When to Hire a Bookkeeper & Your Yearly Financial Timeline as a Business Owner
If you're a business owner wondering when the right time is to hire a bookkeeper, you're not alone. Many entrepreneurs wait until they’re drowning in financial tasks before they seek professional help, but that can lead to costly mistakes and unnecessary stress.
So, when is the ideal time to start looking for a bookkeeper? And how can you set yourself up for financial success throughout the year? Let’s break it down.
When Should You Hire a Bookkeeper?
Signs It’s Time to Hire a Bookkeeper
If any of these sound familiar, it’s time to bring in professional support:
✅ You’re spending too much time on bookkeeping instead of focusing on growing your business.
✅ Your books are disorganized, outdated, or nonexistent.
✅ You’re stressed about tax season and unsure what you’ll owe.
✅ You’re not sure how profitable you actually are or where your money is going.
✅ You’ve hired employees or contractors and need help managing payroll and compliance.
✅ You want to scale your business but don’t have clear financial data to guide you.
The Best Time of Year to Hire a Bookkeeper
While you can hire a bookkeeper anytime, certain times of the year make the transition smoother:
Late Q3 or Early Q4 (September - November): This is the best time to bring on a bookkeeper so they can help you wrap up the year cleanly and prepare for tax season.
Start of the New Year (January - February): If you didn’t bring in a bookkeeper before year-end, starting fresh in January can make sure you have accurate records from day one.
After Tax Season (April - May): If tax season was a nightmare, now is the time to get support so you don’t repeat the same mistakes next year.
No matter when you start, the key is to be proactive, because scrambling at the last minute to clean up your books is never fun.
Your Yearly Bookkeeping & Financial Timeline
To stay ahead of your finances and avoid last-minute panic, here’s what you should be focusing on each quarter of the year:
Q1: Get Organized & Set Financial Goals (January - March)
✔️ Close out the previous year’s books and review your Profit & Loss (P&L) statement.
✔️ Gather all tax documents (1099s, W-2s, receipts, etc.) and prepare for filing.
✔️ Set clear financial goals for the year (profit targets, savings goals, etc.).
✔️ Ensure you have a tax savings plan in place (typically 20-30% of income).
✔️ If you don’t have a bookkeeper yet, now’s a great time to get one.
Q2: Optimize & Plan for Growth (April - June)
✔️ File your taxes (or work with an accountant to file an extension if needed).
✔️ Review Q1 financials to check for trends and make necessary adjustments.
✔️ Ensure your pricing is aligned with profitability and rising expenses.
✔️ Consider hiring or outsourcing to scale your business with confidence.
Q3: Prepare for the Year-End Rush (July - September)
✔️ Conduct a mid-year financial review—are you on track to hit your goals?
✔️ Check for any outstanding invoices or payments and follow up.
✔️ Start prepping for holiday promotions and Q4 sales pushes.
✔️ Assess your bookkeeping process—do you need more support?
Q4: Close the Year Strong & Prep for Tax Season (October - December)
✔️ Make final estimated tax payments for the year.
✔️ Gather all financial records for tax prep (expenses, income, payroll, etc.).
✔️ Conduct a final review of your business profitability.
✔️ Plan ahead for any necessary tax deductions or business investments.
✔️ If you haven’t hired a bookkeeper yet—now is the time.
Bookkeeping Shouldn’t Be Stressful—We’ve Got You!
If your books feel like a never-ending to-do list (or worse, a mystery you’d rather avoid), it’s time to bring in a financial partner who can handle it for you.
At The Summa Collective, we help business owners like you take control of their finances, without the stress. Whether you need ongoing bookkeeping, tax strategy, or financial guidance to scale your business, we’re here to make it happen.
Ready to stop DIY-ing your finances and start making confident, data-driven decisions?
👉 Book a Free Consult Call and let’s chat about how we can help.