Bookkeeping is like dating, ignore the red flags at your own risk.

It might sound ridiculous, but a lot of people treat their business finances like a bad dating app experience, swiping past expenses, ghosting their bookkeeping and ignoring obvious red flags until tax season comes knocking like an ex with “we need to talk” energy. 

If that sounds even a little too familiar, this blog is for you.

Just like in relationships, bookkeeping has its own set of red flags and ignoring them can lead to financial heartbreak. 

Let’s take a look at some common dating … I mean blunders and how to avoid them.

1. Staying in the “it’s complicated” phase

Nothing screams chaos like trying to remember if that fancy dinner was a client meeting or just you treating yourself. Sure, you meant to use the business card, but your personal one was just so convenient. Before you know it, your business expenses look like a tangled mess of personal indulgences and legitimate deductions. 

Want to avoid this nightmare?

Keep separate accounts and use them accordingly. Accidentally use the wrong card once or twice? That’s fine! But staying stuck in the complicated phase just makes everything more complicated. Trust me, future-you will thank you.

2. Ghosting your bookkeeping

Ignoring your finances for months and then panicking when tax season slides into your DMs like, “Hey, we need to talk,” is a classic move. 

But playing hard to get with your bookkeeping won’t end well. Regularly updating your records saves you from last-minute stress and potential financial disaster. 

Want to avoid this nightmare?

Set a date with your books at least once a month. No ghosting allowed.

3. Chasing the one that got away

That missing receipt you swore you had? Yeah, it’s gone. And so is that sweet tax deduction. 

Digging through your junk drawer and the pocket of that jacket you haven’t worn in six months is no way to run a business. 

Want to avoid this nightmare?

Use a digital expense tracker or take photos of receipts the moment you get them. Because let’s face it, those tiny slips of paper have a habit of disappearing faster than a bad Tinder date.

4. Swiping right on bad habits

Relying on memory alone to track expenses? Bad idea. 

"I’ll remember that later" is a lie we tell ourselves, just like "I’ll text them back in five minutes." 

Want to avoid this nightmare?

It’s time to swipe left on bad habits. Keep a system in place. Whether it’s an app, an old-school notebook or a bookkeeper who actually knows what they’re doing, stay on top of your expenses.

5. Ignoring the obvious red flags

Random charges? Inconsistent income records? Transactions that make you go, “Wait … what was that for?” 

These are all signs your books need some serious attention. Surprises can be fun in dating, but not in bookkeeping. 

Want to avoid this nightmare?

If you spot something off, investigate it immediately and figure it out. The longer you wait, the bigger the risk - fraud, errors, or just a giant headache down the road.

6. Rebound spending

Made an impulse purchase and convinced yourself it was a business expense? 

We’ve all been there. But buying a top-of-the-line espresso machine because "networking happens over coffee" might not fly with your accountant (or the CRA).

Want to avoid this nightmare?

Be honest with yourself about what’s essential for your business and what’s just a little retail therapy. P.S. If you work from your house, clothes are not a business expense… sorry.

7. Going back to your ex

Still using that outdated spreadsheet from when you started your business? 

You know it’s holding you back, but you just can’t seem to let it go. Modern bookkeeping software can automate processes, reduce errors and save you time. 

Want to avoid this nightmare?

It’s time to upgrade. Don’t settle for something that isn’t working just because it’s familiar. QuickBooks Online is a great option for $20/month.

8. Looking for a quick hook up

At some point, you realize DIY-ing your finances is like trying to fix a relationship with text messages. It’s not going to end well. 

Want to avoid this nightmare?

It’s time to find "the one" (AKA a good bookkeeper). A good bookkeeper will keep your finances in check, help you avoid mistakes and make tax time a breeze. Investing in professional bookkeeping is like finding a solid partner, supportive, reliable and always looking out for your best interests.

Don’t let your books ghost you

Bookkeeping and dating both have red flags that you absolutely shouldn’t ignore. 

You wouldn’t let someone cancel plans last minute and then ghost you, right? Same goes for your finances! If your records are a mess or you’re avoiding looking at your bank statements, it's time for a reality check. Ignore the warning signs and your financial future could be as awkward as a bad date. 

Keep your books in check and avoid the dreaded "we need to talk" moment. 

Your business deserves better!

(NOTE: While this blog was written by a bookkeeper - it was fact checked by the single lady on our team 😂😂)