Today is Tax Day in the U.S. – the day we’re supposed to file our taxes for the previous year. It’s also the day we should pay any remaining taxes of the prior year and any first-quarter estimated taxes for the upcoming year. Yeah, I know, major eye roll. I don’t know a single person who actually enjoys paying taxes, but alas, here we are. And for many, that’s because they’re either hoping for a major windfall of cash in the form of a tax refund or just hoping not to owe a whole bunch of money to Uncle Sam.
But either way, taxes usually start to move to the forefront of everyone’s mind around this time of year. As a former accountant, I always feel the need to remind folks to keep their tax stuff organized! Nothing costs you more time and money than being disorganized when it comes to taxes. Seriously, it doesn’t matter if you’re filing personal or business taxes—we’ve got to be organized.
I have a blog post and YouTube video that go more into depth on the very simple ways that I keep our tax stuff organized all year long, which you can check out here. But for this post, I’m just going to hit some high notes with basic tax planning for the year that will ensure you’re prepared come tax time next year.
- Review Your Deductions: Make sure you’re taking advantage of all available deductions, such as retirement contributions, charitable donations, or business expenses. I use a spreadsheet, as I show on YouTube, to track all of this. You can see the spreadsheet I use here.
- Tax-Advantaged Accounts: Contribute to IRAs, HSAs, or 401(k)s to lower your taxable income for the year while saving for the future.
- Plan for Changes in Income: If you expect a significant change in income (like a raise or bonus), consider adjusting your withholding or estimated payments.
- Adjust your Withholding: if you keep owing or receiving a significant amount of money every year, review your withholdings and adjust them. No, you don’t want a huge tax refund every year – that’s your money that you’re allowing the government to use all year long, interest-free. That’s money you could add back to your paycheck. Consider changing your tax withholding if you owe a lot of money every year. You can use the calculator found on the IRS website to determine what your withholding on your W-4 should be.
- Consult a Professional: A tax advisor can help you navigate complex tax laws and ensure you’re optimizing your tax strategy.
- Estimated Tax Payments: Speaking of estimated payments – if you own a business or your CPA tells you to pay quarterly estimated taxes, do it. Set a reminder in your digital calendar to pay the amount your CPA determines every quarter. No, it’s not fun paying estimated taxes, but it will help keep you from owing a considerable sum of money come tax time every year.
Now, let’s get into some more details about organizing your tax stuff so you aren’t scrambling around waiting until the last minute to get your taxes done.
1. Create a Central “Tax Zone”
Designate one folder—physical or digital—that becomes the home for all things tax-related. Every W-2, 1099, donation receipt, or deductible expense report goes here as soon as you receive it.
What to use:
A labeled file folder or accordion file (one per year)
A digital folder on Google Drive, Dropbox, or your hard drive
A cloud-based organizer app like Evernote or Notion
If you watched the YouTube video mentioned earlier, you know that we use both a physical file folder and a Google Drive folder. I highly recommend having both a physical place to put stuff and a digital one. This ensures you have a place to store all of your tax documents, and you won’t accidentally misplace them.
2. Know What to Keep
Here’s a cheat sheet of standard tax documents to gather:
Income: W-2s, 1099s, freelance/client income records, interest/dividend statements
Expenses/Deductions: Charitable donation receipts, medical bills, student loan interest, mortgage interest, childcare costs
Investments: Capital gains/loss reports, crypto transactions, retirement contributions
Other: Last year’s tax return, IRS correspondence, business expense reports (if self-employed)
Bonus tip: If you’re unsure about a document, keep it—you can always discard it later. “When in doubt, keep it”.
3. Sort by Category
Within your tax folder, break things down by type:
Income
Deductions
Receipts
Statements
Past Returns
You can use labeled subfolders (or color-coded envelopes if you’re old-school) to make this super visual and easy to browse. I have a spreadsheet we’ve used for years that helps me keep up with the different numbers. You can see that spreadsheet here. I just .pdf the sheets, then attached them to the supporting documents, and submitted them with our tax info to our CPA every year. Keeps us super organized!
4. Go Digital (If You Can)
Scanning receipts and saving PDFs of your statements is a game-changer. Not only does it reduce clutter, but it also makes things searchable. Tools like:
CamScanner, Genius Scan (for phone scanning)
Google Drive, Dropbox, or Evernote (for storage)
Adobe Acrobat (for editing/filling PDFs)
Just make sure you back everything up in more than one place.
5. Track As You Go (Next Year Will Thank You)
Use a simple spreadsheet or budgeting app to log deductible expenses throughout the year. If you’re self-employed or a freelancer, this step is especially helpful. Bonus points if you label expenses by month and category—it’ll make tax prep a breeze.
6. Set a Yearly Reminder
Once your return is filed, move everything into an “Archived Taxes [Year]” folder, and set a calendar reminder for next year to start fresh. Organizing doesn’t have to be perfect—just consistent.
Getting your tax documents organized is one of those “set it and forget it” habits that pays off every single year. Whether you DIY your taxes or hand them off to a pro, having everything in one place makes the whole process smoother.
No more shoeboxes. No more last-minute scrambles. Just peace of mind—and maybe a faster refund.
Getting a handle on the tax stuff now can make things much smoother come tax time. And by staying organized all year long, you can make sure that next year’s tax season is even smoother!
OTHER POSTS YOU MAY ENJOY
Leave a Reply