Paper receipts piled multiple inches high in the corner of your desk. A stack of virtual receipts that makes your inbox-zero friend cringe. And all of it is pulling you away from the day-to-day operations of your company and why you started this business to begin with.
A constantly-moving to-do list item of “catch up on books” that keeps getting pushed further down as you handle more urgent tasks and never actually gets done.
Pair that with the overhanging angst of knowing that tax day will be here before you know it, and the question of “should I hire a bookkeeper?” is on loop in your head.
But are you ready for a bookkeeper? Can you afford to hire a bookkeeper? Is bookkeeping one of those “professional services” that is really a waste of your time and money? Will a bookkeeper actually lighten your load, or will they just give you more financial tasks and responsibilities than you’re already struggling to stay on top of?
Not every small business owner needs to hire a bookkeeper on day one, but if these questions sound familiar, your time has probably come. Though the hiring process can feel a little daunting, the right bookkeeping services can make a bigger difference than you think. Here are 3 things to think about before you hire a bookkeeper.
Is bookkeeping taking away from YOUR time in the business?
One of the clearest signs you’re ready to hire a bookkeeper is when bookkeeping starts pulling you away from the work that actually grows your business—the work you’re good at and really enjoy doing!
Many small business owners who are more than ready to hire a bookkeeper lose an entire day every week categorizing financial transactions, chasing receipts, wrestling with spreadsheets while combing through bank statements until their eyes twitch. When they tell us that, we KNOW it’s time for them to start working with a professional bookkeeper.
You didn’t start your business to become your own part-time bookkeeper, chasing down financial transactions and trying to understand all the financial reports that sound like Greek. If keeping up with the numbers feels overwhelming—or if it’s what’s keeping you up at night—it’s probably time to get support.
Good vs. poor bookkeeping
A good bookkeeper does more than just data entry; they help you understand the financial information that drives your business decisions. Depending on the size of your business, the structure, and how much outside non-biased support you want, that will determine whether you want to hire an in-house bookkeeper, a freelance bookkeeper, or work with one of the local bookkeeping firms in your area.
As much as it pains us to know it, we know that there are some business owners who just ignore bookkeeping altogether and (gasp) guess at deductions and are unable to show receipts.
Not only could this get you in MASSIVE trouble with the IRS down the road, poor bookkeeping practices often lead to poor tax preparation. If you failed to track expenses all year long, it is very difficult to get all of the tax deductions that you are eligible for. In the long run, the work and money that you invest into good bookkeeping practices and managing your business finances will pay dividends in less stress, more time to spend on what you love, AND probably get you more deductions than you would have with an “ignorance is bliss” mentality.
Do you need a system that works specifically for YOUR business?
Most business owners aren’t starting from scratch when it comes to keeping up with bookkeeping tasks. Whether it’s a Microsoft Excel spreadsheet, QuickBooks, Xero, or a more industry-specific bookkeeping software, chances are good that you’re past the paper and pen route.
You probably already have bookkeeping software or a system that helps you track estimates, projects, or invoices. But here’s the thing—just because something works for job costing or payroll doesn’t mean it gives you the kind of accurate bookkeeping and financial reporting your business really needs to make projections and wise financial decisions.
In fact, the wrong system or two different systems that are not connected properly (think project management system not talking to QuickBooks accurately) could potentially lead to miscategorization of expenses, duplicate invoices, major accounting errors, and ultimately lost time and money. Most of these tools CAN be set up to “talk” to each other properly, but it can take someone who knows what they are doing.
We’ve seen tools like Square or custom invoicing platforms that are great for tracking details—but they don’t auto-generate balance sheets or track depreciation the way a savvy business owner needs in order to be a good steward of their business.
There’s a better way
That’s where a good bookkeeper comes in. A skilled bookkeeper can integrate your existing tools into QuickBooks Online or another system and help you get accurate financial records and reports that actually show where your money is going: statement of cash flows, Profit & Loss statements, and balance sheet.
While you do not have to hire the same service professional for your tax preparation as you do for your monthly bookkeeping, we have found that being able to have that Certified Public Accountant and professional bookkeeping services working like team members on YOUR team tends to lead to the best outcome for your small business. Plus, you have a dedicated team providing end-to-end support, helping you achieve your definition of financial success.
Additionally, then there is no confusion about who you need to contact with what questions. If you have a CPA for tax returns but a bookkeeping firm for your bookkeeping, you’re left guessing who you should call for your questions. Having the right financial professional (or multiple professionals) on board is one of the best ways to make sure you are staying on top of all tax guides and income taxes sales taxes.
Can you afford to hire a bookkeeper?
Hiring a bookkeeper is absolutely an investment, but it’s also one of the smartest moves you can make for financial management and peace of mind.
