Tax Day is kinda the pits. All those acronyms and forms can be genuinely confusing and, at least in my imagination, the IRS is populated exclusively by unsmiling men who resemble Tommy Lee Jones' character in Men in Black. At Girlboss, we firmly believe that financial knowledge should not require a law degree, and taxes are no exception.
But here is the thing: tax season does not have to be terrible. Depending on your situation, it can mean reclaiming some of the money you shelled out during the year. And it is worth remembering that while taxes can feel like punishment, they fund things like education, roads, and infrastructure that make daily life work. Worth it, even when it hurts.
In order to make the weeks leading up to April 15 as stress-free as possible, we asked some finance experts for insider insight on how to stay organized and maximize your potential to get money back.
Get Sorted
Around the beginning of the year, the forms documenting how and where you worked should start rolling in. If you were a full-time employee, you will receive a W-2 that documents your wages earned as well as taxes withheld throughout the year. If you were a contractor or freelancer, you should receive a 1099 for any job where you earned $600 or more.
Toneisha Friday, founder and executive director of financial literacy platform Coin Financial, notes that even if you do not receive a 1099, you are still required to report any and all income you received. "Do your best to guesstimate," she says.
You may also receive forms for student loan payments, bank interest, retirement account contributions, mortgages, health insurance, and charitable donations. Friday suggests collecting all your documents in a single folder before you start so nothing gets overlooked. Simple advice, genuinely game-changing in practice.
Figure Out How You Are Going to File
Tax preparation services like H&R Block and TurboTax have made it increasingly simple to file your taxes online, but before you open your wallet, personal finance expert and author of the bestselling book Get a Financial Life, Beth Kobliner, points out that you might be able to file for free.
"If your adjusted gross income was $89,000 or less in 2025, you can file your federal taxes for free," she says. "And if you're getting a refund this year, that basically means you're getting paid to do taxes." Head to irs.gov/freefile for a list of free filing options. The $89,000 threshold marks one of the largest annual increases in the program's history, so more people qualify than ever before.
IRS Free File 2026 (for 2025 taxes)
- AGI limit to qualify: $89,000
- Tax Day deadline: April 15, 2026
- Where to find free options: irs.gov/freefile
Should your situation seem more complicated than the free filing services can handle, Kobliner says consider hiring an accountant, especially if you are a freelancer.
"Remember, time is money. The time you spend poring through your 1099s, W-2s, and receipts could end up costing you more than two hours with a CPA would." — Beth Kobliner
If you are freelancing or managing variable income alongside a full-time role, the tax picture gets more complex fast. This guide to going freelance covers some of the financial planning considerations worth thinking through before tax season hits.
Know Which Deductions Could Save You Money
Whether you enlist the help of a professional or file yourself, Friday suggests taking advantage of the Retirement Savings Contributions Credit, also known as the Saver's Credit.
"The longer you wait to start saving for retirement, the less time compound interest will have to work on your behalf," she explains. "So to encourage people to stash away money in a retirement account, the IRS offers this tax credit." The credit is worth 10, 20, or 50 percent of your retirement contributions, depending on your adjusted gross income.
Saver's Credit 2026 (for 2025 contributions)
- Max contribution counted: $2,000 per person / $4,000 married
- Maximum credit: $1,000 per person / $2,000 married
- Income limit (single): $40,250
- Income limit (married filing jointly): $80,500
- Income limit (head of household): $60,375
Heads up for 2027: The Saver's Credit ends after tax year 2026. Starting in 2027, it will be replaced by the Saver's Match, a new federal matching contribution program. If you are eligible for the Saver's Credit this year, claiming it in 2026 is your last chance before the rules change.
Friday also notes that if you are a freelancer or have a side hustle, you can write off certain business expenses. "If you purchased equipment or office supplies, these costs can be deducted on your tax return. Doing so reduces your taxable income, meaning you would owe less to the government."
If you are building toward that goal, our guide to 401(k)s and Roth IRAs covers how the retirement savings piece fits into the broader picture. And if you are also carrying debt, this story of paying off $102K in debt has useful insight on managing multiple financial priorities at once.
Be Honest With the IRS,They Are More Flexible Than You Think
While you definitely do not want to blow off your taxes or get into murky territory with the IRS, if you end up owing additional taxes or fall a little behind schedule, they can actually be quite reasonable.
"The IRS doesn't mind if you need more time or you don't have the funds to pay the entire tax bill right now," Friday says, "but you must take the proper steps to alert them." For those who cannot pay in one go, payment plans are available and are generally accompanied by manageable interest rates. Those rates are determined on an individual basis with an IRS representative, so it is in your best interest to be as forthcoming as possible.
"It's just like any one of your relationships," says Friday. "Communication is key!"
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