What You Can DIY in Your Bookkeeping vs. What You Will Regret

You started your business to build something great, not to become a part-time accountant. And yet, the further your business grows, the more time you may find yourself spending in your bookkeeping software instead of serving customers or building your team.

At first, handling the books yourself can feel like a smart move. You’re saving money, staying hands-on, and keeping close to your numbers. But as the business grows, so does the complexity. What once felt simple can quickly turn into a source of stress—missed payments, compliance problems, tax headaches, and financial blind spots. That’s the trap too many business owners fall into.

Bookkeeping shouldn’t become a second job. Below, we’ll walk you through which tasks you can handle confidently on your own and which ones you’ll likely regret trying to do yourself.

What You Can Do Yourself (With the Right Tools)

Some parts of bookkeeping are simple enough to handle yourself, especially with the right tools and habits in place. Think of these tasks like brushing your teeth: not glamorous, but they keep things from getting messy.

Entering Sales and Expenses

If you use QuickBooks Online, Xero, or another cloud-based platform, entering income and expenses can become a helpful routine. Most business owners already know when money comes in and goes out, so it makes sense to track it in real time. These systems can sync with your bank account and automate some of the work.

Writing Checks and Paying Vendors

It’s completely reasonable to pay bills and cut checks yourself, especially if you’re using your bookkeeping software to record each transaction. Staying on top of vendor payments helps you avoid late fees and build trust with suppliers.

Creating and Sending Invoices

You know your customers better than anyone. With invoicing tools built into most accounting software, you can create branded invoices, send them directly, and track payments. Many platforms also allow you to schedule payment reminders, which helps with cash flow.

Reconciling Bank Transactions (with Caution)

Modern software can pull in bank transactions automatically. You can then match what shows up in your account with what’s recorded in your books. This step is essential to catching errors, duplicate entries, or missing payments. But keep in mind, even a synced bank feed still needs to be reviewed carefully—this is one of the most common places where small mistakes grow into big problems.

Tracking Mileage and Receipts

Apps like QuickBooks’ mobile tools or Expensify make it easy to snap photos of receipts and track mileage. These records are helpful at income tax time and protect you if your return ever gets reviewed. This is one of the lowest-risk, highest-reward areas where DIY works well.

What You’ll Eventually Regret Doing Yourself

As your business grows, financial tasks get more technical and time-sensitive. What starts as a quick fix, like handling payroll in a spreadsheet or filing your own sales tax, can quietly turn into a bigger issue. Mistakes in these areas often lead to penalties, missed deadlines, or costly rework.

These tasks may seem manageable at first, but complexity builds fast. More employees, more transactions, or new tax rules can turn a simple process into a serious risk. These are the areas where doing it yourself can ultimately prove more costly.

Sales Tax Tracking and Filing

Sales tax is one of the trickiest areas to manage on your own. The rules vary by state, city, and even by what you sell. You may owe sales tax on products, services bundled with products, or even delivery charges. Missing just one deadline or filing incorrectly can result in steep penalties, and most states are not flexible about waiving them.

Payroll and Payroll Tax Compliance

There’s more to paying employees than cutting checks. You’re responsible for calculating the right tax withholdings, submitting regular payroll tax deposits, and filing quarterly and annual forms with both federal and state agencies. These filings are time-sensitive and must be accurate. Errors here can trigger audits, fines, and even a freeze on your ability to hire or pay workers.

Year-End Income Tax Prep and 1099s

Every year, business owners scramble to get ready to file their tax returns. But if your books weren’t kept accurately during the year, your accountant will likely need to do extra work or send it back to you to clean up. If you issue 1099s to vendors or pay contractors, you also need to track those payments throughout the year and file the correct forms. Missing even one form or sending it late can result in penalties.

Catch-Up or ‘Backwork’ Clean-up

Letting things slide for even a few months can create a major backlog. Most business owners don’t have time to sort through months of receipts or transactions and end up rushing to catch up. That tends to create errors, duplicated entries, or missed items—and even more cleanup later.

Misclassifying Transactions

This is one of the most common DIY errors. It’s easy to place a loan payment under “expenses” or mislabel an equipment purchase as a regular vendor payment. These errors throw off your reports and make it hard to understand what’s really happening in your business. They can also increase your income taxes if not caught and corrected before filing.

When DIY Turns Into SOS

Most business owners don’t realize they’re in trouble until something goes wrong. You might think everything looks fine until your balance sheet doesn’t match your bank account, or you discover a major error right before filing your return.

It’s like building furniture without reading the instructions. It seems simple enough, but by the time you realize something important is missing, the whole structure is at risk.

Here are some common signs that it’s time to get professional help:

• You receive tax notices or penalty letters from the IRS or your state
• Your bookkeeping falls behind more than a month
• You’re unsure how much money you’re actually making
• You had a large tax bill that surprised you
• You feel anxious every time you open your accounting software

These are all indicators that your business has outgrown DIY bookkeeping. If you keep pushing forward without the right support, the stress builds, the mistakes multiply, and eventually the cost of fixing it far outweighs the cost of doing it right the first time.

What’s the Real Cost of DIY Gone Wrong?

Trying to do everything yourself may feel like a way to save money, but it often leads to higher costs in the long run—both financially and emotionally.

When DIY bookkeeping goes wrong, it usually means:

• Missed deductions and higher income taxes
• Rework to fix incorrect reports
• Penalties for missed deadlines or incorrect filings
• Delays in payroll or vendor payments
• Loss of visibility into your business’s performance

Time is your most valuable resource as a business owner. If you’re spending hours each week sorting transactions or responding to notices, that’s time you could spend serving customers, improving operations, or planning for growth.

The Smart Approach to Bookkeeping

Running a small business comes with enough challenges. Bookkeeping doesn’t have to be one of them.

You don’t need to hand off everything. Many business owners still handle parts of their books, like invoicing or reviewing reports, but when it comes to payroll, compliance filings, and getting ready for income tax time, the risk of doing it alone is too high. That’s where a reliable accounting service provider makes all the difference.

At TMA Accounting, we help small business owners stay involved without being overwhelmed. We simplify your systems, help you stay on top of deadlines, and clean up any past bookkeeping messes without judgment. We start by understanding what you’re doing now, identifying the weak spots, and creating a better plan—one that supports your business instead of distracting from it.

If you’ve been trying to do it all yourself and it’s starting to feel like too much, now is the time to take the smarter route. Don’t wait until something breaks. Let TMA Accounting help you avoid regret, clear up the confusion, and focus on what matters most: running your business with clarity and confidence.

Book a free call today and find out how we can help.