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Break Up With Your Bookkeeper

Written by Michelle Brown

RED FLAGS that let you know when “it’s time.”

We have all been there, stuck in a relationship that we know in our heart of hearts is no longer a  good fit. That icky feeling when things no longer feel comfortable. You start avoiding meetings and phone calls. Something feels…off.

And that’s where “red flags” come in.

Relationships that turn toxic and/or codependent don’t ONLY happen in romantic scenarios, they are just as common in professional relationships and value partnerships.

It happens with small businesses all the time. You’ve hired someone to handle a big part of your operations. Maybe you have been with them for years and up until now, everything was simpatico or maybe things have been “off” since Day 1.

You get the gut feeling… you know something isn’t quite right. You just don’t feel the love. The relationship has fizzled and the hassle:benefit ratio is waaaay off.

If you’ve exhausted every other avenue, had the authentic, 1:1 conversation and confirmed that there are no personal-life distractions affecting the vibe and nothing seems to be working, it may be time to consider other options.

And if/when you start to see these toxic traits show up, It’s definitely time to break up. And while I can’t advise you on how to break up all relationships, I can tell you when it’s time to break up with your bookkeeper. After 30 years watching business whither grow or wither on the vine, I’ve come to know a few RED FLAGS when I see ‘em.

When to break up with your bookkeeper | 🖐️ FIVE toxic traits to look out for.

  1. Your bookkeeper has all the login information for your bookkeeping platform… and isn’t willing to share. SEASONED ADVICE: Remember these are your books and your finances, dagnabbit. You have every right to review them at any time — and ask someone else to review them, should you see fit. if your bookkeeper is hesitant to share these - BREAK UP WITH THEM.\
  2. Your bookkeeper talks down to you or makes you feel badly about how you want to spend your own money. SEASONED ADVICE: A bookkeeper’s job is to help you track your money and create ways in which you can make good decisions about your money.  If you are hesitant to talk to your bookkeeper or tell them what you need, for fear of “decision shaming,” don’t let them abuse you - BREAK UP WITH THEM.\
  3. Your bookkeeper isn’t reporting back to you regularly with questions about expenses on your bank statement or credit card statement. SEASONED ADVICE: You have hired a bookkeeper to review your banking/credit cards and reconcile them monthly. But you also need them to pay attention to irregularities and redundancies. If they aren’t questioning odd expenses and asking questions - BREAK UP WITH THEM.\
  4. Your bookkeeper just keeps paying subscription fees and contracted payment over and over again without reviewing them. SEASONED ADVICE: Your bookkeeper should be keeping an eye on your bottom line at all times. If they aren’t reviewing contracts for repetitive payments regularly - BREAK  UP WITH THEM.\
  5. Your bookkeeper isn’t flexible and willing to make changes based on the ever-evolving business world. SEASONED ADVICE: Constantly struggling with old fashioned and outdated bookkeeping ideas and is costly and inconvenient for your business….YEP, that is right…. BREAK UP WITH THEM.

As a small business owner myself, I understand that there are many reasons we might not want to break up with our bookkeeper. We know them. We like them as a person. They currently have control over your finances; you may not feel great about ‘rocking the boat.’ Or, you are just a nice person and you don’t want to hurt anyone’s feelings.

But this is your baby… and healthy finances help your baby grow and blossom. Bookkeepers are like the nanny to your child, if they aren’t taking good care of your kid(s) you wouldn’t keep them around… that is for sure.

I know the transition can be hard sometimes, but you deserve a good, healthy, and committed relationship with the person taking care of your baby. (What’s more, the good news is there are a lot of great bookkeepers out there. Just sayin.’)

Breaking up is hard to do, but toxic relationships are harder to ‘do.’


Need help navigating the vital relationship between you, your business, and your bookkeeper? Or, if you’re not sure if you’re reading toxic traits or if your relationship is strained for another reason and you just want to understand the rules of engagement better, reach out to michelle@unleashedfinancialadvocates.com. Future-proofing an empowered business is a tough job, but you don’t have to do it alone.