When Does a Small Business Need a Bookkeeper?
There is no revenue number where a bookkeeping fairy appears and declares that you are officially too successful to categorize your own transactions.
Some business owners hire a bookkeeper almost immediately.
Others comfortably manage their own books for years.
The better question is whether DIY bookkeeping still works for your business.
If the books are accurate, current, manageable, and not taking time away from more valuable priorities, you might be perfectly fine doing them yourself.
But if you recognize several of the signs below, it might be time to reconsider.
1. Your Bookkeeping Keeps Getting Pushed to Next Week
You fully intend to do it.
Just not today.
Then Friday becomes Monday. Monday becomes next month. Eventually you have several months waiting for you.
Occasionally falling behind does not automatically mean you need a bookkeeper.
Consistently falling behind tells you something about the system.
If bookkeeping never makes it high enough on your priority list to actually get done, handing responsibility for it to someone else may be more realistic than promising yourself you'll suddenly start enjoying monthly reconciliations.
Already there? Start with our guide to catching up on months of bookkeeping.
2. You Know What's in the Bank, but Not Whether You're Profitable
Your bank balance is useful information.
It is not your profit.
Money currently sitting in your bank account can include amounts needed for upcoming bills, taxes, debt payments, or other obligations.
Likewise, a business can be profitable on paper while experiencing cash flow problems.
Accurate bookkeeping gives you financial statements that show more than today's bank balance.
If the answer to "How is the business doing?" is always "Well, there's money in the checking account," you could probably use better financial information.
3. Tax Time Requires Financial Archaeology
January arrives.
Suddenly you're searching email for receipts, downloading twelve months of statements, trying to remember what you bought last February, and wondering whether something called SQ *JH4729 was a business expense.
Tax preparation will always require some work.
It should not require reconstructing an entire year of business activity from scratch.
Current bookkeeping means much of that work has already been done throughout the year.
4. You're Doing Bookkeeping Instead of Revenue Producing Work
Suppose you spend four hours every month doing your books.
That may not sound terrible.
But those are four hours you cannot spend serving clients, finding new ones, developing services, marketing your business, or doing something completely unrelated to work.
There is nothing inherently wrong with DIY bookkeeping.
But eventually your time becomes one of the most limited resources in your business.
At that point, the cost of doing something yourself includes what you are not doing during those hours.
5. You're Not Confident Your Transactions Are Categorized Correctly
Maybe your books are current.
You just aren't sure they're right.
You find yourself staring at the category menu wondering whether something is software, dues and subscriptions, office expense, or something else entirely.
Then there are transfers, loan payments, owner contributions, credit card payments, reimbursements, and other transactions that may not behave quite the way an ordinary expense does.
If you're frequently guessing, your reports may not be giving you the information you think they are.
6. Your Business Has Become More Complicated
Think about your business when you first started.
Maybe you had one bank account, a few software subscriptions, and several customers.
Now you might have:
Multiple bank or credit card accounts
More monthly transactions
Contractors
Employees
Loans
Recurring invoices
Vendor bills
Multiple revenue streams
Payment processors
More complicated business expenses
The bookkeeping system that worked beautifully for version one of your business does not have to work forever.
Growth often creates administrative complexity.
That is normal.
7. You're Making Decisions Without Reliable Financial Statements
Should you hire?
Can you afford another software subscription?
Is your new service actually profitable?
Did that increase in revenue translate into more profit?
Can the business support a larger monthly expense?
Business owners make decisions like these constantly.
Accurate financial statements do not make the decisions for you, but they give you better information to make them.
If you rarely look at your P&L or balance sheet because you do not trust that the underlying bookkeeping is accurate, fixing the bookkeeping comes first.
8. Customer Invoices Aren't Getting Followed Up On
You did the work.
You sent the invoice.
Then you got busy.
Thirty days later, the invoice is still sitting there unpaid.
Managing accounts receivable is not relevant to every business, but for businesses that invoice customers, consistent follow up matters.
The sale does not help your cash flow until the money actually arrives.
If invoicing and payment follow up repeatedly fall through the cracks, bookkeeping support that includes routine invoicing may remove another administrative burden from your plate.
9. Your Books Are Already Months Behind
One month behind can become two surprisingly quickly.
Eventually, you reach a point where maintaining the current month and repairing the backlog become two separate jobs.
If this is you, do not assume you need to fix everything before you are "allowed" to hire a bookkeeper.
Cleanup and catch up work exists for exactly this reason.
Mainstay's bookkeeping cleanup and catch up services are designed to bring existing books current before establishing an ongoing monthly routine when needed.
You can ask for help while things are messy.
Really.
10. You Can Do Your Bookkeeping. You Just Don't Want To Anymore.
This one deserves more attention.
You do not have to be bad at bookkeeping to hire a bookkeeper.
You do not need to be hopelessly behind.
You do not need to be confused by your financial statements.
You do not need a dramatic bookkeeping disaster.
Maybe you know exactly how to do it.
And you would simply rather spend those hours somewhere else.
That is enough.
Delegation is not limited to tasks you are incapable of performing yourself.
Successful business owners routinely hand off work they could do because their attention is more valuable elsewhere.
Bookkeeping can be one of those things.
What If I'm Not Ready to Hire a Bookkeeper?
Then don't.
Seriously.
If your business is still simple, your books are current, and DIY bookkeeping works for you, there is no reason to outsource simply because someone on the internet told you that "real businesses" have bookkeepers.
Instead, focus on building a reliable system.
Our beginner's guide to small business bookkeeping can walk you through the fundamentals, and the small business bookkeeping checklist can help you create a weekly and monthly routine.
You can also use Mainstay's free bookkeeping starter resources while you continue managing your own books.
What Should I Look for When Hiring a Bookkeeper?
When you are ready, look for someone who understands the type and complexity of business you operate.
Ask about:
What services are included
How frequently your books are updated
When monthly financial statements are delivered
How questions and missing information are handled
What accounting software they work with
Whether cleanup is available if your books are behind
How pricing works
What responsibilities will remain with you
You should understand what happens after you hand over the books.
At Mainstay, monthly bookkeeping follows a recurring process throughout the month. Transactions and applicable routine invoicing or bill payment are handled as activity occurs, clarification questions are kept concise, relevant accounts are reconciled, and monthly financial statements are delivered by the 15th.
The goal is not simply to make bookkeeping disappear from your to do list.
It is to give you books you can actually rely on.
So, Do You Need a Bookkeeper?
Maybe.
If your books are current, accurate, and easy for you to maintain, you may not need one yet.
If they are constantly behind, becoming more complicated, eating into time you would rather spend elsewhere, or producing financial information you do not completely trust, professional bookkeeping support may be worth considering.
And if your answer is simply:
"I am so tired of doing this myself."
That counts too.
Ready to Buy Back Some of Your Time?
Mainstay provides monthly bookkeeping services for small businesses that are ready for consistent, reliable books without keeping bookkeeping on the owner's personal to do list.
We'll talk about how your business works, what you're currently doing for bookkeeping, and where you could use support. If Mainstay is a good fit, we'll recommend the level of service that makes sense for your business.
Explore Monthly Bookkeeping Services →
Not ready to hand it off? Get the Free Bookkeeping Starter Bundle →