In a recent interview with Lil Yachty, Lil Baby shared a hard-earned lesson from his eight-year career—learning to pay his taxes quarterly. Like many entrepreneurs, he figured it out through trial and error, but now he stays ahead of it. His experience is a perfect example of why understanding tax obligations is crucial for anyone earning income outside of a traditional paycheck.

Why Quarterly Taxes Matter

Let’s be real—taxes aren’t exactly the most exciting topic, but if you’re self-employed, freelancing, or running your own business, this is something you need to know. The IRS expects you to pay taxes throughout the year, not just during tax season. That’s where quarterly estimated tax payments come in.

Instead of waiting until April and getting hit with one massive tax bill, you’re supposed to make estimated payments every few months. This helps you avoid penalties and keeps you from scrambling when tax season rolls around.

When Are Quarterly Taxes Due?

The IRS splits the year into four payment periods:

• April 15 (for income earned January–March)
• June 15 (for income earned April–May)
• September 15 (for income earned June–August)
• January 15 (for income earned September–December)

Miss a deadline? You could owe penalties and interest, which have recently increased to as high as 8%. Letting tax payments slide can quickly become an expensive mistake.

How Do You Pay?

You can make your payments online through the IRS Direct Pay system, EFTPS, or even by mailing a check. Some states also require estimated tax payments, so be sure to check your local rules.

Don’t Want to Pay Quarterly? Do This Instead.

If you’re not ready to start making payments, at least set aside 22-30% of your income every quarter. That way, when tax season rolls around, you’re not caught off guard. Overpay? You might get a refund. Underpay? Expect penalties.

Learning the Hard Way vs. Learning the Smart Way

Lil Baby’s approach to taxes now looks very different from when he started. His story is a great reminder that financial literacy is just as important as talent and hard work. Whether you’re an artist, entrepreneur, or freelancer, staying ahead of taxes isn’t just about compliance—it’s about protecting the future you’re building.

Need Help? We’ve Got You.

If you need accounting and tax help for yourself or your business, we’ve got you covered. Thanks to our strategic alliance with Carson Creative Solutions, led by accounting and tax pro Asia Hill, we’ve built the Tax Ready by Design™ program to help creatives stay compliant and financially sound.

Need guidance? Reach out, and let’s talk.

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