Like Cher, I too sometimes wish I could turn back time.

But alas, that’s not possible (yet!🤞). So instead, I’ve got to put on my big girl pants and turn my mistakes into life lessons — since that’s what us lady leaders are supposed to do.

In my last post, I shared the best decisions I ever made as a business owner. So it’s only fitting I share the worst too, right?

Here are the four worst decisions, based on the 4 S’s of my Bookkeeper’s Business Incubator program (Sales, Systems, Service, and Skills).

Sales: Listening to Others About My Pricing Model

Back when I was a new (and let’s be honest, a little naive) bookkeeper, retainer/value-based pricing was the bee’s freakin’ knees. But you know me, I’m not one for hopping on bandwagons all willy-nilly.

Instead, I was allllll in on my hourly prices. And yet, the so-called experts had me second-guessing what was best for my business. Ugh.

So I let my insecurity get the better of me and hired a — not kidding — Silicon Valley-based data analyst. Who, after much research (and a whole lotta $$$), ended up confirming that I was in fact using the most profitable billing model for my business. 🙄

Yeah, I almost let “experts’ talk me out of my 80% gross profit margin.

Lesson learned: You need to find a pricing model that works for you, whether that’s value-based, hourly, or some sort of hybrid (like my proprietary Value + Based pricing model).

Systems: Choosing the Wrong Project Management Software

A few years ago, my team and I took about six weeks to set up an entire project management system. We were STOKED to have a new shiny platform that would make our day-to-day tasks sooo much easier.

*Narrator voice: It was indeed not easier. In fact, it became much, much harder.*

Ummm yeah. So it was only AFTER we got everything implemented and started to actually use the darn thing that we realized it was a dud (for our team at least). 😫 We invested hundreds of hours into this software only to realize it didn’t have a strong recurring task model, among other issues. For scaling our business, that was obviously no bueno. 

Sooo… we ended up going back to tracking everything on spreadsheets. Obviously not the most scalable solution either, but hey, sometimes lo-fi can be hi-fi in a pinch. 🤷‍♀️

We didn’t give up on our quest for the perfect solution. And eventually, after a lot of research, we found the one 💓. It’s called Teamwork (yup, that’s an affiliate link) and it totally ROCKS.

Service: Onboarding Too Many Clients Too Fast

When you’re a small business owner, every fiber of your being tells you to never say “No” to new business. But you owe it to yourself and your clients to be realistic with your bandwidth and capacity for work before onboarding someone new.

Trust me, this one comes from personal experience. I’ve absolutely bitten off more than I could chew, and I lost one or two great clients because I couldn’t give them the high-touch experience they deserved.

Now, I build a margin into my schedule so I don’t exceed my capacity for work. You and I both know that things don’t always go according to plan. If you try to schedule yourself for every hour of every day, you’re eventually going to run into a problem. Instead, I HIGHLY recommend giving yourself a little wiggle room. It’ll help you account for those urgent, time-sensitive client requests or the days when you have to take care of a sick kid who’s home from school.

Skills: Investing in Programs That Became Shelf-Help

If you haven’t heard the term “shelf-help” before, allow me to explain:

Shelf help = those books, computer courses, or self-guided programs that end up never getting used and collecting dust on your bookshelf or hard-drive.

I’ve spent an embarrassing amount of money on programs that either…

A.) I had no business investing in (prime example: a program on how to run Facebook ads, which I definitely should never, ever do myself).


B.) Were not conducive to my style of learning. In general, I excel with programs that provide live instruction – it’s how I learn best (unless it’s a mini-class targeting a specific topic). 

Because I know I excel with live, hands-on support, I designed my incubator program the same way. It’s a high-touch experience where I teach and engage with students every week and it produces stellar results. 


Just like anything else in life, becoming a business owner is all about learning from the losing. I hope you found this list of “worst decisions” insightful — and hopefully you can use them to better your own bookkeeping business.

Not-so-shameless plug, but one of the most effective ways to fast-track your business without making costly and time-consuming mistakes is to work with a business mentor. The waitlist is currently open for my Bookkeeper’s Business Incubator program!

You’ve got this,