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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.
Does the QBI deduction apply even for side gig income? I thought that was only for like full businesses with employees and stuff.
The QBI deduction absolutely applies to side gig income! It's available for most self-employed individuals, regardless of whether you have employees or not. Even if you just drive for DoorDash or Uber on weekends, that income generally qualifies. There are some limitations and phase-outs at higher income levels (above $170,050 for single filers in 2024), but for most side-giggers, you can take the deduction without complications. It's essentially a free 20% deduction on your net business profit, which can significantly reduce your taxable income.
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!
Yes, the IRS does sometimes grant a waiver for the underpayment penalty for first-time filers who weren't aware of the requirement to make estimated payments. This falls under their "first-time penalty abatement" policy. You generally need to have a clean compliance history for the past three years with no penalties. When you file, you can request this waiver by calling the IRS after you receive a penalty notice, or your tax preparation software might have an option to include a statement requesting the waiver due to reasonable cause. Just be honest about being new to self-employment and not understanding the estimated tax requirements previously.
Thank you everyone for such helpful advice! I've learned so much from all of your comments. I'll check out those resources mentioned and definitely start tracking my expenses better. I'm feeling way less panicked about tax season now!
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Make sure your loan has a reasonable interest rate too! If the IRS thinks the rate is too low, they might consider it a "below-market loan" and apply something called "imputed interest" rules. This could potentially create taxable interest even if no interest was actually paid.
Can you explain more about these imputed interest rules? Our loan is at 3.5% - is that considered reasonable? I don't want to get caught in some complicated tax situation.
Sure thing! The IRS has what's called the Applicable Federal Rate (AFR), which is the minimum interest rate they consider legitimate for loans. If your rate is below the AFR, the IRS might "impute" interest, meaning they treat the loan as if it charged the minimum rate, even if it didn't. A 3.5% rate is likely fine for 2024-2025. The AFR changes monthly, but has generally been in the 2-4% range for mid-term loans recently. As long as your rate is at or above the AFR that was in effect when your loan was made, you should be safe from imputed interest complications.
Has anyone used TurboTax to generate a 1099-INT for family loans? Does it handle these situations well? We've always used it for our regular taxes but never had to deal with issuing forms before.
TurboTax isn't great for generating 1099-INTs. For issuing forms, I've found it easier to just order the official forms from the IRS website or use their online system. Much simpler than trying to make TurboTax do something it wasn't really designed for.
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Has anyone here had their software deductions questioned in an audit? I'm curious what documentation the IRS actually wants to see. I'm about to invest in some expensive quilting design software and want to make sure I'm keeping the right records from the start.
I went through an audit three years ago for my cake decorating business, and they did look at my software deductions. They wanted to see: 1. The receipt/invoice showing the purchase date and amount 2. Proof it was paid from my business account or, if paid personally, documented as a business expense 3. A description of how the software is used specifically for my business 4. Documentation showing I was actually using it for business purposes (I showed them designs I created for clients using the software) Keep all your receipts, maybe take screenshots of business projects you complete using the software, and maintain a clear connection between the software capabilities and your business services. They were actually pretty reasonable about the whole thing.
Don't forget that if you get the subscription software like the ERP system you mentioned, that's considered a regular business expense and gets deducted each year as you pay for it. Only the permanent software license needs the Section 179 vs. Schedule C decision. Also, if you're using a tax preparation software like TurboTax or H&R Block, they'll walk you through both options and usually recommend the simplest approach automatically. That's what I do for my pet portrait business and it's worked fine for years.
This is good advice. I use QuickBooks Self-Employed and it categorizes my subscription software automatically as regular business expenses. Makes tax time so much easier when everything is already sorted correctly throughout the year.
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For your 1099 contractor income, don't forget about estimated quarterly tax payments going forward! Since taxes aren't withheld like they are for W-2 employment, you'll need to make those payments yourself. I learned this the hard way and got hit with an underpayment penalty my first year of freelancing.
Is there a minimum amount of 1099 income before you need to do quarterly payments? Like if it's just a side gig making a few thousand?
You generally need to make quarterly estimated tax payments if you expect to owe at least $1,000 in taxes when you file your return. Even for side gigs, this can happen quicker than you'd think when you factor in both income tax and self-employment tax (which is about 15.3%). A good rule of thumb is to set aside around 25-30% of your 1099 income for taxes, depending on your tax bracket. The IRS has a form called 1040-ES that helps you calculate what you should pay quarterly.
Anyone use anything besides TurboTax for mixed W-2 and 1099 income? Their self-employment section gets expensive real quick...
I switched to FreeTaxUSA and it handles both W-2 and 1099 income really well. Federal filing is free and state is like $15. Way cheaper than what TurboTax charged me for self-employment.
Reginald Blackwell
Have you checked if there were any return of capital distributions in your Webull account? Sometimes these can cause weird reporting issues where Box 5 and Box 1a don't match up. Return of capital reduces your cost basis but isn't taxable as a dividend, which could explain the discrepancy.
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Gabriel Ruiz
•That's an interesting idea! I'm not sure if I had any return of capital distributions. Is there a way to check that on the Webull platform? I'm still pretty new to investing and all these tax forms are confusing.
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Reginald Blackwell
•You can check by logging into your Webull account and going to the "Account" tab, then selecting "History" and filtering for "Dividends." Look for any entries labeled as "Return of Capital" or "ROC." If you see any of these, that's likely your culprit. Return of capital distributions are not technically dividends, but sometimes brokers report them incorrectly. If you find this is the case, you could try explaining this to TurboTax support as the reason for the discrepancy. Alternatively, you might need to manually override TurboTax's error check, though some tax software doesn't allow this without a paid upgrade to a premium version that allows manual entries.
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Aria Khan
I had this exact problem with Webull last year! It's definitely a Webull error. I called their tax support line (took forever to get through) and they admitted it was a known issue with their reporting system. They eventually sent me a corrected 1099-DIV but it took like 3 weeks. If you're trying to file now and don't want to wait, I'd do what others suggested and just make Box 5 equal to Box 1a. It's the technically correct way anyway since 199A dividends can't exceed total ordinary dividends.
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Everett Tutum
•Did Webull send the corrected form to the IRS too? I'm worried about making changes on my end but then having the IRS records show something different.
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