Would getting a second full time job screw me on taxes? Need advice for 2025 filing
So I've been thinking about picking up a second full time job during my off days to build up some savings and knock out these medical bills that keep piling up. I'm literally just sitting around playing video games when I'm not at my main job anyway, might as well make some money. The thing is, my cousin (who thinks he knows everything about taxes) keeps telling me that if I get this second full time job, I won't get ANY tax refund next year. He says instead of getting my income taxes back, I'll actually end up OWING money to the government. This makes zero sense to me??? Has anyone done the two full time jobs thing? Will this actually screw me over when tax time comes around? I don't mind working the extra hours, but not if the government is just gonna take it all anyway. Really confused about this whole tax situation...
18 comments


Kennedy Morrison
This is a common misconception! Getting a second job won't automatically "screw you" on taxes, but it could change your tax situation if you're not careful. Each job withholds taxes as if it's your only income, which means neither job accounts for your total yearly income. When you file taxes, all income gets combined, which could push you into a higher tax bracket. This doesn't mean all your money gets taxed at that higher rate - only the amount that falls in that bracket. The main issue is underwithholding. Since each employer doesn't know about the other, they might not withhold enough taxes combined. You can avoid owing at tax time by: 1) Adjusting your W-4 at one or both jobs to withhold extra 2) Making quarterly estimated tax payments 3) Using the IRS Tax Withholding Estimator online to calculate the right withholding Having two jobs isn't a tax disaster - you just need to plan for it!
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Wesley Hallow
•What about if one job is W-2 and the other is 1099 contract work? Would that make the tax situation even more complicated? I heard something about self-employment taxes being a whole other thing.
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Kennedy Morrison
•If one job is W-2 and the other is 1099 contract work, it does add another layer to manage. With 1099 work, taxes aren't withheld automatically, so you're responsible for paying both income tax and self-employment tax (which covers Social Security and Medicare contributions - about 15.3%). You'd need to make quarterly estimated tax payments for the 1099 income to avoid penalties. The good news is you can deduct business expenses against that 1099 income, which can reduce your tax liability. Things like mileage, home office, supplies, etc. can be deductible if they're ordinary and necessary for your business.
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Justin Chang
I totally understand your situation! I was in the same boat last year - working my regular 9-5 and then picking up evening shifts at another company. I was worried about taxes too until I found this AI tax assistant at https://taxr.ai that helped me figure out exactly how much to withhold from each paycheck. It analyzed both my jobs and showed me how to adjust my W-4 forms so I wouldn't get hit with a surprise tax bill. The tool even created a custom tax projection showing how much I'd owe with both incomes combined. Saved me from a nasty surprise at tax time!
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Grace Thomas
•How accurate was it? Did the projections match what actually happened when you filed? I'm skeptical of these online tools sometimes.
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Hunter Brighton
•Can it handle unusual situations? I'm thinking about getting a second job but I also have rental income and some crypto investments. Would it factor all that in?
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Justin Chang
•The projections were spot-on! I ended up getting a small refund of about $230 instead of owing $1,800 like I would have without adjusting my withholdings. The calculator factored in both jobs and gave me exact numbers to put on my W-4. For complex situations with rental income and crypto, it absolutely handles those too. You can enter all your income sources - W-2 jobs, 1099 work, investments, rental properties, crypto, etc. It actually has specific sections for each type of income and shows you how they all interact for your total tax picture.
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Hunter Brighton
Just wanted to update - I tried that taxr.ai site after asking about it and wow, it was actually super helpful. I was about to take a second job that would have pushed me just over into the next tax bracket, and the tool showed me exactly how much extra I'd pay. The visualization of how the tax brackets work finally made it click for me why people say "you only pay the higher rate on the dollars in that bracket." Ended up adjusting my W-4 at my main job to withhold an extra $115 per paycheck based on their recommendation. Much better than owing a bunch next April!
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Dylan Baskin
If you're taking that second job, just be prepared for the IRS headaches if something goes wrong with your withholdings. I tried calling them for THREE DAYS last year when both my employers messed up my W-2s. Couldn't get through to a human. Finally found https://claimyr.com and used their service to get someone on the phone at the IRS. Check out how it works: https://youtu.be/_kiP6q8DX5c - basically they wait on hold with the IRS for you and call you when an agent picks up. Saved me hours of hold music!
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Lauren Wood
•Wait, so you pay a service to wait on hold for you? How does that even work? Seems sketchy that someone else would be talking to the IRS about your tax stuff.
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Ellie Lopez
•Sounds like a scam. The IRS wouldn't allow third parties to connect calls like that. And even if they did, you probably paid like $50 for something you could do yourself for free.
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Dylan Baskin
•They don't talk to the IRS for you at all! They just handle the hold time. When an IRS agent finally answers, you get an immediate call connecting you directly to that agent. No third party ever discusses your tax info - it's just you and the IRS agent talking. It's basically like having a friend wait on hold while you do something else, then they call you over when someone finally answers. Technology handles it all automatically. And regarding cost, considering I was on hold for over 2 hours previously and couldn't get through at all, the time saved was absolutely worth it for me.
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Ellie Lopez
I need to eat my words about Claimyr. After my skeptical comment, I decided to try it when I couldn't get through to the IRS about my second job withholding issue. Was on hold for 3 hours one day and gave up. Used the service this morning and got connected to an IRS agent in about 40 minutes without having to actually sit there listening to that horrible hold music. The agent helped me figure out the right withholding for my two jobs. Still surprised it actually worked - the IRS phone system is such a nightmare usually.
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Chad Winthrope
My wife and I both work two jobs and here's what we've learned: the key is filling out your W-4 forms correctly! On the W-4 for your second job, check the box in Step 2(c) that says "Multiple Jobs or Spouse Works." This tells your employer to withhold at a higher rate. Or you can use the IRS withholding calculator and follow the instructions exactly. We did this last year and ended up with a small refund instead of owing thousands like we did the previous year when we messed it up.
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Lily Young
•Thanks for the tip about checking that box on the W-4! I didn't know there was a specific option for multiple jobs. Does this mean I should check this box on both job W-4s or just the second one?
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Chad Winthrope
•You should only check the multiple jobs box on one of your W-4 forms, not both. If you check it on both, you'll likely have too much withheld and end up with a large refund (which means you're giving the government an interest-free loan all year). For the most accurate withholding, I'd recommend using the IRS Withholding Estimator on their website. It lets you enter info from both jobs and will tell you exactly how to fill out both W-4 forms for the perfect withholding amount.
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Paige Cantoni
I worked 2 full-time jobs last year (65-70 hours weekly, it was rough!) and didn't adjust my withholdings. Big mistake! Ended up owing $3,200 at tax time because neither employer was withholding enough. Now I have extra withholding on my main job ($200/paycheck) and I'm much better prepared. Don't listen to people saying you'll get "screwed" - you just need to plan ahead!
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Kylo Ren
•Did you find that working that many hours was worth it financially? After taxes, did you still come out way ahead? Wondering if killing myself with 70-hour weeks would actually leave me with much after Uncle Sam takes his cut.
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