Category Archives: Hard Things

What Happens When What Works for Children Doesn’t Feel Good?

Closing schools does not feel good: it’s painful for families, educators, and politicians.

But closing schools, and opening new better schools, can dramatically help low-income children.

Sometimes, the best thing that can happen to a child is for her school to close.

Closing Schools Led to a +.3 SD Gain for Elementary Students in NOLA 

In New Orleans, Tulane researchers found that closing schools and creating new better schools led to very significant achievement gains:


Elementary students who attended a failing school started .1 SD behind their matched peers – two years later, these same students were .2SD ahead of their matched peers.

This +.3 SD impact is higher than the impacts of most educational interventions, and it equates to closing about 33% of the black-white student achievement gap.

You Don’t Have to Harm Existing Children for the Sake of Future Children

What’s incredible about these results is that the students whose schools were closed increased their student achievement.

Before seeing this data, my guess would have been that closing schools slightly harms existing students but is much better for future students who get to attend a better school without going through the disruption of closure.

But the NOLA data indicates that it’s possible to help both existing and future students, which should increase your belief in the benefits of school closure.

You Should Not Close Failing Schools and Send Children to Other Failing Schools 

In Baton Rouge, school closure did not lead to positive effects. This seems to be because these students enrolled into other failing schools after their original school was closed.


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For school closure to work, a city needs to either have open spaces in existing higher-performing schools or be opening new high-quality schools.

There are Good and Bad Ways to Close Schools

School closures are hard, but they can be done with respect. Families deserve to know why their schools are being closed; families should get support (and preference in unified enrollment systems) in finding a better school; and political leaders should ensure that empty school buildings are put to good use for the community.

Unfortunately, in many cities, political officials do not close schools thoughtfully. Instead of being honest with families about the poor performance of the school, they let failing schools linger for year until enrollment dwindles and the school folds academically and financially.

It is Difficult to Scale Something that Causes Political Pain

It is unclear to me whether or not deliberate school closure will scale. Reforms that cause political pain tend not to do well over time.

However, opening new great schools need not be politically painful, which bodes well for continued charter growth.

Of course, continued charter growth can lead to the closure of failing schools – and this is exactly why charter moratoriums have some political support.

Charter moratoriums have the potential to reduce pain for adults even as they inflict pain on children.

Can New Orleans Continue to Close Schools? Should It?

Over the past few years, academic performance has stagnated in New Orleans:


During this time, there has also been a reduction in school closure activity.

So here is an interesting question: has the stagnation in performance been caused because New Orleans ate up most of the low-hanging fruit of closing schools, or has the stagnation in performance been caused because New Orleans has slowed down on closing failing schools?

At this point, I’m not familiar enough with the data to have strong opinions.

But I do worry that New Orleans, especially as it moves toward more local control, may stop using one of the strategies that has proven to dramatically improve the achievement of its students.

Advice -> Endorphins or Habit Change?

There are many inspirational posters on many walls across the world.

Most of these posters do not change the behaviors of those who purchase them, frame them, hang them, and look at them.

Rather, most of the posters deliver a sequence of endorphin boosts that very quickly fade.

In a short matter of time you pass the poster and you feel nothing.

Why Do People Seek Advice? 

Most people who seek advice are not that serious about changing their behavior.

They want to change their behavior, and they want to feel the endorphin rush of wanting to change their behavior, but they do not want to put in the work that behavior change requires.

People like to feel that they can change.

People like to get advice on how to change.

People do not like the process of change.

If you are seeking advice, you’d do well to be aware of why you are seeking advice.

If you are giving advice, you’d do well to clearly articulate what it will require to implement this advice.

Or, at the very least, understand an advice session for what it is: a form of human banter that makes everyone feel good at the time but has little lasting effect.

What Advice Have You Received that Has Become a Habit? 

It’s worth reflecting on what advice you have received that has become a mental habit, both to reflect if you’re doing the hard work of behavior change, as well as to understand why some advice leads to change and some does not.

