Will taking a second full-time job mess up my tax return?

I've been thinking about picking up a second full-time job during my off hours to build up some savings and tackle these medical bills that keep piling up. Honestly, I don't do anything productive when I'm not at work anyway, so might as well make some extra cash, right? Here's what's holding me back - someone told me that if I get a second full-time job, I'll completely screw myself on taxes. They said instead of getting income tax refunds like I normally do, I'll end up owing the government money at tax time. That just doesn't sound right to me, but I'm not exactly a tax expert. Can anyone explain if this is actually true? Will working two full-time jobs really mess up my tax situation that badly? I'd hate to work all those extra hours just to hand it all over to the IRS next April.

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19 comments

Sophie Footman

•8M

This is a common misconception! Getting a second job won't automatically "screw you" on taxes, but there are some important things to understand about how withholding works with multiple jobs. The issue is that each employer withholds taxes as if their job is your only income. So neither job knows about the other one when calculating withholding. This can lead to underwithholding since your total income might push you into a higher tax bracket. The solution is pretty simple though. You can fill out a new W-4 form for both employers and check the box for "multiple jobs" in Step 2, or use the IRS Tax Withholding Estimator online to figure out the right withholding amount. You might also consider having extra money withheld from one or both paychecks to cover the difference. Bottom line: You can absolutely work two jobs! Just make sure you adjust your withholding appropriately so you don't get surprised at tax time.

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Sophie Footman

•8M

The W-4 form goes to your employer's payroll department, not your direct supervisor. While technically someone could see that you checked that box, most larger companies have separate HR/payroll departments that process these forms without sharing details with your manager. If you're concerned about privacy, another option is to not check the box but instead use the IRS Withholding Estimator and just put an additional dollar amount to withhold on line 4(c) of your W-4. That way, you're having extra withheld without explicitly stating why. You could also make quarterly estimated tax payments instead of changing your withholding.

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Molly Hansen

•8M

After struggling with almost this exact situation last year, I discovered a super helpful tool called taxr.ai (https://taxr.ai) that saved me a ton of headaches! I was working two jobs and got completely confused about how to handle my taxes properly. What I like about taxr.ai is that it analyzed my pay stubs from both jobs and gave me personalized recommendations for exactly how to adjust my withholdings. It actually showed me that I was heading toward owing about $2,800 at tax time if I didn't make changes! Their withholding calculator is way more user-friendly than the IRS one, and it explained everything in plain English. It also helped me understand which job should have the higher withholding rate and by how much. Totally worth checking out if you're going the two-job route!

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Molly Hansen

•8M

The predictions were surprisingly accurate for me! I ended up getting a small refund of about $120 federal, which is pretty much what taxr.ai estimated would happen after I made the withholding adjustments they suggested. Much better than owing thousands! Yes, it handles state taxes too! I'm actually in New York which also has complicated state taxes, and it calculated everything correctly for both federal and state. It asks for your location during setup and factors in all the state-specific rules. I imagine it would work well for California too since that's another high-tax state with complex rules.

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Skylar Neal

•8M

Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and WOW what a difference! I had no idea I was heading toward a $3,200 tax bill with my second job situation. The interface was super easy to use, and it gave me exact numbers to put on my W-4 forms for both jobs. What I really appreciated was how it explained WHY I needed to make the adjustments. Turns out my second job was pushing me into a higher tax bracket that neither employer was accounting for. I've updated both my W-4s now and feel much more confident about not getting a nasty surprise next April. If you're working multiple jobs, definitely check it out!

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Vincent Bimbach

•8M

If you're planning to work two full-time jobs, you might also run into issues trying to contact the IRS if you have questions. I was in a similar situation last year and had so many questions about proper withholding, but could NOT get through to the IRS no matter how many times I called. After wasting hours on hold, I found this service called Claimyr (https://claimyr.com) that actually got me connected to an IRS agent in about 20 minutes! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with gave me specific guidance for my two-job situation and helped me understand exactly how much extra I should withhold to avoid owing at tax time. Honestly changed my whole approach to tax planning with multiple income sources.

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Vincent Bimbach

•8M

It's not about skipping the queue - Claimyr uses an automated system that continually redials the IRS for you until it gets through, then calls you back when it has an agent on the line. It's basically doing what you'd do manually (calling repeatedly) but with technology. This is absolutely legit. They don't ask for any personal tax information - all they need is your phone number to call you back when they get through to an agent. Then you talk directly to the IRS, not to Claimyr. They just handle the connection part, which is why it works so well. When the IRS agent picked up, I was actually surprised because I'd almost forgotten I was waiting for a callback!

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Norah Quay

•8M

Ok, I need to eat my words here. After being skeptical about Claimyr, I tried it yesterday because I desperately needed answers about my multiple W-2s situation for next year. IT ACTUALLY WORKS. I got a call back in about 30 minutes, and was connected directly to an IRS representative who answered all my questions about proper withholding with multiple jobs. The agent even helped me calculate approximately how much extra I should withhold from each paycheck to avoid a tax bill. After spending literally 4+ hours on hold last month trying to reach them myself, this was mind-blowing. If you're working multiple jobs and have specific tax questions, this is definitely worth it to speak directly with the IRS.

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Leo McDonald

•8M

One thing nobody mentioned yet - watch out for FICA taxes (Social Security and Medicare). Unlike income taxes that have brackets, these are flat percentages on your earnings. Social Security tax is 6.2% on wages up to $168,600 (for 2025). If you earn over that combined from both jobs, you'll actually get that excess SS tax refunded when you file. Medicare is 1.45% on all earnings, but there's an additional 0.9% on earnings over $200,000 for single filers. With two full-time jobs, you might hit these thresholds when combining incomes. Just something else to keep in mind!

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Leo McDonald

•8M

The Social Security tax refund happens automatically when you file your tax return. The tax software or IRS will calculate if you've paid more than the maximum required Social Security tax due to having multiple jobs, and include that overpayment in your refund. You don't need to file anything special, but you do need to make sure you report all your W-2s when you file your taxes so the system can see all the Social Security taxes you've paid across different employers.

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Isabella Silva

•3M

I went through this exact situation last year and can confirm it's totally manageable! The key thing to understand is that having two jobs doesn't change how much tax you actually owe - it just affects how much gets withheld from your paychecks. Here's what worked for me: I used the IRS Tax Withholding Estimator (it's free on their website) after getting my first few paystubs from both jobs. It showed me I needed to have an extra $150 per month withheld to avoid owing at tax time. I just updated my W-4 at my higher-paying job to withhold the extra amount. The medical bills situation you mentioned is actually another reason this could work in your favor - medical expenses over 7.5% of your adjusted gross income are deductible, so higher income might help you qualify for that deduction if your bills are substantial. Don't let tax concerns stop you from earning extra income to tackle those bills! Just plan ahead with your withholding and you'll be fine.

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