How to know if you're ready to outsource your small business finances — or if you should keep doing it yourself
Hiring a bookkeeper can be one of the most valuable decisions you make as a business owner. But it can also be an unnecessary expense if your business isn’t quite ready.
So how do you know when to bring in help — and when to wait?
Here’s what you need to consider before outsourcing your books, plus how to get the most value from a bookkeeper when the time is right.
What Does a Bookkeeper Actually Do?
A bookkeeper organizes and tracks your business’s financial transactions. This includes:
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Categorizing income and expenses
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Reconciling bank accounts
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Generating financial reports like Profit & Loss statements
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Preparing your books for tax time
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Ensuring your financial records stay accurate and up to date
They do not offer financial strategy, tax filing, or budgeting — those services fall under accounting, tax prep, or CFO-level support.
When You're NOT Ready for a Bookkeeper
Here’s when it makes more sense to DIY your books — for now:
You’re not generating consistent revenue
If your business is pre-revenue or only making a few hundred dollars a month, there’s not enough activity to justify outsourcing yet.
You haven’t separated business and personal finances
A bookkeeper can’t do their job if your transactions are mixed. Before hiring, make sure you have dedicated business bank accounts set up.
You don’t understand your numbers at all
While a bookkeeper helps with organization, you’re still the decision-maker. If you don’t know what you’re looking at in your financial reports, start with education first. The Small Business Planner helps you learn how to review and interpret your numbers before handing them off.
You haven’t chosen a bookkeeping method or software
Before hiring, decide how you want your books managed — cash or accrual basis, QuickBooks or another platform. Otherwise, you’ll be paying someone to build your system from scratch.
When You SHOULD Hire a Bookkeeper
Here are strong signs it’s time to get help:
You’re making consistent monthly revenue
Once you're generating steady income and tracking multiple types of expenses, having a bookkeeper ensures nothing falls through the cracks.
You’re spending too much time on financial admin
If your energy is being drained by receipts, categorization, and spreadsheet updates, your time is better spent on growth activities.
You’re preparing for tax season or a big financial goal
A bookkeeper can get your records clean and accurate so your accountant or CPA can do their job efficiently — and help you avoid costly mistakes.
You’re feeling overwhelmed or behind
If your books are messy or months behind, a professional can catch you up and help you maintain clean records going forward.
What to Do Before You Hire
To get the best results from a bookkeeper:
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Separate your business and personal accounts
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Set up your Core 4 account structure as taught in The Small Business Planner
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Choose and connect your accounting software
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Understand what reports you want access to
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Ask what cadence of reporting and communication they offer
The more prepared you are, the smoother the onboarding will be — and the more value you’ll get from your investment.
Final Takeaway
You don’t need to outsource your bookkeeping right away. But you do need a system.
Start with your own simple structure — track your revenue, expenses, taxes, and pay — and grow from there. Once your business has consistent income and growing complexity, a bookkeeper can free up your time and bring clarity to your numbers.
The Small Business Planner helps you build this structure from day one — so when the time comes to hire, you’re ready.
Explore The Small Business Planner now → https://smallbusinessplanner.com/products/planner