As a workaround, since both forms report income, could you just enter it as 1099-MISC? The tax owed should be the same either way since self-employment tax calculations wouldn't change, right?

I had the exact same issue last year! The key is looking under "Self-Employment Income" rather than searching for "1099-NEC" directly. In TaxAct, go to Federal → Income → Self-Employment Income, and you should see an option to add business income or self-employment income. When you select that, it will ask what forms you received, and 1099-NEC should be listed there. Don't worry about not having a formal "business" - freelance and contractor work counts as self-employment for tax purposes. You can just use your own name as the business name if prompted. The $23,450 you mentioned definitely needs to go on Schedule C (which TaxAct will generate automatically), and you'll also owe self-employment tax on that income, so make sure you're prepared for that additional tax liability beyond regular income tax.

Just an FYI - i made the mistake of just ignoring my quarterly payments one year thinking the penalty wouldn't be that bad. Big mistake! ended up owing about $1,200 in penalties and interest on top of my taxes. they calculate it daily so it really adds up.

I'm dealing with a similar situation right now and wanted to share what I've learned from my tax preparer. One thing that might help with your anxiety is knowing that the IRS has a "reasonable cause" exception for penalty relief when you have unexpected medical expenses. You'll need to document everything - medical bills, insurance statements, etc. - but it's worth keeping track of this stuff as you go. For your irregular musician income, consider setting aside a percentage of each gig payment into a separate "tax account" rather than trying to predict your total yearly income. Even if it's just 20-25% of each payment, it'll help you build up funds for those quarterly payments without the stress of trying to come up with large lump sums. Also, don't forget that you can deduct unreimbursed medical expenses that exceed 7.5% of your AGI, plus all your business expenses as a musician (equipment, travel, etc.). Sometimes people in tight financial situations overlook deductions that could significantly reduce what they actually owe. Hang in there - this stuff is stressful but there are definitely options to work with the IRS rather than just hoping for the best!

Something no one mentioned - if this is your first year as a sole proprietor, you technically qualify for a safe harbor based on last year's taxes. If you had zero tax liability last year, you may not need to make estimated payments your first year.

As a fellow sole proprietor who went through this same confusion, here's what I wish someone had told me clearly: You need to make quarterly PAYMENTS (not file returns) if you expect to owe $1,000 or more in taxes. The deadlines are April 15, June 15, September 15, and January 15. Your 20% savings rate might not be enough - I learned the hard way that you need to account for both regular income tax AND self-employment tax (15.3%). I typically set aside 25-30% to be safe. The easiest way to start is to use Form 1040-ES to calculate your first quarter payment, then you can just make payments online through IRS Direct Pay without mailing forms each time. Keep detailed records of all business income and expenses - you'll need them for your annual Schedule C filing. Don't stress too much about getting it perfect the first year. The IRS understands learning curves, and as long as you're making good faith efforts to pay what you owe, any small penalties are manageable. The key is to start now rather than wait!

I totally get your confusion about Line 20! I went through the exact same thing last year when I switched from using a tax preparer to doing my own return. As everyone else has mentioned, Line 20 is really just a catch-all for unusual situations that don't have their own specific lines elsewhere on the tax forms. Since you're doing Uber and delivery work as an independent contractor, here's what you need to know: all your business-related expenses (car expenses, phone bills, delivery bags, gas, etc.) should go on Schedule C, not anywhere on Schedule 1. This is actually better for you because Schedule C expenses reduce both your income tax AND your self-employment tax. For your W-2 job income, that just gets reported directly on Form 1040. Line 20 would only come into play if you had something really unusual like jury duty pay that you had to return to your employer, certain performing artist expenses, or repayment of unemployment benefits. Since you mentioned you're doing gig work and have a W-2 job, you almost certainly don't have any of these rare situations. Don't stress about trying to find something to put on Line 20 - if it doesn't apply to you, just leave it blank or enter zero. Focus your energy on making sure your Schedule C is accurate for your gig work, as that's where your real tax savings will be!

I went through this exact same confusion when I first started doing my own taxes! As everyone has explained really well, Line 20 is basically a "miscellaneous" line for unusual situations that don't fit anywhere else on the tax forms. Since you're an Uber driver and doing food delivery as an independent contractor, here's the key thing to remember: ALL of your business expenses (car expenses, phone bills, delivery bags, gas, maintenance, etc.) belong on Schedule C, not on Schedule 1. This is actually much better for you because Schedule C expenses reduce your business income before it gets hit with both regular income tax AND self-employment tax. Your W-2 income from your part-time job just goes directly on the main 1040 form - nothing complicated there. Line 20 would only apply if you had really specific situations like having to return jury duty pay to your employer, qualifying performing artist expenses, or repaying certain benefits. For someone doing standard gig work like you, these situations almost never apply. Don't stress about leaving Line 20 blank - that's exactly what most people should do! Focus on getting your Schedule C filled out correctly with all your business expenses, as that's where your real tax savings are going to come from. The IRS designed the forms so that common situations like yours have clear, obvious places for everything.

I just wanted to share an update that might help others still waiting - I finally received my Chase 1099-INT yesterday (Feb 12th), and my Citi forms showed up this morning! So it looks like they're definitely getting them out before the February 15th deadline that Natalie mentioned earlier. For what it's worth, the numbers on my official Chase 1099 matched exactly with what I calculated from my December year-end statement, so using those statements while waiting was definitely the right approach. The Citi form was off by about $0.43 from my manual calculation (probably due to rounding in monthly statements), but close enough that I'm glad I didn't stress too much about the delay. I ended up filing last weekend using my statement calculations, and now I can just keep the official forms for my records. Really grateful for all the advice in this thread - especially learning about the real legal deadlines and hearing from the tax preparer about using alternative documentation. Made this whole situation much less stressful than it could have been!

I just wanted to chime in as someone who's been through this exact situation multiple times over the years. The waiting game with Chase and Citi 1099s is unfortunately pretty predictable - they seem to consistently be among the last major banks to get their forms posted, often right up against that February 15th deadline. One thing I've learned that might help others: if you have multiple account types with the same bank (like both checking/savings AND investment accounts), the different 1099 forms often get processed on completely different timelines. So you might get your 1099-INT for interest income but still be waiting on your 1099-DIV or 1099-B forms from the same institution. For anyone still waiting, I'd definitely recommend the approach others have mentioned about using your year-end statements to get the numbers you need. I've been doing this for years and the official forms have always matched within dollars (usually exactly). The key is making sure you're looking at the right summary - for Chase, look for "Tax Documents" section rather than just regular account statements. Also, if you're really in a time crunch, consider setting up a callback through their phone system rather than waiting on hold. Most of these banks now have options where they'll call you back when a representative is available, which saves a lot of frustration.