How to Transition from Employee to Entrepreneur: A Step-by-Step Guide
Inspired by my conversation with Sasha Eburne on The Audacious Living Podcast
There’s a quiet moment many people don’t talk about.
It’s the one where you’re sitting at your desk, doing “what you’re supposed to do,” yet something inside you whispers, there has to be more than this.
That moment is rarely loud.
But it’s powerful.
I’ve had that moment myself, and I’ve heard it echoed again and again in conversations on the Audacious Living Podcast. One recent conversation in particular reminded me just how quickly life can change when preparation meets courage.
In my interview with business coach Sasha Eburne, she shared how she went from employee to entrepreneur almost overnight. First client in 24 hours. Fully booked in weeks. A team built within months. What stood out wasn’t just the speed. It was the mindset behind the move
If you’re standing at the edge of that same decision, here’s a grounded, realistic, and audacious roadmap to help you make the leap.
Step 1: Get Honest About Why You Want Out
Before strategy comes clarity.
Are you chasing freedom? Flexibility? Fulfillment?
Or are you simply running away from something that no longer fits?
In my own journey, the biggest shifts happened when I stopped pretending I was “fine” and admitted I wanted more autonomy over my time and energy. Entrepreneurship demands effort, but purpose makes the effort sustainable.
Step 2: Start With Skills You Already Have
One of the biggest myths about entrepreneurship is that you need something brand new.
You don’t.
Sasha didn’t reinvent herself. She leaned into skills she’d already built in hospitality, sales, and relationship management and translated them into a service-based business model.
Ask yourself:
What do people already ask me for help with?
What do I do confidently without overthinking it?
What experience do I underestimate because it feels “normal” to me?
That’s often your starting point.
Step 3: Take Imperfect Action
Most people wait for certainty.
Entrepreneurs move with clarity and discomfort.
There’s no such thing as perfect timing. What matters is momentum. Small actions stack fast when they’re intentional. Conversations lead to opportunities. Opportunities lead to confidence. Confidence fuels growth.
Action first. Refinement later.
Step 4: Shift From Worker to CEO Thinking
This is where many people stall.
Running a business is not about doing everything yourself. It’s about deciding what only you should be doing and building support around the rest.
Sasha spoke about stepping into the CEO role early, even when it felt uncomfortable. That shift is what allowed her business to scale rather than stall
Entrepreneurship isn’t just a career change.
It’s an identity evolution.
Step 5: Build Support Before You Burn Out
Here’s something I’ve learned the hard way: resilience isn’t about doing it all alone.
Whether it’s mentorship, community, or outsourcing small tasks, support keeps you grounded when growth accelerates. The strongest entrepreneurs know when to ask for help.
Personal Reflection
What struck me most in this conversation wasn’t the speed of Sasha’s success. It was her decisiveness.
She didn’t wait for permission.
She didn’t overexplain her choice.
She trusted herself enough to move.
I’ve seen this pattern repeatedly. The people who successfully transition from employee to entrepreneur aren’t fearless. They’re committed. They decide, then they figure it out.
Audacity doesn’t mean recklessness.
It means choosing yourself before comfort chooses for you.
🎧 Want to hear the full story behind this journey?
Listen to my full conversation with Sasha Eburne on the Audacious Living Podcast, where we dive deeper into mindset, resilience, and building a freedom-first business.
The Audacious Takeaway
You don’t need a perfect plan to start.
You need a clear intention and the courage to move before you feel ready.
Audacity lives in action, not approval.