Here are some pieces of advice that have truly change how I think and act:

Nobody promised us anything (my father): As my father was dying from Parkinson’s disease, I asked him if he was sad, and he responded: nobody promised us anything. I think about this phrase a lot – as well as a sister phrase that I’ve incorporated into my thinking: the world is not ordered for my own happiness. When I am feel frustrated, indignant, or consumed with self-pity, I say this phrase to myself and, in the moment, reorient my mindset as best as I can, which is often a good amount.

Workout and mediate everyday (self-help books): Basically every self-help / self-improvement book I’ve read and have hammered home the importance of exercise and meditation. And for good reason! It’s taken time, but I’m not at least 5-6 days a week for both. Working out and meditation have become long-term habits.

Lead congruent organizations / teams (Nancy Euske, NSNO management team): After a few initial failures, I am now very deliberate about leading teams and organizations that have an explicitly aligned mission, strategy, culture, structure, tactics, people management systems, and goals.

I’m sure there are other pieces of advice that have become habits – but these standout to me in that they have greatly impacted my life, five years ago I did none of these three with any regularity, and I continually track my behavior to ensure the habits stick.

The Biggest Mistake I Made with Habits

For years, I would read books for knowledge rather than behavioral change. For some types of books (novels, history, etc.) this is fine. For many other types of books (business, self-help, etc.), this is not fine.

But I get high off learning new information, which is dangerous. I used to rip through dozens of business and self-help books a year – and while this made be an interesting dinner party companion (or terrible depending on your conversation tastes) – it rarely led to behavior change.

Now, I only read a business or self-help book if: (1) I have the time to read it deliberately enough to draw out behavior change possibilities; and  (2) I have the time to practice and implement the behavior changes.

The Ability to Adopt New Habits is an Incredible Competitive Advantage

Most people will spend over forty years working.

Over the course of a career, being able to adopt a few important habits a year will provide an incredible competitive advantage over people who do not adopt important habits.

Growth mindset and intellectual curiosity are amazing mindsets – but it’s the ability to form habits that unleashes their true power.

Will America Ever Have Integrated Schools?

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All else being equal, I think it would be better if public schools were integrated. I find the individual and societal rationales for increasing integration to be very compelling.

However, I do not understand how America will achieve integrated public schools in the next few decades.

If others see a realistic path to integration, I’d love to better understand these arguments.


Here is why I am skeptical that we will achieve school integration over the next few decades:

White Families Don’t Want to be in the Minority: As recent research demonstrates, white families want to send their children to schools where they aren’t a signficant minority. Most major urban education systems are 75%+ minority, so the math simply doesn’t work. You can’t scale schools with significant white enrollment when white families only make up a small minority of students.

White Families Won’t Send Their Children to Poor Neighborhoods: I’m skeptical that, at scale, white families will bus their children into poor neighborhoods. This means integrated schools can only really be located in either gentrifying or wealthier neighborhoods. It seems (rightfully) unfeasible that cities will stop operating schools in poor neighborhoods – yet having schools operate in poor neighborhoods will prevent integration.


In short:

  1. If your policy solutions goes against the desires of the vast majority of white people; and
  2. You need white people to participate in your solution; and
  3. Even if you get your policy passed, white people can escape the policy through moving to a nearby town or opting-out of the public system; then
  4. You’re in for a long, hard battle.


All of this being said, I spend most of time working on a strategy that most people think will not scale, so I’m very sympathetic to reformers trying to change the world against tough odds.

But if you’re trying to change the world you need to be able to tell a story of how you might succeed – and, to date, I haven’t been able to understand this story for school integration.

But this might simply be my own ignorance. If anyone can point me to writings that better tell the strategy story, I’ll eagerly dig in.

How Black Lives Matter Has Affected Me


I don’t know that I have anything particularly insightful to say about the deaths of Alton Sterling or Philandro Castile, or regarding the deaths of police officers in Dallas.

