What Prison Taught Me About Leading in Crisis

Every leader faces moments that test one’s ability to remain steady under pressure — and they never arrive with instructions for what to do next.

As a young man, I experienced a personal setback that was extreme and defining. I went to prison after making a decision rooted in rage and grief. At 20 years old, overwhelmed by anger and a misplaced sense of justice, I killed my then-girlfriend’s rapist. I entered Sing Sing prison at 21 years old, facing a sentence that would keep me there for most of my young adulthood.

I didn’t fully know it, but the next 16 years of my life would be a time of near-constant uncertainty, danger, challenge — and opportunity. It turned out to be my training ground for nonprofit leadership.

When I was released in 2008, I came home determined to build a life — and help build organizations that make a tangible difference in the lives of others. Today, I lead a global nonprofit based in the United States that puts out-of-school, out-of-work young people on the path to education, job training, and success.

This work is complex, the stakes are high, and the conditions are rarely stable. I am not alone; the same is true for many executives in our sector.

Here’s what I’ve learned throughout my life and career about leading with strength when certainty is unavailable — and why those lessons matter for all nonprofit executives.

Serious leadership starts with accepting reality.

Denial is dangerous. You cannot negotiate with facts, and you cannot build a future by pretending circumstances are different than they are. Work within the truth of your situation.

From the beginning of my prison sentence, I made a choice that would define everything that followed: I would not minimize what I had done, and I would not spend my life trying to outrun it. I accepted responsibility without excuses and committed myself to making amends.

Radical honesty is imperative: acknowledging what your budget can actually support, what your team can reasonably carry, and what your external environment will tolerate.

Organizations falter when leaders soften hard truths or overpromise certainty they cannot deliver. Radical honesty is imperative: acknowledging what your budget can actually support, what your team can reasonably carry, and what your external environment will tolerate — whether or not those limits are convenient. 

Accepting reality does not mean lowering your standards. It means setting honest expectations rooted in the conditions your team is actually working in. When decisions are tough to swallow, explain your reasoning and hold yourself to the same standards you expect of others.

Smart leaders prepare for every scenario far ahead of time, before the pressure rises. So build plans — lots of them — that take setbacks into account. And never let high emotions harm the relationships you have with your team. Those are some of the most valuable assets you have.

Long-term change requires long-term thinking.

Prison forced me to think in years — not days, not weeks, or even months. It taught me that progress rarely comes from sudden breakthroughs. It comes from discipline, routine, and sustained effort under constraint. 

My prison experience changed when I finally stopped focusing on legal appeals or changes in policy as my way to get home sooner. I embraced the worst-case scenario for my particular sentence and freed myself up to focus on being the person I wanted to be.

When you are looking down a long road, urgency is not always your friend. What truly sustains a leader is clear direction based on values, and the grit to do unglamorous work over time. It’s sheer commitment.

Measure progress in skills built, not just outcomes achieved.

Measure progress in skills built, not just outcomes achieved. Long-term problems demand patience and the courage to stay focused when progress feels slow. Think of it as a strategic plan for yourself as an individual, not just for your organization.

For executives, this often requires protecting core work from constant pivots, or resisting the urge to overcorrect based on short-term signals. Maintaining the right culture, for example, is vital. Stick with the vision. And remember: Communicate repeatedly, to various stakeholders, about why the long view matters. Look ahead five or 10 years and ground yourself in what will still be true — what needs will surely still exist, and how can you align your organization to meet them?

Be a perpetual student.

Education is survival. I studied because learning expanded my sense of possibility and equipped me with the tools I would need long before I knew exactly why I would need them.

Inside prison, I taught fellow inmates to read and write and helped them access high-school equivalency instruction and programs that offered alternatives to violence. I developed a project that provides college-level certificates in ministry and human services to the incarcerated, and I co-founded the first privately funded and accredited college program in New York’s prisons. 

While serving my sentence, I came to realize that in order to survive — both inside and out, during and after — my life’s mission must be to open doors of opportunity for those who need it.

Effective leaders remain students of their work, their teams, and themselves. They seek out perspectives that challenge their assumptions, spend time with people closest to the work, and treat lived experience as seriously as formal expertise. They invite feedback and reflect on failure — especially their own — as carefully as they celebrate success. Leaders who stop learning become disconnected from the realities on the ground.

Staying reflective and willing to adapt is a responsibility. It requires carving out time to listen, read, ask hard questions, and change course when the evidence demands it. 

My dedicated morning routine, for instance, started in prison and continues to this day. It includes a spiritual reading, a learning lesson (on a business concept, for example), meditation, and journaling. It is dedicated time for myself, which sharpens the strategic thinking I need for the rest of the day.

Your vulnerability is your strength.

Suppressing your fear or uncertainty does not make those feelings disappear — it just makes them harder to manage. And when you’re leading a social-change organization, it’s vital that you share your humanity with your team and give them permission to bring their full selves to work.  

Encourage your team to share their worries, but also make sure there’s room to share the positives. Talk about your families, the books you’re reading, the things that matter outside the office. It clears a path for honest, valuable feedback.

When connecting with my CEO peers, I’m reminded of my purpose and that I am not alone.

There is a phrase I return to often: Everything is happening exactly as it needs to for the highest good. For me, this is not about complacency or passivity. It is a forward-looking discipline. It allows me to stay grounded in moments of disruption, absorb uncertainty without amplifying it, and respond rather than react. Leaders must be able to hold complexity, pain, and ambiguity, then distill it for their teams into clarity and forward motion.

Community sustains me in times of opportunity and challenge. When connecting with my CEO peers, I’m reminded of my purpose and that I am not alone. That gives me courage for the road ahead and valuable perspectives that put much of this effort in context. That grounding makes me a better leader and a more responsible steward of the work.

And in stressful times, do not discount the value of finding community with your team. A foundation of trust underpinning you and your staff determines whether people stay engaged, even when the path isn’t immediately clear.

When leaders stay true to themselves, commit to growth, and think long term, institutions don’t just endure. They do the work they were built to do.