The Manager and the Sea: Navigating Leadership’s Loneliest Moments

Leadership often feels like a solitary journey. Whether you’re guiding a team through uncharted waters or making decisions that impact others’ livelihoods, the weight of responsibility can feel as vast and unyielding as the open sea. Ernest Hemingway’s The Old Man and the Sea offers profound insights into the solitude and resilience required in leadership — a reminder that even the loneliest battles can be meaningful.

Santiago, the aging fisherman at the heart of the story, faces days of isolation on the ocean, struggling to reel in a giant marlin. His battle is not just physical but existential. He wrestles with his own doubts, the judgment of his village, and the forces of nature. As I reflect on my journey as an engineering manager, I see parallels between Santiago’s fight and the quiet struggles leaders face daily.

Here are three key lessons Santiago’s story offers to those navigating the lonely seas of leadership.

1. Solitude Is Part of the Job, but It Doesn’t Define You

Santiago’s isolation is not a punishment; it is a natural part of his vocation. As leaders, we often find ourselves making decisions alone — balancing competing priorities, managing conflict, or addressing underperformance. These moments can feel isolating, but they are also opportunities to demonstrate clarity and courage.

However, solitude doesn’t mean abandonment. Just as Santiago has the boy, Manolin, cheering for him from the shore, leaders need allies. Cultivate relationships with peers, mentors, or trusted colleagues who can provide perspective and support. Solitude may be unavoidable in the moment of decision, but it doesn’t have to be a permanent state.

2. The Struggle Itself Is Noble

Santiago’s battle with the marlin is grueling, but it gives his life purpose. “A man can be destroyed but not defeated,” he says — a sentiment that resonates deeply in the world of engineering and tech leadership. Whether you’re untangling technical debt, mediating team conflicts, or trying to ship a high-stakes project, the struggle often feels endless. Success isn’t guaranteed, and sometimes, like Santiago, we come back with only the skeleton of our efforts.

But it’s the fight — the commitment to doing what’s right, even when it’s hard — that defines great leadership. Recognize the value in the effort itself, and take pride in the process, even if the outcome isn’t what you hoped for.

3. Respect the “Marlin” and the “Sea”

Santiago’s respect for the marlin and the ocean reflects a deep understanding of his place in the natural order. Similarly, as leaders, we must respect the challenges we face and the systems we navigate. The “marlin” might be a complex technical problem, an ambitious business goal, or an interpersonal conflict. The “sea” represents the broader organizational or market context in which we operate.

Respect doesn’t mean passivity; it means approaching challenges with humility, curiosity, and adaptability. Instead of viewing obstacles as enemies, see them as worthy opponents that push you to grow. This mindset helps transform frustration into resilience.

Finding Meaning in the Quiet Moments

Santiago’s journey reminds us that leadership is often a quiet, unglamorous struggle. The rewards may not always be tangible, but they are real: personal growth, the respect of your peers, and the satisfaction of knowing you gave everything you had.

In the fast-paced world of technology, where metrics and deliverables dominate, it’s easy to forget the human side of leadership. Hemingway’s tale encourages us to embrace the solitude, respect the struggle, and find meaning in the effort.

As you navigate the seas of leadership, remember: the marlin you pursue matters, but so does the person you become while chasing it.