The Wake You Leave Behind: Reflections From the Middle of the Ocean

The view from my patio - the ship's incredible wake!

There is something powerful about being out in the middle of the ocean: No buildings. No calendar reminders. No noise from the world. Just endless water and the steady hum of a ship that keeps moving forward no matter what the weather brings.

I had the incredible opportunity to join some family members on their birthday cruise last week. Each day, I spent time sitting on the deck of my room, which was on the aft end of the ship. It provided me with a perfect view of the wake trailing behind the ship.

Up close, the wake is bold, bright and loud. It curls and churns as the ship pushes forward. But as the water settles, it stretches into the distance and slowly begins to fade. Even then, you can still see it for miles. A soft but steady reminder that something powerful moved through here.

Leadership is a lot like that.

Leadership Lives in the Wake

We focus so much on the waves right in front of us. The decisions, the conversations, the unknowns. But what really tells the story of who we are as leaders is the wake we leave behind. The culture we shape. The experiences people have when they work with us. The clarity we bring to complex situations. The emotional imprint that remains long after the moment has passed.

Right before this trip, I attended a conference where several members of my former team were present. Walking into that space felt different this time. For years, it was where I belonged. It was where I led, coached, and poured my heart into building a department that could stand strong long after I stepped away, not knowing that day would come sooner than I thought. Seeing them now, united and steady, filled me with something I had not expected. I felt pride instead of hurt, and relief instead of sadness. They were carrying on the culture we built together. They were continuing to use the systems and structures designed to support them. And they looked confident and happy.

Leadership is not about holding the title. Leadership is about building systems, culture, and confidence that last.

When Your Legacy Continues Without You

I will repeat it again... Leadership is not about holding the title. Leadership is about building systems, culture, and confidence that last. This became even more clear a few days later. While I was on the ship, it dawned on me that at that very moment, my old team was back home hosting their annual staff retreat… A retreat I created five years ago that was one of my absolute favorite traditions and day of work each year. It was a day dedicated to genuine connection, teambuilding, alignment, and planning in the most collaborative ways possible. We always worked hard, and played harder on this day of the year. I had a few waves of sadness knowing it was no longer my event to run. But at the same time, I felt a deep sense of pride that it was still happening. It still mattered. It was being carried forward by leaders I helped grow. That realization softened something in me and made me realize something that hit me like a ton of bricks.

My legacy was never tied to the title. It was always tied to the undercurrent.

The Gift of Distance

This season has taught me a great deal about integrity and the quiet strength it takes to honor your own value. Not every leadership environment reflects the depth of connection or authenticity that creates meaningful impact. Sometimes decisions are made quickly or with priorities that do not align with the kind of leader you are striving to be. Even so, I am grateful for the clarity that followed. When the environment no longer reflects who you are, stepping away is not a loss. It is a return to yourself. It is choosing to protect your time, your purpose, and your worth. And it is trusting that the wake you created speaks for itself.

Stepping onto the ship only one day after the conference concluded gave me space to breathe and absorb all of that. The contrast between the conference’s classroom and the open ocean made everything clearer. Leadership, legacy, uncertainty, and renewal were all swirling together in ways I had not fully processed yet. Out there, away from the noise and expectations, I could finally sit with the emotions of this season and see them with a new kind of perspective.

There were moments on this trip that grounded me even more deeply. Watching the sunrise paint the surface of the water. Standing in the rain and remembering how fun it used to feel as a kid to splash and play. Realizing that the rain is not something to fear. Sometimes it is part of the joy. Sometimes it is part of the message.

I felt peaceful in a way I have not felt in a long time. Peaceful with my new direction. Peaceful with my aspirations. Peaceful with the truth that I could have retired in my last job and been content, but contentment was never my ceiling. I am someone who seeks meaning, alignment, and purpose. And when that alignment and purpose faded from my last role and became merely an illusion, it became overwhelming and unavoidable that there is more out there for me. I am so grateful that a values misalignment pushed me from comfort into discomfort, because that shift is what created space for me to chase a dream.

In the middle of the ocean, you cannot help but feel small, yet somehow you also feel steady. There is something grounding about knowing that you do not have to control the water. You just have to keep moving with intention.

On the third day of the cruise, it down poured. It was the kind of rain that makes the sky blend into the water so completely that you cannot see where one stops and the other begins. But out of nowhere, the clouds opened, and the sun broke through for a moment and the rain stopped. It felt like a reminder I needed: Trust that the storm will not last forever. Trust that the sun will return. Trust yourself and your intuition, even when the horizon looks uncertain.

A Wake That Shapes Organizations

For municipal and nonprofit leaders, that trust is not optional. It is essential. Our fields depend on leaders who can align teams around a shared purpose, build a culture where people feel safe showing up authentically, and create structures sturdy enough to support both the mission and the people behind it.

When leaders are clear, grounded, and aligned, they hire better. They retain better. They build workplaces people want to stay in. Their wake becomes a source of stability for the entire organization.

Last week was a much needed pause. It was a reset and a reminder that new adventures will always require us to step into the unknown. It also reminded me that no matter how overwhelmed or unsure we feel in the moment, we are still creating a wake behind us. The wake stretches farther than we realize and touches people in ways we may never fully see.

The ocean has a quiet way of putting everything into perspective. It reminds you that movement matters. Direction matters. Intention matters. Watching the water stretch behind the ship made me think about the systems and structures I built over the years, the ones reflected in my team at the conference and at the retreat. Even when you step away, the work you poured into people and processes continues to move. The wake may fade from sight, but the impact does not. It becomes part of the larger current that carries the organization forward.

My New Horizon

I am carrying a few things forward from last week’s trip:

• A commitment to trust myself in the spaces between certainty and possibility.

• A promise to lead with intention, even when the next step is not fully clear.

• A deeper belief that values alignment is worth protecting.

• A renewed energy for building systems and cultures that outlast any one person.

• Gratitude for the wake I have created in my last role and the one I am creating now.

This trip strengthened something in me. It clarified my purpose and deepened my commitment to the work I am building through Undercurrent Strategies. This business is not just my next chapter. It is my new horizon. It serves as a wide and open place where I can support leaders, strengthen teams, and help organizations create wakes that carry people forward for years to come.

I am continuing to trust myself and my intuition more deeply. To remember that each step I take creates a ripple that can grow into something meaningful. To trust that even in seasons of uncertainty, the undercurrent of who I am is still pulling me in the right direction.

And as I sat there, watching the wake stretch into the horizon, I felt and continue to feel grateful. I am grateful for the clarity, the perspective, the pause, and the reminder that every leader leaves something behind. Our wake shapes the water long after we move on.

Bonus - Photos from the trip!

...because who doesn't love vacation photos?!