separation when it comes to acting with empathy, reducing bias, and developing non zero-sum solutions.

Having the Conversation Beforehand

south carolina panel

I spent the past two days in Charleston, South  Carolina.

My father, who recently passed away, is from South Carolina, so the visit had deep meaning for me.

More importantly, the conversation going in Charleston is steeped in meaning because of the city’s historical racial injustices and the recent horrific shooting at a house of worship.


In education reform, a common critique is that reform is done to a community.

And, to be honest, when I visit cities I often give a talk or two, meet some political and philanthropic leaders, and then fly out.

This is probably the wrong thing to do.

On this trip, our hosts had us spend two hours with teachers and families at a public meeting before we opened our mouths.

I got to hear what some educators and families were going through; what their struggles were; what their hopes were.


The picture above is from a panel that took place at a church the next day.

Before the panel began, an African-American high school student gave an overview of the data of the achievement of his peers.

It was not a white business leader telling a community that the schools weren’t good enough.

It was a black male teenager.


A quick look at the picture above will make it clear that the panel had a diversity of views.

I’m associated with the charter school movement.

The leader sitting to my right, Kaya Henderson, is rightfully considered to be one of the best district leaders in the country.

We’re flanked by Dana Peterson and Chris Barbic, each of whom having been shaped by their own experiences: Dana as a labor organizer and Chris as a charter school founder and superintendent.

It’s rare that you get a former labor organizer, a sitting superintendent, a charter proponent, and a former charter and district CEO sitting on one panel.

All of the panelists, in my opinion, did a great job of being honest about what worked has worked in their cities, being open about what has failed, and clearly stating that the Charleston community has to blaze its own – and inevitably unique – path.


In many cities, panels like this focus on what has happened. Local and national leaders opine on recent reforms efforts.

In Charleston, they are having the conversation beforehand.

Their community has yet to put forth a vision of what the coming years will hold for their schools.

But whatever path they choose, it will have been formed through robust and open public debate.

They are having the conversation beforehand.

The Climb

Every career is different.

But, anecdotally, the below trajectory is a common path I see amongst people who have accomplished a lot for others.

Of course, there are other paths, but for what’s it worth, here are some thoughts on this path.

Screen Shot 2016-02-22 at 10.15.36 PM

High Achiever Phase

At the beginning of your education and career, you are for the most part only accountable for your own performance, as well as perhaps the performance of a few others.

If you can execute, you can get a lot done. This is not to say that there won’t be ups and downs as you progress, but, professionally speaking, the ups and downs will be bound within a reasonable range and the overall trajectory will be up.

Failure, Massive Learning, Recovery

Then, at some point you will really fail.

Sometimes this failure will be known to the world; sometimes it will be known to your management team; sometimes it will be known by your board; sometimes it will only be known to you.

Given that there’s only so much you can fuck up when you’re early in your career and individually executing, your first spectacular failure will generally happen when you’re managing a large initiative, team, or organization.

Some people recover from this and some don’t.

Generally speaking, perseverance, self-awareness, ambition, constant learning, and a deep drive for improvement help someone rebound from major failure (which might be one event or a dark year or two).

I also imagine certain elements of privilege (social capital, race, money, etc.) help, which is unfair.

Sometimes people have to change roles or organizations to fully rebound.

Sometimes they don’t.

The Climb

Ideally, the lessons of your failure are engrained so deeply that you never fail this hard again.

I don’t think it is great for an individual, in the career sense, to fail fast and to fail often.

You should improve enough that you train yourself to mitigate major downsides while giving yourself shots at high upsides.

Some of your upsides will hit for reasonable successes, while some will hit for astounding successes.

But spectacular failures should generally be avoided.

With a good understanding of your own strengths and weaknesses, you should be able to build the right teams and enter into the right situations to give yourself a decent chance of doing great things for others.

Once you’ve entered The Climb, you can get in a virtuous cycle of challenge, growth, and success.

In Sum

Unfortunately, Massive Failure is often the entry ticket to The Climb.

Buckle up.

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.