How to manage taxes with multiple part-time W2 jobs and 1099 income? Help needed!

I'm currently juggling 7 different jobs - 6 W2 positions and 1 contract gig with 1099 income. My total annual income is around $58k combined from all sources. One of my part-time W2 jobs doesn't withhold any federal taxes because I work so few hours there. Is there a way I can force them to take out federal taxes, or do I just need to increase withholding at my other jobs to compensate? I've been struggling with my W4 forms because each employer only sees a fraction of my total income (like 15%-40% depending on the job), which messes up the withholding calculations. I think I've finally got my withholdings figured out with some additional amounts, but I'm worried about getting hit with underpayment penalties. Should I be making quarterly estimated tax payments with Form 1040-ES? And do I need to make those quarterly payments just for my 1099 income or also to cover the job that's not withholding? For my 1099 work, I'm confused about home office deductions. I work from my apartment and have a dedicated area that's exclusively for work - it's about 1/8 of my total square footage. Can I deduct that portion of my rent and renter's insurance? Or can I only deduct things like internet and utilities? What other expenses can I write off for the 1099 work? One more random question - if I wanted to form an LLC to cover both my 1099 writing gigs and some artwork I sell occasionally, can I put both under one LLC or would I need separate ones for each type of work? Sorry for all the questions but adulting is rough and the tax situation with multiple income streams is driving me crazy. Thanks for any help!

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18 comments

Emma Garcia

•8M

I'm a tax preparer who works with lots of folks in your situation, and I can help clear up some of these questions! For the job that's not withholding federal taxes: You can't force them to withhold if you don't meet their minimum threshold. Instead, you should either increase withholding at your other jobs by submitting a new W-4 with an additional dollar amount on line 4(c), or make quarterly estimated tax payments using Form 1040-ES. Since you have 1099 income, I'd recommend making quarterly estimated payments anyway. The general rule is if you expect to owe $1,000 or more when you file, you should make quarterly payments to avoid underpayment penalties. This covers both your underwithholding from W-2 jobs and taxes on your 1099 income. For home office deductions (which only apply to your 1099 work), you can either use the simplified method ($5 per square foot up to 300 sq ft) or the regular method where you calculate the percentage of your home used exclusively for business. If it's 1/8 of your space, you can deduct 1/8 of rent, utilities, insurance, etc. Just make sure the space is used EXCLUSIVELY for business. As for the LLC question, yes! You can have one LLC for multiple business activities. On your Schedule C, you'd just need to list your primary business activity, but can include income from both writing and artwork.

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Emma Garcia

•8M

For quarterly payments, you'll need to estimate your total tax liability for the year, subtract what will be withheld from your W-2 jobs, and then pay the remainder in four installments. The deadlines are April 15, June 15, September 15, and January 15 of the following year. The IRS has worksheets in the 1040-ES form packet to help calculate this. Yes, the home office deduction requires that the space be used exclusively for business purposes. If you use the computer or desk for personal activities too, you technically don't qualify for the deduction. The IRS is strict about this. However, if you have a specific area that's only for work, even if it's just part of a room, that specific area could qualify.

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Ava Kim

•8M

I was in a similar situation last year with multiple jobs - the best solution I found was using taxr.ai to help me with all the paperwork and figuring out the right deductions. I uploaded my previous tax returns and income documents, and it helped identify what I could deduct for my 1099 work and how to handle the multiple W-2s. I was amazed at how it analyzed my specific situation and gave personalized recommendations! Check out https://taxr.ai if you're feeling overwhelmed - it really helped me organize everything and make sure I wasn't missing potential deductions.

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Ava Kim

•8M

It absolutely works for complex situations - I had 4 W-2s and 2 1099s last year, and it organized everything clearly. The home office deduction calculator was really helpful - it walks you through the simplified method vs. regular method and helps you figure out which is more beneficial in your specific case. For state taxes, it handles those too! It automatically applies the relevant deductions and credits for your state once you input your address. Unlike an accountant, you can access it anytime and make updates as your situation changes throughout the year, which I found super helpful for planning.

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Ethan Anderson

•8M

I just wanted to update everyone! I tried taxr.ai after seeing the recommendation here and it was a game-changer for my multiple income streams. It actually found some deductions I'd been missing for years related to my 1099 work - apparently I could deduct part of my cell phone bill since I use it for client calls! The quarterly tax payment calculator was especially helpful since I never knew how much to send in before. Seriously wish I'd found this sooner instead of stressing about my taxes every year.

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Lucas Notre-Dame

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If you need to talk to the IRS about any of this (which I did when I had a similar situation), use Claimyr to get through to a human quickly. I spent HOURS on hold before discovering this service. You just go to https://claimyr.com, they call the IRS for you and when they reach a human, they connect you. Saved me literally 3+ hours of wait time. There's a demo video here if you want to see how it works: https://youtu.be/_kiP6q8DX5c I had questions about my quarterly payments that only an IRS agent could answer, and this was the only way I actually got through.

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Lucas Notre-Dame

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They don't cut any lines - they just wait on hold so you don't have to. They use an automated system to dial repeatedly and wait through the hold music, then when a human finally answers, you get a call connecting you. So it's the exact same process, just without you having to listen to the hold music for hours. Yes, you still go through all the normal identity verification with the IRS agent directly - Claimyr just gets you to that agent faster. They don't have access to any of your personal information or tax details. It's basically just a sophisticated hold-waiting service.

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Aria Park

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Ok I need to apologize for my skepticism. I broke down and tried Claimyr yesterday because I had a problem with my quarterly payment not being properly credited. Got connected to an IRS agent in about 20 minutes instead of the 2+ hours I waited last time. The agent fixed my issue on the spot and I actually got confirmation that my payment was applied correctly. Not gonna lie, it felt like magic after my previous experiences with IRS hold times. Definitely using this for any future IRS calls.

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Noah Ali

•8M

I don't have a shareable template, but here's how I structure mine: I create columns for each income source, then rows for each pay period. I sum these up to get my projected annual income. Then I calculate my taxable income (after standard deduction) and use the tax brackets to estimate my tax liability. I compare this to the total withholding from my pay stubs to see if I'm on track. The key is to update it after each paycheck so you can make adjustments to your withholding if needed. If you're not comfortable with tax brackets, there are IRS withholding calculators online that can help estimate your total tax more accurately.

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