🧠Weekly MindSweep No. 225 | Curated Conversation |Uncertainty
May 2026
*Week 225: Curated Conversation: Uncertainty
Week 226: Mind Your Business: Uncertainty
Week 227: Manage Your Mind: Uncertainty
Week 228: What's On My Mind: Uncertainty
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In the MindSweep this week:
Weekly MindSweep: Past issues live here.
Jamie’s Second Brain Corner: Links to references & MindSweep Mapping
What’s Inspiring Me - The War of Art by Steven Pressfield
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Uncertainty Called. It Wants Credit.
It's time we introduced ourselves properly.
I recently worked with a client who had been developing her landing page for over 6 weeks.
Not because it wasn't good. It was good.
But the email sequence wasn't quite right yet, and you can't launch without the email sequence! Oh, and the social media plan needed to be tightened up first, because what's the point of a great landing page if the algorithm isn't working in your favor? And don’t forget the timing! Everyone knows you don't launch in the third week of the month. Oh, wait, or was it the second week? She needed to look that up again.
The offer itself? Brilliant. She knew it. I knew it. It had been ready for weeks.
But there was always one more thing standing between her and the send button.
I've also worked with a different kind of client — one who called me on a Tuesday afternoon, buzzing with energy.
She had an idea. A live, in-person event. She'd already made the graphic and posted it. People were commenting. There was energy. She was lit up in the way that only happens when something is genuinely alive.
By Thursday, I was gently asking, "Who is this for, specifically?" How do people sign up? What happens after they express interest? What's the experience you want them to walk away with? How are we going to nurture these connections after your event?
She hadn't gotten there yet. She was still in the feeling of the gathering. Imagining the room full of people, the connection, the possibility! But, the logistics, the follow-up, the pathway in and out? Those details hadn't quite made it into the picture yet.
The intention was real. The creativity was real. The heart behind it was completely real.
But the structure that would have made it land? Well…that part was still missing.
Two entrepreneurs. Two completely different ways of moving through the world.
One who could not move forward until everything was perfect. One who moved forward before the path was built.
I've sat across from both of them more times than I can count. And here's what I've learned from watching both patterns up close:
They are not opposites. They are two responses to the same exact thing.
Uncertainty.
How We Got Here
We spent our 5 weeks in April with tolerance and unpacked some uncomfortable awareness. Learning to stay in the creative moment right before the pull to leave. And a lot of you stayed, noticed the micro-adjustments, and tracked the urgency. You practiced staying 10% longer than you normally would.
Along the way, we also uncovered the discomfort of staying too long in spaces and tolerating things we hadn’t noticed before. We practiced letting go of things no longer serving us, personally and/or professionally.
When you stop moving away from a moment as quickly as you used to, you start to see what the moment is actually made of. And underneath resistance, underneath the perfecting and the launching and the list-making and the graphic-creating, there is often the same raw material running quietly in the background.
The fact that we don't know what will happen next.
Oh, hi, uncertainty. You’ve been with us the whole time! Thanks for joining the conversation!
This month, we're bringing it into the foreground.
So, What Is Uncertainty?
Before we do anything with it, let's name it clearly.
Uncertainty is the state of not knowing.
Not knowing what a client will say.
Not knowing if the offer will land.
Not knowing whether the decision you made last Tuesday was the right one or the beginning of a mistake.
Not knowing what comes next in your business, in your relationships, in the world outside your window.
It is the gap between what is and what will be. And your brain lives in that gap as you make decisions every single day.
Uncertainty is not the same as danger. It is not the same as failure. It is not even the same as being lost.
Uncertainty simply means the outcome is not yet written. The road is real. The destination is real. The next mile marker just isn't visible yet.
Your brain, however, does not always make that distinction.
And so it does what brains do: it tries to close the gap. Some of us close it by preparing until we feel ready. Some of us close it by moving so fast there's no time to feel the gap at all.
Both are brilliant unconscious strategies.
But neither approach removes uncertainty.
Why Your Brain Treats "I Don't Know" Like a Fire Alarm
We'll go much deeper on this in Week 3, but for now, let’s just touch on the neuroscience enough to start noticing.
Your brain is a prediction machine. Its primary job, running quietly underneath everything else you do, is to anticipate what happens next so it can keep you safe. When it can make a confident prediction, it feels calm. When the future is genuinely unclear, your brain can register that gap as a threat.
Not a metaphorical threat. A physiological one.
That's why uncertainty doesn't just feel uncomfortable in your thoughts. It often feels like something in your chest, a restlessness you can't quite name, or that particular kind of underlying exhaustion that comes from not knowing.
For people with ADHD, this response can be even stronger. Research on intolerance of uncertainty shows that when the outcome is unclear, the nervous system doesn't just notice and wait. It gets to work, scanning, looping, imagining possibilities, and preparing for many scenarios at once. That's not catastrophizing. That's your brain doing what it's meant to do, just at a volume others might not notice.
