The story of my life is filled with many twists and turns – unbelievable highs and devastating lows. But, through it all, God has revealed a power and purpose deeper than I could ever imagine. By no means am I suggesting that it’s been easy. Far from it. The journey has been incredibly challenging. That said, each passing day reminds me just how fortunate I am for every bit of it – the good, the bad, and the ugly – and how it has shaped the husband, father, and community partner I aspire to be.

The last couple years have been quite heavy for our family. We have felt every emotion imaginable, but we have maintained our strength and resolve throughout. We draw that strength in a multitude of ways. But this week I was reminded, on several occasions, of one of those sources of strength that has been sustaining, encouraging, affirming and validating. And that is the many serendipitous encounters with a wide range of individuals. With each passing week I am uplifted by these serendipitous moments – moments that seem to hit right on time even if I didn’t know or feel it.

For Kids

Some of the most powerful moments come directly from the many former students. Without fail, these tend to come in moments where I may be feeling the lowest. It could be a student I had back in my 9th grade World Geography class, a player I coached, or one of the many students I served as a school administrator. With each encounter I am left with a great sense of joy and purpose-filled. Ultimately, they are why I do what I do and to have so many who have been so gracious to say hello, express their gratitude and share about what’s going on in their lives means the world to me. 

The “Dark Side”

As I entered education I was solely focused on being a classroom teacher and a basketball coach. Never, in a million years, did I imagine I’d take this journey into school administration. I remember when I made the decision to jump into school administration, one of my teaching colleagues said “oh no, James. Don’t go to the dark side!” But as time went on, and I continued my education, I began to see huge gaps in what was being asked of teachers and actions of administrators – why this stellar educator would view administration as “the dark side”. In the classroom, teachers are encouraged to engage their students but I saw little to no true engagement from administrators to teachers. Compliance seemed to be held above engagement and I saw the impact that had on many of my colleagues. 

So I committed to do this work as a school leader in a different way – in a way that uplifts, engages, encourages, celebrates, values, trusts, connects, and empowers educators to bring their full and authentic selves to school each day to do the most important work on the planet – educating the hearts and minds of our young people. Along the way I’ve learned from, and grown with, so many phenomenal educators. By no means do I claim to have it all figured out. In this work, as in life, when you think you’ve got it all figured, rest assured, something will come along and humble you. Instead, I continually seek opportunities to reflect, learn, and grow in my leadership journey.

Be Impeccable with Your Word

And, sometimes, that journey of reflection and growth can come with a seedy dose of self-doubt. Our minds are one of the most powerful tools in the universe. In his best-seller, The Four Agreements, Don Miguel Ruiz discusses being “impeccable with your word”. At its core, this agreement acknowledges the immense creative power of language, acknowledging that our words can either uplift and inspire or inflict wounds and perpetuate suffering. So often, we tend to think about how our words can hurt others. But I want to give a nudge for us to consider how negative self-talk can actually be more harmful than anything we’d ever dare say to another person.

Being impeccable with our word begins within. It calls for self-awareness and a commitment to authenticity. We must find strategies and mechanisms to avoid self-deception or negative self-talk. By using our words and thoughts in a spirit of self-love, we cultivate a positive self-image and strengthen our personal integrity. Believe me, I get it…easier said than done. But that brings me to serendipity.

Serendipitous Encounters: Renewal, Encouragement, and Gratitude

Just as I’ve run into countless former students over the course of my career, I’ve encountered many former educators I’ve served as an administrator. These encounters always leave me feeling renewed, refreshed, and encouraged for our profession. Strangely enough, whether or not I know it heading into these encounters, I leave thinking “that was right on time”. I am so very grateful for the many people out there who take the time from what they’re doing to stop and say “hello”, lend a kind, supportive word, or share some anecdote of how you may have played even a small role in their journey as an educator. It is the ultimate data point for me, as this work is about the people.

Serendipitous Encounters with New Friends and Allies

Over the last couple of years, as my story has played out in local and national media, that circle of educators, parents/guardians, and youth has expanded. With each passing week there’s some sort of serendipitous encounter with someone in one of these groups. From social media messages to emails to chance encounters in public spaces – each interaction stokes my passion and purpose to press on even in the midst of such chaotic and turbulent times. 

One such encounter happened just the other day as our family was out to eat with friends. As I walked to the bar to order a drink for my wife and I, there stood a person ready to greet me with a big smile and an extended hand. As we shook hands they said “Dr. Whitfield, right?” I responded, jokingly, “you got me”, as I lifted my hat to expose my shiny, bald head. After a brief chuckle they went on to share that they’re a principal in a nearby district and just wanted to say hello and let me know how much they support who I am and what I stand for. 

As I thanked them for their kind words they went on to share a bit more background saying, “and I want you to know that my appreciation and admiration goes deeper than all this foolishness that’s been thrown at you and how you’ve handled it with such grace. Actually, I was an assistant principal at a local school when COVID struck. And you were the principal of one of our teachers’ kids. She came in and showed me the videos you were making for the students, staff, and community and I thought ‘that’s some good stuff – I need to follow that dude’, and I have followed your journey ever since.”

They added, “So just know that, for so many, you were, and are, a model for what true leadership should and could look like even before all this came your way.”

Accepting Your Flowers – Appreciation

I’ll just say it – I am terrible at accepting compliments, but have gotten better over the course of time. In full transparency – it was hard to even type the above paragraph because I, in no way, want to self-aggrandize. But my journey has taught me that it’s important to acknowledge and accept these kind sentiments. Doing so shows appreciation to the person who made the effort to share. Additionally, it becomes a powerful tool for being impeccable with my word, allowing myself the opportunity to practice self-love and appreciation.

Gratitude, Purpose, and the Power to Move Forward

This was one of several serendipitous moments that happened over the course of this past week, and each was accepted with deep gratitude. These moments happen to each of us in different ways throughout the course of our busy lives. Sometimes in the form of small whispers. Other times in thunderous applause. Each with the capacity to nudge us along our paths, which can often be mired in the vast complexities of our daily lives. And, while they may not know it right now, I have faith that those reading these words may soon have that moment of serendipity that reinforces their purpose, passion, or simply their will to be. It’s coming. The universe is sending it your way. Listen and/or watch for it. When you hear it and/or see it, embrace it. Then use that serendipitous power to propel you as you move forward.