How to Do Your 2023 Taxes Like a Pro

Table of Contents

1. How Taxes are Determined: The Basics
1. Standard vs. Itemized Deductions
2. Tax Deductions vs. Credits
3. “Above the Line” Deductions
2. How to Do Your Own Taxes
3. What is Tax Planning?
1. Here are a few things to think about while tax planning:
4. How To Organize Your Tax Documents
1. Here are some tax organization tips:
5. What is Tax Preparation?
6. How to Prepare Your Own Taxes
7. What Is The Best Way to File Your Taxes?
8. When Can You File Your Tax Return?
9. 2023 Tax Filing Deadline
10. When Can The Military File Taxes for 2023?
11. When to Expect Your 2023 Tax Refund
12. Taxes Never End

Whether you’re filing taxes for the first time or feel like you’re an expert in military tax filing, the end goals are the same. You want to save the most money on your taxes and (ideally) get the biggest tax refund possible for your situation.

That’s where I come in. I’m a Navy Veteran, Accredited Financial Counselor, and IRS Enrolled Agent with more than a decade of experience in tax planning and preparation. My goal is to help you file your own taxes like a pro.

A successful tax season ultimately comes down to what you do leading up to it.

In this guide, we’re going to discuss tax basics, tax planning, tax preparation and some of the most common questions I get about taxes, so that you can approach your next tax return with confidence.

How Taxes are Determined: The Basics

To understand how the government determines your taxes, let’s start with some basic concepts and then move on to some considerations for your particular tax situation.

First off, all income is taxable unless the IRS says it isn’t. If you have an income source, make sure you know if, how, and when the IRS taxes it.

How much money you make largely determines how much you’ll pay in taxes.

Tax brackets change each year, so keep up to date on the changes to know where you stand. If your income changes during the tax year, make sure you project what that income will be during that year and the ones that follow.

Here are a few more considerations that will determine your taxes.

Standard vs. Itemized Deductions

For most people, the standard deduction saves more money than itemizing.

Itemized deductions include things like mortgage interest, real estate taxes, and charitable contributions. (Though you can deduct some charitable contributions from your 2023 taxes and still take the standard deduction, thanks to the CARES Act).

You should only itemize deductions if they add up to more than the standard deduction.

• To be worth foregoing the standard deduction for tax year 2023, your itemized deductions need to add up to more than $13,850 for single taxpayers (or married filing separately).

• Itemized deductions for head-of-household filers need to equal more than the $20,800 standard deduction.

• If you’re married and filing jointly, your itemized deductions need to add up to more than the $27,700 standard deduction.

Tax Deductions vs. Credits

Credits reduce your tax liability dollar for dollar, while deductions reduce your taxable income. Tax credits go further than deductions most of the time because tax credits take a set dollar amount off what you owe to the government. (Think of a $100 tax credit like a coupon for $100 off your final purchase). Deductions, on the other hand, reduce your taxable income.

The IRS has a great primer on credits and deductions here.

“Above the Line” Deductions

“Above-the-line” deductions are not the same thing as itemized deductions.

Some examples include student loan interest, a traditional IRA deduction or moving expenses. You can subtract these expenses from your gross income to lower your Adjusted Gross Income (AGI).

The IRS limits deductions and credits by income, so the lower your AGI, the better your chance at qualifying for additional tax benefits.

You can find more “above the line” deductions on Schedule 1.

How to Do Your Own Taxes

Doing your own taxes like a pro takes time and reading, planning and preparation. Study up on parts of the tax law and IRS instructions that apply to your tax situation.

Start with Publication 17 and the Form 1040 Instructions. You don’t have to read every word, but pay attention to the sections that apply to you. Service members (and military spouses) should check out Publication 3 as well.

Two more excellent resources that the IRS provides are tax topics and the interactive tax assistant. If you pay state income tax, check out your state’s department of revenue for similar resources.

Once you feel like you know what you’re looking at, doing your taxes like a pro comes down to two things: tax planning and tax preparation.

What is Tax Planning?

In general, tax preparation without tax planning is bad tax preparation.

Tax planning isn’t just about taxes, but your whole financial situation.

You need to sit down and analyze your financial situation to ensure all your pieces work together to minimize your tax liability, save money and reduce tax impact on your finances.

