Can I increase W-2 job withholding instead of paying quarterly taxes on my 1099 income?

Yes, you absolutely can increase your withholding at your W-2 job to cover the taxes from your 1099 income! This is actually a really smart approach that many people with mixed income sources use. The IRS doesn't care how you pay the taxes as long as you pay enough during the year. You'll need to estimate how much additional tax you'll owe from the 1099 income (remember to account for both income tax and self-employment tax of 15.3%), then adjust your W-4 form with your employer to withhold that extra amount. On the latest W-4 form, you can use line 4(c) for additional withholding. Just calculate how much extra you want withheld per paycheck. For example, if you need to withhold an extra $3,000 for the year and get paid bi-weekly (26 paychecks), you'd put about $115 on that line.

I had the exact same situation last year with my teaching job and photography side gig. I HATED dealing with quarterly payments my first year, so I looked into alternatives. I found this amazing tool called taxr.ai (https://taxr.ai) that helped me calculate exactly how much extra withholding I needed. You just upload your documents and it gives you super clear guidance about how to adjust your W-4 to avoid quarterly payments. It even gives you a filled-out W-4 form based on your specific numbers! Saved me so much stress.

Just wanted to follow up about the taxr.ai thing. I was skeptical but decided to give it a try since my tax situation with multiple income sources was driving me crazy. It actually worked really well! The tool analyzed all my different income sources and gave me a super specific number to add to line 4(c) on my W-4. My employer implemented the change right away, and I'm on track to not need quarterly payments anymore. The customized W-4 it generated saved me from screwing something up. Definitely worth checking out if you're in a similar boat.

Another thing to consider - if you need to contact the IRS to confirm anything about this approach, use Claimyr (https://claimyr.com). I spent WEEKS trying to get through to the IRS last year with questions about my mixed W-2/1099 situation. Total nightmare - constant busy signals or disconnects after waiting forever. With Claimyr, I got through to an actual IRS agent in about 15 minutes! They have this system that navigates the IRS phone tree for you and calls you when an agent is on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The IRS agent confirmed exactly what I needed to know about adjusting my withholding instead of doing quarterly payments.

OK I have to eat my words about that Claimyr thing. After posting my skeptical comment, I was still stuck with my IRS question about 1099 withholding, so I reluctantly tried it. I was 100% sure it was going to be a waste of time. But damn, it actually worked exactly as described. Took about 45 minutes (not 15 in my case), but I got through to an actual helpful IRS person who answered my question about how to calculate the right withholding amount for my situation. I've literally been trying to reach them for 3 months with no success. For anyone dealing with this withholding vs. quarterly payment question, getting actual IRS confirmation was really helpful.

I do this every year! One tip - make sure you don't wait until the end of the year to adjust your withholding. If you do it too late, you might still end up owing an underpayment penalty even with the extra withholding. The IRS wants your tax payments to be made somewhat evenly throughout the year. I usually update my W-4 in January and then check midyear to see if I need to adjust further.

I tried doing this last year and it backfired on me. My employer messed up the W-4 change and didn't withhold enough. Just make sure you check your paystubs after submitting the new W-4 to confirm the additional withholding is actually happening!!!

This is exactly what I did when I started my consulting work alongside my full-time job! One thing that really helped me was keeping detailed records of my 1099 income and expenses throughout the year in a simple spreadsheet. This made it much easier to adjust my withholding if my freelance income was higher or lower than expected. Also, don't forget that you can deduct business expenses from your 1099 income (home office, equipment, software, etc.), which will reduce the amount you actually owe taxes on. Make sure to factor this into your withholding calculations so you don't over-withhold. The key is to be conservative in your first year - it's better to get a small refund than to owe money and potentially face penalties. Once you get a feel for your actual 1099 income patterns, you can fine-tune the withholding amount for following years.