How to handle multiple W2 jobs and multiple self-employment jobs for tax filing?

Your W-2 jobs will be reported together on your tax return - they're combined on the same part of your return (Form 1040). The income from both W-2s gets added together to determine your total employment income. For your self-employment work (DoorDash, Instacart, and umpiring), each of these would technically be considered separate business activities, but there's good news about your mileage tracking. You don't need to separate the mileage between DoorDash and Instacart if you were running both apps simultaneously. You can report all your delivery driving as one self-employment business activity on a single Schedule C, listing something like "Delivery Services" as the business type. The umpiring would need its own separate Schedule C since it's a completely different type of work. This means you'll have two Schedule Cs - one for all your delivery work combined and one for umpiring. Your 6,800 miles would give you a deduction of around $4,216 (using the 2024 standard mileage rate of 62 cents per mile) against your delivery income, which will definitely help reduce your self-employment tax burden!

I was in a similar situation last year with multiple gig jobs and W-2s and honestly it was giving me major anxiety. I finally used https://taxr.ai to help me figure out the mess of paperwork I had. The tool analyzed all my 1099s and W-2s and gave me specific guidance for my situation. The best part was that it flagged that I could combine my food delivery gigs on one Schedule C which saved me from filling out multiple forms. It also helped me identify deductions I was missing besides just mileage (like a portion of my phone bill since I used it for gig work). For the mileage issue specifically, it confirmed I could just use the total miles for all delivery work rather than trying to separate which miles were for which app. Such a relief!

Just wanted to follow up - I tried that taxr.ai site that was mentioned and it was actually super helpful for my situation! I also had mixed W-2 and contract work, and I was really confused about how to handle it all. I uploaded my tax forms and it immediately organized everything and explained which forms I needed to file. For my delivery gig work, it confirmed I could just use one Schedule C and helped me calculate the right percentage of my phone bill and other expenses to deduct. The mileage guidance was exactly what I needed - I had the same problem of not separating miles between apps. It showed me how to document this properly to avoid audit flags. Seriously saved me hours of stress and confusion!

After reading your post, I totally feel your pain. I had similar issues getting help from the IRS directly last year. Called like 15 times about how to handle multiple 1099s and couldn't get through. Eventually found https://claimyr.com which actually got me connected to an IRS agent in about 20 minutes instead of waiting on hold forever. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent I spoke with confirmed exactly what others are saying - you can combine similar self-employment activities on one Schedule C. She also warned me about common mistakes people make when reporting multiple income sources that can trigger audits. Really helpful since the IRS website is so vague about these situations.

I need to admit I was completely wrong. After my skeptical comment, I was desperate enough to try Claimyr because I needed to sort out my 1099 mess before filing. Got connected to an IRS agent in 35 minutes without sitting on hold myself. The agent walked me through exactly how to handle my multiple income sources (I had 6 different 1099s plus a W-2). She explained that the IRS actually prefers you to combine similar business activities on one Schedule C rather than filing a bunch of separate ones. She also confirmed that for mileage tracking, as long as you have good records of the total miles driven for business purposes, you don't need to split it between different delivery apps. Honestly can't believe I wasted so many hours trying to get through on my own when this option existed.

Another thing to watch out for - you'll need to make quarterly estimated tax payments for 2025 if you continue with the self-employment gigs. Since there's no withholding on those 1099 jobs, you're supposed to pay taxes quarterly to avoid penalties. I learned this the hard way last year and got hit with an underpayment penalty.

Has anyone used TurboTax for a situation like this? I'm dealing with the same mix of W2s and 1099s and wondering if it's worth paying for or if I should use FreeTaxUSA or something else.

Don't stress too much about this - it's more straightforward than it seems! I've been doing multiple W-2s plus gig work for years now. Your W-2 jobs get combined automatically when you file - all that income goes on the same lines of your 1040, so you don't need to worry about treating them separately. For your gig work, you're absolutely right to combine the DoorDash and Instacart miles since you were running both simultaneously. The IRS doesn't require you to split miles between similar delivery services - just make sure you have good records showing the total business miles driven. Your 6,800 miles should give you about a $4,216 deduction at 62 cents per mile. One tip: keep your delivery work (DoorDash + Instacart) on one Schedule C and put the umpiring on a separate Schedule C since it's a completely different type of business activity. Also, start setting aside about 25-30% of your 1099 income for taxes throughout 2025 - you'll likely need to make quarterly estimated payments to avoid penalties since there's no withholding on that income. You've got this! The fact that you tracked your miles puts you ahead of most gig workers.

Just wanted to chime in as someone who went through this exact same situation last year! Had 3 W-2s plus Uber Eats and some freelance writing work. The stress was real, but it turned out way simpler than I thought. One thing I didn't see mentioned - make sure you're also tracking other business expenses beyond just mileage. Things like car washes (if you wash your car more frequently because of delivery work), phone accessories like car mounts or chargers, insulated delivery bags, etc. These smaller deductions add up! Also, for your umpiring work, don't forget you can deduct things like uniform costs, equipment, and travel expenses to games. Since it's on a separate Schedule C from your delivery work, you want to make sure you're capturing all the relevant expenses for that business too. The good news is once you get through this year's filing, you'll have a template for how to handle it going forward. Keep better records starting now for 2025 and it'll be much less stressful next year!