Why You Shouldn’t Be Afraid to Hire an Entrepreneur (And Why It Might Be Your Smartest Move)
Recently, I heard something that genuinely surprised me:
“We don’t hire entrepreneurs. They never last. They can’t work for other people.”
As someone who has been both an employee and a business owner, I felt a sting of offense. Not because entrepreneurship hasn’t changed me, but because the assumption is backwards.
My years running a business didn’t make me difficult to manage. They made me better at understanding how a business works and what it needs to grow.
Entrepreneurs often make excellent employees. Here’s why.
Entrepreneurs Understand the Weight of Responsibility
When you’ve been the person who makes decisions that affect payroll, customer satisfaction, and day-to-day operations, you don’t show up to work the same way.
Entrepreneurs know:
What it costs when someone is careless
Why clear systems matter
How small details impact the customer
How fragile momentum can be
That experience doesn’t disappear when we join a team. It actually creates respect for the business we’re stepping into.
I don’t just want to do the job in front of me. I want to protect the business. I know what it feels like to build one and keep it alive.
Entrepreneurs Don’t Resist Structure. They Rely On It.
Another myth is that entrepreneurs can’t follow systems.
In reality, most of us love good systems. We’ve worked through the chaos of not having them, and we understand the relief that comes from clear, organized workflows.
We recognize when something is inefficient. We notice when a process doesn’t make sense. And we care enough to fix it, because we’ve seen what happens when small problems turn into big ones.
We’re not here to break structure. We’re here to strengthen it.
We Think Like Owners, Even When We’re Not the Owner
Employees who think like owners are priceless. They see the chain reaction behind every decision. They think in terms of sustainability, consistency, and long-term results.
Entrepreneurs naturally bring that perspective because we’ve lived it.
We notice risks early. We understand the customer’s point of view. We know how to prioritize. And we’re willing to step in where needed, because that’s what we’ve always done.
Hiring someone who thinks like an owner doesn’t threaten your business. It protects it.
So Why Do Some Employers Avoid Hiring Entrepreneurs?
Most of the hesitation comes from assumptions:
They might leave quickly
They might want to change things
They might struggle with authority
But people in any role can leave, resist change, or ignore direction. The difference is that entrepreneurs understand what’s at stake when something goes wrong.
We’ve dealt with the consequences of unclear processes, miscommunication, and poor training. We know how painful those mistakes can be. We’ve done the work to prevent them.
This makes us more reliable, not less.
What Leaders Can Learn From Hiring an Entrepreneur
Instead of avoiding entrepreneurs, ask them questions that let them bring their experience forward. For example:
What systems helped your business grow?
What patterns did you see when things went wrong?
What documentation kept your team aligned?
What would you improve here to help the team save time or reduce stress?
You’ll learn more from that conversation than you might expect. Entrepreneurs are trained to notice what others overlook.
How This Connects to the Work I Do Today
My entire service style comes from this perspective. Whether I’m building SOPs, designing a user guide, organizing a training program, or creating a website, my goal is the same:
Create clarity.
Remove confusion.
Make things easy for the next person.
Think long-term.
Entrepreneurial thinking helps me turn scattered ideas into complete systems that work. It’s the reason I can walk into a messy process and organize it. It’s also why I care so deeply about documentation and training. I know how much they matter.
And above all, I know how much a business owner carries. I’ve carried that weight myself.
If you want someone on your team who brings both structure and ownership thinking, or if you simply want to get your systems, SOPs, or training materials in better shape, I’d love to help.
You deserve clarity. You deserve processes that work. And you deserve support from someone who knows the view from both sides.
Tired of answering the same questions over and over?
My free Stop the Chaos template will help you capture one process and give your team the clarity they need.
