I’ve sat across from countless leaders over the years—some at the pinnacle of their careers, radiating confidence and success, and others in those quiet, dimly lit corners of defeat. While we love to celebrate the victories (and rightfully so!), the unspoken reality of leadership is that disappointment isn’t just possible; it’s inevitable.

When a leader sits before me, shoulders slumped under the weight of a vision that didn’t come to pass or a betrayal they never saw coming, my heart breaks a little. I know that weight intimately. I’ve carried it myself. But I also know that this moment, heavy as it is, holds a profound invitation for growth that success simply cannot offer.

In mentoring, our role isn’t just to cheerlead the wins. It’s to sit in the ashes with someone and help them find the embers that are still glowing—and trust me, they’re always there.

The Silent Weight of Leadership Disappointment

Disappointment in leadership is a unique kind of pain. It’s rarely just about a failed project or a missed quarter. For most leaders I know, our work is deeply woven into our sense of calling and identity. When things go sideways, it doesn’t just feel like a professional setback; it feels deeply personal. It can feel like a complete disorientation of the soul.

When I mentor leaders walking through this valley, I understand the temptation to hide it. We feel we need to keep that “brave face” on for our teams, our boards, and even our families. But here’s the thing—hiding disappointment only allows it to fester into bitterness or cynicism.

The Ministry of Validation

One of the most powerful things we can do as mentors is simply to validate the pain. Sounds simple, doesn’t it? Yet, leaders are so often told to “shake it off” or “pivot” that they rarely get permission to just say, “This hurts like hell.”

When a leader tells me about a key staff member leaving or a strategy that flopped spectacularly, I don’t rush to fix it. I don’t immediately quote Romans 8:28, even though I believe it with every fibre of my being. First, I say, “That must be incredibly hard. I’m so sorry.”

Validation is the first step toward healing. It acknowledges that the loss is real and raw. It tells the leader that their feelings aren’t a sign of weakness, but a beautifully human response to a broken situation. By validating their pain, we create a safe harbour where they can drop anchor, stop drifting, and just breathe.

Moving from Lament to Learning

However, we can’t stay in the harbour forever. There comes a time when we must help the leader lift their eyes from what was to what could be. This is the delicate pivot from lament to learning—and it requires both wisdom and impeccable timing.

Disappointment has a way of revealing our foundations. It strips away the superfluous and forces us to ask those hard questions:

• Was my identity tied too tightly to this outcome?
• What can I learn about my own leadership style through this mess?
• Is there a character issue God is trying to refine in me?

I often tell the leaders I mentor that God is the great Recycler. He wastes absolutely nothing. The pain you’re feeling today? That’s the raw material for the wisdom you’ll share tomorrow.

This isn’t about toxic positivity or pretending the failure was “good.” It’s about stewardship. How will you steward this disappointment? Will you let it harden you, or will you let it soften you, making you more empathetic and resilient?

Reframing the Narrative

One of the most critical skills we can teach is reframing. When we’re in the thick of it, our perspective shrinks dramatically. We see only the immediate loss. As mentors, we have the privilege—and responsibility—of holding the long view.

I think of those great cathedral builders of centuries past. Many of them laid foundations for structures they knew they would never see completed. They lived for a vision bigger than their own lifespan. Now that’s what I call faith in action.

When I help a leader reframe their disappointment, we look for the long arc of God’s faithfulness. Maybe this “no” is protection from a danger we can’t see. Maybe this closed door is steering us toward a path where we’ll be far more effective for the Kingdom.

Reframing doesn’t change the past, but it drastically changes how we walk into the future. It shifts us from victims of circumstance to active participants in a larger, more beautiful story.

A Call to Honest Resilience

If you’re mentoring someone right now who’s ready to throw in the towel, or if you are that leader feeling the sting of a dream deferred, I want to offer you this hope: You are not finished. Not even close.

Your calling as a leader isn’t to be flawless; it’s to be faithful.

Resilience isn’t about never getting knocked down. It’s about how we get back up—with a limp, perhaps, but also with a new depth of character that only the struggle could produce. The most impactful mentors I know aren’t the ones with perfect track records. They’re the ones who can look you in the eye and say, “I’ve been where you are, and I know the way through.”

Let’s be leaders who don’t just survive disappointment but who allow it to transform us into people of greater depth, compassion, and wisdom. The world desperately needs that kind of leader.

Let’s Go Deeper

This topic is so close to my heart that Chuck, Ingrid, and I dedicated an entire conversation to it. In Episode 43 of the Mentored Podcast, titled “Dealing with Disappointment,” we open up about our own struggles and share practical ways to navigate these choppy waters.

We discuss:

• How to manage the complex emotions of setbacks without suppressing them.
• Practical steps for reframing your narrative.
• How to apply faith when your reality doesn’t match your vision.

I invite you to listen. Whether you need encouragement for your own heart or wisdom to help someone else, I believe this episode will be a balm for your soul.

[Listen to Episode 43 on Apple Podcasts here]

I’d love to hear your thoughts on this vital topic.