Disappointment

“In life, you are going to disappoint people. You will not be able to be everything to everyone. But it's not only that! You will also not be able to be everything to people you care about. You will try to be reliable and available, and sometimes you will fail.” ~ Chris Guillebau, author of Time Anxiety

My response when I read this in a recent Susan Cain post was ‘Oof - that’s a bit of a gut punch’! Cain goes on to make the point that the more people we know - the more potential there is for disappointment. “Each person has a reasonable expectation of connection, but the math simply doesn’t work out. Time is finite. Attention is limited.”

There’s a part of many school leaders—especially those who care deeply—who want to be everything to everyone: Supportive to staff. Responsive to parents. Visionary to the board. Compassionate to students. Balanced at home.

But here’s the truth: trying to please everyone is a fast track to burnout—and ultimately, to disconnection from your own purpose.

You will disappoint someone. That’s part of the job.

• You may disappoint a parent by upholding a policy.

• You may disappoint a staff member by making a difficult personnel call.

• You may disappoint your team by setting a boundary or saying no.

And sometimes, you’ll disappoint yourself by not speaking up, not resting, not aligning with your own values.

Disappointment isn’t failure! There’s a difference between disappointing someone and failing them. One comes with the territory of leadership. The other comes when we abandon our principles to avoid conflict.

Part of maturing as a leader is accepting that disappointment isn’t a sign that you’ve done something wrong. Often, it’s a sign that you’ve done something right—that you’ve chosen direction over popularity, clarity over comfort.

This isn’t easy. Especially in education, where so much of our work is relational. But boundaries, honest communication, and aligned decisions are some of the most loving things we can offer.

So the next time you’re at a crossroads—when a decision is sure to upset someone—pause and ask:

If I say yes to this, what am I saying no to?

If I protect someone else’s comfort, do I risk betraying my own values?

Leadership is full of trade-offs. But don’t trade off your integrity, your mission, or your well-being for the illusion of harmony.