Hold on Tight to Optimism

Friday Reflection (No.87)

“Look around, look around
at how lucky we are to be alive right now…
Look at where we are, look at where we started…
the fact that you’re alive is a miracle.”
-That Would Be Enough from Hamilton the Musical

There are times when I need to hear this song more than others, because even in the darkest moments, these lines are true - we are lucky to be alive right now.

The challenge is that our brains and our culture are wired to fixate on the negative. Moreover, we allow the inevitable suffering of life to create layers of mental and emotional scar tissue that can exacerbate this tendency towards disillusion.

And yet in this current period of hyper polarization, the world needs leaders that inspire us to hold on tight to optimism (while still acknowledging the seemingly intractable challenges of this moment).

Leadership Principle: Disillusion, cynicism and inaction are the easy path. Optimism is hard. Choose optimism. Choose action.

In my life, one event, perhaps more than any other, had a profound disillusioning effect on me. What’s surprising is that it is also tied to the person who taught me the most about optimism.

For over a decade, I was actively involved in the Cuban-American community. My passion for youth empowerment and a shared vision with like-minded Cuban Americans led me to support Cuban youth in shaping their own future.¹ After a year or two of working on efforts from the U.S., I felt a pull to travel to Cuba. I wanted to see the reality of my heritage with my own eyes. Not just as portrayed by the media or by family who had left, but to understand the multiple “true” narratives that could only be uncovered by spending time with relatives who still lived there and others ranging from artists to barbers to basketball players.

On my second trip, I met Harold, a Jesuit priest and pro-democracy advocate just a few years older than me. Our first meeting in the city of Camaguey stretched into late-night hours - conversation ranged from his dreams for Cuba, his life’s hardships under a communist regime, and his faith. Surprisingly, we also bonded over a shared love for U2, which led to Harold singing “I Still Haven’t Found What I’m Looking For” as we sat in a plaza near a public fountain.² His quiet conviction and unshakable belief in the potential of our people gave him a magnetic presence that I will never forget.

Harold and me in 2008

Over the years, I returned to Cuba a few more times to learn from Harold. Despite the hardships he faced, he spent every day trying to improve the lives of others.

Then, one day, I received a call that still haunts me: Harold had been killed in a car crash, which was seemingly engineered by state operatives targeting him and another pro-democracy leader. The loss was devastating, and the disillusionment that followed was acute.

For years, I told myself that increased work and family demands were why I withdrew from more formal activism. And while that certainly contributed, when I hold up a mirror, the reason was far more personal: Harold’s death left me questioning whether purity of purpose and courage could make a big enough difference in a world that often rewards cynicism, greed and oppression.

Yet, Harold’s example continues to inspire thousands of activists on the island and abroad. In a different way, it also inspires me daily. Though I’ve yet to fully regain the fervor I once had, his courage and unwavering belief in the power of hope shape how I approach my work with leaders from all walks of life. Whether supporting them to navigate challenges or to inspire their teams, I carry the lessons I learned from Harold with me.

And when I catch myself in moments of pessimism, I return to a book of poems he gifted me during what would be my last visit with him. One line from Dulce Maria Loynaz, a favorite of ours, embodies Harold’s resilient optimism:

“I will be like the river that tumbles and crashes,
leaps and twists,
winding its restless path...
But it reaches the sea!”

I share Harold’s story because, like many, I’ve recently felt the seductive pull of pessimism. Optimism feels scarce, and there is inertia toward cynicism and self-protection. But Harold’s legacy reminds me—and perhaps can remind you—that even in the bleakest of circumstances, we have a choice: Optimism or pessimism; action or inaction.

For most of us, choosing optimism does not need to mean pursuing social justice in every waking moment. In fact, that doesn’t feel like what we need right now.

I’d love to see more leaders that embody Harold’s spirit of temperance and hope, and then take action in big and small ways to ignite optimism in others.

Take Action: Practical and Proven Steps

1. Fortify yourself with optimism and empathy. Put together a list of quotes, stories, poems, songs and other works of art that can pull you out of pessimistic thinking. Spend more time with pragmatic optimists. Moreover, ensure you also spend time seeing the world through lenses of people that you disagree with, so that your optimism does not feel detached from their reality. An old short story by Frank Harris called Magic Glasses is a beautiful allegory for the power of seeing the world through different lenses. (I’ve also written another reflection The Superpower of Skeptical Optimism.)

2. Role model optimistic temperance. As you tackle the next inciting incident in the world or respond to employee activism, focus on the needs of those you lead - demonstrating a service mindset and actively listening to concerns. Once you’ve decided on a course of action, accept that there will be subsections of your employee population that will be disappointed with what you’ve communicated and/or the path you’ve chosen. Don’t let this disappointment cause you to fall into self-righteous defensiveness or worse, to be wishy washy about the optimistic tone you are aiming to set.

3. Prepare for optimistic responses in the face of outrage. A recent interview of Karthik Ramanna outlines principles, mindsets and practical actions to help us lead in the “Age of Outrage.” One such practical action is to designate small committees during the “calm,” so that when an outrage event erupts, they are ready to help outline a path forward for your organization.

Reflect: Some Questions to Consider

1. In moments of disillusionment, what practices or sources of inspiration help you choose optimism and action over pessimism and inaction?

2. Who in your life has shown you the power of optimism, and how might their story inspire your own path forward?

3. What small actions could you take this week to role model optimism?

If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.

1. Several of us co-founded an organization called Raices de Esperanza. Many of these people became close friends - like brothers and sisters. And now nearly two and half decades after its founding, it’s inspiring to see the impact that all of these hermanos have had on the world in spheres ranging from politics to film and from engineering to art.

2. Admittedly I couldn’t help but sing along with him.