There are other more important voices to be heard, including the families of the victims and all of those putting their lives on the line in the on-going protests.

But the events of the past few weeks have surely been cause for further introspection – and in case it’s of use to others – I’ll share those below.

One additional note: for me, there has often been an inverse correlation between the intensity of a situation and my emotional tenor. When blood is boiling around me, my blood cools – this has had both positive and negative effects in my life, and in part explains the tone of this post.


How has Black Lives Matter affected me?

I feel the issue in a way I never did before. Working in education in New Orleans, I’ve surely been exposed to the idea that too often black lives don’t matter. But there is nothing as visceral is video. Watching Tamir Rice being slain; Walter Scott being mowed down – the videos have dug into my conscience – and they have forced me to emotionally and intellectually confront a dark corner of America that I don’t experience in my day-to-day life.

It’s made me question myself. In my younger days, I was more willing to throw myself into the most difficult situations. As a law student, I lived in a war torn Sierra Leone and worked at an international war crimes tribunal because I thought I could be a part of serving those who had been devastated by violence. I thought much less about my own well-being in those days. Now, when I watch the protests, I wonder: do I still have it in me? How much am I willing to sacrifice my own well-being for others? Or am I only willing  to do good if I’m well compensated and get to work with my friends in a cool organization? I also am struck with deep admiration for those who do have it in them.

It’s made me question my role. Due to some combination of temperament, intellectual interest, and ego – I’m wired to be a doer and not an ally. It’s much easier for me to throw myself into something if I’m a leader in the charge. I’m realizing how difficult it is for me to throw myself into something when I’m a walk on player in the fight. Despite my heritage (my father was African-American and mother is an Indian immigrant), I’ve never deeply internalized either of these cultural identities; they are surely part of who I am, and they make me different than white Americans, but still, I find myself on the outside looking in… perhaps I need to broaden my definition of what it means to be a leader.

It’s made me listen more: Reading the twitter feeds and blogs and Facebook posts of Black Lives Matter leaders has drilled into me that you can’t understand something without listening to those who are most affected by it. This doesn’t mean data and analysis is not useful, only that it will always be incomplete. Additionally, I’ve also found myself reading Fox News a little bit more, as I’ve tried to deepen my understanding of those who are troubled by Black Lives Matter. This has also made me empathize with the dangers that good cops face in very difficult situations.

It’s driven home a view that we need to hold physical peace as sacred: In watching the videos of black people being killed – as well as police officers being killed – there has been one constant refrain in my  head: couldn’t death have been avoided? As a nation, if I had one wish, it was that we would be more physically peaceful. Everything can be walked back but death.


So I’ve been affected by Black Lives Matter in deep ways – but what to do?

I’m still struggling with this, so all feedback is appreciated.

First, I want to do my job better. When I’m being lazy, or not thinking things through hard enough, or not being obsessively anxious about solving the hardest problems, I want the videos of the victims to be seared in my brain on replay. I’m in the fortunate position of being able to deploy a lot of capital to increase educational opportunities for black children. And while I don’t think education is the primary issue here, it is the area I have the most control over, so my opportunity for impact is probably greatest. And I do believe that providing great educational opportunities to black children will help them defend themselves against racism, as well as help them fight it. This should not be their burden, but it likely will be.

Second, I want to increase my effort to listen to more diverse voices. It shouldn’t take a video of someone being murdered for me to stay woke. To operationalize this, I’ve set a quarterly goal of reaching out to three people in each city I work in – people who don’t fit neatly into my existing personal and professional circles.

Third – and this more about mindset than immediate action – but I want to better define when and why I’d be willing to accept chaos and upheaval in my own life in order to help others.

It’s Nothing Like Uber


I was recently talking with Kristi Kimball from the Schwab Foundation and our conversation turned to discussing analogies that are used to describe the charter school sector.

We both noted that Uber is sometimes tossed around, in that Uber is often competing with a highly regulated and politically powerful incumbent.


