When to Hire a Bookkeeper: 7 Signs You Needed One Yesterday

You're a couple of years into running your small business, yet you're still shoving receipts into a shoebox. Or maybe you've graduated to a spreadsheet that just makes you feel even more confused. Either way, you're probably wondering when to hire a bookkeeper, and honestly, the answer might be "six months ago."

When you started your business, handling your own books seemed doable. But fast forward to now, and you're spending your Saturday mornings trying to remember if that $47 charge was for office supplies or something else, and you feel like it might be the time to bring in a professional bookkeeper. Here's how to know if you're right!

What Does a Bookkeeper Do?

A bookkeeper handles the day-to-day financial record-keeping for your small business. They're essential to your business's financial health because they make sure that every dollar that comes in and goes out gets properly tracked, categorized, and recorded.

Bookkeepers help small business owners with:

• Transaction Recording: Every sale, expense, payment, and refund gets logged into your accounting system.

• Bank Reconciliation: They match your bank statements with your recorded transactions to catch errors or duplicate charges.

• Invoice Management: They track what money is owed to you and what you owe others.

• Expense Categorization: They sort your expenses into proper categories so you can have a clear idea of where your money goes.

• Financial Reports: They generate reports (usually, monthly financial statements) that show your business performance.

• Tax Preparation Support: They organize everything your accountant needs to create the best tax strategy for your business finances.

Hiring a qualified bookkeeper helps you understand cash flow and make more strategic business decisions because you're clear on how much you bring in revenue and how much you spend in expenses. 

If you don't have that clarity right now, it might be the time for a bookkeeping cleanup.

How Do You Know You Need a Bookkeeper?: 7 Unmistakable Signs

1. You're spending more time on books than you want

When you first started your business, you probably had more time than money. Doing your own bookkeeping made sense because you had fewer transactions, simpler operations, and frankly, you couldn't afford to hire someone else. But as your business grows, all of that changes.

Your time becomes exponentially more valuable as your small business grows.

Every hour you spend on administrative tasks like categorizing expenses or reconciling bank statements is an hour you're NOT spending on strategic planning and business development.

Eventually, you have to start treating your time like it's money. You simply can't AFFORD to spend it on plugging transactions into QuickBooks. You need your brain for strategic decision making!

2. Your financial reports are behind

You haven't opened your accounting software in weeks – maybe months – and you're genuinely afraid of what you'll find when you do. The longer you wait, the more overwhelming the backlog becomes, and the more you avoid it.

This creates a vicious cycle where your financial records become increasingly disconnected from reality.

That's not great for your overall financial management, and it makes it hard to make business decisions because you don't really understand your numbers.

When tax season arrives, you'll have to scramble to reconstruct months of transactions and receipts, which is stressful AND expensive. You'll likely miss deductions, make errors, and spend far more on accounting fees because your CPA has to do detective work trying to make your tax preparation make sense.

3. Your accountant hates you

Okay, your accountant doesn't HATE you, but you're definitely making their job significantly harder. When you send them disorganized records or force them to dig through months of unreconciled transactions, you're making it much harder for them to prepare your tax documents.

To build an effective tax strategy, you need clear, accurate numbers throughout the year.

If your accountant is constantly asking for clarification or requesting additional documents, it'll be hard for them to identify tax-saving opportunities or provide strategic advice that'll help improve your profit margins.

4. You're missing out on deductions

Small business owners qualify for many different tax deductions that can save you thousands of dollars every year. 

However, claiming these deductions requires proper documentation and organized records. If your bookkeeping is inconsistent, you're likely leaving money on the table.

Common business deductions include:

• Home office expenses

• Vehicle expenses for business use

• Professional development and training costs

• Business meals

• Office supplies and equipment

• Professional services (legal, accounting, consulting)

• Marketing and advertising expenses

• Business insurance premiums

• Travel expenses for business purposes

• Software subscriptions

Without organized records, you can't prove these expenses to the IRS, which means you can't claim them. A professional bookkeeper makes sure that every deductible expense is properly categorized and documented. If that's not the case for your business now, that's your sign to hire a skilled bookkeeper!

5. You don't know your company's finances

If your business makes money but finances feel unpredictable, it's likely a good time to hire a bookkeeper. When you can't forecast your cash flow and unexpected expenses blindside you, it's hard to plan for growth, prepare for slow periods, or make informed business decisions.

When you don't have a clear picture of your numbers, your business feels unstable because it actually IS unstable from a financial management perspective.

You might think you're having a great month only to discover major expenses you forgot about, or you might avoid necessary investments because you're unsure about your financial position. This uncertainty about your financial information is stressful, and it keeps you stuck at the same level of growth.

6. Tax season scares you

Tax preparation and quarterly payments shouldn't feel like terrifying guesswork, but when your financial records are disorganized, that's what they become. If you're spending weeks scrambling to gather documents and reconstruct transactions, it's a SURE sign that it's time to outsource bookkeeping tasks.

Good bookkeeping makes tax season routine.

With organized records, you know exactly what you owe, when payments are due, and what deductions you can claim. Your accountant can work efficiently, and you can focus on running your business!

7. You're making more money but not keeping it

Your sales are up, but you're not actually keeping the money and have no idea where it all goes? This disconnect between sales and profit is frustrating, and it's often the result of disorganized books.

When you don't have good expense management and tracking, money disappears into poorly categorized spending and unnoticed subscription services. You might be spending more on supplies than you realize or paying for services you don't use.

Professional bookkeeping shows you where your money goes so you can KEEP more of it.

Is It Worth to Hire a Bookkeeper?

YES! The cost of hiring a professional bookkeeper is almost always less than the cost of not having one.

When you calculate the time you spend on bookkeeping tasks, the deductions you miss, the stress during tax season, and the poor financial decisions you make without accurate data, professional bookkeeping pays for itself.

Our Full Tax + Bookkeeping Service at Desi Tax

At Desi Tax Service®, we help small business owners find clarity in tax season and start saving money you didn't know you had. 

With our Monthly Full Service Tax + Bookkeeping service, you get expert bookkeeping and proactive tax planning, so you have a clear picture of where your money is going!

Learn more about our services or get in touch!