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The Art of Careful Leadership: Lessons from the Principal’s Chair

The Art of Careful Leadership: Lessons from the Principal’s Chair

When I was pursuing my leadership certification, a professor said something that has stayed with me all these years: “It’s lonely at the top.” At the time, I swore it wouldn’t be lonely for me. I had a vision of leadership rooted in connection, compassion, and authenticity. I promised myself I would lead differently—by cultivating meaningful relationships with my staff, building trust, and creating a school community where everyone felt seen, heard, and supported.

And for a time, I believed I had succeeded.

But now, five years into the principalship, I see things with clearer eyes. The relationships I thought were mutual often turned out to be one-sided—me giving, others taking. I extended grace, offered support, gave time, shared resources, and made myself available far beyond the call of duty. I prided myself on being approachable and invested in the wellbeing of my staff. But when a personal and professional crisis hit, the support I had hoped would be reciprocated never came. Instead, I was met with silence, distance, and, in some cases, disappointment.

It’s only in times of crisis that we truly see people’s colors—the good, the bad, and the deeply disheartening. And once you’ve seen it, you can’t unsee it.

So now the question becomes: How do I move forward?

Here’s what I’ve learned, and what I would say to any new leader stepping into this work with an open heart and noble intentions:

Don’t Assume Others Share Your Moral Compass
It’s easy to project your values onto others, especially when you're in a leadership role that demands high standards. But people will show up with their own beliefs, motivations, and moral codes—and they won’t always align with yours. That doesn’t make them bad people; it just means you need to navigate those differences wisely.

Prioritize Relationships, But Set Boundaries
Relationships are at the core of effective leadership, but they must be rooted in mutual respect and balance. Support your team, but don’t lose yourself in the process. Boundaries are not walls—they are the lines that protect your energy, your vision, and your ability to lead with clarity.

True Relationships Are a Two-Way Street
Giving is part of leadership, but giving without receiving leads to burnout and disillusionment. Healthy relationships—professional or personal—require reciprocal energy. If you’re always the one reaching out, checking in, or bending over backwards, it’s time to re-evaluate the dynamic.

Be Compassionate, Not Codependent
Compassion is the foundation of strong leadership, but it can’t come at the expense of your own well-being. Leaders are not saviors. You are not required to carry everyone’s burdens. Support where you can, but empower others to carry their share of the load.

Grow Through the Discomfort
Painful experiences offer clarity. They teach us who’s in our corner and who’s only there when it’s convenient. Let those lessons shape your leadership, not harden your heart. Growth comes when we choose wisdom over bitterness.

Leadership can still be a space of connection and heart—but only when we lead with intention and integrity, and protect ourselves along the way. It’s not about building walls, but about knowing who and what deserves to be let in.

To those stepping into this role: lead with love, but don’t forget to lead yourself with the same care.

photo by Nick Fewing via unspash- Ai assisted

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