From Freelancer to Agency: 6 Lessons I’ve Learned

Two years ago, I was ready to pack it all in and burn my business down.

I felt overworked, underpaid, and definitely under appreciated. I also felt like a total and complete fraud.

What had happened was this: At the beginning of 2016, I made a goal to increase the percentage of my income that came from courses and products instead of 1:1 services. I had an audacious plan to triple my email list in the first half of the year, launch some new live workshops over the summer, and then launch my big signature course at the end of the year.

And while I succeeded at tripling my email list, the workshops didn’t sell nearly as well as I had hoped, and when I launched my course, I came in just under the goal I had set for myself. Overall, I did increase the percentage of my income that came from courses — but only by a few percentage points.

And, me being me, I translated this as a huge and utter failure.  ¯\_(ツ)_/¯

Going into 2017, I felt a deep malaise, and I knew something had to change in my business — but I didn’t know what. I was sick about the massive amount of WORK I had put into trying to achieve my goals the previous year, and how it had barely moved the needle. I was also grumpy about the fact that, while my income had gone up, my profits had not because I had hired a lot more help to accomplish that work.

It felt like a lose-lose situation all around, and I didn’t know what to do other than go back to a solopreneur / freelancer model and just decide that scaling up my business wasn’t for me.

Lesson 1: Mindset over matter

As you can probably tell, I had several big mindset problems happening here:

  • First, I had decided that there was only one way to scale my business, and that was through courses and products — so if that didn’t work, clearly I should pack it all in and give up.
  • Second, I had reached all my goals for the year, but I was berating myself for not exceeding them, which is pretty stupid when it comes right down to it.
  • And third, I was struggling with imposter complex in a big way — because I felt like I had done everything “right”, that I had walked my talk and done what I teach people to do, and it still didn’t “work.”  (See point No. 2 — it did work, just not exponentially the way I wanted it to.)

Luckily, one thing I am pretty good at is knowing when I need help. I knew that I was seeing the glass half empty in my business at that time, and that I needed an outside opinion about how to move forward. Also luckily, a friend and colleague of mine, Breanne Dyck, was offering a brand new kind of coaching that sounded like exactly what I needed — so I signed up.

Lesson 2: There’s more than one way to scale

Hiring Breanne was a very good idea, and there were two very big aha moments that came out of it.

First, she had me list out all my products and services, and then look up how much money I made from each one. Just in doing the exercise, it was abundantly clear that I was spreading myself waaaaaaay too thin trying to make, market, and sell too many things. Even when it came down to my services, nobody (including me) could really explain in one sentence what I did. I was just doing… everything!

And obviously, when you spread your focus around like that, you’re not going to get the same results as when you focus on a single thing.

Second, she asked me a question that completely changed my perspective.

She asked me, “If you were going to double your revenue with half the effort, what would you have to do?”

Immediately I launched into, “Well, I’d have to just double down on writing blog posts for people, and if I were truly going to double my income, I’d have to get a lot more clients, and so I’d need more writers to help me serve them all.”

And, as I remember it, Breanne just sort of smiled at me and waited for the other shoe to drop.

The point is, I already knew somewhere in the cobwebby recesses of my brain that courses weren’t the way I was going to ramp up my business fast — and I also knew that there was way more effort involved in creating and marketing them.


Of course, being me, I had to argue about this. I said to Breanne, “But I don’t want an agency, because I don’t want to manage people.”

And Breanne, with her Breanne Brilliance said, “So hire someone to do the managing for you.”


I had been so focused on the idea that I had to scale by selling courses, that I didn’t even consider there might be another option.

Lesson 3: There’s more to growing an agency than hiring people

It’s important to note that I already had a team at this point. I had two writers and was about to bring on a third, I had a graphics gal, an Infusionsoft support person, a VA, an accountant…

Back it up a couple of years, and I hired my first subcontractor writer without really even thinking about it, at a point when I was getting too busy to handle the workload. And I just kept doing that — which worked fine, but it was really more like a bunch of friends helping each other out.

