Learning to Sail

Becoming a Sailboat vs. a Motorboat: A New Model of Motivation for Leaders

There comes a point in every high-performing leader's journey where the old fuel stops working. The pace that once thrilled you now exhausts you. The urgency that used to motivate now frays your edges. The question becomes not just how do I keep going? but how do I keep going differently? Let’s start with a simple but powerful image: the motorboat vs. the sailboat.

Motorboat Living

A motorboat is fast, agile, and powerful. It can pivot quickly, accelerate hard, and chase down any goal. But here’s the catch: it burns fuel constantly. The moment you stop refueling, it dies. More speed equals more strain. Motorboat leadership looks like long hours, urgent emails, strategy sprints, and a constant push to achieve. It works—until it doesn’t. Until you realize you’re not just tired—you’re running on fumes.

Sailboat Leadership

A sailboat is different. It’s slower, yes. Less flashy. But its power comes from noticing, not forcing. Adjusting sails to meet the wind. It can move forever—no refueling required.

To outsiders, it might look like you’re doing less. But inside? You’re attuned, responsive, and deeply strategic. The wind is always there—you just have to learn to catch it.

The Two Kinds of Motivation

At the heart of this metaphor is a deeper shift: moving from fear-based motivation to surplus-based motivation. Fear-based motivation is driven by the need to avoid failure, insignificance, or shame. It’s reactive, fueled by scarcity, and often rooted in proving something—to others or to yourself. Surplus-based motivation, on the other hand, comes from fullness. It’s the energy of someone who gives because they can, not because they must. It’s grounded in overflow and generosity. It’s the difference between working to survive and creating because you're already full. Fear-based leaders act to stay relevant or validated. Surplus-based leaders act to contribute, to build, to serve. Most of us start in the motorboat. But the sailboat? That’s the future.

The Crisis of Motivation

As fear-driven leaders succeed, their fear diminishes—and so does their drive. That’s when a crisis hits. You’re left asking: What now? Why don’t I feel more fulfilled? How do I stay motivated when I’m no longer scared? You’ve reached the crossroads. And there are three common responses:

1. Coast: Settle. Numb. Distract. Let mediocrity creep in.

2. Reignite fear: Manufacture bigger risks to keep the engine running—often with high cost.

3. Learn to sail: Shift toward surplus. Create from overflow, not obligation.

Examples You May Know

1. Paul Polman

Polman was CEO of Unilever from 2009 to 2019, during which he transformed the company’s mission: rather than chasing profit alone, he guided Unilever toward decoupling growth from its environmental footprint and increasing positive social impact. Wikipedia This is a clean example of the “sailboat” shift: moving from business‑as‑usual, competitive growth to business aligned with meaning, impact, and long‑term value beyond just numbers.

2. Premal Shah

Shah co‑founded Kiva (a global micro‑lending platform) after his time in Silicon Valley, shifting from high‑growth tech to a model built on connecting surplus (capital, networks, innovation) with need (entrepreneurs in emerging markets). Wikipedia His story illustrates the move from “what can I get?” to “what can I give?” and how that motivates with a different kind of fuel.

3. Boeing...

Boeing, once defined by speed, scale, and shareholder-driven urgency, hit a breaking point after crises like the 737 MAX crashes exposed the costs of motorboat-style leadership—fast, forceful, but unsustainable. Under new leadership, the company began a cultural reset: restoring engineering integrity, prioritizing safety, and rebuilding internal trust. What emerged was a slower, more deliberate approach—less about dominating the market, more about aligning with long-term value, societal trust, and systemic responsibility. Boeing is learning to sail: powering forward not by force, but by sensing and catching the winds of what truly matters.

Why This Matters

Sailboat leadership isn’t just gentler—it’s smarter. It’s sustainable. It aligns effort with meaning. It builds trust, clarity, and momentum. Burnout doesn’t come from working hard—it comes from working out of alignment.

The Three-Year Shift: Learning to Sail

This isn’t a quick fix. Becoming a sailboat leader is more like a three-year apprenticeship in a new way of operating. Year One is all about awareness—you begin to notice your fear-based reflexes. You start pausing, listening, questioning the urgency that once felt automatic. In Year Two, the adjustment phase begins. You experiment with surplus, giving where you have more than enough—your ideas, energy, presence. You notice how less effort can yield more clarity. By Year Three, mastery starts to settle in. You no longer rely on pushing. You begin to sense, to align, and to lead with quiet power. Motivation flows because it’s no longer tied to fear—it’s sourced from connection, clarity, and the deep satisfaction of creating from within.

Daily Practice

Morning Alignment Check Start each morning by noticing: what do you have a surplus of today? Maybe it’s time, energy, wisdom, capital, creativity, or simply a calm presence. Then ask: where do I see need? It could be a colleague who’s overwhelmed, a project that needs attention, or a client who needs reassurance. Your job is to connect surplus to need—just once, in a meaningful way, without expectation of return.

Wind Check Before Action Before diving into major work, take a moment to sense the wind. Are you about to push against it, forcing momentum? Or are you trimming sails to catch a natural current? Strain, resistance, and frantic energy are signs you’re slipping back into fear-based proving. Pause. Adjust. Sail.

Micro-Listening In conversations throughout your day, practice hearing what’s unsaid. What are the subtle signals, the emotional undercurrents, the deeper need beneath the surface? Ask at least one question designed to reveal—not assume. Then reflect: did I create stillness and clarity in this interaction, or did I add noise?

Surplus Journal (Evening) At the end of each day, capture three moments where you gave from surplus. Then, name one moment when fear or urgency crept in. What triggered it? How did you respond? How could you have sailed through it differently? Over time, this journal becomes a map of your transition from motorboat to sailboat leadership.

Daily Contribution Each day, commit to one concrete act of contribution that costs you little but matters greatly to someone else. Introduce two people who need each other. Share an insight freely. Offer encouragement or acknowledgment. Anchor it to surplus—only give what naturally overflows.

Evening Stillness Close your day with 5–15 minutes of stillness. Sit quietly. Stretch. Meditate. Picture yourself aboard a sailboat: adjusting sails, catching the wind, moving with grace. Let this image ground you in a rhythm that’s sustainable, spacious, and deeply attuned.

The Choice

You don’t have to quit everything to make this shift. You don’t need a new job or a new title. What you need is a new source of motivation. This is the work of the leader who’s no longer trying to prove anything—only to build something that lasts.  You’ve mastered the motorboat. Now, it’s time to learn to sail.