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The Shift From Solopreneur to CEO: What’s Needed?

May 10, 2022

When you first started your business, it probably felt like you were taking on the world by yourself. Most of us start as a one-person show, and there’s so much we can get done in this phase. We have the energy, the curiosity, the time… and things can start to grow quickly.

In this phase of business, you’re doing everything you can possibly think of with your own two hands. You spend hours down the YouTube rabbit hole trying to DIY your budget, graphics, and emails. 

At some point, though, most solopreneurs will reach a point where they just can’t do it all alone anymore. All that energy, curiosity, and time has been spent on clients and projects — and now you’re full-up and tapped out. This can be both a blessing and a curse. 

On the one hand, you’re making money — go you!

But on the other? The business itself (internal operations, future projects, marketing, etc.) is starting to, or already has, become the last priority in your ever-growing to-do list.

When this happens, it’s a good sign that it’s time to move from solopreneur to CEO. That means changing some of your day-to-day habits and likely outsourcing some work or hiring help. If the idea of stepping into your CEO shoes or leading a team makes you clench up a bit, keep reading.

What Keeps Solopreneurs From Branching Out

The promise of more time and creative energy is usually not enough to help business owners shift into a CEO role or make their first hire. It’s hard to imagine not doing the day-to-day work and not being the one who reviews every tiny detail. It’s also difficult to imagine spending your days doing things that are future-focused rather than fires to put out right now.

And let’s be honest: It’s just really hard to surrender control after being in control of everything for so long. But it’s so worth it. If you’re ready to start making the shift, there are a few things you should know first. 

Progress Will Seem Slow at FIrst

Gone are the days of working on a spur-of-the-moment idea at 11 PM and sending it out to the public the next day. If you have client deliverables, someone new is likely going to take longer to do them at first. 

You will have to give your team time to learn how you work. They will need to hear you articulate your vision and lay out a plan to execute it. They will need to learn your processes or your clients’ needs and learn as they go. That’s just the way it works when you’re a team. 

Communication Isn’t Always Easy

When you’re the only one in your business, the ideas you have can be executed instantly. You don’t have to go through anyone else’s process or worry about clearly communicating an abstract idea. 

This can’t be done with a team. You will have to check on them often and be willing to work through any questions. You also need to plan your ideas out, give clear guidance, and be open to questions, feedback, and changes. 

People Skills Matter

Even in a virtual setting with contracted employees, you’re still responsible for creating a team environment that promotes success, recognition, and open dialogue. You will have to make a bit of an effort to get to know your employees because there isn’t any office water cooler chat. 

Something that’s helped me? Create a profile for each member of your team.

We include work profiles, like their StrengthsFinder results, Love Language preferences, and their Myers-Briggs personality type. We take the extra step to learn a few of their favorite things, so we can easily pop something small in the mail to show our appreciation.

What It Looks Like to Be a CEO (Hint: It’s not what you expect)

The online biz solopreneur is on the go all the time. They have a million ideas in their head at any given moment and there are plenty of things that keep them up all night. Whether it’s a shiny new offer they are itching to create or a client deadline that’s approaching, their minds stay incredibly active. And they have to be, because they are the only ones who can move the needle forward in their business. 

Solopreneurs are scrappy and fast-moving — and there is so much we can get done in this phase of our business. But there’s a downside to doing it all alone.

If they’re not innovating, implementing, and booking new business, no one else will. 

Ever come up with an idea, start working away at it furiously (all-nighters are for big ideas, right?!) but never actually get the project off the ground and launched? You might be a solopreneur.

A CEO, however, is the leader of a company. They still have the same sharp minds and plenty of ideas, but instead of focusing on the nitty-gritty day-to-day execution tasks in their business (like daily operations, client work, marketing assets, bookkeeping, etc.), CEOs can focus the majority of their time and energy on working through their big ideas. 

Of course, becoming the CEO of your business sounds great. You can steer the ship without doing all the grunt work — great. But it’s not all roses and rainbows.

