Filing Your Taxes in 2025
Uncle Sam Season is here and with it comes the emotional rollercoaster—realizing it's tax season, fearing how much you might owe, and then procrastinating like a champ.
But listen, taxes aren't going anywhere.
So instead of spiraling, let's break it down into a simple, doable timeline that'll save your sanity (and maybe some cash too):
Like a monthly money date, set a non-negotiable tax filing date. I’m picking this Friday—last day of the month, work is done, wine is poured, and I’m getting my sh*t together.
Whether you’re DIY-ing or using a CPA, you need your paperwork. That means W-2s, 1099s, interest/dividends income, and any benefits like Social Security or unemployment.
Create a "Taxes 2024" folder on your desktop to keep it all in one place.
Do not walk away from your tax date without a submission deadline. Maybe you finish in one sitting, maybe you book another session in two weeks—but DON’T be that person panicking on April 14th at 11:59 PM.
Don't pay to file your taxes…I REPEAT… DO NOT PAY TO FILE YOUR TAXES! (Unless you're using a CPA or have a super complicated situation.) If your taxes are straightforward, here are great free options:
Cash App TaxesIRS Free File (if you make less than $84K/year)
Ok…Why does this all matter?
Because time is money. The sooner you file, the sooner you:
- Get that juicy refund and put it to work
- Or, if you owe, actually have time to plan a payment strategy
TL;DR: Tax season does NOT start on April 15th. It starts NOW.
Need help deciding if you should file on your own or get help? Take my free tax quiz to help figure it out.