Any recommendations for tracking apps? I have like 5 different side hustles and keeping track of everything is a nightmare.

I've had good results with QuickBooks Self-Employed for tracking throughout the year. It connects to your bank accounts and credit cards, then automatically categorizes expenses. You can also use it to track mileage if you drive for any gigs. It's about $15/month but honestly saves me hours of headaches at tax time. If you want something free, a simple Google Sheet works too - just be disciplined about entering your income and expenses regularly. The key is separating business vs. personal spending, which gets messy fast if you're not tracking consistently.

How much do you need to make before you have to do the quarterly payments? I make maybe $800-1000 a month from my side gig.

Thanks for this additional perspective! I never received any CP2000 notices or any communications from the IRS about this, so I'm guessing they don't have any records of this cash income (it was truly a small cash side gig). As for state taxes, I live in a state with no income tax so thankfully that's not an issue for me. I think I'll follow the consensus advice here and not worry about amending the return at this point. The amount is tiny, I've already overpaid, and it sounds like the assessment period has passed anyway. Really appreciate everyone's input!

You're in a good position then without state income tax concerns and no CP2000 notice. At this point, the administrative burden of filing an amendment likely outweighs any benefit, especially since you've already overpaid. The IRS generally focuses their resources on cases where additional tax is owed rather than situations like yours. Glad you've found clarity on how to proceed! Sometimes the best action is simply moving forward and applying what you've learned to future tax years.

I think this is a good point. Wasn't there a special rule for self-employment tax though? Like you don't owe SE tax if the amount is under $400 for the year or something?

11 Does Cash App Taxes handle 1099 income? I tried using Credit Karma last year but it seemed confused by my freelance income situation.

7 Yes, Cash App Taxes handles basic 1099 income pretty well now. They've improved it a lot since the Credit Karma days. For simple freelance situations, it works fine. However, if you have more complicated self-employment situations with lots of business deductions or inventory, you might want something more robust. For your situation with just one W-2 and one 1099, it should work perfectly and stay completely free. The interface is cleaner now too compared to when it was Credit Karma Tax.

14 The IRS free file is what I use every year! It's buried on the IRS website though. Make sure you go through the IRS site directly (irs.gov/freefile) and not directly to TaxSlayer or other sites, otherwise you might not get the truly free version.

Thanks for the direct answer! I'll definitely get that resale certificate squared away first. For the charitable contribution part - if I explicitly note on the invoice that I'm offering a 5% charitable discount to the nonprofit, can I then claim that 5% as a charitable contribution? Or does it have to be a completely separate transaction?

You can document the discount as a charitable contribution on the same transaction, but you need to explicitly state it as a "charitable discount" or "donation" on the invoice. Keep in mind you're not donating the item - you're donating a portion of its value through the discount. The important thing is clear documentation. Your invoice should show the regular price, then the charitable discount amount as a separate line item (not just a generic "discount"), and note the nonprofit's tax ID number. This creates the paper trail you need. And remember, this has nothing to do with sales tax - it's completely separate.

Direct pay permits saved my sanity! I run a supply company and dealing with all the different exemption certificates was a nightmare. Now about 80% of my tax-exempt customers use direct pay and I don't have to worry about their documentation. Definitely worth asking your customers about.

Thanks for bringing up disability insurance - that's something I definitely need to address. Do you have suggestions on what percentage of income should be covered? And regarding the student loans vs. retirement accounts, would you recommend maxing out all available retirement vehicles before accelerating loan payments?

For disability insurance, most financial advisors recommend covering 60-70% of your income, but as a surgeon, you should look for specialty-specific coverage with true "own-occupation" definition of disability. This means you get paid if you can't perform surgery specifically, even if you could still work in medicine in other capacities. Regarding retirement vs. loans, it depends on the interest rates, but generally yes - max out tax-advantaged accounts first, especially if your loans are under 6-7%. The tax advantages of retirement accounts (particularly when combined with the right business structure) almost always outperform the guaranteed return of paying off low or moderate interest debt. With your income level, you should be able to make significant progress on both simultaneously.

Completely agree. I use Gusto for my S-Corp payroll and it's been seamless. Automatically handles all the tax filings, makes the correct deposits, and generates all the required forms. The reasonable compensation question for S-Corps is where having a good CPA really helps though.