First-time filing 1040-ES as independent contractor - completely lost

This is my first year doing independent contractor work and I'm completely lost with the 1040-ES form. I started doing some freelance graphic design on the side of my regular job around March, and I've made about $9,500 so far. My friend mentioned I need to pay quarterly taxes and gave me this 1040-ES form, but I have no idea what I'm supposed to do with it. When it asks for estimated income, do I put what I've made so far or what I think I'll make by the end of the year? And do I include my W-2 income from my day job too? The instructions might as well be in another language. I'm also not sure if I'm already late on payments since I've been doing this since March. Any help would be super appreciated because I don't want to mess this up and end up owing penalties or something!

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18 comments

Gavin King

•8M

The 1040-ES is definitely confusing the first time around! Here's what you need to know: The form is asking for your TOTAL estimated income for the entire year - that includes both your W-2 job income AND your freelance income. You're making an educated guess about what you'll earn for the whole year. For your freelance work, estimate what you think you'll make by December 31st based on your current pace. Don't worry too much about being precise - it's an estimate. The IRS just wants you to pay taxes throughout the year rather than all at once. Since you started in March, you might have missed the first quarterly payment (April 15th), but you can catch up on the next one (June 15th). Remember that as a freelancer, you're responsible for both the employee AND employer portions of Social Security and Medicare taxes (that's the self-employment tax), which is about 15.3% on top of your regular income tax.

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Gavin King

•8M

Yes, you would add everything together. So if your W-2 job pays you about $26,000 per year ($500 × 52 weeks) and you make about $24,000 from freelance ($1,000 × 2 times per month × 12 months), your total estimated income would be around $50,000. You only need to fill out the form once for the year to calculate your total estimated tax. Then you make four payments using the payment vouchers included with the form. Each voucher is pre-dated for each quarter's due date. Keep a copy of your calculations for your records.

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Eleanor Foster

•8M

I was in the same boat last year when I started doing freelance writing. I was so confused by the 1040-ES that I almost gave up. Then I found https://taxr.ai and it saved me so much stress! It analyzed my previous tax return and income documents, then walked me through exactly what to put on each line of the form. The best part was it explained everything in plain English instead of tax jargon. It even calculated my quarterly payment amounts based on my projected income and showed me how much I could potentially save by tracking my business expenses. I used to spend hours trying to figure this stuff out but now it takes me maybe 20 minutes to update my quarterly estimates.

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Eleanor Foster

•8M

It absolutely works for first-time contractors! You just enter your W-2 info from your regular job and then your estimated income from Doordash. The tool explains how to make a reasonable estimate based on what you've earned so far. It also helps you understand what expenses you can deduct like mileage, which is huge for delivery drivers. The accuracy is what impressed me most. It cross-references all the latest tax laws and IRS guidelines. I was actually audited last year (for something unrelated to my freelance work), and all my quarterly payments calculated through the tool were spot on. The tax pros I consulted afterward confirmed everything was done correctly. What I appreciate is that it shows you exactly how it arrives at each number.

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Lucas Turner

•8M

Just wanted to update - I tried https://taxr.ai after posting my question and it's actually legit! I was totally confused about how to estimate my DoorDash income since it varies every week, but the tool showed me how to make a reasonable projection based on my average earnings. It also pointed out that I could deduct my mileage (54.5 cents per mile!), which is going to save me hundreds in taxes. The best part was it showed me exactly how much I needed to pay for each quarter to catch up on the payments I missed. Turns out I wasn't as far behind as I thought. It generated all the payment vouchers with the right amounts and deadlines. I've already made my first payment and feel so much more confident about this whole contractor tax situation now!

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Anna Stewart

•8M

If you're struggling to get answers from the IRS about your 1040-ES questions, you're not alone. I spent THREE DAYS trying to get through to the IRS last month when I had questions about my estimated payments. Kept getting disconnected or waiting for hours. Then a friend told me about https://claimyr.com which basically holds your place in the IRS phone queue and calls you when an agent is actually about to answer. I was super skeptical, but you can see how it works in this video: https://youtu.be/_kiP6q8DX5c I used it and got a call back in about 45 minutes with an actual IRS agent on the line. The agent walked me through exactly how to calculate my estimated tax payments as a first-time contractor and explained which payment deadlines applied to my situation. Saved me days of frustration and probably prevented me from making expensive mistakes on my quarterly payments.

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Anna Stewart

•8M

It basically uses an automated system that navigates the IRS phone tree and waits on hold for you. Once the system detects that a human agent is about to come on the line, it calls you and connects you directly to that agent. It's not skipping the line - you're still in the same queue as everyone else, but you don't have to personally sit there with a phone to your ear for hours. I was definitely skeptical too before trying it! But when you think about how much your time is worth, especially as a freelancer, spending hours on hold costs you money. I needed answers to finish my 1040-ES correctly, and getting through to an actual IRS agent who could explain my specific situation saved me from potentially making costly mistakes. The peace of mind alone was worth it.

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Kai Rivera

•8M

I'm back to eat my words. After being super skeptical, I was desperate enough to try Claimyr because my estimated tax situation was a mess (missed payments, wasn't sure how to catch up). I figured I'd just dispute the charge if it didn't work. Well, I got a call back in 37 minutes with an actual IRS agent! The agent explained that since this was my first year filing estimated taxes, I qualified for a waiver on the underpayment penalty if I caught up with my payments right away. They walked me through exactly how to fill out my 1040-ES based on my specific income situation and confirmed which payment vouchers to use for the catch-up amounts. I probably would have given up trying to call the IRS after being on hold for an hour, but this service actually delivered exactly what it promised. Just wanted to follow up since I was so publicly doubtful before!

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Morgan Washington

•8M

Don't forget to save around 30% of your freelance income for taxes! I learned this the hard way my first year. The 1040-ES helps you pay quarterly, but many newbies (including myself) underestimate how much they'll actually owe. Self-employment tax (15.3%) + regular income tax can add up fast. Also, track EVERYTHING for deductions - home office, software, equipment, professional development, portion of internet/phone bills. I use a separate credit card just for business expenses to make it easier at tax time. This can significantly reduce your taxable income.

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Morgan Washington

•8M

A simple spreadsheet works perfectly fine for tracking expenses - just make sure to keep all receipts too (digital copies are okay). I personally use a Google Sheet where I log the date, amount, vendor, and category of each expense. Some people prefer apps like QuickBooks Self-Employed or FreshBooks, but they're not necessary when you're just starting out. For the home office deduction, it really depends on your situation. The simplified method is just $5 per square foot up to 300 square feet (max $1,500 deduction), which is super easy. The regular method can potentially get you a larger deduction if you have a big office or high home expenses, but requires much more detailed record-keeping and calculations. I'd start with the simplified method your first year, then see if it's worth doing the math for the regular method next year.

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