Financial Planning for Geeks

The Geek’s Guide to Tax Prep

- Taxes

Happy 2025! If you’re like me, the first thing you think about on January 1 is filing your tax return for the previous year.

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I count a dozen little tax deductions here.

OK, maybe that’s not the first thing I think about, but I really do start preparing for tax season in January. This is Financial Planning for Geeks, right? Even if you aren’t going to jump out of bed tomorrow to get this done, I have some tips to help you get ahead of tax season and make sure you’re up to date on any relevant changes.

First, let’s go through what you’ll need to prepare for tax season. Many of these documents will be available to you online, so if that’s an option through your employer, mortgage holder, investment institution, bank, or other organizations, you can start downloading last year’s documents right away.

1.        Last year’s tax return and other IRS-related documentation: If you’re preparing your return yourself, you’ll need some numbers from last year’s return, including Social Security numbers for you, your spouse, and your dependents, as relevant. If you paid estimated taxes along the way last year, you will want to have those amounts handy. And if you got any notices or correspondence from the IRS last year, they should be part of your prep file.

2.        Income documents: You will need W-2 forms from all of your employers, 1099 forms for freelance or other types of work, and records for any other income you earned from unemployment, gig work, rental properties, card games in Vegas, or other sources. Your employer is required to get you your W-2 by Jan. 31, so make sure to follow up if you don’t have it by then.

3.        Credit and deduction documents: First of all, do you itemize deductions? Most people don’t, because the standard deductions end up being greater than any deductions they could itemize. For most people, the largest itemized deductions are available for charitable contributions, mortgage interest, medical expenses, education and childcare expenses, and business-related costs. If it’s more advantageous for you to itemize deductions, you’ll need to pull together your receipts and documents to substantiate these expenses. You can stay up to date on the standard deduction amounts by checking the IRS website under “Credits & Deductions.”

4.        Investment documents: You will also need any 1099 forms you received from banks or investment companies for interest, dividends, and/or capital gains. You will also want to have your retirement account contribution amounts handy.

5.        Business-related documents: If you are self-employed or running a small business, you will also have income and deduction documentation for that side of the house. Make sure your deductions include home office expenses and mileage tracking, as relevant.

6.        Health insurance forms: If you got your health insurance via the Marketplace, you will need Form 1095-A to document that. For other types of health insurance coverage, you will need Form 1095-B or 1095-C.

7.        Accountant data sheet and/or other forms: If a tax professional does your taxes, they may need you to complete other documentation. For example, our accountant has an annual intake form, including a checklist so she knows if our situation has changed during the past year. We also sign off on the cost and terms of engagement before she starts.

Please note that you may not need to submit all of these documents to the IRS, but they do need to be part of your file. Most pros recommend you keep these tax records and returns for at least three years after you file or pay any tax that was due, whichever is longer.

There are also some things you can do to make this year even better from a tax perspective.

1.        Understand any IRS rule changes that might affect you: You can check the IRS website, and Newsweek summarized some key changes for 2025. If tax brackets or certain deductions or limits change, there may be something you can do right away to improve your situation. In fact, check all the relevant facts I’ve given you here, because tax law changes all the time and what I’ve said won’t stay current forever.

2.        Review this year’s return: Look for areas where you might have overpaid or missed deductions (if you itemize) so you can optimize your tax setup for this year. If you owed significant tax when you filed your return, start making estimated payments and/or change your tax withholding so you can avoid paying next time. If you got a significant amount of tax back, reconsider your interest-free loan to the government and change your withholding.

3.        Maximize contributions to your retirement accounts: This lowers your taxable income and makes your retirement that much more secure. The IRS increases contribution limits most years, so make sure you stay maximized. And if you’re 50 or older, make sure you take advantage of the catch-up contributions, which allow you to sock away even more money. The catch-up amounts go up most years, too.

4.        Direct (more) money to other Tax-Advantaged accounts: Consider contributing to a Health Savings Account (HSA) if it’s available to you. Unused contributions can roll over indefinitely, and contributions reduce your taxable income. A Flexible Spending Account (FSA) can also be beneficial by reducing your taxable income, but you can only roll over a portion of unused contributions until March 31 of the following year. And if you pay state income tax, you might also contribute to a 529 Plan for education savings. Some states will give you an income tax deduction or credit for your contributions.

5.        Pay estimated taxes if relevant: If you’re self-employed or earn a lot of gig income, you will want to work with a tax professional to make appropriate quarterly estimated tax payments. If you don’t, you might have to pay a penalty (and all those taxes) at the end of the year.

6.        Do some tax-loss harvesting: If you pay significant capital gains taxes on your investments, it might be worth offsetting your gains by selling some investments that returned a loss during the year. You can use capital losses to offset gains during the tax year when they occurred, and/or carry them forward to offset gains in future years. Capital losses can also offset up to $3,000 of your ordinary income every year.

7.        Create a system for tracking deductions: If you’re one of the few people who itemizes, it’s worth having a process for tracking deductions like charitable donations, medical expenses, home office costs, and state and local taxes. You might just throw the receipts in folders, you might put them into an Excel spreadsheet, you might use an app, but whatever you do, don’t wait until the end of the year to pull it all together. What a pain in the nether regions.

8.        Use IRS Online Tools: You can create an IRS online account to review documents from previous years, make payments, and stay informed about the status of your refund, among other things.

Fellow geeks, I wish you all the best as you prep your taxes, and I hope you’re able to use some of my tips to improve your situation next time. May your tax season be as smooth as your favorite code running with no bugs in sight!

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Penny Farthing

I, Penny Farthing (non-wizarding name Kerry Read ), actually have a day job in the world of finance. This blog came into being because of my deep and abiding love for geeks and Personal Finance.