For most of us, that means reducing our overall taxable income, managing tax withholding and taking advantage of available tax deductions and credits. For folks with more complicated tax returns, it might mean looking years ahead and determining whether or not to shift income from one year to another to minimize taxes.

Any time your income or family situation changes, you need to review the impact on your finances. You may need to adjust your withholding, change your investment strategy or begin to pay estimated taxes.

At a minimum, I recommend that you sit down and plan out your taxes once a year. If you do this in December you can cover two tax planning events:

1. First, you can do projections for the next year, set your tax withholding for the start of the year, and set your tax and financial goals.
2. Second, you can do a final check of your current year’s tax situation and look for any last-minute moves that may benefit you.

I recommend taking an additional look at your finances in late summer or early fall, to ensure you’re on track to receive a refund if you’re expecting one.

If your income varies significantly throughout the year you may want to project your tax return results and your tax liability more frequently to avoid surprises when you file your tax return. The more complicated your finances and tax situation, the further out you should plan.

Here are a few things to think about while tax planning:

• How much tax should you withhold from your pay?

Generally speaking, you don’t want a tax refund, outside of tax credits. You don’t want to owe taxes either.

In an ideal world, your tax withholding is just enough to cover your tax liability for the year. When you over-withhold taxes to get a bigger refund, you’re increasing your taxes’ impact on your finances throughout the year.

While you’re waiting to get your money back in a refund, you’re missing out on investment or debt payoff opportunities. Your dollars may also lose value due to inflation.

If you’re not comfortable with your projections, it may make sense to withhold a small “buffer” to avoid penalties for not withholding enough. If you don’t need it, you’ll receive it in a refund.

The IRS tax withholding estimator can help you calculate your withholding, and so can this 1040 Tax Calculator.

• How should you handle a bonus?

If you received a bonus that bumped you into a higher tax bracket, you have a couple of options.

If you received the bonus in a combat zone, your bonus is already tax-free. You can even invest it 100% tax-free in a Roth TSP, 401k or IRA. (you don’t have to pay taxes on combat pay before you deposit it, and you won’t owe taxes on Roth contributions when you withdraw them!)

If you weren’t in a combat zone but you don’t want your bonus to impact your taxes, you can invest some or all of it into a traditional pre-tax TSP, 401k or IRA.

(Or, if you’re ok with paying taxes on it now for the promise of tax-free growth, you can still invest it into a Roth).

• Has an income increase disqualified you from a tax credit you expected to receive?

Some tax credits have phase-out limits. These limits reduce the value of a tax credit as a taxpayer’s income goes up. If you’re in this situation, you should carefully weigh the value of the tax credit to determine if it’s worth it to move your money to qualify for it.

Let’s say, after deductions, a military couple expects their taxable income to exceed the phase-out limit for the American Opportunity Tax Credit (AOTC) by about $11,000. If they chose to put $11,000 of their income into a traditional (pre-tax) TSP account, they could lower their taxable income for the year and receive the tax credit.

The couple would need to weigh whether or not receiving a $2,500 tax credit now is worth deferring taxes on their TSP investment until retirement.

• Do you need to move money to avoid a tax penalty?

If you’re investing in a qualified retirement plan that has a contribution limit (like a 401k, 403b, TSP or IRA) and you accidentally over-contributed, you have until the tax filing deadline to fix it. But, it’s a good idea to fix it before the end of the calendar year to simplify your reporting and tax records.

Remove excess contributions from your retirement plan, along with any gains from the excess contribution (called Net Income Attributable or NIA). If you don’t remove your excess contributions, your penalty for over-contributing is 6% for each year the funds remain in your account.

• Are you planning to sell any of your investment assets?

If you have stock or cryptocurrency assets that you’d like to sell for gain, you can minimize taxes by selling them when you’re serving in a combat zone, because your tax-free combat pay lowers your taxable income.

Other events that lower your tax rate include permanent changes of station (PCS), periods of unemployment or separation from the military.

You can also time your offloading of bad investments to offset capital gains taxes in an act called tax-loss harvesting.

For example, if one stock lost you $1,000 and another made you $1,000, selling both at the same time results in a zero gain. Tax-loss harvesting can be a valuable strategy if you invest in a lot of individual stocks or cryptocurrencies.

