Learning to Trust That What Is for Us Will Find Us
Those who regularly read my writing know that I often focus on leadership—particularly the realities of navigating the superintendency and serving in educational leadership roles during extraordinarily complex times.
Over the past several months, I have written about the loneliness of leadership, the weight of difficult decisions, the fragility of trust, the emotional toll of public service, the uncertainty facing schools, and the growing tension that exists within and around public education. These topics remain deeply important to me because they reflect the lived experiences of so many educators and leaders I know, admire, and respect.
But this post is different.
While it is still rooted in lessons learned through leadership, it is ultimately about something much more personal and universal. It is about disappointment. It is about identity. It is about the opportunities we pursue, the ones we lose, the ones we outgrow, and the difficult realization that not everything we want is meant for us forever.
In many ways, this may be the most important leadership lesson I am still learning—not how to acquire opportunities, but how to release them. Not how to force outcomes, but how to trust timing. Not how to hold on tighter, but how to recognize when a season has fulfilled its purpose and the next season awaits.
The challenge is that I understand this lesson far better than I consistently live it.
I can often see the wisdom in it.
I can even offer it to others.
Yet when it comes to my own life, I still find myself looking backward for confirmation of what my future should look like. I still compare what is unfolding to what I once imagined. I still struggle to accept that the next chapter may not resemble the one I had planned.
And perhaps that is why I am writing this.
Because sometimes the greatest growth in our lives begins when we stop fighting for what is leaving and start trusting what is becoming.
The Hardest Part Was Never the Closed Door
For much of my life, I assumed the greatest pain came from losing opportunities.
The position I did not get.
The role that did not materialize.
The path that unexpectedly changed.
But with the passage of another birthday last week, the more I realize that some of my greatest pain has not come from the opportunities I lost.
It has come from my refusal to accept that they were never mine to keep in the first place.
There are moments throughout my leadership journey when the evidence is clear.
My path is moving in a different direction.
New and different opportunities are emerging.
New lessons are presenting themselves.
New seasons are beginning.
Yet part of me remains standing in front of a door that has already closed.
Pulling.
Pushing.
Negotiating.
Trying to convince myself that if I work harder, wait longer, explain better, or sacrifice more, the outcome might somehow change.
I know better.
And yet I still do it.
Not because the opportunity is necessarily right for me.
Not because the season is meant to continue.
But because letting go often feels like losing something I have attached to my identity.
The Cost of Resisting What Is Already Leaving
What I rarely acknowledge in those moments is the emotional toll that resistance takes.
Disappointment is only part of it.
There is pain.
The pain of watching a vision I created for myself collide with a reality that refuses to cooperate.
There is vulnerability.
The uncomfortable realization that no amount of preparation, effort, intelligence, or determination can guarantee a particular outcome.
There is shame.
The quiet fear that perhaps I have somehow failed because the future I imagined, or what I imagine others have imagined for me, is no longer unfolding before me.
And perhaps most difficult of all, there is the loss of identity.
Because leadership has a way of intertwining who we are with what we do and we start to recognize ourselves only in that fashion.
We introduce ourselves through our titles.
We attach meaning to our positions.
We connect our sense of worth to our accomplishments.
And when an opportunity disappears—or a season ends—it can feel as though part of us is disappearing too.
Not because it actually is.
But because we mistakenly believed the role was the source of our identity rather than an expression of it.
I know this.
And still, I struggle with it.
Life Keeps Moving While I Keep Looking Back
One of the most humbling realizations I continue to have is that life rarely stops moving forward.
Even when we do.
And while this reflection is deeply personal, I have come to believe it is not uniquely mine. In conversations with leaders across the country—particularly those who have sat in the superintendent’s seat and even those who occupy those chairs currently—I have discovered that many of us carry similar thoughts, questions, and struggles.
We rarely talk about them publicly.
But they are there.
The opportunities we did not receive.
The roles we thought would be ours.
The districts we imagined leading.
The careers we envisioned for ourselves.
The versions of success we carefully constructed in our minds.
For many leaders, especially those who have served in the superintendency, there are moments when we find ourselves looking backward while life continues moving forward.
