I remember exactly where I was when my certainty blinded me.

I was in a corner conference room that was brimming with the morning light that shone through its large, floor-to-ceiling windows. The tables and chairs were placed in a large u-shape and were scattered with printed agendas and half-empty coffee cups. I walked to the front of the room and faced over twenty five central office administrators and staff as their new executive director and began briefing them on what I described confidently as a straightforward fix to the current curriculum issues. The problem, as I saw it, was clear: the school district invested too many resources into the internally developed curriculum to simply discard it for an off-the-shelf product. The solution, I insisted, was equally clear: implement a tightly structured review process based on research-based standards in order to identify and address deficiencies. I had data, I had slides, and I had examples from other school districts, including the one I had just left. Most importantly, I had conviction. I remember telling myself, This is what leadership looks like. People need clarity, direction, and someone who knows what’s going on.

As an executive director of curriculum and instruction—new to the district, but not new to leadership—I believed this was the moment to show I could take control of a messy situation. In many respects, the district was unstable. The superintendent had just departed under controversial circumstances two weeks before I arrived. I was the third executive director of curriculum and instruction in four years. The curriculum had been revised repeatedly over the same period of time, and test scores refused to cooperate with anyone’s plan of improvement. To make matters worse, I joined mid-year as an outsider, and I knew it.

Friends and colleagues had warned me before I took the role. “Are you sure this is the right move?” they asked. Some tried to tell me about the district’s internal politics, long-standing racial tensions, and the weariness of teachers and administrators who had seen too many reforms come and go. I listened politely, and, then, I ignored much of it.

Part of me framed their concern as caution. Another part, if I’m honest, read it as doubt on their part. The doubt, I believed, was something I already had outgrown. I had earned a doctorate, successfully led district-wide initiatives before, including curriculum development, and had proved myself in three other school systems. What I didn’t yet understand was how thin the line is between confidence and blindness.

The plan passed. The initiative launched, and, then, quietly at first, it began to unravel. Increasingly the politics clouded our focus, which turned some my team members against me and led others to outright undermine or sabotage my decisions. Revisions took longer than expected, and I quickly became the perfect scapegoat for everything that wasn’t right. What I had framed as a clear solution was being framed as complicated, unclear, and unnecessary. What I had seen as structure felt, to them, like another bureaucratic obstacle.

No one stood up in a meeting and supported me when the pressure and accusations started flowing. Essentially, it was the beginning of the end for me, but, for a while, I was in denial, thinking things were not as bad as they seemed. That gap, between how sure I felt internally and what was happening externally, was the beginning of a reckoning.

What I Now Recognize as Overconfidence

Looking back, the pattern is embarrassingly clear. I projected more certainty than my evidence warranted. I underestimated the complexity of the system, leadership instability and character, internal politics, institutional history, and culture. And, I confused being articulate and knowledgeable with being right. In education leadership, those errors are easy to make and hard to detect. The feedback loops are long, and the outcomes are ambiguous.

By the time you know whether a decision helped or harmed, the context will have changed already. This is what psychologists call a noisy environment: one where cause and effect are delayed, obscured, or contradicted?. The field of education is full of noisy environments which make calibration, the relationship between how confident you say you are and how often you are actually correct, difficult. For example, if I say I’m 80% confident, I should be right about eight times out of ten. In practice, most of us aren’t. Classic studies show that when people report being 90% certain, they’re often right closer to 70–75% of the time. Even worse, when people claim near-absolute certainty, accuracy can drop to little better than chance. I didn’t know those statistics at the time, but I lived them. What made me especially vulnerable was the social reward structure around confidence. As an administrator and leader, I was subtly, and sometimes explicitly, rewarded for sounding sure. Clear answers were praised, hesitation was read as weakness, and ambiguity made people uncomfortable. So, I learned, without realizing it, to compress uncertainty into confident language.

