Leading with a heavy heart

Disbelief, discouragement, and grief are plaguing our nonprofit sector this January. The days are shorter, the sun seems to come and quickly go, and the world feels heavy in ways we can’t ignore. Changes in government policies are already rippling through the communities we serve, natural disasters keep us awake at night and glued to our screens, and the challenges we face—personally and professionally—often feel relentless.

In times when I feel unmoored, I find myself leaning on the wisdom of two individuals I’ve studied over my leadership journey and continue to admire: Admiral James Stockdale and Fr. Gregory Boyle. They come from vastly different worlds—one a decorated naval officer and Vietnam POW, the other a Jesuit priest and founder of Homeboy Industries. When I find myself in a season of heavy-hearted leadership, I call upon the lessons I’ve learned from these two leaders. These lessons provide a path forward when the weight of the world feels unbearable. I hope they do for you as well.

Confront the Brutal Facts

Admiral Stockdale endured seven years of brutal captivity during the Vietnam War. He survived through what’s now known as the Stockdale Paradox:

"You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be."

What are the brutal facts of your current reality? Have federal funds suddenly and without cause been “paused” for the children and families you directly serve? Has someone recently resigned from your already small team, and now you’re struggling to find talent? Has a key donor shifted priorities without warning? Are you parenting teens and tweens in this digital age with no roadmap? Are you caregiving for an aging parent while maintaining a full-time leadership role? Are you grieving the death of a loved one? Are you worried about your neighbors, colleagues, family, and friends for any number of reasons? We live in a broken world. These are brutal facts.

Have you ever worked with someone who consistently pretends everything is fine? It can be exhausting. Denial doesn’t serve us, especially as leaders. We need to name what’s hard—honestly and courageously. Whether it’s staff burnout, funding cuts, administrative changes, or personal struggles, confronting reality is essential. It makes people feel seen, and acknowledging our own pain helps us move forward.

Stockdale reminds us that facing the truth isn’t a sign of weakness but rather the foundation of resilience. In the Gospel of Matthew, even Jesus himself said, “Come to me, all you who are weary and burdened, and I will give you rest.” He didn’t say, “Stop complaining!” He said to come to Him because He acknowledges our weariness and burdens.

Have you done this for yourself this week? Have you done this with your team?

Verne Harnish wrote a guide that I referred to often while leading an organization during the COVID-19 pandemic. He calls it The Five C’s of Crisis. His first C? Communication. Daily. Hold a team huddle, staff meeting, or record a video and send it. It might say something like this:

"I know the weight of everything around us feels hard right now. It certainly does for me. I want you to know I see you and value you, and I acknowledge the realities we are facing together.”

Next, avoid jumping to silver linings or forced optimism. Instead, shift toward what’s possible. Don’t sugarcoat it or gloss it over.

“While the hard might remain, here’s what we know about where we are, what we don’t know yet, and what we’re going to do to figure it out.”

Give your team something to anchor themselves in for the future—small possibilities.

This leads us back into hope.

Don’t Stop Believing

Stockdale’s words remind us that hope is not a passive feeling or blind optimism. It’s the ability to face the hard truths of the moment and then keep holding onto the belief that you will make it through.

Fr. Gregory Boyle, founder of Homeboy Industries—the largest gang rehabilitation and reentry program in the world—takes this a step further. He reminds us that hope isn’t just a belief, it’s practice. He says:

"The feeling of hope always disappoints me; the habits of hope sustain me."

Boyle’s work is grounded in this idea. At Homeboy Industries, hope is built through action: offering kinship, job training, healing, and second chances to people who might otherwise be discarded by society. He meets people where they are, acknowledges their pain, and walks alongside them as they build something new.

What are the small, tangible things you can do to sustain hope, not just for yourself, but for your team?

These habits might include:

• Rest and reflection: Take a clarity break. Step away from the noise, particularly on social media, to recharge. See Cal Newport’s book Digital Minimalism as a guide.

• Prayer practices: Seek out the Creator for sustaining strength and courage to continue.

• Complete the stress cycle: The research is clear—getting outside gets us out of our heads. Get some exercise, outdoors whenever possible.

• Radical transparency: Be honest with your team about challenges and invite them into problem-solving.

• Kinship and connection: Build trust, one conversation at a time. Recognize humanity in each person you lead and invite them to recognize it in each other. Spend extra time in community.

• Small wins: Focus on what is possible, even when big solutions feel out of reach.

Remember that staff huddle you’re going to host or email you’re going to send? The next part goes like this:

“We’ve faced hard things before, and we’ve made it. We will again. Don’t stop believing. And thank you for being a part of this journey.”

Invite your team to commit to building habits of hope. Give them the strategies outlined above plus your own that will build confidence and culture as you move forward, together.

Take Care, Lead Well, Keep Going

Leadership is hard. And leading when the world feels heavy? That’s even harder. But I see you. I see the weight you’re carrying, the decisions you’re making, and the heart you’re bringing to the work.

You are not alone.

As Stockdale teaches us, face reality with unflinching honesty. And as Boyle reminds us, sustain hope through daily habits. In times of uncertainty, both courage and hope are choices we make—not just once, but over and over again.

If you’re looking for more resources on leadership and coaching, visit my website: www.aftondevosconsulting.com.

And if you haven’t yet read Tattoos on the Heart by Fr. Gregory Boyle, Good to Great by Jim Collins (especially the story of Admiral Stockdale), or Digital Minimalism by Cal Newport, consider adding them to your list. They’ve been invaluable to me, and I hope they will be to you as well.

Take care, lead well, and keep going.