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Surf Lessons for Leadership: We cannot measure success by how many waves we catch

Published January 29, 2025
by Stephanie Ockerman

After years of learning to surf, I’ve discovered powerful leadership lessons that apply far beyond the ocean. Today’s lesson is simple yet impactful: we cannot measure our success by how many waves we catch.

When we focus solely on achievements (riding the wave), we often miss the deeper story – the learning, growth, and countless attempts that got us there. It’s about intentionally reflecting, adapting our approach, and practicing micro-skills until they become intuitive.

While this applies to many aspects of life, let’s focus on business agility and leadership.

Agility is simpler than we make it out to be. It’s about being adaptive, innovative, flexible, and resilient. It means approaching creative work in complex environments in ways that enable early feedback, frequent validation, and more ease/ less waste in responding to change.

We are navigating uncertainty, complexity, and ambiguity. We have to do a lot of work to get to the “wins” – to ride those waves. So we cannot just measure our success by how many waves we catch.

Here’s the challenge: Agility was meant to be the antidote to treating people like machines and focusing purely on efficiency. Yet many organizations use “agile” practices to control people and outcomes.

Why this misalignment between intention and impact? I believe our relationship with success – and how we use goals and measures – plays a crucial role.

What if we completely changed our relationship to even the idea of measuring success? What if success wasn’t about good/bad, win/lose, right/wrong? That binary thinking is too simplistic for complex work in changing environments.

Yes, we need to measure outcomes. But we also need:

  • A broader perspective on the journey itself
  • Understanding of the experience that leads us towards outcomes
  • To treat measures as neutral information that guides us toward goals

Otherwise, we end up gaming the measures and creating ineffective goals.

So how do we break out of this trap?

Here are four key pillars for adaptive planning when dealing with uncertainty:

  1. Run experiments to seek towards goals (which will evolve as we learn)
  2. Goals are most useful when they focus on outcomes (instead of activities or outputs)
  3. Use measures as information (not a judgment), and that information helps us navigate towards goals.
  4. Maintain multiple perspectives when measuring (because complexity demands it)

Note: These pillars are inspired by the Evidence-Based Management (EBM) framework. I am teaching a live virtual EBM training in March if you want to go deeper.

My invitation to leaders: Let’s stop attaching our worthiness and happiness to achievements.

Instead:

  • Regularly reflect on the micro-skills you practice, the hard work and determination.
  • Regularly reflect on your process, taking an experimental approach, adapting and learning as you go.
  • Celebrate these aspects of your work and how you show up in the world.

Because these are the elements that will set you up to catch that next wave.

Want to experience this leadership lesson firsthand? Join my Agile Leadership Surf Camp in Costa Rica, where we use learning to surf as a tool to more deeply embody agility and grow our leadership capacity.

And if you find this inspiring and want to apply these concepts to grow your leadership skills to be more adaptive, innovative, and resilient, sign up for my newsletter Leaders Ride the Waves.

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