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What Sitting Down with Leslie Shields Reminded Me About Business (Besides the Fact That Entrepreneurs Need More Sleep)
- RED Development Group Admin
- Jul 8
- 4 min read
A Letter to Every Business Owner Who’s Working Hard, Wearing Every Hat, and Wondering Why Their Calendar Needs Therapy
When I had the opportunity to sit down with Leslie Shields on the Life, Business, and Everything in Between podcast, I expected a conversation about entrepreneurship.
What I didn’t expect was a reminder of why so many business owners unintentionally become employees of the very companies they created.
If you’ve ever found yourself answering emails at 11:47 p.m., eating lunch in your car because “it’s efficient,” or convincing yourself that vacation is something other people do, this one’s for you. . . Pull up a chair. Let’s talk.
Somewhere Along the Way, Entrepreneurs Started Glorifying Busy
Entrepreneurs wear “busy” like it’s an Olympic medal. Someone asks, “How are you doing?” And we proudly answer, “Busy!” As if exhaustion is proof of success. Imagine if doctors answered that way. “How’s the surgery going?” “Busy.” Not comforting. Yet, business owners have somehow convinced themselves that working 70 hours a week is evidence they’re winning.
Here’s what I shared with Leslie:
"Being an entrepreneur and being a business owner are not the same thing. (YouTube) One creates work. The other creates systems that produce results. There’s a difference. A very profitable difference."
The Day You Become the Bottleneck
Every founder has experienced it. Your team asks where a file is. You know. A client needs an answer. They call you. A proposal needs approval. It waits on your desk. Payroll question? You. Vendor issue? You. Printer jam? . . . still somehow you. At some point, your business quietly stops running because of you and starts running through you. That isn’t leadership. That’s dependency dressed in business casual.
Your Business Shouldn’t Require Your Constant Presence
During the podcast, Leslie and I talked about systems. Not because systems are exciting. Let’s be honest. Nobody wakes up saying, “Today I hope someone teaches me Standard Operating Procedures.” But everyone wants the outcome of systems.
They want:
Freedom.
Consistent revenue.
Better teams.
Less chaos.
Predictable growth.
The funny thing? All of those are side effects of good operations. People often ask me, “What’s the secret to scaling?” They’re expecting some magical marketing trick. Instead I tell them something wildly disappointing . . . Document your processes. I know. Not nearly as exciting as a viral social media strategy. But infinitely more profitable.
The Myth That You Have to Do Everything
Business owners are some of the most talented people I know. Which is wonderful. And dangerous. Because talented people develop a terrible habit. They say, “I’ll just do it.” Again. And again. And again. Until one day they realize they’re the:
CEO
HR Director
Marketing Department
IT Help Desk
Office Supply Coordinator
Customer Service Representative
Emergency Coffee Procurement Specialist
No wonder you’re tired. Your organizational chart has one name on it. Yours.
Systems Don’t Replace People
They Empower Them. One of the biggest myths in business is that systems make work robotic. Actually, systems make people confident. Imagine joining a company where:
Nobody knows how onboarding works.
Every manager explains things differently.
Every client gets a different experience.
Every employee has “their own way.”
That’s not culture. That’s improvisation. And improvisation is a terrible long-term operating strategy. Systems don’t eliminate creativity. They eliminate confusion. There’s a big difference.
Freedom Is Built, Not Found
One of my favorite moments from the conversation with Leslie was discussing what business owners are really chasing. Most people say they’re chasing money. I don’t think that’s true. I think they’re chasing freedom.
Freedom to spend time with family.
Freedom to travel.
Freedom to think strategically.
Freedom to stop answering emails during dinner.
Money is often just the vehicle. Systems are the engine. Without systems, more revenue simply creates more complexity. More clients become more fires. More employees become more questions. More growth becomes more stress. That’s not success. That’s multiplication without infrastructure.
Here’s My Challenge to You
Ask yourself one question. If you disappeared for two weeks:
Would your business continue moving?
Or would your phone explode like it just received an emergency weather alert?
If the answer is the second one, don’t feel discouraged. Feel informed. Because now you know exactly where your next level of growth lives. Not in working harder. Not in another productivity app. Not in another color-coded planner. It lives inside operational excellence.
The Real Goal
At RED Development Group, we often say we help businesses become sustainable, agile, and profitable. Those aren’t just nice words. They’re outcomes. Sustainability means your business doesn’t collapse when you’re unavailable. Agility means your team can adapt without panic. Profitability means your company rewards your leadership instead of consuming it. That’s what we’re building. Not just businesses. Businesses that give founders their lives back.
One Final Thought
If my conversation with Leslie reminded me of anything, it’s this:
The businesses that change lives aren’t always the ones with the biggest ideas.
They’re the ones with the best execution. (YouTube)
Ideas inspire.
Systems sustain.
Processes multiply.
And leadership isn’t measured by how indispensable you become.
It’s measured by how well your business performs because you built something bigger than yourself.
So the next time someone asks how business is going instead of saying, “Busy.” Imagine saying, “It’s running.” Now that’s a conversation worth having. If you haven’t had a chance to listen to my conversation with Leslie Shields on Life, Business, and Everything in Between, I hope you will. We dive deeper into the difference between entrepreneurs and business owners, why systems create freedom, and how building a sustainable company is one of the greatest gifts you can give yourself, your team, and your family. It was a conversation I thoroughly enjoyed, and I think you’ll walk away with practical ideas you can put to work immediately. (YouTube)
Here’s to building businesses that work. Even when you don’t.
An Invitation
If your business feels:
Reactive
Overwhelming
Founder-dependent
Operationally inconsistent
Don’t waste the crisis. Use it.
Let RED help you:
Identify operational blind spots
Clarify systems and accountability
Strengthen leadership infrastructure
Build sustainable operational rhythms
Through the RED Executive Assessment Suite, we help founders turn pressure into process and crisis into clarity. Because sometimes the breakthrough is hidden inside the breakdown. Wise leaders never waste the crisis.
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