Category Archives: Advice

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.

Every Mentor Should Become Your Peer

I. Rigorous Thinking and Effectiveness 

The most effective people that I’ve worked with, or engaged with online, are extremely rigorous thinkers.

This, in some sense, is satisfying.

To the extent that the connection between effectiveness and rigorous thinking is causation rather than correlation, then increasing the rigor of one’s thinking can help lead to greater effectiveness.

II. Implicit and Explicit Instruction 

Of the extremely rigorous thinkers I’ve interacted with, only some of them are good at explaining why they think the way they do.

All of them, on the other hand, have been good at telling me when my thinking has not been rigorous enough.

Given the above, I’ve spent a lot of time trying to take their implicit and explicit instruction in order to improve myself.

One incredibly positive aspect of the internet is that it opens up thousands of avenues to learn how other people think.

III. Mentorship 

Another way to say all this: the value of a mentor (either in person or online) is that she should significantly increase the rigor of your thinking.

When you communicate with her, you should run as many cycles of feedback as you can –  pitching your ideas, getting her critiques, and learning.

But, at some point, this can lead to laziness: you might rely on your mentor to do the thinking for you rather than doing it yourself.

One way to test your potential laziness is to continually take stock of the delta between the rigor of your thinking and the rigor of your mentor’s thinking. If you are not closing the gap between the rigor of your thinking and your mentor’s thinking, then you are, in some sense, exploiting your mentor.

Ultimately, every mentor should become your peer. This should be the goal of all involved.

IV. My Journey in Unrigorous Thinking 

For whatever it’s worth, my biggest obstacles to rigorous thinking have come from the following:

1. Yearning for Silver Bullets: Very few quick fixes exist for hard problems. In part, I think I was drawn to law school because of the idea that passing the right law could fix things quickly. As it happens, this is very rarely true. Hard problems tend to have decade long answers.

2. Yearning to Have My Problems Solved: Related but slightly different: when confronted with thorny day-to-day problems, I’ll sometimes gravitate toward the easiest or first solution rather than taking the time to rigorously analyze the issue. This is nothing more than intellectual laziness but it is difficult to control, especially when you’re moving fast and making a lot of decisions each day.

3. Ignoring Politics: I’ve also succumbed to spending a lot of time on ideas or programs that never had a chance of being political viable.

4. Ignoring Executing at Scale: Even ideas that might be politically viable may not be possible to scale operationally. Especially earlier in my career, I deeply underestimated execution as a limiting variable.

5. Wanting to be Agreeable: The desire to please or get along with others sometimes trumps my effort to push to get to the right answer.

Those are the big ones: I could have avoided many of the biggest mistakes of my career had I been more rigorous at avoiding these pitfalls.

I suspect I’m not the only person in my line of work to make these types of mistakes.

V. Thinking More Rigorously Hurts Until It Becomes a Habit 

For all of the above issues, there has either been a professional failure or extremely direct piece of feedback that has provided a wakeup call that I need to be thinking more rigorously.

Even after knowing I have a problem with the way I think, many times the only way I’ve been able to make progress  has been by being exposed to leaders who are adept at avoiding these pitfalls.

This often all rather painful.

For me, it literally hurts to think more rigorously in an area where I have not previously been a rigorous thinker.

In some instances it feels like being a child who knows his parents are right but doesn’t want to admit it even though it is in his best interest to (1) admit it and (2) incorporate his parent’s way of thinking into his world view.

Eventually, it gets less painful – and then it becomes a habit.

And then it’s on to the next one.

VI. Accountability is an Accelerant 

One last point: putting yourself into situations with high accountability for outcomes is one of the best ways to increase the rigor of your thinking.

If you are not accountable for outcomes, then you will be tempted to avoid the pain that comes with thinking more rigorously.

If you are accountable for outcomes, then the pain of potential failure helps offset the pain of thinking more rigorously.

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.