Thinking About Filing Your Own Taxes? Ask These 3 Questions First

Nov 25, 2023 By Susan Kelly

As tax season approaches, the choice between filing your taxes or seeking professional assistance looms large. While opting for DIY tax filing can lead to savings on preparation fees, it's a decision that demands careful consideration. To empower you in making an informed choice, we've outlined three pivotal questions to ponder before venturing into solo tax filing.

These questions will help determine whether your financial situation aligns with the DIY approach or if it's wiser to enlist professional help. Remember, your tax return is not just about filing but ensuring accuracy and efficiency, and making the right decision now can save you valuable time and money down the road.

Question 1: Do You Have a Simple Tax Situation?

The first question to consider is the complexity of your tax situation. Not all tax returns are created equal. Some are straightforward, while others resemble a tangled web of deductions, credits, and income sources. If your tax situation is relatively simple, filing your taxes might be a breeze. But how do you know if your taxes are on the simpler side?

Here are some characteristics of a simple tax situation:

Standard Deduction: You plan to take the standard deduction instead of itemizing deductions. For many individuals, especially those without significant mortgage interest, medical expenses, or charitable contributions, the standard deduction is the way to go.

Few Income Sources: Your income primarily comes from a single job or a few predictable sources, such as interest, dividends, or retirement distributions. Multiple streams of income can make things more complex.

No Major Life Changes: You haven't experienced any significant life events during the tax year, such as getting married, having a child, buying a house, or starting a business. These events often introduce tax complexities.

No Self-Employment: You're not self-employed or a business owner. Self-employment income often involves additional tax considerations like estimated tax payments.

If your tax situation aligns with these characteristics, it's more likely that you can successfully file your taxes. Tax software programs and online services make it easier than ever to navigate simple tax returns, guiding you through the process step by step.

However, if your situation is more complicated, with multiple income sources, deductions, and life changes, you may benefit from professional tax help. Tax professionals are well-versed in handling intricate tax scenarios and can maximize your deductions and credits while ensuring compliance with tax laws.

Question 2: Are You Comfortable with Tax Regulations and Software?

Even if your tax situation appears straightforward, you still need to ask yourself if you're comfortable with tax regulations and the software required to file your taxes. Tax laws can be complex, and they change regularly. If you're not up to date with the latest tax rules, you might overlook deductions and credits that could save you money.

Furthermore, using tax preparation software or online platforms requires a certain level of tech-savvy. These tools are designed to simplify the process, but you'll need to input your financial information accurately. A simple typo or misunderstanding of how to use the software could lead to errors on your tax return.

Here are some tips to consider:

Education: Take some time to educate yourself about the tax regulations that apply to your situation. The IRS website is a valuable resource, and you can find information specific to your circumstances.

Choose the Right Software: There are various tax preparation software options available, ranging from basic to advanced. Select one that aligns with your comfort level and provides adequate guidance.

Double-Check Your Work: Even if you use tax software, review your return carefully before submitting it. Check for accuracy and make sure all your information is complete.

Consider Support: Many tax software packages offer customer support in case you run into difficulties. Don't hesitate to reach out if you have questions or encounter problems.

If you're not confident in your ability to handle the technical aspects of tax preparation, it might be best to hire a tax professional. They have the knowledge and expertise to navigate the complexities of tax laws, ensuring your return is accurate and optimized.

Question 3: Do You Have the Time and Patience?

Completing your tax returns can be quite a lengthy process, especially when dealing with a more intricate tax situation. It's not something you can rush through on your lunch break. You need to set aside sufficient time to gather your financial documents, input your information accurately, and review your return carefully.

Consider these time-related factors:

Gathering Documents: You'll need to collect various financial documents, such as W-2s, 1099s, and receipts for deductions. This can take time, especially if you're disorganized.

Data Entry: Inputting your financial information into tax software or forms can be time-intensive. Any mistakes can lead to delays and potential errors.

Research: If you encounter unfamiliar tax situations or have questions about deductions and credits, you'll need to invest time in researching and understanding the relevant tax rules.

Review and Submission: Even after completing your return, it's essential to review it carefully before submission. Skipping this crucial step can result in expensive errors.

Patience is another critical factor. Filling out tax forms and dealing with financial data can be tedious. If you become frustrated or overwhelmed easily, it may be wise to delegate the task to a tax professional who can handle the details for you.


Filing your taxes can save money, but it's not for everyone. Ask three key questions: 1) Is your tax situation simple? 2) Do you understand tax rules and software? 3) Do you have time and patience? If you answered "yes," go ahead. If not, consider a tax pro. Accurate filing matters. Choose wisely and save time and money.

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