Say Yes Before You’re Ready

Reflections from my [CLIC] Connect conversation on leadership and risk in hospitality

Our episode on [CLIC] Connect, a hospitality, travel, and tourism interview series hosted by Craig Sullivan of [CLIC] Media, and co-hosted with Rachel Humphrey of Women in Hospitality Leadership Alliance.

The [CLIC] Connect panel began with a simple question: What led you to hospitality?

But the conversation quickly turned to something deeper — what it takes to say yes before you feel ready.

As someone who’s built a career evaluating hospitality investments, I’ve learned that few opportunities come gift-wrapped in certainty.

When I was invited to speak on a panel earlier this year about AI and hospitality investing, my instinct was to say no. I’m not a technologist. I use AI the way most people use Excel — to make good work sharper.

But the organizers weren’t looking for a tech expert. They wanted a practitioner. So I said yes.

That yes reminded me of what hospitality has taught me again and again: real progress usually starts before you feel fully prepared.

Hospitality is built on uncertainty — a new guest, a shifting market, a deal that doesn’t quite pencil on paper yet.

The discipline is staying present anyway.

And that’s true in investing too.

You don’t build credibility by being perfect. You build it by engaging honestly — staying curious, making thoughtful decisions even when the outcome isn’t guaranteed.

That same openness is what makes teams and organizations stronger. When leadership reflects a broader range of perspectives — especially at the ownership and investment level — the work gets sharper.

Representation isn’t optics. It’s operational intelligence. Expanding who’s in the room sharpens the questions, challenges assumptions, and strengthens outcomes.

The Women in Hospitality Leadership Alliance is helping make that possible through its Speaker Directory, which connects conference organizers and media outlets with experienced female executives from every sector of hospitality. It’s designed to make industry stages — and boardrooms — more representative of the talent that already exists.

The [CLIC] Connect conversation explored exactly that — how leadership, risk, and representation intersect when we choose to show up before everything feels certain.

🎥 Watch the full discussion with Craig Sullivan and Rachel Humphrey →

If you’re an investor, operator, or leader navigating your own version of “not yet ready,” this conversation is worth your time. It’s about how presence — not polish — creates credibility that lasts.

That’s the mindset we’re building at Jane Hospitality: grounded leadership, clear structure, and the willingness to say yes before the perfect moment arrives.