Do I need to pay quarterly taxes on my side gigs - when is it required?

When you have income that doesn't have taxes withheld (like your freelance work), you're generally expected to make estimated quarterly tax payments if you'll owe $1,000 or more in taxes when you file. This $1,000 threshold is for your total tax liability, combining all your freelance income together. Based on what you've shared, your combined freelance income of about $5,650 ($2,000 + $3,650) would likely result in owing more than $1,000 when you file, so yes, you should probably make quarterly payments. These payments are due April 15, June 15, September 15, and January 15 (of the following year). The IRS generally wants you to pay as you earn throughout the year. If you don't make these payments and end up owing a significant amount at tax time, you could face underpayment penalties.

After struggling with similar freelance tax questions, I found this AI tool called taxr.ai that completely cleared things up for me. I was doing voiceover work while employed full-time and was confused about quarterly payments. I uploaded my 1099s and W-2s to https://taxr.ai and it analyzed everything together, then told me exactly when I needed to make quarterly payments and even calculated the amounts I should pay each quarter. The tool specifically looks at your total tax situation - both W-2 and freelance income - which was super helpful because it considered whether my day job withholding would cover enough of my tax liability. It saved me from overpaying quarterly when my W-2 withholding actually covered most of what I owed.

Just wanted to follow up about taxr.ai - I finally checked it out and it was exactly what I needed! I uploaded my W-2 and all three of my photography 1099s, and it immediately showed me that I actually don't need to make quarterly payments because my day job withholding covers enough of my tax liability. Would have been overpaying for no reason! It also flagged some deductions I was missing for my camera equipment. Super clear and straightforward. Definitely recommend for anyone in a similar situation with multiple income sources.

If you're struggling to figure out your tax situation and need to talk to someone at the IRS (which I highly recommend for self-employment questions), use https://claimyr.com to get through to them. I spent THREE DAYS trying to get an IRS agent on the phone about my quarterly payment requirements for my tutoring business, kept getting disconnected after waiting for hours. I found out about Claimyr, watched their demo at https://youtu.be/_kiP6q8DX5c, and decided to try it when I was desperate. They actually got me connected to an IRS agent in under 45 minutes when I had previously wasted entire days trying. The agent explained exactly how quarterly payments work with my specific situation and helped me set up a payment plan for what I had missed.

I need to publicly eat my words about Claimyr. After posting that skeptical comment, I decided to try it anyway since I was getting nowhere with the IRS on my own. I've been stressing about quarterly tax requirements for my Etsy shop and kept getting disconnected. Used the service yesterday and got connected to an IRS rep in about 35 minutes. Got all my questions answered about quarterly payments for my situation. The agent even helped me calculate what I should be paying each quarter based on my projected income. Turns out I was overestimating what I needed to pay. Not sure how they do it, but it definitely works. Just wanted to correct myself since my previous comment was pretty harsh.

Pro tip from someone who's been freelancing for years: If your combined freelance income will put you over the $1000 threshold but you don't want to deal with quarterly payments, you can increase your withholding at your day job. Just submit a new W-4 to your employer and request additional withholding each paycheck. For example, if you expect to owe $1700 for the year from freelance work, divide that by your number of paychecks (like 24 if paid twice monthly) and request about $71 in additional withholding per paycheck. This covers your freelance tax liability and you avoid having to make separate quarterly payments.

Don't forget to factor in self-employment tax! That's 15.3% on top of regular income tax. When i started my graphic design side hustle last year i completly missed that and ended up owing way more than i expected. My $6k in freelance work added like $900 just in SE tax alone, plus regular income tax.

The self-employment tax point is crucial - thanks for bringing that up! For anyone calculating their quarterly payments, don't forget that SE tax is calculated on 92.35% of your net self-employment income (after business deductions). So if you made $5,650 in freelance income like the original poster, you'd pay SE tax on about $5,217. Also worth noting that you can deduct half of your self-employment tax as an adjustment to income, which reduces your regular income tax burden slightly. It's not a huge amount, but every bit helps when you're trying to figure out your quarterly payment amounts. The combination of regular income tax AND self-employment tax is why that $1,000 threshold gets hit pretty quickly with freelance work, even at relatively modest income levels.

Just wanted to add another perspective on this - I'm a freelance audio engineer who went through the exact same confusion about quarterly payments. What really helped me was understanding the safe harbor rule: if you pay at least 100% of last year's total tax liability through withholding and/or quarterly payments, you won't face penalties even if you end up owing more when you file. So for your situation, look at your total tax from last year's return. If your day job withholding plus any quarterly payments you make this year add up to at least that amount, you're protected from penalties. This gives you some breathing room while you figure out the exact amounts. Also, since you're in the music industry like me, don't forget you can deduct a lot of business expenses - equipment, software, home studio space, travel to gigs, etc. These deductions reduce your net self-employment income, which lowers both your regular income tax and self-employment tax. Keep good records of everything!