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3 Steps to Survive Any Bookkeeping Head Scratcher

Aug 01, 2025

Ever had a bookkeeping situation so bizarre even Google’s like, “Yeah… good luck with that”? 🙃

We've ALL been there. Weird client workflows, oddball setups, or unusual bookkeeping scenarios that feel impossible. Here are three things I do when I hit one of those head scratchers:

 

1. Simplify First 🧘‍♀️

It's easy to overthink complicated situations, especially if someone walks you through a complex 20 step process just to get one entry or number.

Try stepping back and asking:

"Okay, what ACTUALLY happened here in the simplest, real life terms, and how can I clearly record that?”

For example:

  • A client made a business purchase. (Sure, they accidentally used their mother in law's card and repaid her from another business, making everything messy.) BUT at its core, it's just a business expense.

  • CompanyABC made a sale. (Yeah, they want it recorded across 27 accounts, codes, departments, different tax setups, and to a related company, okay, weird.) BUT at its core, it's just one sale.

 

2. Quick Expert Check 💡

Platforms like Fiverr and Upwork have legit pros! People with experience, credentials, and specialized knowledge.

Paying a specialist a couple hundred dollars for an hour might seem steep, but if that bit of spending:

  • Saves hours of your own time

  • Prevents costly mistakes

  • Eases your stress

  • Teaches you something you can reuse...

Then it might actually be worth it!

Pro tip: Always vet your expert first, check credentials and reviews!

 

3. Build a Trusted Network 🤝

Sometimes you just need someone who gets it to set you straight.

I've got a friend who's basically my personal "weird tax situation" guru. He always knows the answer or at least where to find it. His entire practice revolves around tricky tax scenarios, and he's spent enough years in school to be a surgeon (but just for tax!).

Other bookkeepers running similar businesses? They're honestly my best friends for sanity checks, like, "Am I crazy, or does this make sense? How would you handle this?"

 

Doing bookkeeping solo can feel rough! 😅 That’s why we created a group specifically for bookkeepers who want another set of eyes on those tricky situations. Want more details? Here's where all the info is!

 

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