Pay estimated taxes if you need to
If you have substantial income from a source other than a traditional job – whether it’s investment income, self-employment, or a side job where you’re treated as an independent contractor rather than an employee – then you might need to make quarterly estimated tax payments. Failing to have enough tax withheld can lead to penalties if you don’t, so take a look at Form 1099-ES and run the numbers to see whether you should be paying quarterly estimates and if so, how much will be enough to stop you from getting penalized.