The Human Costs of Being Too Sure

The impact of being overconfident don’t just derail projects, they can also negatively affect the team dynamics and culture. For my team, my certainty translated into rigidity. Procedures designed to “help” became blunt instruments. Struggle was interpreted too quickly as lack of competence and effort. Team members’ voices were narrowed to fit the initiative, not challenge it. I see now how confidence can silence nuance, not by shouting it down, but by leaving no room for it to surface. I thought I was inviting collaboration. In reality, I was often inviting agreement. For me, the emotional toll was real. When the initiative faltered, I felt embarrassment first, then defensiveness. The temptation to double down was strong; after all, reversing course would mean admitting that my confidence had outpaced my understanding. That gap, between my identity as a reflective educator and my behavior as a leader, was painful to confront.

How I Calibrate Confidence Now

I don’t try to eliminate confidence, as that would be both unrealistic and irresponsible. Confident leadership is still necessary for decisive action, but calibration is required to ensure sound decisions are made. So, to calibrate, I work to make my uncertainty explicit. I say things like, “I’m about 60–70% confident this will work, and here are the assumptions I’m making.” That language does something important: it models that uncertainty is not incompetence, it’s honesty. I also focus on improving feedback loops. Before launching initiatives, I now ask, What would tell us early that this isn’t working? I commit, in advance, to revisiting decisions if specific indicators don’t improve within a certain time frame. That makes revision a feature, not a failure.

Another key to my calibration is seeking structured dissent from my team or colleagues. Sometimes I pay attention to the skeptic in the room to see what captures their attention. Or, I listen longer to the quiet, outlier perspectives in the room, who I used to brush aside because they complicated my narrative. The biggest feature of my calibration is reflecting on my optimism. This is an informal but intentional action to notice how often I am overly optimistic about timelines, resistance, or my ability to explain change into existence. The more I reflect, the more patterns emerge if honest with myself. These practices have changed how I lead meetings, design programs, advise team members, and respond to students. I speak more slowly, ask more questions, and revise more publicly.

Returning to the Conference Room

Experiences like this, which I used to try move on from because I saw them as failures, I now embrace fully to improve my leadership style One improvement is that I have shifted from projecting certainty to hosting uncertainty responsibly. If I were back in that conference room today, I would still act with confidence, but differently. I would ask what I didn’t yet understand. I would test assumptions before enforcing structure. I would create space for doubt before insisting on clarity. The posture I now aspire to model for students, my team, colleagues, and myself, is simple but demanding: be confident enough to act, humble enough to revise, and honest enough to say, I don’t know yet.

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When I first became an educator, I believed the work would be demanding but straightforward—teach well, serve students and families faithfully, and trust that my impact would speak for itself. Like many educators, I entered the profession with a clear moral compass and a strong sense of purpose. I assumed that meaningful contribution would naturally translate into recognition, trust, and professional regard.

What I did not anticipate was how disorienting it can feel to contribute deeply and still feel invisible within an institution. Over time, I learned that feeling undervalued is rarely just an emotion. It is often a signal of recognition, influence, growth, and respect, leading to a difficult, unsettling question: If others do not acknowledge my contribution, is it still meaningful?

That question did not arise because I lacked commitment or competence. It emerged precisely because I cared deeply about the work.

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A Nonlinear Beginning

I did not follow the traditional path into the field of education. Actually, my academic training began in physics. After graduating from college, I planned to pursue a career in engineering, and when launching that career proved more difficult than expected, I enrolled in graduate school for electrical engineering. On paper, I was moving forward, but internally, I was quietly unraveling.

It was during that season, while attending graduate school, that I stumbled into education almost by accident through a substitute teaching opportunity. At the time, I felt disoriented and behind, unsure whether my previous educational pursuits had been in vain. I wondered if I had misread my own aptitude or misunderstood the map I was supposed to follow.

That uncertainty lingered until my father offered advice that would shape my professional life more than any credential ever could: Let your identity come before your title. He went on to tell me that jobs will change and titles will come and go. He advised me, “Decide early who you are, what you stand for, and how you will work, regardless of who is watching.”

So I did.

