“i okay” — Moving Forward with Curiosity & Confidence

As our family explored the world together, I watched Ash’s little legs struggle with steps too tall for their stride. Instead of asking for help, they’d dust themselves off after every stumble and declare with fierce determination: “i okay.”

That phrase became our family mantra—not because everything was always okay, but because it reminded us that we could move forward with courage and curiosity, even when the path seemed impossible.

I didn’t realize then that I’d spend the next decade ignoring my own version of those steps.

The Steps That Don’t Fit

After 30 years of working in the luxury travel industry and brand leadership, I’ve seen people and organizations trying to navigate steps that aren’t designed for them.

Generational workforce shifts that demand new approaches. Evolving consumer expectations that outpaced strategy. The urgent call for authentic inclusion in industries built on exclusion. And instead of pausing to understand these new realities, we default to old solutions and quick fixes.

The hospitality industry taught me that extraordinary experiences begin with deep listening and understanding what someone truly needs, often before they realize it themselves. Yet I watched companies implement diversity programs without understanding inclusion. Mandate new policies without asking why their current culture wasn’t connecting. Rush toward solutions for problems they hadn’t fully grasped.

I saw the gap. I felt it in my bones. And for years, I did nothing about it.

Because seeing the problem and having the courage to do something about it are two vastly different things.

The Voice You Keep Ignoring

When do you finally listen to that little voice in your head?

You know the one. The voice that whispers when you’re pretending to pay attention in a meeting. The one that surfaces at 2 a.m. when you can’t sleep. The voice that says, “This isn’t it. There’s something more. Something different. Something that matters.”

For so many years, I lacked the courage to listen.

I was on a treadmill—just moving from one day to the next. Making excuses about why I couldn’t make a career change or even find the time to sit still and think, reflect, and be honest with myself. I was paralyzed by guilt. I worried about hurting people if I left. I was terrified of failing if I tried something new.

I recently looked at the notes section on my phone. I found over fifteen different entries going back seven years—all variations on the same theme: “KWW 2.0.” Ideas about what I could build. Questions about what I was meant to do. Dreams that I was too afraid to speak aloud.

Clearly, I took my sweet time listening to the voice in my head, but that’s okay; moments of leadership transformation often start quietly.

The Question That Changed Everything

Then one day, this question started haunting me:

What legacy are you building with the questions you’re not asking?

Not the questions I was asking clients. Not the strategic frameworks I was developing for brands. But the questions I was avoiding in my own life:

Why am I staying in something that no longer fits?
What am I afraid will happen if I pursue this idea that won’t leave me alone?
What if the voice in my head isn’t a distraction—what if it’s the point?
What would courage look like?

I thought about Ash on those steps, dusting themselves off and declaring “i okay”—not because they weren’t struggling, but because they were brave enough to keep trying. And I realized: I’d been stuck on my own set of impossible steps, pretending I was fine, when what I really needed was the courage to climb differently.

Choosing Courage Over Comfort

So, what gave me the courage to resign? To take time to focus on what I’d been whispering about for seven years. To start Keep Wondering Why (KWW Inc.)?

Honestly? It wasn’t one dramatic moment. It was the accumulation of small realizations:

The cost of staying became greater than the fear of leaving. Every day I ignored that voice, I was choosing someone else’s version of success over my own. I was building someone else’s legacy instead of my own.

I realized courage isn’t the absence of fear—it’s acting despite it. I was still terrified. I’m still terrified, let’s be honest. I left a stable executive role at an amazing company with no real plan for what’s next. But waiting until I wasn’t scared would have meant waiting forever.

I saw the gap between my values and my actions widening. I was teaching organizations about authentic leadership and generational readiness while ignoring the generational shift happening in my own industry. I was advocating for inclusive cultures while staying in spaces that no longer included the fullest version of me.

I understood that my experience of it was the point. Thirty years in luxury travel. An LGBTQ+ perspective in an industry that wasn’t always ready for it. Navigating multi-generational family business dynamics. These weren’t obstacles to overcome; they were the unique lens that could help others.

I finally asked myself: What if the voice in my head knows something I don’t know?

Here’s what I know now: Organizations don’t transform because they find the perfect strategy. They transform because someone has the courage to ask the questions everyone else is avoiding.

• What if generational differences aren’t a challenge to manage—but a superpower we’re failing to unleash?
• Why do we invest in leadership readiness programs that prepare executives for yesterday’s workforce instead of tomorrow’s multi-generational reality?
• What would shift if we stopped trying to make Gen Z “fit” our culture and started asking what their perspectives reveal about where our culture needs to evolve?
• When did authentic inclusion become a compliance initiative instead of a competitive advantage?
• Why do LGBTQ+ leaders still have to edit themselves in industries that claim to value “authentic luxury experiences”?
• Why do our luxury brand values sound like legacy statements when next-gen consumers are asking us to prove our purpose, not just polish our image?

What opportunities are we missing by treating differences as obstacles instead of as the diverse thinking that drives innovation?

The same is true for us as individuals. We don’t transform because we suddenly have all the answers. We transform because we finally have the courage to ask ourselves the questions we’ve been avoiding and be willing to get uncomfortable while you grow and evolve.

When I watch organizations struggle with generational readiness, inclusive leadership, and authentic transformation, I see my own seven-year delay reflected back. The notes app entries. The “someday” promises. The voice we keep silent because listening feels too risky.

But here’s what Ash taught me with their “i okay” declaration: Courage isn’t about being ready. It’s about being willing to try, even when the steps seem impossible.

Your Turn to Wonder

So, I’m wondering: What’s your little voice telling you?

What have you been noting on your phone for years but never acted on? What career change, creative pursuit, or courageous conversation have you been postponing? What questions are you avoiding because you’re afraid of the answers?

What if the gap between your values and your actions is an invitation—not a judgment, but a doorway?

What if that voice in your head isn’t unrealistic or impractical? What if it’s the most practical thing of all—your deepest wisdom trying to get your attention?

And here’s the question that still haunts me, in the best possible way:

What legacy are you building with the questions you’re not asking?

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Ash was right. We are okay—not because the steps are easy, but because we keep climbing. Not because we have all the answers, but because we have the leadership courage to keep wondering why.

Maybe it’s time to listen to that little voice. Maybe it’s been right all along.

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I’d love to hear from you

What’s the idea or change you’ve been noting on your phone for months or years? What would it take to find your voice and finally listen?

Open that note and revisit what sparked it. Give it a moment of attention — not to act, but to see what emerges.And if you’re a leader feeling the gap between where you are and where you need to be—in your career, your organization, or your approach to transformation—let’s talk. This is the work I do, helping leaders and organizations find the courage to ask the questions that change everything.