But now imagine that if instead of working with drivers who provided their own cars, Uber had to buy or lease taxis from the taxi companies that they were competing with, or they had to buy a new fleet of cars everytime they entered a market.

Now imagine if these cars were not cars but were school buildings that cost about $20 million a piece.

Now imagine if buying or building these cars schools buildings often required the permission of another government agency, so entering the market required the approval of two regulators, not just one.

Now imagine if instead of being a billion dollar for-profit company with access to capital,  Uber was a non-profit organization reaching out to a capital market that was just beginning to understand what their company does.

Now imagine if instead of having to hire people for a skill that most of us learn when we’re sixteen, Uber had to hire people who could do one of the hardest jobs in the world – a job so hard that if a teacher changes professions he or she inevitably looks back and says: that was the most difficult job I ever had.

Now imagine if, instead of hiring a recent business graduate as a general manager to lead their city operations, Uber had to hire people to do a job (lead a high-poverty school) that one business school professor described to me as the hardest leadership job in the country save for being in combat.

Now imagine if instead of being judged on whether or not the company could get someone from point A to point B for a decent price, Uber was judged on whether or not it could put a dent in centuries of historical poverty and racism and help all students complete an education that enriches their lives and puts them on track for a good job.

And now imagine that Uber’s ultimate aim was not simply to win, but to make everyone better – so much so that they spent significant resources on documenting their best practices, publicly sharing all they know, and providing direct training to their “competitors” – with the hope that everyone can get better and innovate as quickly as possible.

I wish it were like Uber. But it’s not.

It’s much, much harder.

And it’s much more important.

The teams of educators, in charter and district schools alike, who are achieving great things in partnership with communities deserve our highest praise and support – as do the students and leaders in these communities who are doing the hardest work of fighting for a better tomorrow.

These educators, students, and community leaders are tackling problems that most private sector companies can’t even begin to understand.

The Challenge of Separating Emotional and Intellectual Agreeableness

There is a decent amount of research showing that agreeableness (as measured by the five factor personality test) is not always associated with strong professional outcomes.

Specifically, agreeableness can reduce results orientation and create opportunities to be taken advantage of by colleagues who better use power to achieve their desired ends.

That being said, agreeableness need not be all bad: to the extent that it helps cultivate large, loose networks, agreeableness is likely of use to leaders in attracting talent and coalition members, especially in the non-profit sector.


Many times, I’ll be in a conversation with a colleague, grantee, or potential grantee and there will be a small war going on my head: part of me wants to nod my head, smile, and ask probing but pleasant questions – while another party of me wants to dig in very hard on everything that might be wrong about what we’re discussing.

I have a strong desire to be both emotionally agreeable and intellectually disagreeable.

Which begs the question: is it possible to be emotionally agreeable while being intellectually disagreeable?


I’m not sure. But here’s some things I try to do:

  • Utilize processes that create a safe space for intellectual aggression (i.e., assigning someone to be the devil’s advocate in a meeting).
  • Using hedging phrases such as “I might have this wrong, but….” that soften the blows of intellectual aggression.
  • Trying to separate my empathy for a person with my disagreement with her ideas – so that my intellectual disagreeableness does not bleed into full blown personal animosity.

If you have any other tools, let me know.

I struggle to get the balance right.

Sometimes I feel like I’m too agreeable, and sometimes I feel like I’m too intellectually aggressive.

Having the Conversation Beforehand

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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 Hard Thing About Hard Things in Education Reform

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I’m rereading Ben Horowitz’s The Hard Thing About Hard Things. If you haven’t read it, it’s well worth reading.

The book is an attempt to be brutally honest about how hard is to build a company, as well as give some advice on how to survive the hard times.

I learned a lot from reading about Ben’s experience.

So in case it’s of use to you, here’s some summaries / lessons from my very hard times in my own professional career.

Leading School Development Work Without Instructional Knowledge

NSNO had two experienced educators leading our new school creation work. It was very hard to find two top notch instructional people and we’d done a lot of recruiting to get these awesome folks and I thought we were in good shape staffing wise. I was wrong. They both had children at roughly the same time and I ended up leading our school support work while they were out.

