Let Go or Be Dragged

There’s an old saying that goes, “Let go or be dragged.” At first glance, it sounds simple, almost flippant. But the truth embedded in those words is anything but easy to embrace. Letting go is one of the hardest lessons we face in life. Whether it’s a job, a relationship, or even an identity we’ve outgrown, knowing when to leave is an art and science

And yet, if we don’t heed the gentle tugs telling us it’s time to move on, we risk doing harm—not just to ourselves, but to the people and spaces around us.

I know this lesson intimately. While at Vista Academy, I poured everything I had into transforming the school. I led renovations that gutted bathrooms, cleared out hoarded storage spaces, and reimagined the physical environment for the community. It was intense, emotional work—tearing down what no longer served us and building something better in its place. But when all the physical changes were complete, I noticed something unsettling: I was still deeply triggered by the smallest imperfections—a pencil scribble on a desk, a vandalized wall poster or a broken chair. These things gnawed at me because they felt like insults to the immense effort I had poured into creating what was now the new standard.

No one else was triggered in the same way.

The growing body of students and staff weren’t there for the late nights of demolition or the painstaking decisions about every detail. They didn’t carry the same emotional investment in what the space had become because, for them, it had always been that way. There was no general calculus of the opportunity cost of spending time at work instead of at home. My over-investment began to manifest as frustration and overreaction, and I realized that by holding on so tightly, I was doing more harm than good. My inability to let go of my emotional ties to the work risked undermining the very community I had worked so hard to support.

Overstaying—whether in a job, a relationship, or a phase of life—rarely serves anyone.

When we hold on too long we hurt the people we care about, the organizations we love, and the communities we’re a part of. Our toxic parts—the parts of us that are frustrated, resentful, or simply depleted—start to leak out. We lose the ability to show up as our best selves, and in doing so, we risk eroding the very things we worked so hard to build.

This is where self-awareness becomes critical.

Self-awareness is more than just recognizing that something feels off; it’s about identifying the source of that feeling. Are you experiencing decision fatigue, emotional disconnection, or the physical toll of stress? Are you clinging to something out of fear, habit, or misplaced loyalty? When we develop the language to describe what’s happening—when we move beyond vague phrases like “I’m just tired” to specific insights like “I’m drained because I feel unappreciated”—we take back control. Language gives us clarity, and clarity is power.

Leaving when the time is right is an act of love.

It’s a way of preserving the good that we’ve created and protecting the people we’ve invested in. It’s about recognizing that our presence—when it’s no longer fueled by purpose or alignment—can do more harm than good. And it’s about trusting that by letting go, we create space for something new to emerge.