What began as a temporary job quickly revealed something I had not anticipated—a genuine calling. Teaching gave my work meaning in a way I had never experienced before. I went on to earn a master’s and doctorate in education, completed my certification, and committed fully to the profession. From that point forward, I treated every opportunity with intention, focusing not on position but on impact.

I learned a lesson that would later become essential: my value should not be anchored in how others perceive me.

Growth, Risk, and the Visibility Paradox

Throughout my career, I took several pivotal risks that pushed me beyond my comfort zone. The first was leaving my initial high school teaching role at Pinkston High School to join the School for the Talented and Gifted, an environment with dramatically different expectations, norms, and pressures. The second was transitioning from the classroom into a central office role, where my sphere of influence expanded but my distance from daily classroom validation increased.

The most transformative risk, however, was leaving K–12 education altogether to enter higher education. That move broadened my reach, deepened my leadership responsibilities, and allowed me to engage in systemic change that affected entire communities rather than individual classrooms.

Each transition elevated my professional growth and expanded my capacity to serve others. Yet, in every role, there were moments when I felt deeply valued and others when I did not. Recognition was inconsistent and, at times, disconnected from the actual impact of my work. As I assumed more responsibilities, I increasingly realized the hard truth that contribution and visibility do not always move in parallel.

A Familiar Tension

Like many workers, I am sometimes unsure whether my supervisor or institution fully acknowledges my contributions. For many educators and educational leaders, like myself, whose work is often mission-driven and relational, the perception that your institution doesn’t recognize your worth can be demoralizing.

Over time, I realized that “feeling undervalued” was too imprecise a diagnosis to be useful. The real understanding took place when I started asking a simple question: What would make me feel valued? The answer changed depending on my role and the season. Sometimes I wanted acknowledgment. Other times, I wanted clearer pathways for advancement or greater influence over decisions that directly affected my work. Naming those distinctions mattered. Without clarity, dissatisfaction becomes diffuse, and diffuse dissatisfaction is nearly impossible to address productively. Now I believe that feeling undervalued may be less about the recognition of my contributions and more about the misalignment between my expectations and the organization’s mechanisms for acknowledging contributions.

A More Grounded Response

Practically, this realization reshaped how I respond to feeling undervalued. I now gather evidence of impact, maintaining a simple “wins file” that documents key projects, outcomes, data, and feedback. This is not self-promotion; it is accuracy. In parallel, I protect my well-being by cultivating peer recognition, seeking mentors and sponsors who understand my work, and tracking small, daily wins that remind me why the work matters.

I have also learned to initiate direct, yet collaborative, conversations with supervisors. Rather than framing discussions around dissatisfaction, I frame them around contribution and growth. I might say something like, “I’d like to talk about my impact and how I can continue to grow in this role.” These conversations do not always lead to immediate change, but they restore agency. They clarify my and the organization’s expectations and help me make informed decisions about whether to stay, adapt, or move on.

Underlying all of this is a commitment to intellectual humility. I treat my assumptions like hypotheses rather than truths. I seek perspectives that challenge my interpretations. Before reacting, I ask, “What might I be missing?”

What Feeling Unseen Taught Me

Looking back, the moments when I felt undervalued were not detours from my professional growth. They were formative tests. They forced me to clarify what I needed, advocate with humility, and anchor my sense of worth in something deeper than recognition.

My value did not begin when someone noticed it. And it does not disappear when someone overlooks it. I have learned that stewarding my work also means stewarding my voice. Leadership, especially in education, requires choosing clarity over resentment, courage over silence, and purpose over approval.

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Turning 50 this year sharpened that realization. Life is too short to reserve gratitude for a single Thursday in November. If anything, Thanksgiving should be a daily mindset, a way of inhabiting our work, our relationships, and our inner lives.

But how do we actually do that? What does it look like in practice? And how do we measure whether we’re living with a grateful, grounded awareness rather than reacting to whatever the day throws at us?

These questions have been on my mind for months.

