Taking The Leap: From Solopreneur To Entrepreneur

April 23, 2026

There’s a vast difference between being an independent operator and being responsible for employees and, indirectly, their families. If you have been a “solopreneur” and are planning to make the entrepreneurial leap, or you’ve already made the leap, this is essential to recognize.

Being an entrepreneur requires you to be fearless to a certain degree. It takes courage and an innate desire to take the risk to create something from nothing and convince people to follow you. There is nothing as equally invigorating and as nerve-racking as starting a business, then adding sentient beings to the mix (i.e., your employees), that you have to manage.

Transitioning from “I” to “we” isn’t just about paperwork and payroll—it’s about fundamentally changing how you think about and run your business.

First, you’re going to need to make a significant mindset shift around fear, perfectionism, and control. Sure, you’ve already proven you’ve got the guts to leave the corporate world behind for the promise of independence and better control over your life. But what about when it comes to hiring, managing, and sometimes firing people? That’s a whole different ball game.

Only two out of ten small business owners make the leap to true entrepreneurship by hiring employees. Why? It means letting go of the security blanket of doing everything yourself and trusting others to do what you’ve hired them to do. The biggest reason I see people struggle with jumping the chasm boils down to fears that the people they’ve hired won’t be as good as they are.

It comes back to perfectionism and the need for control, which are inextricably intertwined. They both stem from our fear of letting go and then failing. You’ll need to be prepared to embrace the fact that you won’t be perfect when you launch your venture, particularly as a bootstrapped founder. Your employees won’t be perfect, but you have to let go of your need to control and let them grow. The more you allow them to grow on their own, the more you as a company can grow.

Moving from being an independent contractor to an employer is an emotionally complex journey. So, before taking this significant step, stop and ask yourself:

  • Can you allow your employees to learn and grow so they can work toward delivering the quality of work your clients expect, and are you ready to trust them to do so?
  • Do you have the mindset and skills to be an effective leader rather than just a talented individual contributor?
  • Are you prepared to step back from hands-on client work to focus on strategic business growth?
  • Can you let go of the tasty dose of dopamine that comes from directly serving your clients and solving their problems?
  • Are you ready to find satisfaction in your team’s successes rather than your own tactical wins?

Shifting from solopreneur to entrepreneur is not easy, but the rewards are tremendous. You will experience the thrill of the build and all the impact you’ll have on those you employ and the customers and clients you serve. And as you stretch outside of your comfort zone, you will grow personally and professionally.

Making the leap from solopreneur to CEO can feel overwhelming, but I’ve found that putting your ideas on paper helps crystallize your vision and helps manage all the emotions that come with the human side of your business.

Originally posted on Forbes.com