5 Signs It’s Time to Outsource Your Bookkeeping

(And Why Doing It Sooner Can Save You Time, Stress & Money)

Let’s be honest — for most people (not us nerds though!), bookkeeping isn’t the most exciting part of running a business. But it’s one of the most important. And it has to be done. It’s your legal requirement as a business owner in Canada.

Still doing it yourself? That’s totally normal at the beginning. Many solopreneurs can handle a simple set of books, looking at them monthly or even annually.

But as your business grows, your time becomes more valuable — and mistakes become more costly. We’ve seen many business owners dive into growing and scaling their business like superstars. Unfortunately the books may go neglected, resulting in costly cleanup work and penalties from the CRA and other agencies (WSIB, etc.).

The good news is that if you know when it’s time to outsource, you can be proactive and keep your books in tip-top shape. That’s why we’ve come up with these 5 signs that it might be time to call in the pros.

✅ 1. You're Always Behind on Your Books

If your bookkeeping feels like an “I’ll get to it later” task... and later never comes, you’re not alone. As a small biz owner, you’re bound to procrastinate when it comes to your books. The question is, are you ever actually getting them done on time? Falling behind schedule is a costly mistake and means:

• You don’t have accurate financial data

• You’re scrambling during tax season

• You might be missing important deadlines or deductions

📌 If your books are still sitting in a shoebox (or an inbox), it’s time.

✅ 2. You Dread Tax Time

If tax season fills you with panic, that’s a red flag. An outsourced bookkeeper keeps everything clean, organized, and CRA-ready — year-round.

Imagine being stress-free at tax time… better yet, imagine smiling knowing you’re being audited! It’s possible with a professional bookkeeper. We keep your books CRA-compliant and audit-proof.

💬 “They go above and beyond to make sure I get the best service and money back when it comes to tax time.” – Doreen Wilton, Jewels Trees

✅ 3. You're Spending Too Much Time on Admin

As a business owner, your time is best spent running and growing your business. You're an entrepreneur because you're good at it! However, not every entrepreneur is a bookkeeper. Your skill set is developed for:

• Finding new clients

• Building your brand

• Growing your revenue

Good bookkeeping requires a different skill set - knowledge of GAAP (generally accepted accounting principles), legal filing requirements, and software proficiency, for example.

Your time is precious, and learning the ins and outs of your books instead of scaling (or resting!) can cost you hundreds of hours every year that you can’t get back.

If bookkeeping is eating into your evenings or weekends, it’s costing you more than just time — it’s costing you opportunity.

✅ 4. You’re Not Sure If You’re Making or Losing Money

If questions about your finances leave you guessing, you’re not alone—but you are flying blind. Without clear financial insight, every business decision is a gamble. A professional bookkeeper gives you the clarity and confidence you need to understand your numbers and take control of your business future.

If you can’t confidently answer questions like:

• “What’s my monthly profit?”

• “Where is my money going?”

• “Can I afford to hire?”

A professional bookkeeper gives you financial clarity, so you can make smarter and faster decisions.

✅ 5. Things Are Getting More Complicated

As your business grows, so do the responsibilities. Maybe you’re

• Hiring your first employee

• Registering for HST/GST

• Thinking about incorporating

These are exciting milestones—but they also come with a heavier compliance load, more paperwork, and greater financial complexity. What used to be a simple spreadsheet quickly becomes overwhelming, and mistakes can lead to penalties, missed opportunities, or cash flow issues.

Outsourcing a professional bookkeeper at this stage isn’t just helpful—it’s essential. They ensure everything is set up properly, keep you compliant, and help you stay organized as you scale. With an expert on your side, you can navigate new challenges with confidence and focus your energy on growing your business—not untangling financial red tape.

🎯 Bottom Line: If You’re Feeling Overwhelmed, You Don’t Have To Do It Alone

Outsourcing your bookkeeping isn’t a luxury — it’s a smart growth move. At Simcoe Office Solutions, we help small business owners across Canada and beyond stay organized, reduce stress, and reclaim their time.

📞 Let’s chat — book a free consultation today and see what a difference professional bookkeeping can make.