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Diary of a Leader: When Growing Your Business Starts to Feel Like a Trap
- Lindsay Sheldrake
- Mar 8
- 4 min read
Updated: 3 days ago
Welcome to Diary of a Leader: Real Stories, Leadership Lessons, and Personal Growth
Ah, founders.
Few experiences in business are more disorienting than building something successful and then feeling trapped inside it.
It shows up in conversations. A founder will describe how well things are going. Demand is strong. The team is talented. The work is good.
And then they pause.
"But somewhere around twenty people, something shifted."
Welcome back to Diary of a Leader, where we explore what is really happening beneath leadership, growth, and the structures meant to support both.
This week is about the moment growing businesses start to feel harder to run than they used to. Because that feeling is not random. And it is not a leadership failure.
It is a structural signal.
When Growth Starts to Feel Like the Problem
I have had versions of this conversation several times recently. Different industries, different business models, different founders. But the pattern is remarkably similar.
Up to a certain size, the business works because the founder holds it together. They know every client. They understand every project. They are close enough to every decision that things move because they are in the room.
Then the team grows. More clients. More projects. More people doing good work.
And somehow, the founder ends up more involved, not less.
Communication starts to fragment. Decisions that should be simple start traveling upward. Teams begin waiting rather than moving. And the founder, who built something successful, starts to feel stuck inside it.
The work is not harder. But the business has become harder to run.
This Is Not a People Problem
The instinct in this moment is often to look at the team.
Are the right people in the right roles? Does someone need more training? Is there a communication breakdown that better meetings could fix?
Sometimes those things matter.
But in most of the conversations I have had recently, the team is not the problem. The structure is.
When a business is small, informal systems work because the founder fills every gap. They are the decision flow. They are the communication system. They are the accountability structure. Not by design, just by proximity.
That works at eight people. It starts to strain at fifteen. By twenty, the gaps in the structure are no longer small enough for one person to fill.
And yet most businesses at this stage have not yet designed anything to replace what the founder was doing alone.
Growing Business Operational Structure: What Actually Needs to Change
The honest answer is that nothing sudden happens at twenty people.
What happens is that the distance between the founder and the work increases gradually, until one day it is too large to bridge informally.
Decisions that used to happen in a hallway conversation now require a meeting. Information that used to travel naturally now gets lost between teams. Accountability that used to be obvious now needs to be explicit.
None of this is a failure. It is a predictable stage of growth.
The businesses that move through it well are not the ones with the best talent or the strongest culture. They are the ones that recognize the shift early and design for it intentionally.
They stop relying on proximity and start building structure.
The Question Worth Asking
Most founders in this situation ask: what is going wrong?
The more useful question is: what is this business still relying on me to hold together that a structure could hold instead?
That single shift changes where you look for answers.
Reflection Questions
At what size did your business start to feel harder to run than it used to?
Where do decisions slow down, and what does that reveal about how authority is defined?
What are you still personally holding together that a structure could hold instead?
What would need to be true for your team to move without you in the room?
Wrapping Up: Growth Reveals Structure
The twenty-person wall is not really about headcount.
It is the moment when the gap between how the business was built and how it now needs to operate becomes visible.
Founders who move through it well are not the ones who work harder or hire faster.
They are the ones who stop and ask: what does this business actually need to carry its own weight?
That question, asked early enough, changes everything.
You Don’t Need to Solve This All at Once
f this resonated, that is enough for now.
Awareness comes first. Clarity follows. Change comes later.
When you are ready to look at the structure underneath your business, that is where the real work begins.
When you're ready, you can reach out at SOLVED Collective.
Continue Reading
If this resonated, these posts go deeper:
Stay tuned for more real-world reflections on leadership, operational clarity, and purposeful growth in the next installment of Diary of a Leader.