I’ve tried gratitude journals with limited success. I tend to record only the “big” moments, forgetting that gratitude is a muscle built on small repetitions. I’ve also tried lengthening my prayers, adding more intentional thankfulness. Helpful, yes — but still reactive. Still dependent on moments where I pause after the day has already happened.

Then, unexpectedly, a clip of Maya Angelou stopped me cold.

In an interview, she described her philosophy of being present and giving everything she has to every moment. The simplicity and power of her words hit me harder each day I replayed them. After reflecting, I realized what had been missing in my efforts to move beyond a one-day Thanksgiving mindset:

I was being grateful, but I wasn’t being fully present.

Gratitude without presence becomes a list.

Presence without gratitude becomes a performance.

Angelou attempted both — courageously, wholeheartedly, daily.

Here are five concepts I’ve learned from her and how I’m applying them to my life and work.

1. Presence as Foundational

Angelou’s reminder is simple: Be fully here.

Not halfway. Not distracted. Not on autopilot.

Presence means giving your moments the gift of your attention.

For me, this changes:

• Deep work: Fewer distractions, less multitasking, more whole-self focus.

• Relationships: Showing up fully, listening deeply, contributing meaningfully.

Presence is not passive awareness — it’s active engagement.

2. Giving Everything You’ve Got

Angelou doesn’t encourage participation; she encourages wholehearted investment.

“Give everything” is a radical statement.

For us as thinkers, creators, leaders, and educators, this includes:

• Bringing full clarity and intention to our work

• Showing generosity with insights and support

• Avoiding the comfort of half-effort thinking

It’s not about being perfect — it’s about sincerity of effort toward perfection.

3. Gratitude + Humility

Then comes the part many of us skip.

Angelou pairs presence and effort with a posture of gratitude and humility:

“Be present in all things and thankful for all things.”

This reminds me to appreciate:

• The process of deep thinking

• The opportunity to do meaningful work

• The people who journey with me

• The tools and resources we have access to

Humility reorients the work. It reminds me that I’m serving something larger than myself — ideas, truth, community.

4. Courage to Engage Fully

Being present isn’t easy. Giving everything isn’t easy.

Both require courage to face discomfort, uncertainty, and vulnerability.

Angelou always emphasized courage as the foundation of character.

In my work, courage looks like:

• Confronting hard questions

• Staying with discomfort

• Exploring unfamiliar ideas

• Resisting shallow, reactive thinking

Being Present + Giving Everything = Risk.

But the alternative is stagnation.

5. Aligning Purpose with Action

Gratitude isn’t philosophical—it’s active.

So, it isn’t enough to reflect. I must act.

Angelou’s approach creates a feedback loop:

Being Present → Wholehearted Giving → Purposeful Action → Deeper Gratitude

It is a daily cycle of intentional living rather than an annual holiday reflection.

Why This Matters for You and Me

• It elevates output: Deep thinking is less about time and more about quality of attention.

• It shapes culture: Presence and gratitude transform how teams interact and collaborate.

• It gives meaning to work: We stop executing tasks and start embodying values.

• It builds resilience: Because when gratitude and presence anchor you, burnout loosens its grip.

You can watch the clip yourself — it’s brief, but the wisdom is timeless:

This is the mindset I’m committed to carrying into every day, every interaction, and every endeavor.

Not Thanksgiving as a holiday.

Thanksgiving as a lifestyle.

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When I was a child, I had a single question that could test the patience of any well-meaning adult: “But why?”

It started innocently enough. My parents would offer an answer, something practical, tidy, meant to end the conversation. But the moment they did, another question would escape before I could stop it. “But why?” Why was the sky blue? Why did grown-ups have to work? Why did some rules seem to bend and others didn’t?

At first, my parents indulged me. Then they sighed. Eventually, they resorted to the parental fallback: “I don’t know, son.” Later, when I was a little older, the answer shifted to something that changed me: “Why don’t you look that up and let me know?”

That single sentence did more than redirect my curiosity; it honored it. It told me that wondering wasn’t a problem to fix but a spark to follow.

