The secret trap keeping freelancers and coaches from growing their businesses

by | May 27, 2020 | Entrepreneurship, Leadership, Strategy | 0 comments

When I started my business, I knew exactly what I wanted to do: I wanted to help entrepreneurs feel calm and organized and in control. And I knew what I wanted my life to look like: I wanted to have the freedom to travel, or take a day off for my birthday, or go to the zoo with my family on a Wednesday.

I wanted to log in each day with a clear list of meaningful, challenging, and achievable projects in front of me. And I loved the idea of building something bigger than me so I could hire other people who also wanted that freedom.

I just didn’t know how to get there.

So I started out as a freelancer. I connected with people who needed help, and I helped them.

Slowly but surely, more people said yes. A year after I started my business, I was taking care of ten clients at once, had no time to work ON my business, and regularly skipped holidays…and I was 6 months pregnant.

I had hit the freelancer ceiling.

I tried a variety of solutions – some worked, some didn’t. I doubled down on some things, abandoned some projects and started over, and learned a lot of things the hard way.

Over time, I began to learn how to be a bona fide CEO of a business that could grow beyond me.

Have I “arrived”? No, and I’m not certain there’s such a thing as arriving in entrepreneurship. But I have learned a few things about this freelancer ceiling – the trap that keeps many entrepreneurs stuck and frustrated – and how to move beyond it.

What is the Freelancer Ceiling?

Freelancers, by definition, offer their expertise to companies for project-based or contract work. Most business owners in the service industry start out here. It’s a natural first step. But as they establish themselves and begin to grow, a few things often begin to happen:

  • They get swamped with client work, leaving them in a feast or famine cycle where they’re either hustling to keep up with deadlines or desperately hustling to find new clients if the work dries up.
  • They’re continuing to get better at their craft, allowing them to raise their prices and work with better clients, but the value they’re creating is for others’ businesses, not their own – they have to start all over with each new client.
  • They reach a point where they can’t raise their prices any further if they want to keep the same target market.
  • They try to hire a virtual assistant to get more time back. It doesn’t work out.
  • They try a software tool a friend swears by. It doesn’t work out.
  • They hire people to get them out of the weeds. They get caught in a constant cycle of chaos with their team.
  • They struggle to keep the quality of their work high as more people come through the door.
  • They do a marketing campaign – it works like gangbusters. This is very bad news because they don’t actually have time to deal with all these new prospects.
  • They get sick of doing one-on-one client work altogether and don’t know where to go from here.

This doesn’t happen to everyone. Some freelancers are happy to raise their prices further, work with more sophisticated clients, and keep their companies small and exclusive.

Others are able to build a bigger business by sheer force of will and charisma.

But too many get stuck right here.

It doesn’t have to be this way.

If this is you, there IS a way forward.

Step One: Take Command of the Transformation

As you move beyond the freelancer ceiling, the first thing to understand is that freelancing isn’t a direct path to entrepreneurship. Instead, it’s a platform you can use to prepare for, fund, and grow your entrepreneurial business.

A business that can grow beyond the freelancer ceiling has a different DNA from the work you’ve been doing. You should be proud of what you’ve accomplished – none of your work has been wasted. But the skills that got you here aren’t going to get you there.

It’s time for your caterpillar freelancer self to become a CEO butterfly. And you can expect that process to be as seemingly slow and messy and uncomfortable as the chrysalis experience is for butterflies.

Bracing yourself to undergo some big changes will make the process much easier. You’ll need to start seeing yourself as a CEO, and changing your habits. The first and hardest one? Getting organized.

Step Two: Get Organized and Focused

As a CEO, being able to manage yourself effectively will either make or break your fledgling company. It’s time to get focused, clear, and strategic.

Everyone has their own way of being organized, and finding what works for you will be a lifelong journey rather than a destination. Expecting yourself to achieve superhuman productivity will only hold you back. But saying “I’m just not an organized person” and going along with old habits won’t help either.

The goal of organization isn’t to buy a label maker. The whole point is to arrange your resources (especially your time) and your energy towards the things that matter most to you. If you want to build a steady business that gives you freedom, having a clear, single-minded purpose is no longer optional.

Step Three: Find Creative Ways to Leverage Your Expertise

If you watch Shark Tank, I’m sure you’ve seen how much the entrepreneurship space is focused on products. The general logic is that products are scalable, while services are not.

I call BS.

You CAN grow a service business, and selling courses isn’t the only way to do it. With a little creativity, you can come up with a long list of interesting options to explore.

This is the hardest step, and you’ll always be iterating and experimenting, but it can also be incredibly fun if you embrace the process.

What if you could add a group element to part of your program without losing the one-on-one experience? Or loop in course modules only for the pieces of your service that are consistent from client to client while keeping some pieces customized?

You could sell an intensive where you deliver a project that normally takes weeks in one day, or train and certify others to follow your signature style.

Think about the ultimate outcome you want your clients to achieve, and all the ways you could get them to that outcome. Start brainstorming, and let yourself think outside the box.


My daughter just turned one, and I still have a lot of work to do. But I can say one thing for sure – my business gives me the freedom I longed for, and I can see a clear path forward for continuing to grow without giving up that freedom. I’m leaning into the discomfort of the transition, becoming more organized and focused, and experimenting with new and better ways to get my clients the outcome they need.

The freelancer ceiling doesn’t have to keep you stuck either. Try this out, and you’ll find yourself emerging as a calm, collected CEO at the helm of a dynamic, thriving business.

And I can’t wait to see it happen for all of us.


Ashlee Berghoff, MBA, is the founder of A Squared Online, which turns freelancers and coaches into CEOs by helping them adopt the practices and systems of a flourishing business. As her clients become more effective and productive, they can cut out the noise, experience real momentum, and build bona fide businesses that keep growing even while they’re on vacation.

Ashlee is certified in the Fix This Next methodology, which was created by bestselling author Mike Michalowicz to help entrepreneurs identify their one core vital need and fix it. She has been featured on the Copywriter Club Podcast, Reigniting Main Street, and the Formula Publisher Podcast. She also recently taught copywriters how to serve more clients in less time at the annual Copy Chief Live conference in Florida.

You can take our Fix This Next Assessment for free at