Even writing this now, I feel some sense of embarrassment and guilt as I was 100% not ready for the job. I remember being very anxious and feeling dread going into the schools we working with. They were all start-up schools that needed excellent support and I knew that I personally could not give them the support that they needed.

There is really nothing more to say other than I showed up and did what I could and kept the work moving until our team was reassembled.  The only thing I think I did well was stay calm and focused. I never freaked out publicly and I kept our support visible. We kept on showing up to schools. I’m not sure there is anything I could have done different. It was an external shock and sometimes when external shocks happen you just have to survive.

Failing in Raising a Major Fundraising Round

NSNO was trying to raise somewhere around $15 million for the city and we arranged a final pitch day for our biggest funders. They flew in from all over the country and for the day we put them in front of high status speakers and panels full of our best educators. Then, at the end of the day, they said they needed some time to debrief. So our leadership team, including our board chair, left the room for about an hour. Then we came back in. The funders proceeded to tell us that they weren’t ready to make another major investment; that they still had too many questions.

I was shocked. I thought we had everything lined up. I thought we put on an awesome day. And I felt passionately that the work had to continue; that we were on the cusp of something very very important and that they were going to abandon us. With as much calm as I could muster, I told them this; that they needed to invest. I was very young at the time and if my voice wasn’t shaking audibly my mind surely was shaking. They said they understood where we were coming from but that they weren’t ready to invest. The meeting ended. I went up home to my girlfriend and cursed loudly about how the funders were abandoning us. Then I drank a few bourbons and went to bed.

Shortly after, we told the staff that were unsuccessful in getting the commitments we needed. I forget what we said or how we said it. Mostly what I remember is creating a plan to go back to each of the funders individually and figure out what their concerns were and make sure we fixed it. This is what we did. Eventually we raised more than we had initially set out to raise.

The reason the day was a failure was all our fault. Instead of understanding our funders’ concerns and having deep discussions about these issues, we put on a dog and pony show for them. They were rightful frustrated, and, I think, felt like they had wasted much of the day. Putting on this dog and pony show both kept them from getting the information they needed and made us look like we did not have our shit together. The reason we were able to get through it is that we were very dogged; we did not hold grudges; and, ultimately, we put forth a realistic and compelling vision of what we could accomplish as a city.

Failing to Lead the NSNO Management Team

When I first became CEO everyone on our management team was much more experienced than I was. And while I was confident in my ability to develop our organizational strategy and communicate this vision to internal and external stakeholders, I was not confident in my ability to manage senior staff who had more content knowledge than I did. So instead of building a management team I simply met weekly with our senior staff to make sure the work was moving. I did not set high expectations for the work; I did not build trust amongst the team; I did not provide thoughtful feedback; I did not create an atmosphere of debate.

During our first 360 performance review, I received brutal feedback. The management team made it very clear that I was failing to lead them. It was extremely, extremely difficult to hear. I was emotionally hurt and for about a day couldn’t even really deal with it. Then I got my act together and met with each of them to figure out how I could get better. I built a plan to become a true leader of the management team and mentally committed myself to deliberately managing the team. Soon after, we did an off site retreat and got much more vulnerable with each other; we began to push each other; and I began to internalize the fact that perhaps the most important role I had was leading the management team. Overtime, the management team became, in my opinion, very high-performing and all members stayed with me through my tenure.

Not leading the management team was 100% my fault. I was unprepared to be an effective CEO and if I had prepared more fully I could have avoided some early mistakes. The only reason I survived is that I think every member of the team knew two things: (1) I was passionate about NSNO and (2) I was an extremely committed constant learner.

If people believe you care and they know you want to get better and they trust that you can get better they will forgive you when you fuck up.

Anyways, those were some hard things. I’m sure I got some of the details wrong. But, at the very least, that’s how they felt.