You can’t read the label from inside the jar

You know what’s frustrating?

Being the person everyone else trusts to see the obvious next move… and then looking at your own business like someone dumped the contents of five different notebooks onto the floor and said, “Good luck, CEO.”

I see this all the time with really smart business owners (myself included).

They can walk into a client’s business, spot the problem, name the pattern and give the client a path forward before the coffee even gets cold. Then they turn around and try to do the same thing for themselves, and suddenly everything feels foggy.

The half-built projects all feel like they could matter, but because everything feels important, nothing really is.

The systems are almost working, but only because you’re still the one remembering how all the pieces are supposed to connect.

Rest assured this is not a sign that you aren’t good at what you do or even a general character flaw. It’s what happens when you’re “trying to read the label from inside the jar.”

Here’s a perfect example of what I mean by that… I was on a consulting call recently with a client who is genuinely brilliant at business strategy.

She helps female service providers grow their businesses through coaching and a multi-track program built around client acquisition, leadership, and sustainable growth.

She is the person her clients come to when they need help seeing what is happening in their business, making better decisions, and getting traction on the next stage.

BUT, her own business had a lot moving at the same time. She runs multiple group coaching calls every week. She has team members, clients, systems, SOPs, and more ideas than time.

So she is not new to business strategy. She is just very much inside her own business.

Honestly, we ALL are.

Most entrepreneurs have brains that are very good at seeing possibility. They can connect dots quickly, imagine what something could become, and start building before the average person has even found a pen.

That kind of brain is powerful. It is also fully capable of getting 30%–40% into a project, losing momentum, circling back weeks later, and realizing you now have to spend half your energy just remembering what “Past You” was trying to do.

I will bet my left eye that you don’t need someone to help you come up with good ideas. You had plenty of those.

What you need help with was deciding which ideas deserved to be finished, which needed to be simplified, and which could be released without turning it into a whole identity crisis.

Guess what? You’re not alone.

Wanna know what I have done with MANY clients, both 1:1 and inside my program? We have literally sat together and worked through their task lists, line by line, because they were afraid to take things off.

Every item felt “urgent” even if it really wasn’t. Every idea felt “important” even if it was still half-baked with no deadline as far as they can see.

Every “I should probably do that” was treated like it belongs next to actual client work, sales follow-up, or delivery tasks.

And THAT is the metaphorical jar, my friend.

(which is why I’m pretty sure this needs to become a whole separate webinar training down the road; stay tuned!)

From inside, it all looks connected and it all feels like it matters, but it’s more like a tangled rope than a step ladder. Both are designed to help you climb, but only one is set up to do so quickly and easily.

Instead of sorting things by what they actually are, you end up giving the same level of energy and brainpower to everything.

And that is where outside perspective helps… Someone who’s outside the jar and can read the label.

You are not brand new anymore. You have clients, revenue, offers, proof, ideas, systems, and momentum. But you also have more complexity than you used to, so you start wondering why you can’t just “figure it out.”

It’s not that you lack business brilliance so much as you are often too close to all the moving parts to separate what matters most from everything that simply feels important.

And if we are just going to go one level deeper in the mindset work (which, tbh, I avoid whenever possible, which is why I hired a coach!), this is where a lot of people quietly start beating themselves up.

They assume needing help means they are somehow less credible and if they need a coach or mentor to help them sort through the swirl, maybe that means they should have been further along by now.

But that is just ego getting in the way of growth. Great leaders do not prove their competence by trying to make every decision in isolation.

They build a circle of people who can help them see the business from a cleaner angle, who can see what they see, but without being buried under the same emotional attachment, history, pressure, and “but this could be something” energy.

When you’re inside the business, everything has context, but an outside perspective helps you tell the difference between something that needs follow-through and something that is only hanging around because you do not want to waste the work you already put into it.

That distinction matters, especially if you have a pattern of starting strong and fading before the finish line.

Weekly Challenge

This week, the goal is to find the pattern. Where do you keep getting tripped up?

Look at the places in your business where you keep circling, not as proof that you are failing. Look at it as information. Patterns are useful when you stop using them as evidence against yourself.

This week, take 10–15 minutes and write down the repeat offenders in your business.

1. Where do you consistently lose traction?
2. Where do you keep making the same decision over and over?
3. Where do you have a pile of almost-finished things that may need to be completed, simplified, delegated, or tossed?

Then bring that pattern to someone outside your business. It could be a mentor, a coach, a consultant, or a peer who knows how to ask good questions.

Or want the AI prompt that I wrote specifically for this challenge? It’s in my new free Skool Community!

Instead of pretending you have perfect decision-making skills or proving you can do everything alone, learn where your objectivity disappears and build support around that.

Because you can be excellent at what you do and STILL need perspective and still need another set of eyes on the business you are standing inside every day.

That is the real work of getting through the messy middle and it doesn’t make you less of a CEO. It makes you a smarter one.

Speaking of which, if this is the season you’re in…

Join my NEW Notion AI Skool Community

It’s where I’m gathering CEOs who are in the messy middle, but have no plans to stay there!

We’re using Notion, AI, and cleaner systems to make better decisions, finish what actually matters, and stop letting every good idea turn into another open loop.

Inside the community, you’ll find past

• Webinar replays that are no longer available publicly.
• Practical Notion AI demos.
• Behind-the-scenes walkthroughs of my Notion AI-powered business.
• And the AI prompts that go with these weekly challenges.

Just a heads up, while the community is launching, early members get free access to the AI prompt library from past newsletter challenges. As the community grows, that library will eventually move behind a paid tier, so this is the window to get in while it’s included.

If you want to be around other CEOs who are sorting the swirl, taking action, and building businesses they do not have to mentally babysit all day, come join us in Notion AI Skool.

Bring the pattern you keep getting stuck in.

We’ll help you see it from outside the jar.