The First Bookkeeping Tasks Small Businesses Should Outsource
If you’re a small business owner who has tried to juggle bookkeeping on the side, you already know the truth: bookkeeping isn’t difficult because the math is hard — it’s difficult because it’s relentless.
It’s every day. Every week. Every month.
Every coffee purchase. Every subscription. Every deposit. Every invoice. Every little thing that happens in your business creates a ripple in your books.
Most business owners eventually hit the same moment:
“I can do this myself… but should I?”
If you’ve reached the point where bookkeeping is draining your time, confidence, or energy, outsourcing might be the smartest next step — and it doesn’t have to be all or nothing. You can start small and only hand off the tasks that make the biggest difference.
This guide breaks down the first bookkeeping tasks most small businesses should outsource, why they matter, what they include, and how doing so can save you hours every month.
Let’s make bookkeeping a whole lot easier.
Why Small Business Owners Struggle With DIY Bookkeeping
Most business owners don’t start their journey thinking, “Wow, I can’t wait to categorize transactions for the rest of my life!”
Bookkeeping often lands on your plate simply because it feels too early to hire help. But even businesses with low transaction volume eventually realize DIY bookkeeping creates problems like:
Falling behind
Scrambling during tax season
Guessing instead of knowing
Losing receipts
Inconsistent categorizing
Mismatched bank balances
Late invoices or forgotten bills
Stress every time you open QuickBooks
And here’s the real issue:
Bookkeeping mistakes compound over time.
One small error in March can turn into a much bigger problem in December — and you usually don’t notice until something goes wrong.
That’s why outsourcing even a few key tasks can give your business instant clarity and stability.
The First Tasks Small Businesses Should Outsource
These are the bookkeeping responsibilities that make the biggest difference. You can outsource one at a time or bundle them together. Either way, each one provides immediate relief.
1. Monthly Transaction Categorizing
This is the quiet time-eater. Every purchase, sale, deposit, invoice payment, refund, fee, subscription, and transfer must be assigned the correct category.
Done right?
You get clear financial statements and accurate taxes.
Done wrong?
Your numbers become unreliable.
Why this is the #1 task to outsource:
It takes the most time.
It’s the easiest to get wrong.
It must be done consistently.
It’s the foundation for all other financial reports.
A bookkeeper will:
Categorize every business transaction
Clean up incorrect categories
Separate personal purchases
Flag questionable charges
Ensure IRS-friendly bookkeeping
Maintain clean, precise books month after month
It’s the quickest win for your sanity.
2. Bank and Credit Card Reconciliations
Reconciliation is the process of comparing your books to your bank accounts to make sure they match.
Most business owners don’t realize how crucial this is. Reconciliation is how you catch:
Duplicate transactions
Missing income
Missing expenses
Bank errors
Accidental double-charges
Fraudulent charges
Without monthly reconciliations, your financial reports can be off by hundreds or thousands of dollars without you ever noticing.
A bookkeeper will:
Reconcile every bank account
Reconcile credit cards and loan accounts
Identify and correct errors
Keep balances accurate
Flag any concerns
This one task alone makes your financials dramatically more reliable.
3. Invoicing & Accounts Receivable
Cash flow is the heartbeat of your business, and slow invoicing is one of the biggest culprits behind cash flow issues.
Common DIY problems:
Forgetting to send invoices
Forgetting to attach W-9s or receipts
Mis-typing invoice amounts
Sending invoices late
Not following up on overdue payments
A bookkeeper can:
Create and send invoices
Track who has paid and who hasn’t
Send reminder emails
Organize payment records
Maintain an organized invoicing system
When someone else handles this, your revenue becomes more predictable, and your stress level drops.
4. Bill Payment Tracking (A/P)
This doesn’t mean handing over your bank login or letting someone else pay your bills directly.
Many business owners feel nervous about this part — and that’s completely understandable.
Fortunately, there’s a safe, structured way to outsource this:
A bookkeeper tracks your bills and prepares everything for you to approve.
They will:
Organize vendor bills
Track due dates
Prevent late fees
Keep you informed of upcoming payments
Streamline your payment workflow
This alone prevents last-minute chaos and protects your cash flow.
5. Monthly Financial Reports
Most business owners don’t need complex, accountant-level financials.
What they do need is clarity — clear reports that help them make decisions confidently.