Yet somewhere between childhood and adulthood, that spark dims. Not because we lose interest in the world, but because the world teaches us that answers matter more than questions.

The Great Trade: Curiosity for Competence

In school, the very place meant to nurture inquiry, curiosity often becomes collateral damage in the pursuit of efficiency. The questions that once bubbled up in the back seat or at the dinner table are slowly replaced with those that fit neatly on standardized tests.

By middle school, students learn that curiosity is risky, takes time, invites uncertainty, and rarely guarantees the “right” answer. By the time we reach adulthood, many of us have mastered the art of suppressing wonder in favor of getting things done.

Leaders, especially in education, feel this acutely. The more we’re responsible for, the less curious we allow ourselves to be. Systems reward decisiveness and certainty. Meetings reward concise answers, not open questions. Somewhere along the way, curiosity becomes a luxury instead of a leadership habit.

But curiosity isn’t a luxury—it’s fuel.

The Curious Principal

A few years ago, I met a school principal, let’s call her Dr. Alvarez, who understood this better than most. Her school was struggling: morale was low, innovation had stalled, and teachers were quietly burning out.

When she arrived, she resisted the usual leadership impulse to fix things quickly. Instead, she asked her team a disarming but straightforward question: “What are we not seeing?”

At first, people stared back, unsure how to respond. They were used to directives, not questions. But Dr. Alvarez kept asking, patiently, sincerely, with the same wide-eyed curiosity of a student trying to understand the world.

Gradually, her team began to open up. Teachers shared frustrations that had gone unspoken for years. They started experimenting again, trying new lesson formats, co-teaching across subjects, and exploring creative assessments.

Within a year, student engagement was up. Staff turnover dropped. The change didn’t come from a new program or policy; it came from a cultural shift sparked by one leader’s curiosity.

When I asked Dr. Alvarez what made the difference, she smiled. “I stopped pretending to know and started asking to learn,” she said.

Why Curiosity Powers Leadership

Curiosity does more than satisfy a passing interest; it rewires how leaders think and connect.

It keeps the mind flexible. A curious leader resists the trap of certainty. Instead of defending old assumptions, they test them. They look for new data points, new voices, new ways of seeing a challenge.

It deepens empathy. When we’re curious about people, not just their performance but their perspectives, we listen differently. We see what drives them, what frustrates them, what ideas they’ve left unsaid. Curiosity transforms conversations from transactions into relationships.

And it fuels creativity. Most innovation isn’t born from genius; it’s born from asking slightly better questions. Psychologist Francesca Gino’s research at Harvard found that teams led by curious managers perform better because they feel safer exploring new ideas. Curiosity signals humility, and it tells people, “Your insight matters.”

In other words, curiosity doesn’t just help us lead better; it helps others think better.

Becoming a Student Again

Here’s the paradox: the best leaders don’t outgrow their student mindset; they return to it.

Leaders who stay students treat challenges like coursework. They don’t rush to the answer key. They dig in, test ideas, and learn through iteration. They make time for exploration, like reading outside their field, observing how others solve similar problems, and letting reflection do its quiet work.

They ask better questions. Instead of “How do we fix this?” they ask “What’s really happening here?” or “What’s the question behind the question?” Those shifts sound small but create entirely new pathways of understanding.

They surround themselves with a menagerie of thoughts and perspectives—people who think, teach, and work differently. Curiosity thrives in diversity because every perspective holds a puzzle piece we didn’t know we needed.

And they extend curiosity inward. True curiosity isn’t just external; it’s introspective. It’s the willingness to ask, Why did I react that way? What might I be missing? What am I still learning?

When leaders give themselves permission to stay curious, they create the same safety for others.

The Courage to Not Know

Curiosity requires courage; the courage to admit you don’t know, the courage to explore what might fail, the courage to lead with questions when people expect answers.

But that’s the quiet superpower of leaders who stay students. They don’t equate uncertainty with weakness; they see it as an invitation to grow.