I wasn’t technically a “solopreneur” any more — but I also wasn’t exactly an agency, either. That’s because everybody working for me was a contractor. There are pros and cons to having contractors versus employees, but frankly I’d always been scared of the idea of hiring an employee and then basically being responsible for that person’s salary and therefore mortgage and life. (P.S. That is bull hockey, but just the way my brain works.)

So for most of 2017, I focused on ramping up my 1:1 services again, and played around with the idea that I was running an agency. I was still trying to manage everything myself — even though that’s expressly what I told Breanne I didn’t want to do — and trying to figure out what running an “agency” meant to me. Things kept ticking along, but there were also little harbingers of the growing pains we would begin to experience in the transition.

Lesson 4: There’s a difference between thinking like a CEO and thinking like a freelancer

All this time, I’d really been acting like a freelancer — not like a CEO — but I didn’t know it.

In early 2018, a client of mine, Adrienne Dorison, was hosting her first of a new kind of workshop called Run Like Clockwork, aimed at helping business owners set up their businesses to run without them. It sounded like exactly what I needed and I signed up to go and bring two of my team members with me.

Most importantly, I brought my long-time team member, Teri Vannoy, who had been my manager in a previous life. She and I had been dancing around the idea of her coming on as a project manager in my business for more than a year, but hadn’t actually committed to what that would mean or look like. I think part of the reason we hadn’t made it official is that I couldn’t get off my butt to define what it was I wanted her to do, or what the role would look like.

The biggest change for me was in thinking about what MY role in the company ought to be — instead of chief cook and bottle washer. Right now, that means I am in charge of sales and marketing as well as big picture strategy for clients — pretty much everything else should be handled by somebody else. Which is weird and freeing. (I do take on a few writing projects each year, but that’s really not the majority of my role any more.)

In addition, I had to make sure I was setting up my team to actually handle that stuff. People need to have the resources and be empowered to make decisions on their own — instead of coming to me for everything.

We walked away from the event feeling like we had the tools to finally make this happen. I sat down and wrote out a job description for Teri and a mission statement for the agency, and we actually made it official September 1 of 2018.

So we’re only a few months in as of this writing, but I can’t tell you how exciting it is when my team makes decisions without me!

Lesson 5: A team requires different structures and systems

As we’ve grown into these new roles, we’ve also discovered that teams that work well — and are empowered to make decisions and manage their own stuff — require different structures and systems than a freelancer working with her buddies.

I realized that I was keeping a lot of the information about the business in my head, and if it was really going to be able to run without me, all that info needed to live somewhere, in formats other people could understand and make use of.

This caused us to really reexamine the systems we had in place (because we did have some!) and ask if they would continue to work going forward. We’re still in the phase of auditing, analyzing and moving to a new system, but I have no doubt it will help us be more productive in the future.

We’re also experiencing some growing pains in offering a completely smooth customer experience. But these are learning experiences that we’re growing and improving from every day.

Lesson 6: It’s an ongoing process

Frankly, we’re still very new to all of this, and we’re learning as we go. I’m extremely lucky and grateful that the women I’ve surrounded myself with on my team are all incredible, self-starters, kind, generous, and experts at what they do. I’ve decided that keeping some of them as contractors — who are building and growing their own businesses — is actually a win/win for all of us right now.

I’ve also found that being able to offer a load of powerhouse experts in a single package is a very strong selling point to the right kind of client.

I’m still working out exactly how to market to and reach that kind of client consistently, but I already know that when they do find us, they are amazed and excited about what we can do for them. We’re also working and improving all the time on making the client experience seamless and enjoyable.


What else would you like to know about my transition from freelancer to agency owner? I wrote this post in response to requests from my community — and so I’d be happy to answer any more questions you may have. Just leave them in the comments below.

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