Last Thursday, I announced my decision to join Wizly, an AI startup revolutionizing how experts build and share their wisdom. The opportunity aligned perfectly with my long-term vision — both for Solo CEO and my broader goals — and came about through a serendipitous LinkedIn connection (yes, another life-changing one!).

If you read that announcement, you likely felt my unbridled excitement about joining a mission that could transform how we, as knowledge professionals, build the businesses we deserve.

And hell yes, I'm still pumped.

But you probably didn't sense, because I didn't talk much about it, how incredibly difficult it was ultimately to make that decision.

But you probably didn’t sense, because I didn’t talk much about it, how incredibly difficult it was ultimately to make that decision.

Even after I felt like I probably would join the team, I wavered. I hemmed and hawed. I waffled. I struggled something fierce.

I spent hours talking through it with my husband, Andy, overthinking every possibility, and doubting myself all along the way.

And of course, throughout it all, the stress, the distraction, and the self-doubt were eating away at me. The emotional whiplash of one moment saying “Hell yes!” and the next, “I can’t do this!” left me anxious and exhausted.

The effects were noticeable:

It became harder for me to show up for Solo CEO members and my 1:1 clients with the kind of presence, focus, and authenticity I pride myself on. I wasn’t sure what the future would look like, so I found myself swinging wildly between possibilities —jumping to build new programming and experiences before quickly realizing I was being unnecessarily reactive.

I wasn’t following my own advice to be intentional in my actions, and I definitely was betraying my theme for 2025 of “Slow is smooth. Smooth is fast.”

On top of that, I wasn’t taking great care of myself physically — having too much wine with Andy, sleeping like shit, and in general just feeling worn down.

I felt both stuck and lost all at once. I was frozen, unsure of what to do or where to focus my time. And yet, I also felt ungrounded, flighty, and untethered from my purpose and what I truly wanted.

It was haaaaard.

In the midst of my uncertainty, I found myself on a cross-country flight from Portland. I've long said I'm most productive on airplanes, but as I sat there at 20,000 feet, staring at my laptop screen, I couldn't focus on anything practical.

And so, finally, I decided to ask for help — from Future Me.

Note: If you’re unsure of what I’m talking about, watch this and learn about how you can turn Future You into your coach, mentor, and spiritual advisor. Truly, my conversations with her have been downright life-changing.

I want to be clear. Throughout all of this, I was also conducting the thoroughly practical process of due diligence — talking to lawyers, evaluating financials, and researching my options. And Future Me served as a thought partner and advisor in the more nuts-and-bolts strategic and logistic planning.

I think part of me assumed that once I felt good about the terms of our agreement, the self-doubt would resolve. It didn’t.

And, for some reason, before this point, I hadn’t asked Future Me to help me delve deeper into what I truly wanted or to get curious about the hesitation that kept percolating beneath the surface.

I knew that there was one big question I was grappling with, and I asked Future Me to help me figure it out.

If you’re not aware, I have a tattoo across my right forearm, “Throw off the bowlines,” which is from a quote that I believed was by Mark Twain, but I have since learned is not (sigh).

On LinkedIn, I shared a whole story about that tattoo and how it foreshadowed my divorce. No matter who originally said it, I believe in its sentiment and try to follow my curiosity, live a life of adventure, and take chances to soak it all up.

So, I pulled up ChatGPT, and found my Conversations with Future Me project, opened up a new chat, and asked (I even maintained my original typos here, so you can see its authenticity):

These are the questions Future Me (via ChatGPT) asked me:

Neither is better. But one will feel more aligned right now.

Now flip it:

Is there something I keep pushing down—about my desire, my fatigue, my excitement, my boundaries?

What's the truth I haven't said out loud yet?

Not the fantasy. Not the pressure. The fire. What version of the future makes me nervous in a good way?

That's the one you're drawn toward.

I spent the vast majority of my 5+ hour cross-country flight journaling about these questions, slowly peeling back the layers of my fears and uncovering the root of what I really wanted and why.

Here’s what I discovered:

This wasn’t a binary decision. This was the moment to ask myself:

“Am I ready to let go of control…in order to grow?”

Because that was the deeper dynamic at play here. Not just Solo CEO vs. Wizly. But

My desire to make a lasting, monumental, legacy-building impact was real. The fear of surrender was real, too.

I was not clinging to Solo CEO because it was the better path.

I was clinging to it because it felt safer to be in full control — even when that control was limiting me and sometimes exhuasting me.

And what was I being invited into?

It was trust.
It was a leap.
It was co-creation.

It was a step toward a version of myself who doesn’t carry it all alone.

As someone who has spent the better part of a lifetime hyper-independent (thank you, trauma response), and feeling like she needed to do everything herself, that idea was scary. It still is.

But answering these questions for myself helped me understand that I was ready to face that fear.

And that shrinking away from it would go against every part of who I am and who I am becoming.

Looking down at the tattoo on my forearm as I write this, I realize I'm living its wisdom in real time:

I'm not giving up my dream. I'm setting sail for wider waters.

I'm not walking away from my brand. I'm catching new trade winds.

I'm not losing control. I'm leaving the safe harbor of sole ownership for the adventure of collaboration.

I'm not quitting. I'm exploring, dreaming, discovering.

I share this deeply personal journey not to control the narrative, but because I know how challenging it is to leave the safety of the harbor.

Big, life-changing decisions require both courage and wisdom — the courage to throw off the bowlines, and the wisdom to know which winds to catch.

If you take away just one lesson from all of this, let it be this: Your inner wisdom is wise. But she won't ever yell to be heard.

It's your job to create the quiet moment, away from the noise of the harbor, where you can hear her whisper which way to sail.

Here’s to the wind in your sails,
Kasey