Should you pay estimated taxes?

For today’s finance topic…..should you pay estimated taxes? As always, the answer is “it depends”. I will give you a few examples.

If you find yourself paying thousands of dollars each year in taxes and it’s just based upon a normal year (meaning no major events such as home sale/purchases, stock market wins/losses, etc) then yes, you would save yourself the pain of paying out a large amount each year. On the other side, if you find yourself getting a large return each year, maybe you should adjust your withholdings so you keep more of that money in your pocket during the year. If you seem to break even or close to it each year….don’t change a thing. That is the goal.

A good accountant or CPA can help you figure out your estimated taxes after a short conversation based on previous returns and events you expect in the upcoming year. I say a good accountant for a reason. In the past, I have both owned a lot and have received a few large returns. Though the big check feels nice…I’d rather keep that money throughout the year.

Now that the tax deadline has passed and you can already begin to pay estimated taxes, take a look at your situation now to make the 2026 tax season a little less painful and a little more easy to handle.