A bookkeeper can provide monthly reports such as:
Profit & Loss
Balance Sheet
Cash Flow Overview
Spending Summary
Revenue Trends
Month-over-month Comparison
The real value?
A bookkeeper helps you understand what the numbers mean, not just what they say.
6. Clean-Up and Catch-Up Work
If you’re behind, this is one of the most impactful tasks to hand off.
A bookkeeper can bring your books from “months behind and overwhelming” to “fully accurate and caught up.”
This is especially helpful if:
You’re not confident your books are correct
You’ve mixed business and personal expenses
Categories are messy
Your balances don’t match your bank
You’re preparing for taxes
You want a fresh financial start
Cleanups often reveal issues you didn’t even know were hiding in your books.
7. W-9s, 1099s, and Contractor Tracking
This is one of the most overlooked areas of bookkeeping.
Many business owners wait until January to think about 1099s — which usually leads to stress, missing information, and last-minute scrambling.
A bookkeeper can:
Collect W-9s before contractors are paid
Track contractor totals throughout the year
Prepare everything needed for 1099 filing
Prevent IRS penalties
Keep your year-end smooth and stress-free
This is the easiest place for a bookkeeper to save you from January chaos.
How Outsourcing Bookkeeping Saves Small Businesses Time and Money
You may be wondering whether outsourcing now is “worth it.”
Let’s break it down.
1. You’ll save hours every month.
Even small businesses spend 8–15 hours a month on bookkeeping. What could you do with that time?
2. You’ll make better decisions.
Clean financials help you understand:
What’s profitable
Where to cut expenses
How much to pay yourself
When to hire
When to raise prices
3. You’ll reduce tax season stress.
Clean books = easier filing = lower CPA bill.
4. Your numbers become accurate and trustworthy.
No more guessing. No more surprises.
5. You can grow with confidence.
Good bookkeeping supports smarter business planning.
FAQs About Outsourcing Bookkeeping
Q: Do I have to give my bookkeeper access to my bank account?
No — you stay in full control of your financial accounts. At Managed Mayhem, we use QuickBooks Online’s secure, view-only bank feeds, which allow your transactions to sync automatically without ever giving us your banking login or password.
You maintain full control over your accounts, and we receive only the transaction data needed to keep your books accurate and up to date.
Q: Can I outsource only one or two tasks to start?
Absolutely. Many clients begin by outsourcing just one or two high-impact tasks — often categorizing, reconciling, or invoicing — and expand over time. Managed Mayhem is designed to grow with you at your pace, not overwhelm you.
Q: What if my books are a mess or I’m really far behind?
You’re not alone — messy books are more common than you think. At Managed Mayhem, we specialize in judgment-free cleanup and catch-up work, whether you’re a few months behind or haven’t updated anything all year. We’ll get everything cleaned up, organized, and running smoothly.
Q: How do I know it’s the right time to hire a bookkeeper?
Most business owners outsource when bookkeeping starts taking too much time, creates stress, or feels uncertain. If you’re behind, confused, or avoiding your books, that’s usually the sign. If your business is growing, outsourcing becomes even more valuable.
Q: Will outsourcing bookkeeping save me time?
Yes — often more time than clients expect. Tasks that take you 10–15 hours each month may take a bookkeeper only 1–2 hours. That’s time you get back to focus on growth, clients, or simply breathing a little easier.
Q: Do you work with businesses that are new or very small?
Yes. Managed Mayhem supports businesses of all sizes — including new entrepreneurs, established small businesses, and businesses with low monthly transaction volume. You don’t need to “hit a certain size” before getting help.
Q: Do I need QuickBooks Online to work with Managed Mayhem?
Yes. We use QuickBooks Online exclusively because it provides secure bank feeds, reliable reporting, and efficient monthly workflows. If you don’t have QBO yet, we can help you get set up correctly from day one.
How to Start Outsourcing Your Bookkeeping (Without Overwhelm)
You don’t need a full-time bookkeeper. You don’t even need to outsource everything. You just need help with the tasks that are costing you the most time and clarity.
The easiest way to get started? Pick one task from this list — and hand it off. Then build from there.
Ready for Stress-Free Books?
If you’re ready to get organized, stop guessing, and finally feel confident in your numbers, I can help.
Send me a message anytime, and I’ll help you decide which tasks to outsource first — based on your business, your goals, and your budget.