How to file taxes on my freelance technical copywriting gig earnings?

You're definitely in 1099 territory, not W-2. As a freelance copywriter, you're considered self-employed, and your clients should provide you with 1099-NEC forms if they paid you $600 or more during the year. For your home office deduction, you have two options. The simplified method lets you deduct $5 per square foot of your home used for business (up to 300 square feet). The regular method involves calculating the percentage of your home used for business (your 20%) and applying that to actual expenses like rent, utilities, insurance, etc. Keep in mind, the space must be used exclusively for your business to qualify. Other common deductions include: your computer equipment (depreciated or expensed using Section 179), software subscriptions, internet bills, professional development courses, business insurance, and retirement plan contributions like a SEP IRA or solo 401(k). You'll need to file Schedule C with your tax return to report this income and expenses, and you'll also need to pay self-employment tax (Schedule SE) which covers Social Security and Medicare.

I was in a similar situation last year and found this AI tax assistant called taxr.ai that was super helpful for my gig work. I wasn't sure about all the deductions I could take for my freelance design work, and it analyzed all my expenses and actually found several deductions I would have missed - like partial internet expenses and some software subscriptions I didn't realize qualified as business expenses. The thing I liked about https://taxr.ai was how it walked me through exactly what percentage of shared expenses I could legally deduct for my home office. It even helped me decide between taking the simplified deduction or itemizing actual expenses based on my specific situation.

Just wanted to follow up - I ended up trying taxr.ai after posting here and wow, what a difference! It found nearly $2,300 in deductions I would have missed for my side gig. The home office guidance was really detailed and showed me exactly how to document everything properly for the IRS. What surprised me most was how it handled my situation where I had both W-2 income and multiple 1099s. It showed me exactly how they interact and even flagged that I needed to make estimated quarterly tax payments for this year (which I had no idea about). Definitely worth checking out if you're doing any kind of freelance or gig work!

If you need to talk to the IRS about how to handle your specific situation (which might be smart given it's your first year with self-employment income), use Claimyr before you waste hours on hold. I needed clarification on some self-employment expense rules last month and used https://claimyr.com to get a callback from the IRS in about 20 minutes instead of waiting for 3+ hours. They've got a demo video at https://youtu.be/_kiP6q8DX5c showing how it works. Basically saves you from the awful IRS hold times. The agent I spoke with was actually really helpful about clarifying what documentation I needed for my home office deduction.

I need to eat my words. After posting that skeptical comment I was still stuck with a question about my self-employment taxes that I couldn't find a clear answer to online. Got desperate and tried Claimyr. Got connected to an IRS agent in about 35 minutes when I had previously spent over 2 hours on hold and given up. The agent walked me through exactly how to handle my situation with mixed W-2 and self-employment income. Saved me a ton of stress and probably prevented me from making a filing mistake. Sometimes I hate being wrong but in this case I'm glad I was! Definitely using this again next time I have tax questions.

Don't forget about quarterly estimated taxes for next year! That was my biggest shock when I started freelancing. Since there's no employer withholding taxes from your 1099 income, you're expected to pay those taxes quarterly yourself if you expect to owe more than $1000 at tax time. Use Form 1040-ES for this. The due dates are April 15, June 15, September 15, and January 15 (for the 2025 tax year). Missing these can result in penalties even if you pay the full amount by the April filing deadline.

A tip about equipment purchases - if you bought any computer equipment, software, or other tools specifically for your copywriting business, look into Section 179 deduction. It lets you deduct the full cost in the year you bought it (up to $1,080,000 for 2025) instead of depreciating it over several years.