I’m an accidental entrepreneur. Ten years ago, I quit my job and started doing contract work while I figured out what to do next. I never wanted to work for myself, but I knew my nine-to-five wasn’t giving me what I needed.

My first jobs were managing projects I had managed before and working for people who knew me and my skill set. I also started picking up other contract gigs offering operations support for solopreneurs who wanted to scale but didn’t have the capacity they needed.

Eventually, I realized that being a solopreneur was what I was meant to do and officially incorporated my company. At this point, I had a solid client load, managing projects that were squarely within the wheelhouse of what I knew how to do before I went out on my own. I also knew that I would need to start picking up more work if I wanted a sustainable business.

I positioned myself as a generalist. I was very aware of the skills I had that businesses needed, but I marketed them in an “anything goes” type of fashion. Anyone I met had a problem that I could solve in one way or another, so I would propose services based on what they thought they needed, even if that meant that I was doing many different types of things for different people.

When people asked what I did, I gave them examples of past projects and clients instead of positioning myself as a business that solved a specific problem for a particular person.

Many freelancers start like this. You start getting some success in one thing, so you keep doing that without considering how it plays into a more targeted business model or the life you want to live. Along the way, you lump in or add on adjacent things so that eventually, you’re a Jill-of-all trades but master of none.

When I teach people how to start a business, I have them start with a business model first, built around what makes them happy and what they’re good at. But the truth is, we all have to go through this trial-and-error period because that’s how we figure out what we like best and what we’re uniquely positioned to offer in the market. The trick is, if you start more intentionally, that trial-and-error period can be shorter, and you can get to a more replicable, sustainable business model faster.

In my work with solopreneurs, I’ve identified a few different phases of business model development. These are not linear. One person might stop at one of these phases and be perfectly happy staying there, another person might cycle through these every few years, and someone else might start in the middle and then bounce around until they figure out what works. The point of identifying the different phases is to understand better where you’re at and think about where you might go next.

The accidental entrepreneur

Whether you still have a nine-to-five, made the leap to solopreneur, or were pushed by a layoff, you started picking up independent work for one reason or another. Often this is because someone you knew asked you to do a one-off thing for them, and then someone else did the same, and then they told a friend, and now you’re officially a business of one. You didn’t have a plan and probably never even had a written scope or contract for those first few gigs, but now you’re in a place where you’re known for doing this specific thing, and it turns out you’re pretty good at it.

The Jill-of-all-trades

You have the curse of competency. When you worked for other people, this meant that everyone came to you whenever a new project or problem needed to be solved. You (smartly) decided to leverage your competency to solve these problems independently and get others to pay you for it on your own terms.

Now you’re positioning yourself as anything to anyone, which means you’re picking up work (because you’re good at many things), but you’re not as strategic as you could in leveraging your specific talents.

For me, this looked like project management, business development, systems implementation, program design, strategic planning, program management, automation, or, or, or …. I would network with anyone and then tell them I could do anything, meaning I was selling nothing to no one.

I still built a successful business because I’m good at many things, but it wasn’t scalable. I was still operating with an employee mindset, approaching my clients with my skillset (e.g., my resume) instead of my value proposition as a business.

My business also wasn’t something that maximized my joy because I wasn’t trying to focus my business on what I wanted to do; I was picking up clients to get paid.

The scaling solopreneur

You’re at the next level from accidental entrepreneur and/or Jill-of-all-trades. You’re so good at what you do, even though it doesn’t have a ton of structure, that clients are coming out of the woodwork. The band-aid measures you’ve used to get this far aren’t cutting it anymore, and you’re starting to drop balls. You’ve outgrown your business model.

You’ve got to get more focused, and fast because there are a few things that can happen here:

• Burnout: Instead of focusing your structure and systems, you muddle through with sheer force of will and many more hours than any human should work.
• Bust: Your clients start to think you’re not good at what you do because you’re constantly dropping balls, and they leave.
• Bottom-out: You start dropping clients and losing income because you can’t keep up.

The micro-business

You’ve likely gone through the phases above, learned what you were best positioned to do, and built a strategic business around it. You know who you serve and how you serve them, and you have a structure for each engagement that makes it replicable. You’ve got it dialed in.

You also might be in a place where you have more work than you can handle and are thinking about (or already have) added capacity to help you serve more clients.

You’re living the dream.

But…there are two downsides to this phase:

• Disconnection: You’ve gotten big enough to hire other people, which is excellent, but now they’re doing all the work you used to love to do, and all you’re doing is managing people.
• Dissatisfaction: Sometimes, when we dial things in, we miss the chaos and the process of building something new.

But here’s the good news…you’re an entrepreneur! You can change what you do and how you do it whenever you want. You can go back to any phase and start over. You can use your replicable structure and systems to sell off your business or hire someone to take it over completely.

The trick is not to get stuck in any of these phases if they’re not making you happy or giving you what you need. The whole point of working for yourself is to find fulfillment and create new things, not get stuck doing stuff you hate.