The educator Parker Palmer once said, “We teach who we are.” The same is true for leadership: we lead who we are. If we’ve stopped learning, we lead from what we already know. If we stay students—curious, humble, inquisitive—we lead from possibility.

Coming Full Circle

Every so often, I hear my younger self again, the child in the back seat asking, “But why?”

It reminds me that leadership isn’t about mastering the answers. It’s about protecting the questions that keep us growing.

Because when curiosity leads, learning follows.

And when learning leads, leadership thrives.

So stay a student. Keep asking why.

That’s where your next breakthrough will begin.

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My Father’s Wisdom

My father was a remarkable man who taught through stories, always colorful, sometimes exaggerated, but always packed with wisdom. I didn’t appreciate them fully back then. Like many sons, I assumed I knew more than I did. It wasn’t until I found myself teaching my own sons, repeating his words almost verbatim, that I understood the weight behind them.

Lately, I’ve been feeling what many midlife professionals quietly admit: that sense of being stretched thin, unclear, and disconnected. The responsibilities pile up, work, family, health, faith, and somewhere between doing everything and meaning everything, we lose our why.

When that happens, autopilot takes over. We keep moving forward but without enthusiasm or direction. And that’s when my dad’s voice comes back to me:

“Son, sometimes you just gotta want to.”

I was seventeen when he first said it. Stressed about school, sports, and life, I told him I just didn’t have the energy to keep trying. He listened patiently, then smiled and said, “You’ve got to want to!” I remember snapping back, “Of course I want to!”

But that wasn’t what he meant.

Over time, I realized his phrase wasn’t about desire, it was about alignment. He was teaching me that real willpower doesn’t come from emotion or adrenaline; it comes from connecting your will to a deeper purpose.

The Nature of Willpower

Willpower, what we often call self-control or discipline, isn’t just mental toughness. It’s the conscious ability to direct attention and energy toward what matters most, even when comfort or distraction beckons.

Neuroscience tells us that willpower lives in the prefrontal cortex, the brain’s control center for planning and decision-making. But this system is finite, it tires under stress, fatigue, and uncertainty. That’s why forcing yourself through life on sheer effort eventually fails. What sustains you isn’t willpower alone, but willpower with meaning.

Align Your Will to Something Bigger

In faith traditions, we’re taught to align our will with God’s. Through prayer, Bible study, and meditation, we seek to live according to divine wisdom. But even outside of religion, the principle holds: aligning our personal will to a higher purpose, a calling, a cause, a set of core values, fuels resilience in ways brute discipline never can.

Modern psychology calls this value congruence: the alignment between what we do and what we deeply believe. When our actions match our values, motivation becomes renewable. When they don’t, we burn out, no matter how hard we push.

Neuroscience reinforces this: acting in alignment with purpose activates reward pathways and buffers stress responses. Stoic philosophy echoes it too, Marcus Aurelius and Epictetus taught that peace comes not from controlling outcomes, but from aligning one’s will with nature, reason, or Logos.

Across disciplines, the message is the same:

Strength of will is not about domination—it’s about direction.

Clarifying Your Higher Purpose

So how do we bring this alignment into focus? Start by making your higher purpose visible.

• Name it. What do you ultimately serve, faith, family, freedom, growth, contribution?

• Write it down. Purpose gets stronger when you can articulate it clearly.

• Check your alignment. Do your daily decisions and goals reflect that purpose?

When you can see your purpose on paper, your will has something to aim at. You no longer rely on fleeting motivation, you draw on conviction.

Returning to My Father’s Lesson

As I’ve faced new seasons of stress and uncertainty, I’ve realized my father’s phrase, “You gotta want to”, was his simple way of saying: Your will must serve something worthy.

You can’t sustain focus by forcing yourself. You can only sustain it by wanting something big enough to orient your entire life toward it.

So the next time your energy wanes or you feel aimless, ask not just how hard can I push? but what am I aligned to?

Because true willpower isn’t about control, it’s about connection.

And once your will is aligned with purpose, you won’t just move forward. You’ll move forward with meaning.

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