April 20, 2026
Kimberly’s Wanderings & Wonderings – April 2026
Muddy Boots & Blooming Opportunities
Picture This: You are five years old. It has just rained. There is a puddle. A magnificent, enormous, perfectly muddy puddle, right in the middle of the sidewalk.
You don’t think twice. You jump.
Both feet. Full commitment. Splash everywhere. And you laugh. That whole-body, completely unselfconscious laugh. Pure joy.
Now fast-forward. You are an adult. Same puddle. Same rain. And what do you do?
You most likely walk around it. Carefully. Maybe even a little proud of yourself for being so practical.
Somewhere along the way, we learned to stay clean. To stay composed. To choose the safe path around the mess rather than through it. And listen, there is a time and a place for that. But I have been wondering lately: what have we lost in all that careful stepping around?
April has been one of those months that answered the question for me. A full, messy, surprising, wonderful month. The kind of month that leaves you a little muddy and completely grateful.
When was the last time you experienced getting a little muddy and feeling completely grateful?
This month, I am giving you, and myself, permission to jump in the puddle and get a little messy.
A few weeks ago, I attended my annual YPO (Young Presidents Organization) Forum retreat. During the retreat we had a facilitator trained in doing “shadow work.” I will be honest; I had no idea what I was walking into. Hard doesn’t begin to cover it. But it was amazing. The stories written in childhood have a way of running the show long after we think we have outgrown them. And when you think about it, we don’t arrive as adults from nowhere. Something or someone (or both) shaped us. And most of us never stop and ask what or why. We just did.
What came out of those days was something I had been searching for: finding my voice.
Not performing it.
Not polishing it.
Actually, finding it messy and imperfect as it is.
And I realized: you can’t find your voice if you are always afraid of getting your boots muddy.
And another uncomfortable truth that came up for me was, “Who in your life will give you truly unvarnished feedback?”
Not the cheerleaders. Not the people who love you so much, they soften every truth. The ones who will look you in the eye and say the thing you need to hear. Wow…that question sat with me.
So, this April, the invitation is this: Where might you need to get a little messy? Where has the pursuit of perfect been keeping you from the puddle?
If you want to discover more about shadow work and what I learned, click here to read my recent blog. (add it in once blog is done)
What’s Emerging
April just keeps on giving. This month, I also had the chance to attend Tomorrow’s Talent Today, part of the Seatrade cruise conference at Florida International University (FIU) and it was one of those experiences that leaves you full.
The conversations kept circling back to something that felt deeply relevant: grit and resilience. Not just as buzzwords, but as the actual lived experience of people who build careers and lives through the “messy middle,” through the hard moments, the pivots, the seasons that didn’t go as planned.
It got me thinking about my own story. In 1995, I joined the family business, Valerie Wilson Travel. I helped start our cruise division, Cruises of Value. We even launched a website when the internet was unknown and not mainstream. I had no idea what I was doing, honestly. It was uncertain and exciting and completely imperfect. And yet, 31 years later, I still get a little thrill when I talk about cruises as a segment within travel, hospitality, and tourism.
That hasn’t faded. If anything, it’s grown. I am proud to be part of this world of travel. Proud of what it does for people, the wonder it creates, the connections it builds, the doors it opens.
The future of travel? I am beyond excited about it and grateful for my career path. And events like, Tomorrow’s Talent Today, remind me why.
Getting Comfortable With Being Uncomfortable
This month I was also honored to be featured as a Trailblazer by photographer Priyanca Rao, a conceptual photoshoot designed to capture personal stories and empowerment through photography. I had no idea how transformative it would be.
The images told a story I had not quite found the words for yet. More color. More fun. More authenticity. A woman stepping into her next chapter – laying down the bricks she no longer wants to carry, finding her voice, and embracing her calling to help others. Sometimes you need someone else’s lens to see who you are becoming.
Messy, emotional, and exactly on theme for this month. Read the full feature.
P.S. — Why Wednesdays continues! Each week on social, I am posting a question designed to slow us all down before we rush to the answer. Follow along and wonder with me.
Featured Perspective
Sea Cloud: Where the Senses Come Alive
A few weeks ago, I experienced a wonderful 7-day Caribbean cruise of the Sea Cloud II with my husband and several dear friends from the travel industry. Pinch me! It’s been a month!
There are some experiences you don’t quite have words for until you are in the middle of them. Sea Cloud is one of those.
If you have never seen one of their ships, it is the kind of vessel that defies easy description. It is part ship, part yacht, part sailboat, and all at once makes you stop mid-sentence because you realize you have been staring. It is a step back in time. The crew works their magic against a backdrop of extraordinary decor, details, and care taken in every corner.
And then, the sails go up.
It is a slow thing, gentle yet firm if that makes sense. And that is exactly the point. You are encouraged to relax, reflect, dream, escape. The ocean does its part. The sails do theirs. And somewhere in between, you remember how to do yours.
Sea Cloud awakens the senses in a way that feels almost surprising because how often do we let that happen? How often do we give ourselves the space to simply be present to what is beautiful?
I found myself wondering: what would it look like to bring even a little of that spirit into everyday life? To let ourselves slow down enough to actually feel the moment we are in, rather than plan for the next . Not criticizing the details and overthinking. Just be present. Fully present.
That is the question I am still sitting with. I hope it finds you, too.
One Small Shift
Plant the Seeds (5 Minutes)
Spring doesn’t happen all at once. It starts underground, quietly, before there is anything to see. You plant, and then you wait. You water and nurture, and then you wait. And then, without warning, something starts to bloom. Like ideas. Relationships. Dreams.
Your prompt this month:
- What is ONE seed you want to plant this spring, personally, professionally, or both?
- What would need to be true for it to grow?
- Who is in your garden with you? Who waters you, who challenges you, who gives you unvarnished truth?
Write it down. Even one sentence. That is the planting.
Messy handwriting welcome. Muddy metaphors encouraged. 😊
Wonder Together
This month’s question is the one I keep turning over myself:
“Where has the fear of being messy or imperfect been keeping you from jumping in?”
I would love to hear from you. Hit reply, send a note, find me on social. Let’s wonder about this one together.
And if you feel like it, what seed are you planting this spring? I would love to know.
In case you missed it, here are some other recent blog posts that might interest you:
Until next month, keep wondering, get messy, and plant some seeds,
