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Lead Learner

“If you look back on yourself a year ago and aren't shocked by how stupid you were, you haven't learned much. - Ray Dalio

Consider the decisions you have made over the past year. Is there something you did where you ask yourself, "What the (heck) was I thinking?"

While agonizing over every mistake is not constructive, understanding we have the ability to learn from our experiences is one of the greatest powers we have as humans.

Rather than squander limitless potential, those who embrace lifelong learning understand every day is an opportunity to improve.


If you think I've always enjoyed learning - you're wrong.

After graduating from college I believed learning was done. At 22 years old, I was convinced everything worth knowing had already been uncovered. My previous 16 years were spent in the classroom - what else was there to know?

Sadly, the beginning of my professional teaching career made it blatantly obvious there was still plenty to learn.

My first couple months of teaching high school math were a breeze. The kids were well-behaved, and I was doing something I enjoyed. "I can't believe they pay me to do this!" I recall thinking.

However, I pity anyone who visited my classroom after October. Do you recall the scene in Kindergarten Cop where the kids are running around out of control and Arnold Schwarzenegger eventually yells "SHUUT UUP!"? Unfortunately, that scene was recreated far too often in my classroom.

But typical of many prideful rookies, I didn't think my struggles meant I had more to learn. "I just had a rough group of students," I justified after finishing the year.

Year two was basically a repeat of year one. The fall months went fine, but as winter approached I once again lost control of my classes. "I don't need to change - the students need to change," I reasoned upon finishing my second year.

Years three and four were more the same. My third year I blamed upbringing: "No wonder these kids don't want to learn - look at their parents!" My fourth year I blamed school administration: "It'd be nice if the principal would give me some support!"

At age 26 and four years of teaching under my belt I was ready for a change. School administration didn't look too difficult, so I applied for a few jobs and managed to land a middle school assistant principal gig.

"This leadership thing can't be too complicated," I predicted while preparing for my new endeavor.

It didn't take long to discover I was in over my head. Whereas I survived teaching through determination, perseverance, and Red Bull, I couldn't fake my way through supervising 70 adults. Once they saw past my charismatic personality, the staff quickly detected I knew little about organizational leadership.

There came a moment when I realized if I didn’t learn how to effectively manage employees I would forever be miserable at work ... or get fired.

As someone who was entrusted to lead a team of educators, I had forgotten the core business of our profession was learning. How could I require "high levels of learning for all" if I didn't model those expectations in my own behavior?

I needed to become a lead learner.


As I brainstormed ways to enhance my job performance, attention centered around earning my superintendent's license and PhD in educational leadership. While the notion of earning another degree was admittedly depressing, a colleague who was already registered convinced me to enroll.

When I showed up to my first superintendents' class I felt out of place. I was an inexperienced, insecure assistant principal surrounded by veteran, confident head principals and district office administrators.

"I'm way out of my league," I thought as we wrapped up the first day.

However, I knew significant improvement would require me to push beyond my comfort zone. Even though quitting crossed my mind numerous times, I ignored the self-doubt and immersed myself in the work.

As I progressed through the coursework something started to change. The more I learned in class, the more comfortable I felt in my job. Workplace problems that usually gave me fits were now manageable thanks to newly-acquired knowledge. My confidence grew with each passing week.

Whereas adult learning always felt like a chore, it began to feel - dare I say - enjoyable.

After six difficult but satisfying years I finished my doctorate. While some opt for a professional learning sabbatical after writing the dissertation, my appetite for learning was growing. I found fulfillment in exploring the work of proven experts and testing their theories in my own setting.

Although my curiosity originated with leadership and education, it was clear that continuous improvement was possible across many life pursuits. Soon I was soaking up information on such topics as fitness, nutrition, personal finance, relationships, and psychology.

As an educator who finds pleasure in helping others, I felt compelled to share my discoveries with others. However, I had doubts about publicly voicing my thoughts. "Do I even know what I'm talking about?"

Furthermore, I was worried about looking vain. "Will people accuse me of being a know-it-all?"

Nervously, I began to share my ideas in meetings, at conferences, and on social media. To my surprise, others found value in my perspective. Not only did they embrace my thoughts, they also began using my suggestions in their own settings.

With the increasingly positive feedback came a willingness to take bigger chances. First a website. Next a blog. Then a newsletter. And finally a podcast.

“What about a book?” some folks asked.

“Me?" I'd reply, chuckling at the idea. "Maybe when I'm older. I have waaay too much to learn.”

However, the more my audience grew, the more I realized they enjoyed hearing about my journey. Readers voiced their admiration for my willingness to share my successes - and failures - while trying to get better professionally and personally.

"If you wait 20 years to write your book, will remember going through the process?" questioned one colleague. "No one has written a book quite like this."

She was right.

My personal development journey resulted in reading hundreds of leadership, education, and personal growth books. Although many of these books were remarkable and completely transformed my life, there were two bothersome patterns.

First was the authors. Most leadership books were written by business CEOs with no connection to schools. Most education books were written by consultants no longer employed by schools. And most personal growth books were written by social media influencers with little interest in schools.

Second was the content. While countless authors did a masterful job covering the topics of leadership, education, and personal growth either individually or in pairs, very few books attempted to navigate the obvious intersection of all three themes.

"No one has written a book quite like this."

Until now.


This book is comprised of three sections: Leadership, Education, and Personal Growth. All three parts contain numerous bite-sized pieces of content related to the overarching section. To give the book a natural flow, similar topics are pieced together.

Despite its deliberate structure, there is no right way to read this book. Feel free to read from cover to cover, or bounce around and choose topics that pique your interest. Think of this book as a buffet. You can start with the salad bar and proceed to the main course ... or you can go straight for dessert.

Given this book tackles several different issues, there may be sections that do not pertain to your current setting. Simply skip those sections and come back when you believe the subject is more applicable.

However, understand books change as you undergo different life experiences. As time passes, concepts initially deemed unimportant may later prove meaningful. Avoid permanently rejecting any ideas as they may deliver future value.


Stephen Covey once said, "The single most powerful investment we can ever make in life is investment in ourselves."

My hope is that you view this book as an investment. Whether you are looking for a few helpful ideas, or are searching for a complete mental makeover, realize lifelong learning is always time well spent.

What are you waiting for?

Let's get started.



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