Small business owner reviewing paperwork and asking whether to hire a bookkeeper or keep doing it themselves

Should You Hire a Bookkeeper or Do It Yourself? A Mid-Year Reality Check

Still managing your own bookkeeping? Here’s how to know if it’s time for support.

If you’ve made it this far into the year doing your bookkeeping on your own, well done. Truly. It’s no small task to stay on top of invoices, receipts, reconciliations, and cash flow while running your business.

But now that we’re mid-year, it’s worth asking:
Is your DIY system still working for you? Or is it quietly holding you back?

Here’s a gentle check-in to help you decide whether to keep going solo or bring in some help.

1. How Much Time Are You Spending on Bookkeeping?

Be honest with yourself. Is it 1–2 hours a week? Or is it creeping into evenings, weekends, or the hours you’d rather spend growing your business?

Hiring a bookkeeper doesn’t mean you’ve failed; it means you’re valuing your time.

Your zone of genius is running your business. Ours is keeping the numbers clean.

2. Are You Confident Your Records Are Accurate?

A missed deduction. A miscategorized expense. A bank account that hasn’t been reconciled in three months.

These small mistakes can add to stress, lead to penalties, or create missed opportunities. If you find yourself second-guessing your books (or ignoring them altogether), that’s a signal that it may be time to hand them off.

3. Is Your System Working, or Just “Working Enough”?

Spreadsheets, paper folders, apps that only kind of work together—if your current setup is a patchwork of “good enough,” it might cost you more friction than you realize.

A good bookkeeper will help you set up a system that works for your business and grows with it.

Small business owner reviewing paperwork and asking whether to hire a bookkeeper or keep doing it themselves

4. Are You Ready to Make Bigger Financial Decisions?

Whether hiring, investing, or applying for a loan, clean financials give you the confidence to move forward—and the proof to back it up.

If your books are up-to-date and professionally managed, it’s easier to make smart, strategic moves (and sleep at night).

5. What Would It Feel Like to Let It Go?

This isn’t about giving up control. It’s about getting support.

Many small business owners don’t realize how much mental space bookkeeping takes up until it’s off their plate. What would it feel like to know your numbers are handled, checked, and easy to understand?

The Mid-Year Takeaway: Bookkeeping Should Work for You

Whether you’re ready to delegate or just want help improving your current system, you don’t have to go it alone. At Numble, we work with business owners across Canada to make bookkeeping less stressful and more useful.

Want to explore what working with a bookkeeper could look like for your business? Let’s talk.

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