Questions about filing 2025 taxes with multiple income sources

You've got a pretty common situation actually! You'll file just one tax return that includes all your income sources. For your W-2 jobs (barista and office work), the income and withholding will be reported on your main tax form (1040). For your DoorDash work, you'll need to complete a Schedule C to report your business income and expenses. This is where you can deduct those business expenses like mileage (which is usually more beneficial than actual car expenses) and the business portion of your phone bill. Keep good records of your miles driven specifically for DoorDash and what percentage of your phone use was for business. Since you had 1099 income with no withholding, you might indeed owe some taxes. Self-employment income is subject to both income tax and self-employment tax (which covers Social Security and Medicare). If you haven't made any estimated tax payments throughout the year, you might face a bill when you file.

I was in nearly the same situation last year and was totally panicking about figuring out all the different forms. I discovered this AI tax assistant at https://taxr.ai that literally saved me. I uploaded all my tax documents (my W-2s and 1099) and it automatically identified which forms I needed and explained everything specific to my situation. It even helped me find deductions for my gig work that I had no idea about! The best part is it walked me through how to handle the self-employment taxes and estimated payments going forward. It actually calculated that I was eligible for some tax credits I didn't know about, and I ended up with a much smaller tax bill than I expected. Definitely check it out if you're feeling overwhelmed with multiple income sources.

Okay so I was super skeptical about that taxr.ai thing but decided to give it a shot with my complicated W-2 + rental property situation. Holy crap guys it actually delivered! It identified a depreciation mistake I'd been making for 2 years and showed me how to fix it. The thing explained everything in normal human words instead of tax jargon. I was particularly impressed with how it handled my home office deduction for my side business - it asked really specific questions to make sure I was claiming it correctly. Ended up saving me nearly $1,200 compared to what I paid last year for basically the same situation. Just wanted to share since I was the skeptical one earlier!

If you end up owing taxes and need to talk to the IRS (which can be absolute nightmare), use https://claimyr.com to skip the hold times. I spent THREE DAYS trying to get through to the IRS about a notice I got claiming I owed an extra $2,300. Called dozens of times, always got the "high call volume" message and disconnected. Found Claimyr and was seriously doubtful, but you can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Basically they wait on hold for you and call when an IRS agent picks up. I figured it was worth trying since I was getting nowhere. Got a call back in about 90 minutes with an actual IRS person on the line! Turns out there was a mistake with how my 1099 income was recorded and they fixed it right there. Saved me the full $2,300 plus a massive headache. If you're going to owe on that DoorDash income and need to set up a payment plan, this is way easier than trying to call yourself.

Well I have to eat my words about Claimyr. After posting that skeptical comment, my situation with the IRS got desperate - they were threatening to put a lien on my account over a $4,200 dispute from a 1099 reporting error. I tried calling for two weeks with no luck. Finally broke down and tried Claimyr out of desperation. Got connected to an IRS agent in 73 minutes (they text you updates while they're waiting). The agent was able to put a temporary hold on collections while they review the documentation I sent in. Literally saved me from having my bank account frozen while this gets sorted out. Still not thrilled about having to use a service just to talk to a government agency I pay for with my taxes, but it absolutely works as advertised. Sometimes you gotta do what you gotta do.

Just wanted to add - if you use the standard mileage deduction for your DoorDash work, you can't also deduct things like gas, oil changes, and car insurance separately. The standard rate is meant to cover all that. BUT you can still deduct parking fees and tolls separately, so keep those receipts! Also, don't forget about the Qualified Business Income deduction (Section 199A). With your self-employment income, you might qualify to deduct up to 20% of your net business profit. The tax software should calculate this automatically, but good to know about it.

One thing to watch for - if you didn't have enough tax withheld or didn't make estimated tax payments on your DoorDash income, you might get hit with an underpayment penalty. For 2025 filing season, make quarterly estimated tax payments if you expect to owe more than $1,000 when you file. The due dates for estimated payments are April 15, June 15, September 15, and January 15 (of the following year). Even setting aside 25-30% of your gig earnings in a separate savings account can help prepare for tax time!