You can also minimize taxes on your investments by holding onto an asset for at least a year to receive the lower, long-term gains tax rate.

How To Organize Your Tax Documents

Organizing your tax documents is another key component of tax planning.

If you are the one doing your taxes, you should organize your tax documents in a way that works for you. Again, the more complicated your tax situation, the earlier you should start this process.

You might need to organize tax documents on an ongoing basis.

Here are some tax organization tips:

• Keep both electronic and paper copies of tax documents and tax returns.

Keep at least seven years of tax documents and tax returns.(Personally, I prefer 10 years.)

• Create a document checklist.

Keep a checklist of documents you expect to receive during the tax year, plus a final tax preparation checklist to use when you file your taxes.

• File tax documents or supporting documents as they come in.

Start the year off in January with folders for the new tax year – both electronic and physical.

• When in doubt about a document, keep it.

If you aren’t sure if something can help you on your tax return – whether or not it is a tax document – keep it. This point is also important for documents that could help you on your tax return, but typically don’t.

For example, many people stopped itemizing in tax year 2018 because it was not helpful. However, tax laws change and sometimes change retroactively. If you retained documents to support itemization for the years you didn’t itemize, (like property tax statements and mortgage interest) you may benefit later if the law or your tax situation changes.

• Organize your documents in a way that makes sense for data entry.

Often, married couples will provide me with tax documents separated by spouse, even though they intend to file jointly. Software isn’t typically organized that way.

Group documents like W-2s together and separate income from expenses. If you’re self-employed or own your own business, keep all related income, expenses, and other items separate from the rest of the tax documents.

I like to separate items supporting specific deductions and those supporting specific credits, although it can also be good to keep all items related to a child together.

• Keep all IRS (or state and local tax authority) correspondence.

In January 2023, most taxpayers will receive one or two letters from the IRS.

If you received a third stimulus or economic impact payment in 2023 you will receive IRS Letter 6475 detailing how much you received. If you received Advance Child Tax Credit payments you will receive letter 6149 providing the total amount of your payments. You’ll need to enter both of these letters into your 2023 tax return.

What is Tax Preparation?

Tax preparation is the process of filling out your tax forms and filing them. The United States has a pay-as-you-go system for personal income taxes. This means you must pay your income taxes throughout the year.

Most taxpayers do this by withholding taxes from their salaries or retirement income. Some taxpayers pay estimated taxes every quarter for income that doesn’t have withholding as an option.

During tax preparation, you are essentially making sure that you paid the correct amount of taxes for your individual tax situation. If you paid too much during the year or if you are eligible for some assistance through refundable credits then you may get a refund. If you didn’t pay enough you will owe money when you file your tax return.

If you owe “too much” you may have to pay a penalty for “underpayment of estimated tax.” Most taxpayers avoid this penalty if they owe less than $1,000 in tax or paid withholding and estimated tax of at least 90% of the current year’s tax or 100% of the tax shown on the return for the prior year, whichever is smaller.

How to Prepare Your Own Taxes

By now, you’ve already engaged in some tax planning. You’ve made a note of any changes to your tax situation that might impact your tax return and you know how to address them (or maybe you already have!)

Here’s how to start preparing your taxes.

1. First, see if anything has changed with the tax code.

You can subscribe to the IRS newsletter to hear about tax changes as they come out. You can also check IRS publications and instructions, which will summarize any recent changes. Don’t forget to keep up to date on any state income taxes that apply to your tax situation.

2. Gather your documents.

Verify on your document checklist (see “How to Organize Your Taxes” above) that you have everything. Make sure you keep your previous year’s tax return handy for reference.

3. Start working in your tax software.

If you used it the previous year, some information will carry over. Verify that information remains accurate. The IRS will send all correspondence to the address you use when filing your tax return.

4. Re-read questions to make sure you understand them.

Make sure you understand what your tax software is asking you before you enter information to answer the question. Often, tax software will have tips or help tools that you can reference if you’re not sure.

If you still have questions, consult IRS publications and instructions. The 1040 instructions, publication 17, and publication 3 (for service members and military families) are always helpful.

If after some research you are still uncertain about a question or result, seek outside professional assistance.

