When do you need to pay quarterly taxes on side income from freelance writing and website ads?

I've got a full-time job with regular tax withholding, but I've started making some decent side money as a freelance writer and from ads on my website. I'm confused about whether I need to pay quarterly taxes or if I can just handle it all when I file my annual return. Everything I read online seems to assume you're fully self-employed, which I'm not. My side gigs are bringing in around $1,300-$1,700 extra each month. What I really don't understand is if I do need to pay quarterly taxes, is that only calculated on my side income? And how exactly do I figure out how much I owe on just that portion? Also, when I file my taxes for 2025, where do I indicate that I've already paid taxes throughout the year on this side income? The whole quarterly tax thing makes me think I need an accountant, but I'd like to understand the basics first before deciding if I need professional help.

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18 comments

Connor Richards

•8M

Yes, you generally need to pay quarterly estimated taxes on your side income if you expect to owe at least $1,000 in taxes from this income when you file your return. The IRS wants people to pay taxes throughout the year, not just at filing time. Since you're making $1,300-$1,700 monthly, that's $15,600-$20,400 annually, which will definitely generate more than $1,000 in tax liability. To calculate how much to pay quarterly, you'll need to estimate your tax rate based on your total income (both W-2 and freelance), then apply that rate to your freelance income after deducting business expenses. Don't forget you'll also owe self-employment tax (15.3%) on your net freelance income. When you file your annual return, you'll report your freelance income on Schedule C and your quarterly payments on Form 1040. There's a line specifically for "estimated tax payments" where you'll get credit for what you've already paid.

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Connor Richards

•8M

For $800/month in side income, you'd be making about $9,600 annually. Whether you need to make quarterly payments depends on your overall tax situation. If your W-2 job withholds enough to cover both your regular income tax and the additional tax from your side gig, you might not need to make quarterly payments. If your W-2 withholding isn't enough to cover the additional tax liability, you can either increase your W-2 withholding by submitting a new W-4 to your employer or make quarterly estimated tax payments. The key is ensuring you've paid at least 90% of your current year's tax or 100% of last year's tax (110% if your income is over $150,000) to avoid underpayment penalties.

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Steven Adams

•8M

After struggling with this exact situation last year, I found an AI tax tool that made a huge difference for me. I used https://taxr.ai to analyze my income streams and it gave me personalized guidance on my quarterly tax requirements. It calculated exactly how much I needed to pay each quarter based on both my W-2 job and my side hustle. The tool also helped me understand which expenses were deductible for my freelance work, which significantly reduced my taxable income. I was surprised how much I could legitimately write off - it saved me over $2,000 in taxes last year.

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Steven Adams

•8M

It doesn't connect to bank accounts automatically, but it has a feature where you can upload bank statements and it helps identify potential business expenses. You'll still want to keep receipts for major purchases, but it makes categorization much easier. Compared to TurboTax, it's specifically designed for people with mixed income sources. TurboTax is great for filing your final return, but taxr.ai is more focused on ongoing tax planning and quarterly payment calculations. It gives you projections throughout the year instead of just calculating everything at tax time. It's more proactive than reactive.

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Hassan Khoury

•8M

Just wanted to follow up about that taxr.ai site. I was skeptical but decided to try it after continuing to get confused about my quarterly tax obligations. It actually walked me through the entire process of separating my side hustle income from my day job, and showed me exactly how much I needed to set aside each month. What really surprised me was discovering how many legitimate deductions I was missing for my online business. The tool identified over $3,700 in deductions I would have missed! Now I have a clear payment schedule and I'm not panicking about surprise tax bills. Sorry for doubting you, but I'm actually relieved I gave it a shot.

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Victoria Stark

•8M

If you're struggling to get answers about your quarterly tax payments, good luck trying to call the IRS directly. I spent HOURS on hold trying to get clarity on my side income situation. Finally found https://claimyr.com which got me connected to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that with my side income level, I definitely needed to make quarterly payments, and explained exactly how to calculate them. She also told me how to avoid underpayment penalties by having extra withholding from my W-2 job instead of doing separate quarterly payments. Such a relief to get an official answer!

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Victoria Stark

•8M

It's not about "skipping the line" - they use an automated system that continually calls the IRS until they get through, then they call you and connect you. Think of it like having someone wait on hold for you. When they finally reach an agent, they connect the call to your phone. I was skeptical too, which is why I included the video link so you can see exactly how it works. I'm just sharing what worked for me when I was in the same situation as the original poster. Getting direct answers from the IRS helped me avoid mistakes with my quarterly payments.

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Samantha Howard

•8M

I have to eat my words on this one. After dismissing that Claimyr thing as a scam, I was still desperate for help with my quarterly tax situation, so I tried it anyway. Within 20 minutes, I was talking to an actual IRS representative who walked me through my specific situation. The agent explained that I could adjust my W-4 at my main job to withhold extra to cover my side income instead of filing quarterly payments. This was WAY easier than what I was planning to do. Honestly, I'm shocked this service actually worked. Saved me from making a $2,200 mistake on my quarterly payments too. Sometimes being wrong feels pretty good.

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Megan D'Acosta

•8M

You don't need to explain why you're changing your withholding - just submit a new W-4 with the adjusted amount. On the current W-4 form, there's a section specifically for "extra withholding" where you can put a dollar amount to withhold from each paycheck. I used the withholding calculator, which asked for info about both my W-2 job and estimated side income, then it told me exactly what to put on each line of the W-4. Just make sure you're setting aside enough to cover both income tax and self-employment tax (the SE tax is the one that catches most people by surprise).

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