Why You Can’t Keep Up With Your Bookkeeping (And What To Do About It)

Every month you look at the growing pile of receipts in your office and wonder, Why can’t I get this under control?

You’re not lazy. You’re not broken. And you’re definitely not the only small business owner who feels this way. In fact, after many (many!) conversations with clients, I’ve realized that there are three main reasons entrepreneurs consistently fall behind on their books.

If any of these sound familiar, you’re in the right place. Let’s unpack them one by one, and more importantly, talk about what you can do to finally stop the cycle of stress.

1. I’m Just Not Good With Numbers

This is the one I hear most often. And honestly? Sometimes it’s true. There really are people whose brains just aren’t wired to comfortably work with numbers. If this is you, there’s no shame in admitting it. Bookkeeping isn’t everyone’s strong suit, and that’s okay.

But here’s the thing: if numbers feel like an impossible mountain to climb, this is an area of your business you need to outsource sooner rather than later. The longer you struggle with it, the more time-consuming (and expensive) it will be to clean it up later. Please don’t wait until tax season when the stress is at its peak and deadlines are looming.

Now, for many solopreneurs, the “I’m not good with numbers” story comes from somewhere else entirely. It’s not that you can’t understand bookkeeping, it’s that no one has ever shown you how. You were handed receipts, bank statements, and accounting software without any real guidance. Naturally, you felt lost.

The good news? That’s fixable. If you fall into this camp, you don’t need to give up or outsource right away. You just need the right tools and a bit of direction. That’s exactly why I created my DIY bookkeeping templates and why I run my Facebook community, The SoloPreneur Hub. With a clear system and some encouragement, you’ll be surprised how quickly it clicks.

2. I Just Don’t Have the Time

If you’re a solopreneur, you already know what it feels like to juggle everything. You’re the CEO, the marketer, the product creator, the customer service rep—and the janitor, too. Finding time to sit down and reconcile your books often feels impossible.

But here’s the hard truth: bookkeeping isn’t optional. Whether you love it or hate it, those numbers eventually lead to taxes. And the CRA or IRS don’t care how busy you are—they still expect accurate filings, on time, every time.

So what do you do when time is the issue? You really only have two options:

1. Restructure your schedule to make room for bookkeeping.
   This might mean setting aside an hour every Friday, blocking a half day at the end of each month, or using a simple weekly checklist. The key is consistency—because once you fall behind, catching up becomes overwhelming fast
2. Hire someone else to do it.
   Sometimes, no amount of time management hacks will change the reality that you have too much on your plate. Outsourcing isn’t failure, it’s a smart business move.

One of my business coaches, Janell Connolly, shared a piece of wisdom at a retreat that I’ll never forget: “Drop the balls that bounce.” In other words, you can afford to let some things slide. But bookkeeping isn’t one of them. It’s more like glass, drop it, and it shatters into a stressful, expensive mess.

3. Money Feels Stressful, So I Avoid It

This last one is the least talked about, but it’s a biggie. If you grew up with financial insecurity, or if you’ve been in a relationship where money was a constant source of conflict, it makes sense that you’d want to avoid it. For many people, not doing their books isn’t about time or skills, it’s about unrecognized trauma.

Your brain is doing what it thinks is best: protecting you from stress. It whispers that looking at your numbers will only lead to pain, so you shove the receipts into a drawer and promise to deal with them “later.”

Here’s the problem. Avoidance might protect you in the short term, but in the long term, it only makes things worse. When tax time comes, or when your business starts to grow, the stress doubles.

If this is your reality, please give yourself some grace3. You’re not lazy or irresponsible, you’re coping. And coping mechanisms are hard to undo.

In this case, the best next step might be twofold:

• Outsource your bookkeeping while you work through the underlying emotional piece with counseling or coaching.
• Reframe your relationship with money by learning to see your numbers as information, not judgment.

Over time, as you heal, you may find you can handle your own bookkeeping again. But in the meantime, outsourcing ensures your business doesn’t suffer while you’re doing the deeper work.

What All Three Reasons Have in Common

Whether your struggle is about numbers, time, or money mindset, the end result is the same: falling behind on your books creates stress and costs you money.

The solution doesn’t have to be complicated. You either:

• Get the right tools and training so you can manage your own bookkeeping with confidence, or;
• Hire help so you can focus on other parts of your business.

Both are valid, and the right choice depends on where you’re at in your business and life.

The First Step to Getting Back on Track

If this post has you nodding along, here’s my challenge to you: don’t just close the tab and go back to ignoring that stack of receipts. Choose one action you can take this week.

• If you’re struggling with know-how, grab my Map Your Money Income & Expense Tracker to simplify your system.
• If time is your biggest hurdle, set aside a recurring appointment in your calendar right now.
• If money feels like the enemy, consider whether outsourcing might give you the breathing room you need.

Your future self will thank you.

Final Thoughts

Bookkeeping doesn’t have to feel like an endless, shame-filled cycle. The first step is recognizing why you’re stuck. Once you understand the root cause, you can make a clear decision: learn it, schedule it, or delegate it.

Your numbers are the story of your business and the path to your dreams, and they deserve more than being shoved in a shoebox.