Military OneSource offers free tax consultations. Most tax software companies offer some tax consulting at a low price. Even tax professionals consult each other sometimes – don’t feel weird about asking for help.

5. Keep track of which documents you’ve used.

If you have more than a few tax documents, mark them off as you enter the data from them. I simply put a checkmark on each paper copy I’ve used. I move electronic copies into a “completed” folder.

6. Pay attention to software tips, questions and warnings.

Most tax software checks for general errors and provides suggestions and cautions. Review these to ensure that you don’t need to take any further actions. These suggestions and comments can save you money and keep you out of tax trouble.

But, keep in mind that software providers don’t always cover user mistakes. Double-check any data entries and review your data totals (such as summaries for multiple W-2s) to make sure they make sense.

7. Save your progress and step away from your computer.

Come back to review your return with fresh eyes after a day or so. Re-read everything before filing. Accuracy is important because once you file your return electronically, the IRS will not accept another tax return electronically with the same social security numbers.

Do what I call the “idiot” checks. Is there something obviously missing or “off?” I like looking at all the lines on the actual tax forms during this step.

Does the child tax credit total match up to the amount expected for the number of children? Are you expecting the saver’s credit but don’t see it? Is your reported interest supposed to be $20 but you entered $200?

8. Confirm acceptance.

After you file your tax return make sure the IRS and your state accept it. You may get the confirmation within minutes, hours or even days (particularly with state tax returns). Usually, your state won’t accept your electronic return until the IRS does.

What Is The Best Way to File Your Taxes?

When choosing a method to file your taxes, look for the least expensive option that reliably suits your needs.

• With that in mind, consider free options first.
  • For service members and military families, Military OneSource provides free tax filing software. The site also has tax consultants available to help you if you get stuck.
  • If the tax software at Military OneSource doesn’t meet your needs, then IRS Free File may work for you. IRS Free File partners provide free filing services for taxpayers with income below $72,000. If your income is above $72,000 the IRS will provide free fillable forms you can file electronically. However, these forms will only perform the most basic calculations. It doesn’t provide software that can check your returns for errors.
  • Voluntary Income Tax Assistance (VITA) sites – located at or near military bases – provide free in-person tax preparation help. Some VITA sites limit service member eligibility by income, pay grade and complexity of your tax returns.

• If you go shopping for tax software make sure you compare your options. 
  • Price: First, compare prices for the software version that best meets your needs. More complicated tax returns may need an advanced or deluxe software package. If you pay state taxes, check to see whether the price for your package includes a state tax return, and whether adding additional states requires additional payment.
  • Guarantees: Take a look at what guarantees the software offers at no additional cost. Factor in any extra guarantees you’d be willing to purchase for an additional fee.
  • Support: Does the software offer tax consultations or help finishing your return? Does it feature a helpline or virtual chat option to get expert help when you need it? If so, when are they available and how fast do they respond?
  • Ease of use: How easy is it to use? Can you upload, scan or take pictures of tax documents to automatically transfer information to your tax software?

If you find taxes confusing or if you prefer to spend your time and effort on other things, consider hiring a tax professional. Ask friends or colleagues in similar tax situations for a referral. Someone who has just one W-2 for their tax return may have a great tax pro, but if you own a rental house, you might be better off asking for a referral from another landlord.

Check out the IRS tax professional directory to see a list of options near you.

When Can You File Your Tax Return?

The IRS typically doesn’t accept electronically filed returns until late January.

If you’re planning to file for the Earned Income Tax Credit or the Additional Child Tax Credit, the IRS doesn’t begin processing those until after Feb. 15.

Taxpayers with these two credits are lucrative targets for tax identity thieves. To mitigate this, the IRS spends extra time comparing your W-2 and 1099 tax documents with your tax return. But, no system is perfect. If your tax return gets rejected because an identity thief already filed under your social security number, file your return by mail, along with a tax identity theft affidavit (Form 14039).

Whether you’re using one of the tax credits or not, you don’t have to wait until Jan. 31 (or Feb. 15 for EITC and ACTC) to file your taxes if you have all the tax documents you need.

Many tax software companies will permit you to prepare and submit a tax return before the IRS begins accepting them. Your software will hold the tax return until the IRS is ready for it.