While we are grieving one opportunity, another is quietly emerging.
While we are focused on the door that closed, another path is already opening.
While we are questioning what we lost, we are simultaneously becoming someone we could never have become had everything unfolded according to our original plan.
Yet many of us miss that.
Not because we lack gratitude.
Not because we lack perspective.
But because we are human.
We compare the future to a version of the past.
We measure what is emerging against what we expected.
We evaluate new possibilities through the lens of old ambitions.
We try to determine whether the next chapter looks enough like the one we thought we wanted.
And in doing so, we sometimes fail to appreciate what is actually being offered.
I suspect many former and current superintendents understand this feeling intimately.
After all, leadership often requires years of sacrifice, relentless commitment, and a willingness to tie ourselves to a mission larger than ourselves. When a chapter ends unexpectedly—or when an opportunity never materializes—it can feel like more than a professional disappointment.
It can feel personal.
Because what we are releasing often represents years of effort, aspiration, sacrifice, and hope.
Growth requires release.
But release is difficult when the thing we are letting go of once meant so much.
And perhaps that is why so many of us struggle with it.
Not because we do not know better.
But because some parts of our hearts are still trying to hold onto what our minds already know has passed.
Some Things Are Meant for a Season
One of the hardest truths I continue to wrestle with is that not everything that is good for us is meant to remain with us forever.
Some opportunities are seasonal.
Some relationships are seasonal.
Some roles are seasonal.
Some versions of ourselves are seasonal.
There are positions I once wanted desperately that, had I received them, might have taken me away from experiences I now value deeply.
There are chapters of leadership I fought to preserve that, in hindsight, had already taught me everything they were meant to teach.
There are opportunities I still occasionally revisit in my mind, even though I know they no longer align with who I am becoming.
The season changed.
I simply was not ready to accept it.
And perhaps that is the deeper lesson.
Not every ending is a failure.
Sometimes it is simply completion.
The Difference Between Ambition and Attachment
There is nothing wrong with ambition.
Ambition has carried many of us through extraordinary journeys.
But attachment is something different.
Ambition says:
“I will pursue this opportunity with excellence.”
Attachment says:
“I cannot be okay unless I get it.”
Ambition fuels growth.
Attachment creates suffering.
Because attachment convinces us that a particular outcome is necessary for our happiness, our success, or our identity.
And when life moves differently than we expected, attachment makes us feel as though we have lost ourselves.
When in reality, we may simply be losing a version of ourselves that we have already outgrown.
The challenge is that I often recognize the difference only after the struggle has already begun.
What I Am Learning
Today, I am learning—sometimes reluctantly, sometimes stubbornly—that not every opportunity requires me to fight for it.
Sometimes the most courageous thing a leader can do is release.
Release the title.
Release the plan.
Release the timeline.
Release the expectations I place on myself and the expectations I imagine others have of me.
Release the version of the future I carefully constructed in my mind.
Not because I have given up.
But because I am trying to trust that my purpose is bigger than any single opportunity.
The truth is that I still struggle with this lesson.
I still look backward.
I still compare.
I still wonder.
I still revisit old ambitions and old definitions of success.
I still occasionally grieve things I know are no longer meant for me.
But I am beginning to understand that letting go is not a single decision.
It is a practice.
A continual choice to release what no longer serves us.
A continual choice to trust what we cannot yet see.
A continual choice to believe that our future does not have to resemble our past to be meaningful.
The truth is that many of the things I have fought hardest to keep were never intended to remain forever.
They were chapters.
Important chapters.
Meaningful chapters.
Necessary chapters.
But chapters nonetheless.
And had they remained, I might never discover the next part of the story.
I might never become the person I am still being shaped into.
I might never be open to the wonder, growth, and possibility waiting on the other side of letting go.
Perhaps that is the lesson I am still learning.
Not everything we lose is meant to be recovered.
Not everything that ends is meant to be restarted.
Not everything we want is meant to stay.
And sometimes the greatest act of faith is believing that what lies ahead can be more beautiful than anything we are still trying to hold onto behind us.