Adjust Expectations

When you transition into the CEO role, you’ll find you have to (gasp!) trust other people. You will have to hire help. And you will need to be open to feedback because you will make mistakes.

You’ll also have to alter your behaviors, expectations, and possibly even your business operations. But if you do it with strategy and with the right people in the right places, you’ll be amazed at the results.

Create New Habits 

There’s a common sense of relief when solopreneurs start growing their businesses and stepping into their CEO roles. I’ve heard so many people say (myself included) that there’s less chaos and more white space in your day, and it’s nice to be able to stop doing the things that you have no interest (or skill) in doing, like bookkeeping or social media. 

You’ll also have more time to dive into your passions and get (re)connected with the reason you started your business in the first place. But this doesn’t happen overnight.

Solopreneurs-turned-CEO have to almost re-train their brains to stop stepping in to fix everything and do everything themselves. (And maybe even adjust their perfectionist expectations a tad, too.)

You will need to train your team and let go of the fact that they aren’t doing everything the same way you would. And it may feel like you’re spending way too much time training someone else to do something that you could do in a matter of minutes — but a CEO leads, rather than monopolizes.

You’ll have to put in a lot of your own work to stop reacting to every email or trying to redo things exactly how you’d do them. And you’ll have to spend more time training than you might expect. But once you’ve stopped the muscle memory that tells you to “do” everything and your team has time to get comfortable, things will run smoothly without you. What a relief that is! 

Trust the Experts

When you have multiple people working on a team with you, you get expert eyes on your most important work. You won’t have to know if the sales copy flows well or if your social media plan is comprehensive enough for your next launch. 

Contractors or people you employ part-time or full-time can take these elements of the task and use their expertise to get it done on time and well.

Think about all the time you’ve spent as a solopreneur trying to research best practices for an industry you know little to nothing about. When you become a CEO, it’s all about trusting the experts you hire — and allowing that trust to give you more time to do things that CEOs do (like dream up the next biggest idea). 

Forward Thinking

The beauty of having a team is that it creates more space for you to work on the things that propel a business forward and help it reach its goals. As a CEO, you’ll have more time to focus on your business operations, your processes, your offers, and your profit and revenue. 

You will also have more time to do higher-level tasks in your business, such as hosting sales calls, attending conferences or masterminds, speaking on podcasts or at events, and even investing in your own development.

With a solid team to support you, you can make significant progress you otherwise wouldn’t have been able to make. And that’s what it’s all about. 

Supported Hand-off

As the CEO, you’re the captain of the ship. You can pivot however you want. Just because you’re hiring help doesn’t mean you’re giving away all control to someone else. Your brainchild isn’t going anywhere. 

But you can’t just hand off work and walk away. You have to also lead that ship

Training your team isn’t a one-and-done event, either. You have to be willing to invest time in training people correctly, and in creating spaces that help them do their best work. This is where self-development really comes in handy because many of us never really thought we’d be leading a team! These are new skills for most of us, so it’s OK if you need to work on them a bit. 

Becoming a CEO Doesn’t Happen Overnight — or Without a Plan

So… are you ready to step into a CEO role within your business? Or does the solopreneur route seem right for you for a little while longer? 

You’ll have to determine that answer for yourself — and it’s OK if you’re not ready to become a CEO. Not everyone needs a large team, but I’m willing to bet even the smallest of businesses (and one-person shows) could use a helping hand. 

Before you hire any help, though, you need to make sure that your business is organized and that your systems are clear. This makes it much more likely that the people you hire will be successful faster.

From project management to client management, business operations templates can get you (and your team, if you hire one) organized and moving forward in far less time than it takes to Google and modge-podge a process together. 

If you’re ready to scale your business and maybe even grow a team, you can check out a few of the templates I’ve created, including:

The business owners who become the best CEOs know they don’t have to create everything from scratch — or do everything themselves. It’s time to find the help you trust, and give them the tools they can use to help take your business to the next level. 

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