The entrepreneur refining her landing page for the sixth week isn't being difficult. Her brain is working overtime to manufacture enough certainty to feel safe moving forward.
The entrepreneur who posted the event graphic before the sign-up link was ready isn't being careless. Her brain found a different way to reach the same goal: generate momentum, create energy, and make something feel real so uncertainty has less space.
Both approaches are responses to the same uncertainty.
Where Uncertainty Shows Up for Creative Entrepreneurs
Uncertainty doesn't always announce itself. It rarely walks in and says, " Oh, hi, hello, I am the thing making this hard. It tends to arrive in either an over-the-top or completely thrown-together costume.
Let’s begin by taking notice of how it can look completely different depending on how your brain responds to not knowing. Here are a few places you might recognize it this week.
In the pause before you hit publish. You've written the thing. You know it's good. And you still hover, because you don't know how it will land. Or you post it immediately, before you've read it back, because waiting feels worse than going to a BNI meeting.
In the pricing conversation. You've done the math. You know your worth. Still, something feels tense when you say the number out loud, so you keep adjusting the offer until it feels safer to share. Or you name a number quickly, before you can second-guess yourself, and then spend the next three days worrying you went too low.
In the quiet after a big decision. Not regret, exactly. Just the hum of I made a move, and now I have to wait. That hum is uncertainty, and it can be relentless in an ADHD brain that is still turning the decision over, looking for the confirmation that hasn't arrived yet. That silence? Deafening.
In the comparison. When you look at someone else's timeline and measure yours against it, you're often really looking for evidence that your unknown future will be okay. You're borrowing certainty from someone else's story because yours isn't written yet.
In the to-do list that keeps growing. One more thing to prepare, one more detail to fix, one more reason it's not quite time yet. The list is long and keeps getting longer, because finishing it would mean stepping into the unknown.
In the idea that becomes a graphic before it becomes a plan. The energy of starting something new is real. It temporarily closes the gap. But when the momentum fades, the uncertainty is still there, along with new logistical questions.
We'll dig into all of this much more in the weeks ahead. For now, the invitation is simply to start noticing where uncertainty already lives in your days and how it manifests for you specifically.
This Week: Just Notice
We are not trying to “fix” or “manage” anything just yet. Let’s not even try to get comfortable with uncertainty today.
Let's just name it, point at it, and say: “Oh! There you are! I see you, you little rascal!"
Because here's what I know from the work I do with entrepreneurs every week and from my own experience as a business owner moving through a world that offers very few guarantees: you cannot change your relationship with something you haven't acknowledged is there.
Uncertainty drives your business actions, decision-making, creativity, and sense of safety. This month is about seeing it clearly and understanding its influence.
This week, try this:
When you feel the urge to over-research, over-plan, delay a decision, or scroll someone else's page looking for reassurance, pause for just a moment and ask: Is there something I don't know here that I'm trying to fix by doing this?
And if you feel the urge to move fast, post early, say yes before you've thought it through, or create momentum before the structure is there, pause and ask the same question: Is there something I don't know here that I'm trying to outrun?
You don't have to answer perfectly. You don't even have to stay in it long. Just notice if uncertainty is underneath the behavior.
That noticing? Bring it to our Curated Conversation community next Monday.
My questions for you this week:
Where do you feel uncertainty most in your body, and when does it tend to show up in your business?
What does "I don't know" feel like for you in your thoughts, in your body, in your behavior?
Reply and share with me!
✨ You Belong Here. I can help.
If you've ever made a decision just to make the uncertainty stop — or stayed stuck because moving forward meant not knowing what would happen — you are not alone. Welcome to being a creative entrepreneur!
This is the exact territory we can navigate together in the MindSweep Mapping Session. We slow it down, look at what's underneath the behavior, and build awareness and a strategy to move from a place of clarity instead of pressure.
It starts with a conversation. Book a free consultation!
Curated Conversation
You Read It. Now Come Sit In It.
Uncertainty called. It wants credit. And this month, we're finally picking up the phone.
In May, we're spending four weeks getting properly introduced to the thing that's been running your business patterns in the background — the preparing, the launching, the comparing, the stalling. It all leads back to the same place. We're going there together.
Curated Conversation meets live every Monday morning. We read the current issue aloud, sit with two discussion questions, and close with a five-minute guided meditation with Terri Hamilton. It's the Weekly MindSweep, but in community and in real time.
If you've never joined us, your first month is free.
You've been reading the room for weeks. Come sit in it.
Listen if you want. Speak if you're ready. Stay if it feels like home.
Mondays at 8 a.m. EST. Start with coffee. Belonging included. đź’ś
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What I’m reading
The War of Art
by Steven Pressfield
If you create anything — a business, a brand, a body of work — this book will name something you’ve been living but couldn’t quite articulate.
What has stayed with me is recognizing how sophisticated Resistance can be.
In other news…
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