I hit a milestone on October 17, 2025: my 700th cold dip in Lake Ontario.

What began almost three years ago as an experiment in courage has become a practice in presence, patience, and adaptability. Each dip—whether in snow and deepest winter wind chills or under relaxing summer skies—has taught me something essential about how to stay centered when conditions are unpredictable.

In today’s workplace, adaptability isn’t optional. Leaders and teams are navigating constant change, new technologies, and shifting expectations. Those who thrive aren’t necessarily the fastest or the most experienced. The people thriving and ready to take on the future are the ones who can stay grounded, curious, and responsive when the environment keeps changing.

Reflecting on this milestone, here are five lessons from the cold water that apply just as much in leadership as they do in life.

1. Expect Awkward

Doing anything new will feel uncomfortable. You’ll question your judgment, your timing, and even your motivation. The first time I waded into near-freezing water, every instinct screamed to get out. But I’ve learned that awkwardness is a sign of growth, not failure.

Leaders experience the same thing when navigating uncharted territory—implementing a new process, stepping into a senior role, or addressing difficult feedback. The initial discomfort doesn’t mean it’s wrong; it means it’s unfamiliar.

Tip: Discomfort is the doorway, not the danger. Expect the awkward stage and move through it instead of backing away.

2. Ask A Better Question

Early in my dipping journey, I’d stand on the shoreline asking, “Will the water be cold?” Of course it would. That question focused on fear, not opportunity. Eventually, I replaced it with, “How can I meet the cold water today?”

In leadership, the same shift applies. When facing disruption, many leaders ask, “How will I get people to accept this change?” A more empowering question is, “What could this change make possible for my team?” That subtle reframe and pivot unlocks possibility, creativity, and forward momentum.

Tip: Change the question, change the outcome. Lead your team with curiosity rather than control.

3. Watch For Your Inner Critic

As my dip count climbed, a sly inner voice tried to steal the joy. “You should’ve started earlier,” it said. “You can’t count summer swims—they’re too easy.” That voice shows up for leaders, too, especially under stress: “I should have known that.” “I’m not doing enough.”

When you stretch into new territory, expect your inner critic to try to pull you back into old patterns. Instead of wrestling with it, recognize it for an unconscious attempt to keep you safe in the familiar. Simply say, “Thanks for sharing, but I’ve got this,” and continue forward.

Tip: Notice the critic, but don’t negotiate with it.

4. Celebrate Showing Up

Recently, I met a new dipper who had seen me dipping and we had a conversation lakeside. He asked how often I dipped and his energy started to drop. He then sheepishly told me, “I’ve only done two.” I smiled and said, “That’s amazing! You showed up—that’s how it all starts.” His smile returned.

Brené Brown said, “Sometimes the bravest and most important thing you can do is just show up.” In leadership, that’s true too. When your team feels overwhelmed or progress stalls, your role is to recognize the effort, not just the results. Encouragement fuels perseverance.

Tip: Recognition fuels resilience. Catch effort early and praise it often.

5. Track Your Progress

At some point, I began marking each dip on my calendar. It felt a little nerdy, but it was motivating to see the pattern of consistency and momentum grow. The same principle holds for leadership. We tend to measure organizational outcomes—revenue, performance, KPIs—but neglect to track the small, repeatable actions that build adaptability.

Record the daily moments of alignment: one honest conversation, one decision delegated, one pause before reacting. Integrating a methodology to sustain change is an important component of my work with teams because it allows me to provide insight as to what’s shifting, and where people might be stuck, so we can course correct along the way. Progress becomes visible when you measure what you can control.

Tip: Track consistency, not perfection. Momentum builds from what you repeat.

Seven hundred dips later, I can confirm the water hasn’t gotten warmer—but I now embrace and look forward to being in it.
That’s the real work of adaptability. The conditions won’t always be comfortable, but the more you practice meeting challenges with curiosity, awareness, and steadiness, the stronger and more resourceful you—and your team—become.

If you’d like support with leadership within your organization or team, let’s connect to explore whether the Adaptive Advantage (™) program or Level Up Leadership executive coaching program can help!”