Do I have to make quarterly estimated tax payments as a new freelancer?

So if I don't make any income in the first quarter, I don't need to make an estimated payment for that quarter, right? And how do I even calculate how much I'll owe when I don't know how much I'll make?

That's right! If you don't earn any income in the first quarter, there's nothing to pay estimated taxes on for that period. For calculating when you don't know your income yet, you'll need to make your best projection and adjust as you go. A good rule of thumb is to set aside about 25-30% of your freelance income for taxes. Once you start earning, you can use the IRS Form 1040-ES worksheet to get a more precise figure. The key is to keep good records of your income and expenses so you can make adjustments to your estimated payments each quarter based on your actual earnings.

Does it work with irregular income? My freelance work comes in chunks - sometimes I make nothing for 2 months then get a big project. Would it still calculate everything correctly?

I'm skeptical of these tax tools. Does it actually connect to the IRS systems or is it just making estimates? I've been burned before by apps that claim to handle taxes but then miss important details.

Yes, it actually works amazingly well with irregular income! That's one of the features I love most. I'm a graphic designer and sometimes go weeks with nothing, then land three big projects at once. The tool adjusts your tax projections based on your actual cash flow patterns, not just assuming steady income. For your question about IRS connections - it doesn't directly connect to IRS systems (which is actually good for privacy). Instead, it uses the actual IRS tax calculation formulas and updates whenever tax laws change. It's much more comprehensive than those basic calculator apps. It tracks your deductions, business expenses, and even helps identify write-offs you might have missed, which has saved me thousands.

How does this even work? I thought it was impossible to get through to the IRS. Do they have some special connection or something?

Yeah right. There's no way this actually works. The IRS phone lines are a disaster - everyone knows that. Sounds like another scam trying to profit off desperate freelancers.

It works by basically navigating the IRS phone system for you and holding your place in line. The system calls the IRS, works through all the automated menus, waits on hold for you, and then calls you when they get an actual human agent on the line. It's not a special connection - just clever technology that does the waiting for you. Honestly, I was skeptical too. I tried calling the IRS directly three different times and gave up after being on hold for over an hour each time. With this service, I went about my day, and my phone rang when they had an agent. Completely changed my perspective on dealing with tax questions - I actually got answers instead of giving up in frustration.

But what if my income this year will be way higher than last year? Last year I was a part-time student with minimal income. This year I'm expecting to make quite a bit more with freelancing.

That's actually where the safe harbor provision helps you! If your previous year's tax liability was small, you can use that amount as your safe harbor target and avoid penalties even if you end up making significantly more this year. For example, if you only owed $2,000 in taxes last year, you could make quarterly payments totaling $2,000 for this year ($500 each quarter), and you wouldn't face underpayment penalties even if you end up owing $10,000 when you file. You'd still need to pay the remaining $8,000 when you file your return, but without penalties for underpayment.

Is there a good app for tracking all these expenses? I'm terrible at keeping receipts.

For expense tracking, I've been using Receipt Bank (now called Dext) which lets you just snap photos of receipts with your phone. QuickBooks Self-Employed is another solid option - it automatically categorizes transactions and has a mileage tracker too. Since you're in video production like the original poster, don't forget you can also deduct things like: - Camera equipment rentals - Stock footage/music licenses - Travel expenses to client locations - Even a portion of your phone bill if you use it for business The key is being consistent about tracking everything from the start - it's so much easier than trying to reconstruct everything at tax time!