Starting Over Is Not Failure

April 18, 2026

Story

There was a time in my life when I would have looked at starting over and seen it as a loss.

A step backward.
A sign that something did not work out.
A quiet kind of failure.

But life has a way of teaching us what success alone never can.

After nearly 30 years in public education, including the last five as superintendent, I made the decision to leave a role that had defined so much of my professional life. School leadership is for the faint of heart. The responsibility of leading people in a school organization–students, parents, teachers, other school leaders, tax payers, board members–is immense. But I thrived in the environment. Until I didn’t. It was not a decision I made lightly. Titles like that do not come quickly. They are built over years of hard work, long days, sacrifice, and commitment. 

When you have spent so much of your life climbing, it can be difficult to imagine what it means to step away. And yet, deep down, I knew I was being called to something different.

What followed was not neat or easy. Some parts of my life were shifting in ways I never would have chosen. I was carrying the weight of change, loss, uncertainty, and questions I could not yet answer. There were moments when I wondered whether I was unraveling something I had worked so hard to build.

But what I could not see then, I can see more clearly now:

Starting over is not failure.

Sometimes it is courage.
Sometimes it is surrender.
Sometimes it is the first honest step toward the life you were meant to live.

We live in a world that teaches us to value achievement. We are taught to keep climbing, keep producing, keep proving. And for many of us, our identity quietly becomes tangled up in what we do, how we are seen, and how well we perform.

We become the title.
The role.
The reputation.
The one who holds it all together.

Until one day, life asks a deeper question:

Who are you when the title changes?
Who are you when the role ends?
Who are you when the life you planned no longer fits?

Those are not easy questions. In fact, they can feel disorienting. But they can also be clarifying questions. Because sometimes, what feels like an ending is really an invitation. An invitation to return to yourself. To return to God. To return to the parts of your life that were waiting patiently beneath all the striving.

Reflection

For me, starting over did not just mean changing jobs. It meant reimagining what it meant to live with integrity and faith. It meant trusting that peace mattered more than prestige. It meant believing that even after heartbreak, life could still hold beauty. It meant opening my heart again and discovering that love can find us, even after seasons that leave us wondering if it ever will.

None of that happened all at once. And none of it came without pain.

Finding a new role in school leadership in a Catholic setting was unexpected, but so fulfilling. Returning to my roots, the familiarity of my own Catholic education felt like the comfort of long forgotten safety that I didn’t know I lost. The most fulfilling of my days in this new role has been sitting in chapel mass with some of my students and marveling at the reality of this new opportunity. 

Finding an amazing partner was also unexpected. Since meeting we’ve referred to that day as Amor Fati–a Latin phrase popularized by philosopher Friedrich Nietzsche that “represents the mindset of not merely accepting, but embracing and loving everything that happens in life—good, bad, or painful—as necessary, purposeful, and fuel for growth.”

But that is often how second beginnings work. They do not usually arrive with a trumpet blast and a perfect plan. They arrive quietly. Through a nudge. A discomfort you cannot ignore. A truth you can no longer deny. A door opening where you did not expect one. A strength you did not know you had.

And if we are brave enough to say yes, those beginnings can change us.

Not because they erase the past, but because they redeem it.

I think many of us reach a point in life when we realize that achievement alone cannot sustain us. Success may look good on paper, but eventually we begin to ask different questions. Questions about meaning. About peace. About purpose. About who we are beneath the resume, beneath the image, beneath the expectations.

That is not weakness.
That is wisdom.

There is humility in beginning again. There is vulnerability in laying down what is familiar and stepping into what is new. But there is also freedom.

Freedom to stop pretending.
Freedom to stop performing.
Freedom to choose a life that is more aligned, more grounded, more true.

Maybe starting over in your life does not look dramatic. Maybe it is not a career change or the end of a relationship or some visible reinvention. Maybe it is quieter than that.

Maybe it is finally setting a boundary.
Maybe it is healing from something you have carried for too long.
Maybe it is letting go of the version of yourself that was built for survival, and stepping into the one built for wholeness.
Maybe it is allowing yourself to believe that your story is not over yet.

Because it is not.

There is something deeply hopeful about second beginnings. Like the line from one of my favorite songs, Closing Time: Every new beginning comes from some other beginning's end…”

They remind us that we are not finished just because one chapter ends. They remind us that God is always at work, even in the unraveling. They remind us that the most meaningful parts of our lives are not always found in the climb, but often in the surrender that follows.

So if you are in a season of starting over, I hope you will resist the urge to label it as failure.

Maybe this is not the end of your story.
Maybe this is the place where your truest life begins.
Maybe this is not falling apart at all.
Maybe this is becoming.

Question

What part of your life might be waiting for a second beginning?

Until next Saturday, choose presence.