Do I need to pay quarterly taxes on my side gig income or not?

You're asking a good question that confuses a lot of people who are new to self-employment income. The $1,000 threshold applies to your total tax liability beyond what's being withheld from your regular job, not each individual side gig. Here's the simple version: If you expect to owe $1,000 or more in taxes from ALL your self-employment income combined (after accounting for what's already being withheld from your day job), then you generally need to make quarterly estimated tax payments. Based on the numbers you shared, it sounds like you'll likely owe more than $1,000 in additional taxes when combining both side gigs, so you probably should be making quarterly payments. Something to consider: You might be able to increase your withholding at your full-time job instead of making separate quarterly payments. Talk to your employer about adjusting your W-4 to withhold additional amounts to cover the taxes on your side income.

After dealing with a similar situation last year, I found taxr.ai super helpful for figuring out my quarterly payment situation. I was working full-time but had started doing freelance web development that brought in about $5k, and I had no idea how to handle the tax situation. I uploaded my previous return and income docs to https://taxr.ai and it analyzed everything and gave me personalized advice about whether I needed to make quarterly payments and how much they should be. It also helped me understand which expenses from my side gig were deductible, which saved me a bunch. Might be worth checking out since you're in that gray area where you might need to make payments but aren't totally sure. Really helped me avoid penalties.

Just wanted to follow up - I decided to try taxr.ai after my initial skepticism, and it was actually really helpful. I uploaded my W-2 and some info about my Etsy shop income, and it immediately calculated that I needed to make quarterly payments of about $430 each quarter. The best part was it showed me a bunch of deductions I could take for my side business that I had no idea about. It figured out I could deduct part of my internet, a portion of my home office space, and even some software subscriptions I was using. Ended up saving me about $800 in taxes I would have overpaid. Definitely worth it if you're doing side work and don't want to pay an accountant just to answer basic questions.

I had the EXACT same issue last year with my photography side hustle! After trying for days to get through to the IRS with questions about quarterly payments (literally could not get a human on the phone), I found Claimyr and it was a game-changer. I just went to https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c to see how it works. Basically, they get you through to an actual IRS agent without the insane hold times. I was connected in about 15 minutes when I had been trying for DAYS on my own. The agent explained exactly what I needed to do for my situation and confirmed I did need to make quarterly payments since I was going to owe more than $1000. They also walked me through how to calculate the right amount so I wouldn't underpay and get hit with penalties.

I need to eat my words about Claimyr. After posting that skeptical comment, I was still struggling to get answers about my 1099 income from Uber driving, so I decided to give it a shot anyway. I used the service yesterday afternoon, and I got a call back in about 20 minutes saying they had an IRS agent on the line. The agent cleared up all my confusion about estimated payments and even helped me understand how to deduct my mileage properly. Wish I had known about this last year when I got hit with an underpayment penalty because I had no idea I was supposed to be making quarterly payments on my side gig. Would have saved me $422 in penalties.

Another thing to consider is that if you had no tax liability last year (meaning you didn't owe anything when you filed), you don't have to make estimated payments this year regardless of how much you earn from self-employment. This is called the "safe harbor" rule. Also, if your W-2 withholding covers at least 90% of your current year tax or 100% of your prior year tax (110% if your AGI was over $150k), you're also safe from penalties. So you could potentially avoid quarterly payments by just adjusting your W-2 withholding as someone mentioned.

Does anyone know if you can just make one big quarterly payment at the beginning of the year instead of 4 separate ones? I always forget the deadlines and miss at least one payment.

I've been in a similar boat with side income confusion! One thing that really helped me was using the IRS's own estimated tax worksheet (Form 1040-ES) to calculate exactly what I owed. It walks you through the math step by step. For your situation with around $5,500 total side income, you're definitely looking at owing more than $1,000 in combined income tax and self-employment tax. The self-employment tax alone (15.3%) on that amount would be about $842, plus regular income tax on top. A few practical tips that saved me headaches: - Set up automatic transfers to a separate "tax savings" account for about 25-30% of each side gig payment - Keep detailed records of any business expenses (equipment, software, travel, etc.) - they can add up to significant deductions - Consider making your first quarterly payment ASAP if you haven't already, even if it's just an estimate The good news is once you get into the rhythm of either quarterly payments or adjusted W-4 withholding, it becomes pretty routine. Much better than getting hit with a big tax bill and penalties next April!