Since I facilitate a leadership community for school administrators, by default I recommend books for them. I write about it all the time, including this post highlighting our reading list for SY 20-21.

Here is a post I wrote on the best books for leaders in education or this post answering the question, “What should I read as a school leader?”

In today’s blog, I’m going to share what I read to develop professionally and read for enjoyment personally this past year. 

In an effort to be precise, I will share a very brief comment so you can make an informed choice as to whether my recommendation is right from you. 

For books about business, I’ll bridge the gap between education and business to show you how it will help you lead in your specific context.

If I read a book that I wouldn’t recommend, it didn’t make this list.


Here is a Table of Contents in case you want to jump to a specific section.


Stubborn Attachments. Explore multidisciplinary thinking, thought experiments, and whether economic growth is good for society.

Thinking in Bets. Upgrade your thinking by considering probabilities. Taught by a World Series of Poker champion.

Atomic Habits. Learn how to develop the habits you want and shed the ones that hold you back.

The Big Leap. Learn how to expand in abundance, success, and love every day. Eliminate your upper limit challenges.

The Inner Game of Tennis. Inward journey looking at the two selves. It will benefit you to operate in a flow state versus evaluating your every move.

Reboot. A radical inner exploration of self.

The Art of Gathering. Create better gatherings that dazzle your community.

Dare to Lead. A playbook on how to lead well.

Emotional Intelligence 2.0. Leaders that invest in developing their EQ are more effective and making more money than peers who do not.

The Inevitable. Learn what the future holds and how to build a school that is future ready.

Rework. How to work better and build a better school of the future.

Stop Talking, Start Listening. Neuroscience shows the reader how to tell better stories and have more influence. Author was on the podcast.

The Great Mental Models Volume 1 & The Great Mental Models Volume 2. Learn models that will improve your decision making in a variety of situations (e.g Hanlon’s razor, Second-order thinking, evolution, etc.)

When. Scientific secrets to timing should challenge you to adjust how learning happens within schools. Dan Pink was on the podcast too.


Supercoach. What if you believed you were born happy? What changes? Learn to live from the inside out.

The Coaching Habit. Contains essential questions all coaches should ask.

Trillion Dollar Coach. A silicon valley coach who helped all the big companies (e.g. Google, Facebook, etc.) become a success. Bill Campbell coached greatness through candor and compassion.


Creative Quest. A book by Questlove, enough said. 

On Writing. Stephen King writes a part memoir, part guidebook for authors.

Cartooning. A multi-week course on doodling and creativity.

Steal Like an Artist. Take a great idea, remix, make it your own.

Show Your Work. Do your work in public. This is the new resume. I can relate.

Bird by Bird. The best book on writing, hands down. 

Understanding Comics. An in-depth exploration of comics as well as how to tell stories.

The War of Art. How to be a professional and move past “The Resistance” (aka the imposter syndrome).


This is Marketing. Amazing book on leadership and influence. Reading will help you be more empathetic and more effective.

The Infinite Game. You have a choice. Make decisions for short term benefits or play the long game to build something of significance that will last (and be better for society, the environment, etc.).

Anything You Want. Contrarian thinking on how to build a business. True Ruckus Maker. It will improve your ability to question why we do what we do in education and make it better.

Business Model Generation. A robust look at building a business. Apply the business model canvas to your school to consider all the angles. Includes the empathy map I wrote about here and here .

Blue Ocean Strategy. Don’t compete in a red ocean full of sharks. Create a category and be the only competitor. If schools did this, they would be remarkable. 

Digital Minimalism. Turn off your damn phone and log off social media. It is making you dumb and wasting your time.

Work Less, Make More. Questions if you are the only one that can do a specific task. If school leaders thought this way they would be more productive.

The Virgin Way. Richard Branson is an original Ruckus Maker. Learn from how he lives and build businesses to make better schools.

Linchpin. Make yourself indispensable by creating so much unique value in your district that you can become a linchpin.

Measure What Matters. Transformed how I think about and achieve my goals. I wrote an in-depth post on the content here.

Company of One. Growth for growth’s sake isn’t necessarily a good thing. Staying small is at times the best option.

Perennial Seller. How to create in a way that stands the test of time. 

Purple Cow. Create in a way that is memorable and spreads by word of mouth.

Who Do You Want Your Customers to Become? For schools the question is, “Who do you want your students to become?”


Leonardo da Vinci. One of the most intelligent and talented men to ever live. The Journey of Crazy Horse. A Lakota hero and inspiring leader. I recommend the audio version.

Philosophy / Spirituality

The Fifth Agreement. I read these agreements every morning: 1) Be impeccable with your word, 2) Don’t take anything personally 3) Don’t make assumptions, 4) Always do your best, & 5) Be skeptical but learn to listen.

The Pema Chodron Collection. Amazing teachings on meditation.

Wishes Fulfilled. Interesting book on imagination and making your dreams a reality.

The Little Book of Hygge. Add a bit of happiness to your life from this Danish practice.

Letters of a Stoic. Seneca on Stoic philosophy. 

Discourses. Epictetus sharing Stoic philosophy.

Meditations. Marcus Aurelius’s personal journal considering life through a Stoic perspective. My favorite Stoic book.

On Having No Head. A book on living where you aren’t at the center of the universe. This is “No-self” or “headless” living. 

Zen in the Art of Archery. A beautiful book on presence, focus, and living in effortlessly.


Thug Kitchen. Great recipes and cursing. What’s not to like? How Not to Die. My wife wanted to explore a healthier diet due to a medical condition. She is an epidemiologist by training and really cares about science. According to her, the research in this book is sound. This is where our plant based journey started. A documentary you may want to check out on this topic is The Game Changers which is all I needed to be convinced that I would survive on a plant based diet. Zaika. I love Indian food. This is a plant based Indian cookbook. 


Fiction & Poetry

Life isn’t all business. Read fiction for fun and read poetry to nurture your soul.
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