The IRS might process your return early if it uses it to test its system before the official acceptance date. But, be wary of any companies or tax advisors promising early processing. No one can guarantee that.

2023 Tax Filing Deadline

For 2023, the individual tax return filing deadline is April 15.

If you can’t file by this deadline, make sure you fall under a tax return extension.

You can read about tax return extensions here.

Most tax return extensions extend the time to file, but not the time to pay. This is true of the most common extension request on IRS Form 4868, the Automatic Extension of Time to File.

This is a six-month extension. You should file Form 4868 if you don’t have all of your tax documents and information gathered or you aren’t able to finish the return on time for some reason.

You should not file an extension just because you owe taxes or just to delay paying taxes. If you owe taxes, interest and penalties for failing to pay taxes begin adding up the day after the filing deadline.

If your tax return is ready to file, you should file it even if you owe money that you cannot pay.

The penalty for failing to pay taxes you owe is only .5% per month. Failing to file your tax return or a Form 4868 by the filing deadline incurs a larger tax penalty – up to 5% of the owed amount each month.

Setting up a tax payment plan is easy and can be done online.

If you are getting a refund and you file your tax return late or not at all, then you will not pay a penalty for failure to file or failure to pay because the IRS assesses the penalty based on what you owe to the U.S. Treasury.

In nearly all cases, you will not receive a refund at all if you wait longer than three years to file a tax return.

When Can The Military File Taxes for 2023?

Sometimes military members experience circumstances that keep them from filing during the normal tax season.

I have seen service members file two or three years of tax returns at once because it wasn’t convenient for them to file earlier.

Again, if you do this for federal tax returns that you’re receiving a refund for, you won’t be penalized. But make sure you’re right about that. If you delay filing past the filing deadline and you owe money you’ll be subject to interest and penalties.

Service members who will be deployed or unavailable during tax season may want to grant their spouse or another trusted family member Power of Attorney (POA) to complete their tax return when they won’t be available to do so. You can do this through your legal office, or use IRS Form 2848.

Military members stationed overseas or in combat zones are eligible for certain tax extensions. Some of these extensions require requests, but some do not. You can read more about extensions here.

Read about other situations in which a service member’s spouse may sign a tax return without a POA in IRS publication 3, the Armed Forces Tax Guide.

When to Expect Your 2023 Tax Refund

Most taxpayers get federal tax refunds. Right now, the IRS expects to deposit most refunds within 21 days of accepting an electronic return. If you opt to receive a check instead of direct deposit, it can take up to four weeks.

But, these timeframes are not guaranteed. If the numbers you enter into your tax return for the third stimulus payment or the advance child tax payments do not match IRS records, your tax refund may be delayed while the IRS adjusts the amount.

Your adjusted refund could be smaller or larger depending on the mismatch. If the IRS adjusts your refund, it will send you a letter telling you why and what you can do if you disagree with their decision.

Normal reasons for tax refund delays include:

• Selection for a random identification confirmation

• Failure to provide some required information for the tax return (I’ve seen this most often for individuals who received subsidized healthcare insurance under the American Care Act, but didn’t include Form 1095A information in their tax return).

• Incorrect direct deposit information.

Additionally, filing a paper tax return or an amended tax return may cause significant delays. The IRS encourages taxpayers to file returns electronically when possible.

You can check on the status of your tax refund using the IRS “Where’s my refund?” tool or using the IRS2Go app. Some tax software programs offer refund updates too, but if the IRS doesn’t have an update, won’t have one either.

It can take a day or two for an electronic return to show up on the “Where’s my refund?” tool. Updates on paper returns may take a couple of weeks or more to show up.

Taxes Never End

Tax season doesn’t truly end when you receive your tax refund (or pay taxes, if you owe them). Tax preparation and planning is an ongoing process. The better you keep up with it throughout the year, the easier it will be to file (and avoid surprises when you file!)

One of the tools the IRS has to help you with this process is your online tax account. If you don’t have one yet, set it up. This will make it easier for you when you need to figure out what is going on, make payments, or consult your tax records.

After reading all of this you may be thinking, “I’d rather just answer the questions in the software instead of doing all that work”. For many taxpayers, that is just fine. But, if you want optimal results – particularly if you have a complicated tax situation – then it is better to do taxes like a pro.

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