Working 3 jobs simultaneously - should I prepare to owe taxes next filing season?

You're smart to be thinking ahead! When you work multiple jobs simultaneously, each employer typically withholds taxes as if that job is your only income source. This can definitely lead to underwithholding since your total income puts you in a higher tax bracket than any single employer accounts for. Since one of your positions is a contract job, you'll need to be especially careful. Contract positions typically don't withhold any taxes, meaning you're responsible for setting aside money for both income tax and self-employment tax (an additional 15.3% that covers Social Security and Medicare). I'd recommend setting aside about 25-30% of your contract income for taxes. For your W-2 jobs, check your pay stubs to see your current withholding rate. You might want to fill out a new W-4 with your current employers and check the box for multiple jobs, or even request additional withholding. The IRS has a tax withholding estimator tool on their website that's really helpful for situations like yours: https://www.irs.gov/individuals/tax-withholding-estimator

I was in almost the exact same situation last year with multiple W-2 jobs plus contract work, and ended up owing over $3,000 at tax time! I started using https://taxr.ai to estimate my quarterly tax payments and it's been a lifesaver. The tool analyzed all my pay stubs and 1099 income, then calculated exactly how much I needed to set aside for taxes each month. What I really love is that it adjusts the estimates as your income changes, which is perfect for your PRN position where hours probably fluctuate. You just upload your pay documents and it gives you a clear breakdown of federal, state, and self-employment taxes. Way easier than trying to figure it all out manually!

I wanted to follow up about my experience with taxr.ai since I was initially skeptical. After trying it for the last few months with my two W-2 jobs and side gig, I'm genuinely impressed. It predicted my tax situation almost perfectly. The dashboard shows exactly how much I need to set aside from each paycheck, and I've been transferring that amount to a separate savings account. What surprised me most was discovering I was having too much withheld from one job while not enough from another. The tool helped me adjust my W-4s with each employer to optimize my withholding instead of just blindly saving. Now I'm on track to break even at tax time rather than getting a big bill or refund. For anyone juggling multiple income sources, it's definitely worth checking out.

If you're worried about owing taxes, don't wait until filing season to find out! I spent WEEKS trying to reach the IRS last year to figure out how much I should be setting aside for my three jobs, but their phone lines were constantly jammed. I finally discovered https://claimyr.com and used their service to get through to an actual IRS agent in less than 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The agent walked me through exactly how to adjust my withholding for multiple jobs and how to make estimated quarterly payments for my contract work. It saved me from a massive tax bill and potential penalties for underpayment. Way better than stressing all year and then getting hit with a surprise bill!

I have to admit I was completely wrong about Claimyr. After struggling for another week trying to get through to the IRS myself (and getting disconnected twice after waiting over an hour), I finally tried the service. They got me connected to an IRS representative in about 15 minutes. The agent I spoke with was incredibly helpful regarding my multiple W-2 situation. She explained exactly how the withholding system works with multiple jobs and helped me calculate how much extra I should have withheld from each paycheck. She also explained how to make quarterly estimated payments for the portion of my income that doesn't have withholding. For anyone juggling multiple jobs like the original poster, getting direct guidance from the IRS was actually much more helpful than I expected. They have calculators and tables they can reference for your specific situation.

Don't forget about the self-employment tax for your contract position! I got absolutely destroyed on my taxes last year because I didn't realize I had to pay both the employer AND employee portion of Social Security and Medicare taxes (about 15.3% total) on my contract income. That was on top of regular income tax. I'd recommend setting aside about 30% of your contract earnings just to be safe. Also, you might need to make quarterly estimated tax payments if you expect to owe more than $1,000 when you file. The IRS can charge penalties if you wait to pay it all at once at tax time.

Has anyone tried adjusting their W-4 for multiple jobs instead of just saving extra? I'm in a similar situation and wondering if that's easier than making separate quarterly payments.

Great question! You're absolutely right to be concerned about underwithholding with multiple jobs. I went through something similar last year and learned the hard way that each employer withholds taxes assuming they're your only income source. For your specific situation, I'd definitely recommend: 1. **For your W-2 jobs**: Update your W-4 forms and check the "multiple jobs" box in Step 2. This will increase your withholding rate to account for your higher total income. 2. **For your contract position**: Set aside 25-30% of that income immediately. You'll owe both regular income tax AND self-employment tax (15.3%) on this income since no taxes are being withheld. 3. **Consider quarterly payments**: Since you're earning $1,920/month from your contract work (assuming 20 hours × $24), you'll likely need to make quarterly estimated payments to avoid underpayment penalties. The IRS withholding estimator tool is really helpful for calculating exactly how much extra to withhold or pay quarterly. Also, keep detailed records of all your income and any business expenses related to your contract work - those expenses can reduce your taxable income. Better to overpay slightly and get a small refund than to owe thousands plus penalties!

You're definitely smart to think ahead about this! I was in a very similar situation a couple years ago with multiple W-2 jobs plus freelance work, and I ended up owing about $2,800 at tax time because I didn't plan properly. Here's what I wish I had done from the start: **For your W-2 jobs:** Fill out new W-4 forms with both employers and check the "multiple jobs" box in Step 2. This tells them to withhold at a higher rate. You can also request additional withholding on line 4(c) if needed. **For your contract work:** This is where you need to be most careful. Set aside 30% of every contract payment immediately - don't touch that money! Contract work means you're paying both the employer and employee portions of Social Security and Medicare taxes (15.3% total) PLUS regular income tax. **Track everything:** Keep detailed records of all income and any business expenses related to your contract position. Things like mileage, supplies, home office space, etc. can reduce your taxable contract income. The IRS withholding estimator is your best friend here - plug in your expected income from all three sources and it'll tell you exactly how much you should be setting aside or having withheld. Since you're making good money from multiple sources, you'll likely need to make quarterly estimated payments to avoid underpayment penalties. Better to be safe than sorry!