Should You Transition From Solopreneur to Entrepreneur? Here’s How to Know

You’ve been in business a couple of years, and you’re at the re-evaluation stage, wondering if you should change things up. Do you want to keep doing it on your own as a solo operator? Or would you rather be a systems operator with processes in place that can help you grow with a team? As of 2019, 41.1 million Americans were solopreneurs—comprised of freelancers, contractors, consultants, and business owners without teams.

Being a solopreneur is exciting. You have a business that you’re passionate about. You have no one to answer to. And everything is on your time. 

The downside?

Everything is on you. 

Not every solopreneur is meant to stay a solopreneur throughout their business journey, and many are. It all depends on your goals, your fulfillment, and how you want to structure your life. 

Here’s everything you need to know about if and when you should (or should not) make the transition from solopreneur to entrepreneur.

The difference

Many solopreneurs consider themselves entrepreneurs—and they’re not wrong. Solopreneurs are simply entrepreneurs who have chosen to rely predominantly on themselves to execute their vision in the business instead of building an in-house team to support them. This means everything in the business that allows it to run, from marketing to bringing in sales to client delivery, is reliant on the business owner. Solopreneurs may hire freelancers or companies for specialty projects like graphics or logos. Perhaps, solopreneurs may also hire freelancers to outsource the tasks where they’re weak or have zero interest, however, most of the business execution is handled by the solopreneur. This can make many solopreneurs reliant on constant effort for the cash flow in their business, especially if they are some kind of specialist with custom deliverables. 

Entrepreneurs typically focus on building a system and a team, to remain in the visionary role as much as possible. They desire to scale the business, bring on more people, add more services or products, and expand the business without limits. Entrepreneurs may learn how to do most of the things in their business as it pertains to the execution and delivery in case they need to step in, but this is not where they spend their day-to-day efforts. Instead, entrepreneurs focus on business growth. They’re primarily pouring their energy into ways the business can continue to scale, even if they step away. 

Who the switch is right for

If you’re a solopreneur and you are considering switching to becoming an entrepreneur, chances are you’re overwhelmed and overworked. You’ve been carrying the load on your own, maybe even thought of selling your company and let’s face it, it can get heavy without support.

Social media, ads, and funnel strategist, April Wilhelm of Wilhelm Media Group, says she knew the switch from solopreneur to entrepreneur was right for her when she found herself getting burnt out and doing work she wasn’t excited about every day. “I was extremely successful as a solopreneur,” Wilhelm said, “but as my business grew and my personal life changed…I was getting burnt out and needed more flexibility while still having the same success.”

However, the process isn’t always linear. After a while, Wilhelm went back to solopreneurship, but is slowly rebuilding her team after learning the leadership skills required to be CEO in her company.

If you have no desire to grow a business beyond yourself or beyond your lifetime, and you’re more ease-oriented than ROI-oriented (meaning you’d rather work four days a week than make more money), chances are that you simply have a systems problem. You may need to delegate to a freelancer virtual assistant five hours per week. You may need some more automation in your business for your sales and marketing processes. Look at where there may be some time and energy leaks in your business and see if there’s a system, process, or automation that can plug that hole for you. This may mean hiring a coach or consultant to help you identify where you can strengthen and streamline your business. But it may not require you to bring on a team.

TD, a copywriting business owner, made the decision to move from entrepreneur with a team to a solopreneur. When asked about why she chose solopreneurship, TD said, “I wanted to be a better businesswoman, and I felt really disconnected when I wasn’t focused on the business end of it all. I’m more nimble this way. I can act in the moment as inspiration strikes.” Making the change from entrepreneur to solopreneur let TD have more direct control over the business. 

If you have decided that you want the business to run without you or that you want to build a legacy-focused business that will continue to grow after you die, then switching to entrepreneurship may be right for you. Many solopreneurs struggle to bring in enough income to get the business to perform on its own so that they can take vacations, rest periods, or even work on the business instead of in the business. This can lead to serious burnout with mental, emotional, and physical health complications as a result. Hiring a team to take the load off of you and grow the business whether you’re present every day or not is a great reason to hang up the solopreneur hat—but it doesn’t have to be drastically different from what the business looks like today. 

For example, you may only need to hire a virtual assistant in order to get the tasks off of your plate that aren’t allowing you to grow or take care of yourself. If you struggle with organization or project management, then you may need to hire an online business manager (OBM). If sales aren’t your favorite thing, you may need to hire a small sales team to take over your sales process for you. Regardless of who you bring on, you don’t have to go from zero to a full-fledged company overnight. It’s a process, and you start one hire at a time based on your most pressing need. 

There is another time to switch, but instead of from solopreneur to entrepreneur, you make the switch from entrepreneur to solopreneur. This can happen for many reasons, some of which include divorce, changing businesses, starting over, growing out of business, or having other financial shifts. Personal branding strategist, Kimra Luna, said, “Being on this (solopreneur) path right now has primarily been because I’m rebuilding my brand, starting over, and really wanting to take things slow. I learned a lot of things from hiring in the past, and so now it’s made me more mindful about how quickly I hire.” 

When asking Luna what led to the decision to start over as a solopreneur instead of going straight to entrepreneurship, she replied, “I know how to grow, I’ve done it before. And I want to do things in a slow, more mindful way. So that I, for one, don’t burn myself out. But for two, once you have people on your team, you’re managing more than just yourself. Now you’re actually managing multiple people, and that can become very draining as well. So I want to make sure that I really have the capacity—energetically, timewise, and financially —to bring on people in the right roles.” 

When to switch

If being a one-person show doesn’t work anymore, and you want the business to scale without you (or you’re experiencing burnout and you’re considering burning your business to the ground—which is more common than you’d think), you may want to consider switching to entrepreneurship. But before you make that decision, here are the things to try (and ask yourself) first.

1. Have you implemented all of the automated systems that will help you run your business, and you’re still experiencing burnout?
   
2. Have you outsourced the menial, specialized tasks, like graphic design, webpage design, video editing, and other project-based tasks already?
   
3. Have you created systems and processes that optimize your time and streamline your work? Standard operating procedures, project management tools, and time management calendar blocking aren’t just tools for companies. They’re life-savers for solopreneurs too.
   
4. Has your vision for your business changed, and do you now want to move more into a legacy-based business model?

Your answers to these questions will let you know if it’s truly time to make a change or show you exactly where you should focus your efforts first if you do want to stay a solopreneur. 

Solopreneurship is a powerful journey, and like anything worthwhile, there’s a lot of trial and error. It’s normal for there to be seasons of overwhelm in your business, especially if you’re just starting or in the process of growing. However, if there’s sustained overwhelm, check your systems, processes, and automation first. If those things are on point and working for you, then it may be time to reconsider your business structure.