Kimberly’s Wanderings & Wonderings: Summer 2026

Picture this: You are sitting on a deck or patio (or perhaps out on a boat or standing on a beach), watching the sky go through six plus different colors in the space of twenty minutes. Magic. You cannot tell exactly when it changed from gold to pink to that deep almost-purple. It just… did. All at once and not at all at once.

If I am honest, that feels like my summer. All at once and not at all at once. You know what I mean? How is it that we only have two more weekends left (and Labor Day is as late as possible this year). It is like a bonus weekend.

Here is the thing about momentum, though, much like a sunset, you cannot actually point to the moment it starts or when it progresses. It just moves in continuous motion. On August 19th, I will hit the one-year mark since KWW Inc. was legally incorporated. Papers filed, box checked. Quiet. Nobody knew.

But if you asked me when this really started, I would say something different.

The Other Reset Button

We are in the dog days of August. You can feel it changing. The sunsets are a little earlier. You feel an urgency to “get it in” before summer is over. I can feel the other season creeping in at the edges.

Budget season. Back-to-school. Fall routines quietly rebuilding themselves before Labor Day even shows up. My inbox already has the first “let’s get 2027 planning on the calendar” email sitting in it, and for years I would have called that an intrusion. Summer is not over yet. Let me finish.

But here is what I have finally admitted to myself: it is not an intrusion. It is my favorite part.

I was that kid who lived for new school supplies. Crisp notebooks, sharpened pencils, the smell of a fresh box of crayons (I still love to get a fresh box of crayons as coloring is therapeutic). It was not about school. It was about possibility. A blank page that had not been written on yet. And somewhere along the way, that feeling never left me. It just changed shape. Now it shows up as a new strategy session. An idea that has not been tested yet. A potential new client I want to pitch. Everyone talks about January as the reset button. Mine has always lived in September.

So, maybe what I am feeling right now is not obligation pulling at summer’s edges. Maybe it is joy, just early.

Breaking the Mold, Out Loud

Somewhere between my last newsletter in June and now, Keep Wondering Why stopped feeling like something I was building and started feeling like something that was building.

A travel trade publication (Travel Weekly) wanted my perspective about what is refining hospitality, especially with the LGBTQ+ space, and learn about my journey since selling Valerie Wilson, joining Chase Travel Group, and starting my company.

What struck me most in putting my thoughts together was not specific to any one community, it is a principle that applies to every guest, every client, every person walking through your door:

Luxury today is defined by personalization, not standardization. But you need language so standardization can be personalized.

Another podcast called me a “Trailblazer,” a word I am still getting used to hearing about myself. The conversation talked about my brand journey from breaking the mold, rewriting the rules, and leading with courage. Real leadership is not about fitting in. It is about creating a new way forward.

And I keep catching myself doing the thing you do with a sunset: stopping mid-motion, a little stunned at the beauty and change. You pause and think, when did this happen?

Check out the podcasts:

Travel Weekly 

Her Brand Story – Trailblazer Kimberly Wilson Wetty

Back-to-School Shopping

Be honest. You loved getting new school supplies too? Right? That feeling does not have an age limit. And with so many of us heading back to the office this fall, there has never been a better excuse to bring a little of that energy back.

What is something you want in your version of back-to-school shopping:

• A new pen – one that actually feels good in your hand
• A fresh journal or notebook, blank and waiting
• Ten minutes to rearrange your desk, even just moving one thing
• Yes, even a new lunch box, if “return-to-office” is suddenly your reality again

None of this needs to be productive. That is the point. It is not about the supplies. It is about feeling possibility. And giving yourself permission to feel like September again, even if you are fifty-five, like me, and the “first day” is just a regular Tuesday.

What is your one small shift this week?

Wonder Tree: Swim Across America

I have grown to love swimming. The repetition of the laps. The feel of the water, especially in the summer in an outdoor pool.

On Friday, July 24th, I swam a 5K: two hundred and twenty laps, one hour and fifty minutes, for cancer research. The next day, I stood on the water’s edge at Swim Across America’s Long Island Sound swim and cheered on the open water swimmers.

I will admit there was a small pang of guilt for not being in the open water. Some friends and donors teased me for doing a pool swim. I am learning that comparison is a trap. Swimming two hundred and twenty laps is still swimming two hundred and twenty laps. And our small, but mighty Team BeachBum raised over $30,000, the event raised $1.5 Million. It is easy to hear a number like $1.5 Million and let it stay this abstract thing. It is much harder to hear a doctor or survivor say that money buys hope. I left inspired, and more hopeful than I walked in.

This is The Wonder Tree in action. Keep Wondering Why’s commitment to showing up for causes that matter, whether it is a client’s chosen charity or one close to my own heart. Swim Across America is one of the causes we champion, and this summer reminded me exactly why.

With curiosity, inspiration, and back-to-school shopping vibes,