The Magic of the Messy Middle: What It Really Takes to Scale
- Liz Short
- Jul 30
- 3 min read
Every business owner chasing real growth eventually hits it.
The Messy Middle.
You know the place.
You’re knee-deep in progress, the “fun” phase is long gone, and now it’s just… meetings, setbacks, and second-guessing everything.
Not glamorous.
Not cute.
But absolutely necessary.
Whether you're rolling out new tech, launching a new revenue stream, or trying to shift your whole strategy without setting your team on fire, there's one hard truth: big moves come with big messes.
The Myth of the Perfect Plan
Let’s stop pretending that strategic planning makes everything smooth.
It doesn’t.
It just gives you a smarter starting point before things get chaotic.
And trust me, they will get chaotic.
The bigger your goal, the more curveballs you’ll catch.
Yes, you need a plan.
But no, you won’t be able to spreadsheet your way out of every unknown.
If you're scaling, shifting, or shaking things up, welcome to the part of the journey where things get weird.
Change Management Is More Than a Checklist
Scaling your business is less “just follow the plan” and more “herding caffeinated squirrels through a maze.”
Change management isn’t about handing your team a timeline and calling it a day.
It’s about navigating the people part of progress.
The doubt, the resistance, the “Wait, why are we doing this again?”
The strategy?
Important.
The human stuff?
Critical.
So build in flexibility.
Make space for real talk.
And know when to shift gears without burning the whole thing down.
What It Takes to Scale: Make Peace with the Pivot
Say it with me: pivoting is not failure.
It's feedback.
It’s leadership.
It’s knowing when to cut your losses or rework the timeline so your team doesn’t riot.
The plan you kicked off with might’ve looked great on paper.
But if the reality has shifted (and it will) you’ve got two options: adjust or stall out.
Smart leaders adjust.
So don’t cling to the plan.
Learn to read the room, rework the strategy, and keep things moving.
What Actually Works When You’re in the Thick of It
Here’s what’s saved my sanity in the messy middle:
Check in. Often. Not just with your KPIs, but with your people.
Normalize the mess. It’s not broken. It’s just in process.
Ask for help. Get a coach, a consultant, a unicorn ops person—whoever helps you see clearly when you’re too deep in the weeds.
Remind yourself why you’re doing this. Because the middle will make you forget.
And don’t just “hope for the best.”
Hope is not a strategy.
A well-timed pivot?
That’s strategy.
My Own Messy Middle
Look, I’ve been running this business for 2.5 years and spoiler alert: the messy middle isn’t a phase.
It’s a recurring event.
Some days I’m high-fiving myself like a boss.
Other days I’m wondering if I’ve actually lost my mind.
Welcome to entrepreneurship!
What keeps me grounded?
Knowing perfection’s not the goal, progress is.
That, and having a go-to crew of smart humans I can lean on when the wheels feel wobbly.
Growth Is Messy for a Reason
If you’re deep in a growth spurt right now, I want you to hear this: you’re not doing it wrong.
You’re just in the middle.
The messy middle isn’t just a hurdle—it’s where you figure out what it takes to scale with intention, resilience, and a whole lot of flexibility.
So embrace it.
Don’t polish it.
Don’t panic.
This is where the good stuff starts.
I've been right where you are now: spinning wheels in the messy middle. Let’s untangle your growth strategy together! Together we'll make a plan that works, especially when things get a little wild.
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