Introduction:

"I remember year five."
Four simple words that validated everything I'd been experiencing as an entrepreneur. When Michelle Mitchell said that to me, it was like someone finally turned the lights on in a dark room I'd been stumbling through.
Year five isn't random. It's when you stop running a business and start owning one. It's when the employee mindset finally breaks, patterns become visible, and you realize—for the first time—what you're actually building.
But here's what nobody tells you: most entrepreneurs never make it to year five. And the ones who do? They're often too burned out to appreciate what they've learned.
Michelle Mitchell has been doing this for 15 years. She's not just survived the milestones—she's documented them, learned from them, and built a business that runs without her.
This conversation is about the patterns you can't see until you've lived them. And why recognizing them earlier could save you years of unnecessary struggle.

Real Story (one person, one action, one result)

I hit year five thinking I'd figured it out. I knew my business. I understood my market. Revenue was coming in.
Then I had a conversation with Michelle.
"Yeah, I'm starting to figure some things out," I told her. "I knew what I knew, but I didn't know the things I didn't know."
Her response stopped me cold: "Year five. I remember year five."
That's when it hit me—this wasn't just my experience. There were milestones, checkpoints, patterns that everyone goes through. I wasn't alone. I wasn't behind. I was right on schedule.
But here's the shift that changed everything: Michelle explained that in those first five years, you're still stuck in employee mindset. You're working certain hours because that's what you're "supposed" to do. You're doing things the corporate way because that's all you know.
The breakthrough? Realizing you get to call the shots. No one is motivating you—it has to be internal. The regular paycheck is gone, and it won't be regular for quite some time.
Michelle put it bluntly: Some people think they're running a business, but what they really have is a nonprofit—because they don't understand how to position their expertise, attach transformation to it, and put a dollar figure on it.
So they just don't sell anything.
The action? She started documenting patterns. Reflecting on what worked, what didn't, and why. Every client interaction. Every pricing decision. Every moment of hesitation.
The result? Fifteen years later, she's built a team she can trust, created courses that teach financial literacy, and stepped into the CEO role where the business runs—with or without her.

The Truth (why it matters)

Most entrepreneurs are living the same five years over and over.
They're stuck in hustle culture—believing they need to be on every platform, attend every event, and work 24/7 to prove they're serious. They've traded one grind for another.
But here's what Michelle knows that most don't: There's a time to hustle. But you shouldn't always be hustling.
If you're not being retrospective—learning from the hustle, documenting the patterns, setting yourself up for flow—you'll crash and burn.
The truth about timing:
You don't know if you missed an opportunity or caught it at the perfect time until it's already passed. So you take time to reflect. You go back and ask:
● Did I hesitate too long?● Did I jump too fast?● What lessons did I miss?

Michelle is clear: "You have to reflect on the things that have happened to you in business. If you didn't do it at the end of the year, now is the time."
Because when you reflect, you start seeing patterns:● The clients who drained your energy (and why you said yes)● The pricing mistakes you made out of desperation● The opportunities you hesitated on—and what that cost you

The employee-to-entrepreneur shift isn't just mindset. It's accountability.
When you work for someone else and mess up, they handle the client. You might get reprimanded, maybe fired—but it's not on you.
When you're the business owner? Every decision is yours. Every client interaction. Every reputation hit. Every consequence.
That's why Michelle says: If you have baggage with money in your personal life, you'll have baggage with money in your business. The patterns follow you.
But if you document, reflect, and learn—you shorten the curve. You build the foundation. And when life throws the unexpected (like her MS diagnosis six months after starting her business), you've built something strong enough to survive it.

What To Do (one clear everyday action)

Stop moving. Start reflecting.
At the start of this year (or right now), take time to look back at what already happened. Don't just look at revenue. Look at patterns.
Here's Michelle's framework:Ask yourself:● What worked for me last year?● What didn't serve me?● What do I need to stop doing?

Document it. Write it down. Track it. Because:
● If you don't document, you won't remember● If you don't reflect, you'll repeat the same mistakes● If you don't learn the lessons, you'll stay stuck

Give yourself permission to quit things that don't serve you.
Michelle is adamant: "I give you permission to stop doing things that do not serve you. Period."
That platform you're forcing yourself to show up on? Stop.
That pricing model that keeps attracting the wrong clients? Change it.
That "guru" advice that's not working for your business? Ignore it.
The goal isn't perfection. It's pattern recognition.
Once you see it—you can't unsee it. And that's when growth happens.

Conclusion

Year five isn't magic. But it is a milestone.
It's when you stop thinking like an employee and start thinking like an owner. It's when patterns become visible. It's when you realize the business model you brought from corporate doesn't work in entrepreneurship.
But you don't have to wait five years to learn these lessons.
Michelle spent 15 years documenting, reflecting, and learning—so you don't have to take as long.
Her question sits with you: "Where are you today? Where do you want to be? Who do you need to become to get there?"
The gap between where you are and where you want to be isn't filled with more hustle. It's filled with reflection, documentation, and the courage to stop doing what doesn't serve you.
Ready to stop repeating the same patterns?
Download Michelle's free guide: 3 Simple Financial Habits Every Entrepreneur Needs
These aren't generic tips. They're the foundational habits that helped Michelle build a business that runs without her—and they'll help you spot the patterns before they become problems.

About the Guest

Michelle Mitchell helps entrepreneurs understand their business finances, call out patterns that don't serve them, and build businesses that support their life goals. Diagnosed with MS six months after starting her business, she built a team and systems that allowed her to step into the CEO role—and eventually shareholder—while maintaining her health and passion for financial literacy.
Connect: YouTube | LinkedIn

What Patterns Are You Missing?

This episode is part of an ongoing series on business milestones and decision-making. Drop your questions in the comments—we'll address them in upcoming episodes.
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