Imagine if instant success just came naturally to you. Everything is easy, breezy, beautiful. You’ve got the Midas touch that turns every idea into gold. No mistakes, no challenges. Just $$$, baby.

Hahahaha – alright big dreamer, come back down to Earth.

I was recently asked in my free Facebook group this question:

“How were you able to scale to a multi-6 figure firm?”

The short answer is, not easily. In fact, sometimes I still shake my head and wonder that myself. While I look like I have my sh*t together today, I promise you it took a looooot of courage and little heartbreak to get here.

Before going all-in on my bookkeeping business, I freelanced for 10 years. But there came a time when I had to make a decision: commit completely to building my business or *gulp* go work for someone else. You might’ve guessed, that latter wasn’t an option.

Fast forward a few years, and I have a wildly successful business that’s scaled to become a 6-figure firm. Now, I can share my experience on growing from freelancer to founder with others looking to do the same.

The Chicken or Egg Problem

This is actually a pretty common issue across service-based industries. In order to grow your freelance gig into a business, you need more clients. But to obtain more clients, you need more support.

Uh, so which comes first? It’s a chicken or egg problem. 

You need to onboard new clients to scale your business, but you want to make sure you have a team in place to continue providing a great customer experience. Onboard too many clients without enough staff, and….rut roh….you don’t have the bandwidth to meet their needs.

Hire too many team members before bringing on new clients, and you risk not being able to fill their time. You want your salaried employees to have enough work so they aren’t sitting around getting paid to do nothing. And contractors appreciate having consistent hours.

I’ve faced this problem and it wasn’t pretty.

When I first launched my bookkeeping firm, I quickly grew – but – whoops – I onboarded more clients than I should have. I was excited to grow my business, but realized quickly that I was in over my head. Without a team in place to meet the demand of a growing clientele, I lost some clients pretty quickly.

The good news is, a few of my spinning plates have fallen, and I still live to tell the tale. 

To answer the question “Which comes first?” – design a flexible team that can handle fluctuating demand. I did this by creating a small army of part-timers until I was in a position to hire full-time staff.

Get a Bookkeeping BFF

If you aren’t ready to hire employees yet, find yourself a bookkeeping BFF! 

When you get in a jam with too many clients, send some of the overflow to your partner. In return, they can send more work your way when they’re slammed.

Eventually, you’ll still want to work on building your team. But during the transitional time from freelancer to founder, creating a strategic partnership can be a lifesaver.

Prepare for More Meetings

Here’s what nobody told me about becoming my own boss:

I’d better start loving meetings. Because I’m in them all. the. time.

But that’s the gig! The more you grow your business, the less time you have to be hands-on with client work. Your focus will shift to business operations and LMA – lead, manage, and accountability (LMA is part of the EOS process and discussed in the book Traction by Gina Wickman).


The transition from side hustle to full-blown business is exciting – and a little scary. More clients = more money, but only if they stick around. Unhappy clients can mean a hit to your reputation and loss in revenue.

I suggest ramping up slowly. Diving all in makes it harder to keep your head above water. Track your time carefully, talk to other bookkeepers, make goals, and proceed with confidence. 

Remember to learn from your mistakes. Better yet, learn from the mistakes of others (like me) who’ve been around the block a time or two.

You’ve got this, mama 💪


P.S. On the prowl for a Bookkeeping BFF? Come join my Facebook group and hang with like-minded mamas in the bookkeeping field!