Most entrepreneurs start businesses to escape structure.
We want freedom. Control. The ability to make our own decisions without someone looking over our shoulder.
Then we build companies that become prisons.
I’ve been thinking about this a lot after my conversation with Leslie Hassler on the En Factor podcast. She is a small business scaling strategist who transformed her first business from what she calls “a prison of my own making” to Your Biz Rules, her “playground.” The difference wasn’t working harder or finding better clients.
It was structure.
The Efficiency Pathway
When we can create structure, it allows us to shorten our decision-making process. It creates a pathway for more efficiency.
Think about it this way: every time you make a decision from scratch, you burn mental energy. Should I respond to this email now or later? Which task comes first? How do I handle this client situation?
Structure answers these questions before you ask them.
When we have this pathway to efficiency, we shorten the amount of time required to do those things that need to be done. It opens us up to do the things we want to do beyond those day-to-day check-the-box tasks.
This is where most entrepreneurs get it wrong.
We assume structure is too binding. That it doesn’t give us the freedom and independence we need to be creative and innovative and do what we need to do as entrepreneurs to be successful.
But it’s really just the opposite.
I teach this when I teach about creativity. It’s not about a free-for-all. It really is about understanding the boundaries and knowing when to push those and knowing when to change them.
Structure doesn’t mean you’re locked in. Structure gives you the freedom to be innovative and to live the life you want. Maybe balanced isn’t the right word, but integrated.
A life that integrates all the aspects of who you are.
Uncertainty As A Constant
Leslie challenges something most entrepreneurs believe: that uncertainty is new.
Uncertainty has always existed. We just weren’t always aware of it.
When something becomes a constant and we frame it that way, we build a strategy around how to deal with it. But when we think of it as something that’s not supposed to happen, something to be feared and pushed away, it becomes more challenging.
Right now we live in a very uncertain business climate. It’s challenging to predict the future and plan.
So here’s what I’ve learned: if we can recognize that uncertainty is part of life and we have to live in the moment, it becomes powerful.
Obviously we need to continue planning. But recognizing that those plans are based on assumptions, and those assumptions may change.
The more we recognize the presence of uncertainty, the more we take note of those assumptions. Otherwise we walk around making assumptions without even being aware of them.
But when we’re aware that we need to bring these assumptions top of mind and note them, we can always look back and say, “Those assumptions don’t hold anymore. What do I need to do about changing my plans?”
This is structure too. A structure for thinking about uncertainty.
The Control Trap
Here’s the hard truth: entrepreneurs like being in control.
That’s partly what led us down the path of entrepreneurship. We like being our own boss.
But this personality trait creates a massive blind spot.
Leslie shared a powerful story about a client who systematized operations and empowered her team. The owner took a month-long honeymoon. When she returned, the business was running better without her direct involvement.
That’s not failure. That’s freedom.
But getting there requires confronting something uncomfortable: we often derive our value from the work itself rather than the impact.
When you’re the one doing everything, you feel needed. Essential. Valuable.
When systems run without you, it can feel like you’re not contributing. Like maybe you’re not as important as you thought.
This is ego talking, not strategy.
Leslie’s approach to this is practical. She helps entrepreneurs take situations that are ambiguous and lacking structure and create a pathway forward. That’s a very powerful skill.
Most entrepreneurs can learn this. But working with someone who can hold up that mirror, who can see what you can’t see about yourself, jumpstarts the process.
Communication As Infrastructure
One specific example of structure creating freedom: centralized communication systems.
Leslie’s team uses one main platform as their “hive mind.” All work-related communication happens there. Not scattered across texts, Slack messages, and email threads that aren’t scalable or easily referenced.
This seems simple. Almost too simple to matter.
But think about how much time you spend searching for information. “Who said that? Where was that decision made? What did we agree on?”
When communication has structure, everyone gains freedom. Freedom from constant interruptions. Freedom from information anxiety. Freedom to work asynchronously without losing context.
This is especially critical for remote teams. Without physical proximity, structure becomes the connective tissue that holds everything together.
Your Superpower
One of my biggest takeaways from talking with Leslie: everybody has a superpower.
The way we become successful is by focusing more on our strengths than on trying to compensate for our weaknesses.
We talked about surrounding yourself with people who can fill in gaps. But also recognizing your superpower and how to play to that.
Leslie’s superpower is visibility. She helps people see where to build structure to give them freedom.
What’s yours?
You can’t operate in your zone of genius if you’re trying to be good at everything. You can’t do that if you’re spending your time on tasks that drain you instead of energize you.
Structure allows you to delegate everything outside your superpower. To build a team where everyone operates from their strengths.
Action Over Waiting
Leslie says something that cuts through all the noise: “Wait and see is not a strategic plan.”
You will always experience growth through action, whether it’s what you wanted or not.
This is critical right now. When uncertainty is high, the temptation is to pause. To wait until things become clearer.
But clarity comes from action, not contemplation.
Both successes and failures provide learning opportunities that guide you to your next breakthrough. The only way you don’t learn is by not moving.
This doesn’t mean reckless action. It means structured experimentation. It means making your assumptions explicit, taking action, and adjusting based on what you learn.
It means building systems that allow you to move fast without breaking things.
The Integration
So here’s what I want you to take away from this.
First, don’t be afraid to get help and support. Sometimes we need guidance from experts who can see what we can’t see about ourselves.
Second, self-awareness is incredibly important. Someone else can hold that mirror up for us. They can show us things we see or don’t see about ourselves that can be very helpful.
Third, shift your mindset to understand that structure is not confining. Structure can give you the freedom to live life and build a business more fully, more passionately, more in line with the life and work you imagine.
The entrepreneurs who thrive aren’t the ones who resist structure.
They’re the ones who build it deliberately. Who use it to create space for what matters. Who understand that freedom isn’t the absence of constraints but the presence of the right ones.
Structure doesn’t trap you.
The lack of it does.
Tune into the full episode with Leslie Hassler to hear more about her story and incredible insights for entrepreneurs.
