Self-Employed vs. Business Owner: Which Stage Are You In?

After spending 2 months in spring 2025 undergoing and healing from emergency spinal surgery it got me thinking ... if YOU got laid up and couldn't work for 2 months, would your business go on without you?

Self-employed vs business owner are similar but not the same! Most service-based entrepreneurs, coaches, and consultants start out self-employed (you get paid to do all the work) but staying there forever means your business can only grow as far as your personal time and energy will stretch.

Here’s the truth: being self-employed isn’t “bad.” It’s actually a vital stage of growth where you learn the ins and outs of your work, your clients, and your systems. From there, you get to decide how (or if) you want to evolve into a business owner.

In September's Shop Talk (catch the replay below 👇), we explored the difference between being self-employed and running a business, plus the steps to elevate your mindset, vision, and model.

Self-Employed vs Business Owner: What stage are you in?

The 4 Stages of Growth (and Why Each One Matters)

Stage 1: Self-Employed

• You’re delivering the services, coaching the clients, or building the products yourself

• Why this stage matters: You learn exactly what your clients want, what works (and doesn’t), and start building your own proprietary processes

• The win: You know your business inside and out, which helps you decide what to automate, delegate, or outsource later

Stage 2: Structured & Streamlined

• You package services, create repeatable offers, and put simple systems in place

• Why this stage matters: You reduce decision fatigue, get more predictable revenue, and lay the foundation for future team support

• The win: Freedom from “custom everything” and more mental energy for growth

Stage 3: Supported & Shared

• You hire subcontractors, employees, or facilitators to help deliver

• Why this stage matters: You shift from “I do everything” to “the business serves clients”

• The win: More capacity, less burnout, and a business that doesn’t pause if you take time off

Stage 4: Scalable Assets

• You turn your expertise into courses, memberships, templates, or certifications

• Why this stage matters: Your intellectual property works for you, creating revenue without more hours

• The win: Recurring income, thought leadership, and freedom to focus on your vision

Reflection Questions for Entrepreneurs

These came directly from our Shop Talk conversation. Take a few minutes to jot down your own answers.

1. If you stepped away from your business for a week or a month, what would keep going, and what would stop?

2. Which stage do you feel you’re in right now, and what are the benefits of being there?

3. What would your day look like if you were showing up as a business owner instead of self-employed?

4. What’s one task you could delegate, automate, or systematize tomorrow?

5. What feels exciting (and what feels scary) about letting go of some control?

Common Questions Entrepreneurs Ask

During our discussion, a few themes popped up again and again:

• “How do I know if I’m ready to hire help?” → Start with small, repeatable tasks that eat up your time. Even 5 hours a week off your plate is a win.

  
  

• “What if I love the hands-on client work?” → Great! Staying self-employed is valid. Scaling doesn’t always mean an agency or no longer doing the work you love. It can mean productizing your expertise, creating group offers, or just working smarter.

  
  

• “How do I keep my business personal if I bring in a team?” → Document your processes, values, and client journey. That’s what makes the business feel like you, even when others are involved.

  
  

• “Is it too soon to think about systems if I’m brand new?” → Nope. Even simple systems (like saving email templates instead of rewriting them every time) make your life easier and prepare you for growth.

Why This Matters for Local & Online Entrepreneurs

Whether you’re a service provider in Vancouver, a coach with global clients, or a digital product creator, the principle is the same:

👉 Your business should work for you, not the other way around.

Each stage is part of your evolution. The key is recognizing where you are right now, leaning into the benefits of that stage, and making intentional choices about what comes next.

Your Next Step

Take 5 minutes to answer the reflection questions above. Then choose one small action that moves you a step closer to the business you want to build, whether that’s documenting a process, delegating one task, or mapping out a product idea.

And if you want to go deeper, watch the full Shop Talk replay and join us live next month for more honest conversations about building a profitable, scalable business without the burnout.

Join the Ick-Free Sales Community

Have more biz questions than answers? Great! That's a normal stage of early entrepreneurship and our Ick-Free Sales Community will help you find the answers, get sales, and grow your brand ... your way!

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Howdy, I'm Lindsay aka The Radical Connector. I've been teaching entrepreneurs how to stop burning out on busy work (that doesn't work), ditch the chaos & overwhelm of growing a new business, focus on the right sales & marketing activities (the stuff that actually works) and to step into their role as CEO and visionary so they can bring their epic business dreams to life for over 20 years.

If you're ready to grow and scale a business without burning out, selling out, or doing it all alone, you're going to love it here!

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