It’s tax-deductible, helps improve operational efficiency, and gives you back time to focus on high-level leadership and customer service. We always ask clients: How much time are you spending trying to do your own bookkeeping, and how much more income could you generate with that time if you were able to work in your zone of genius? Sometimes, breaking down the cost to an hourly rate or opportunity cost can help you truly understand the value of hiring a bookkeeper for your small business.
We’ve seen what happens when business owners let things slide for months, then January hits and they lose two solid weeks scrambling to get ready for tax filings—digging through those piles of receipts and trying to remember “now what was that expense for?”
The real question is, can you afford NOT to hire a bookkeeper?
Bookkeeping isn’t just about getting through tax season. It’s about financial clarity, confident planning, and long-run business success.
Another aspect that is not discussed often enough is the importance of balance, mental health, and truly prioritizing family time, even when running a small business. If you are drowning in the day-to-day work of running a business, outsourcing your bookkeeping is one of the easiest tasks to hand off.
Additionally, how much do you think your mental health is potentially suffering if you are spending hours and hours on bookkeeping tasks that make you want to scream or cry, or both? We all (hopefully) start businesses to help other people while doing the things we are good at and love doing. If bookkeeping isn’t on your “love to do” list, then it is stealing time, energy, and joy. Worth it? We think not.
Are your bookkeeping tasks taking away from what matters most in your life? Here at Lauren Hale CPAs, we believe that strong businesses and healthy families can coexist-that you can be a great spouse, parent, and friend while also running a profitable and successful business. One of the key elements of success in this constant juggling act is knowing what you can (and should) outsource and what only YOU can do.
In all seriousness, when your kids are grown and out of the house, are you going to wish that you had spent MORE time keeping up on your books and less time playing with them? Hiring a bookkeeper is a good place to start, having more time to do what matters most.
FAQ: Should You Hire a Bookkeeper?
What does a bookkeeper actually do for small businesses?
A bookkeeper handles your day-to-day recording of receipts, categorizes financial transactions, and reconciles bank accounts. They prepare financial statements, such as an income statement and balance sheets, and help maintain accurate financial records. They may also assist with payroll services, invoicing, and generating financial reports that guide better business decisions.
Do I need a certified bookkeeper or a CPA?
Technically speaking, not every business needs a certified public accountant for everyday bookkeeping tasks. A certified bookkeeper or experienced bookkeeping services provider can offer everything from monthly bookkeeping to cash flow tracking and QuickBooks Online setup. However, for tax preparation or advisory services, we strongly recommend working with a CPA.
We are obviously biased, but we see great benefit in working with a CPA firm that will manage your tax preparation and monthly bookkeeping to ensure nothing slips through the cracks or gets lost in communication.
Is it better to use freelance bookkeepers or hire in-house?
That depends on your specific needs, the size of your business, and your budget. An in-house bookkeeper can provide easy access and deep familiarity with your business processes. However, the cost of having an in-house bookkeeper will rival that of hiring another full-time employee.
Most small businesses don’t need that many man-hours spent on bookkeeping tasks. For many small business owners, working with a virtual bookkeeper or a team from a local bookkeeping firm is more cost-effective, while still offering professional bookkeeping services and peace of mind.
What should I look for during the hiring process?
Look for someone with a strong track record, understanding of small business accounting, and the ability to provide accurate bookkeeping and data-driven insights. The best bookkeepers will be familiar with tax laws, best practices, and work with your accountant to categorize expenses properly so the IRS doesn’t give you the side-eye during an audit.Your bookkeeping candidates should obviously have experience with a bookkeeping software like Microsoft Excel or QuickBooks Online.
Is bookkeeping really worth the cost?
Absolutely. When you factor in your hourly rate and the opportunity cost of doing your own bookkeeping, the value becomes clear. A dedicated bookkeeper frees you up to lead your company well, sell more products or services, and serve your people better ALL while giving you accurate financial data and professional help that leads to long-run financial success and less stress.
What’s the difference between a bookkeeper and a fractional CFO?
A good bookkeeper focuses on the day-to-day recording of receipts, categorizing financial transactions, and maintaining accurate financial records.
A fractional CFO, on the other hand, takes a more strategic role—offering financial advisory insight, helping with forecasting, and advising on high-level business decisions. Most small businesses benefit from having a skilled bookkeeper handle the financial tasks that keep everything running smoothly. But when you’re looking at big-picture growth, funding, or long-range planning, a fractional CFO may be a smart next step.
Do I need to do anything to prepare before I hire a bookkeeper?
The best candidates will help guide you through the setup process—but yes, there are a few things you can do to make onboarding easier. Start by gathering your recent bank statements, organizing login access to your bookkeeping software, and reviewing any systems you already use (like payroll services or invoicing tools).
It also helps to write down your specific needs AND questions: Do you want help with sales taxes? Monthly bookkeeping only? Someone who will work directly with your CPA? A little prep goes a long way toward building a productive partnership.
