You should look into filing as an S-Corp if your business continues to grow. I switched from sole proprietor to S-Corp once I was consistently making over $40K in profit, and it saved me thousands in self-employment taxes. You pay yourself a reasonable salary (which is subject to FICA taxes) and can take the rest as distributions (which aren't). There are additional costs like incorporation fees and more complex tax filings, but the tax savings can be substantial once you reach a certain income level.

Connor, based on your numbers ($6,500 in sales), you'll definitely need to file taxes if your net profit exceeds $400. The key word here is "net" - so you'll subtract all your legitimate business expenses (materials, workspace costs, etc.) from that $6,500. Here's what you'll need to do: • File Schedule C (Profit or Loss from Business) with your Form 1040 • If your net profit is over $400, also file Schedule SE for self-employment tax • Keep meticulous records of ALL business expenses - they're your friend for reducing taxable income • Consider setting up a separate business bank account to make tracking easier going forward Don't worry about not being formally registered - the IRS considers you self-employed regardless of business structure. Start gathering those receipts now and consider using accounting software like QuickBooks or even a simple spreadsheet to track everything. Better to be over-prepared than caught off guard!

Just to add a small clarification that might help - there's also a separate ordering rule for Roth IRA withdrawals that determines what comes out first: 1) Regular contributions come out first (always tax and penalty free) 2) Conversion contributions come out next (might be subject to penalties if within 5 years of conversion and under 59½) 3) Earnings come out last (subject to tax and possibly penalties if you don't meet requirements) Since you're over 59½ and if your first Roth contribution was indeed in 2019, then starting in 2024, everything comes out tax and penalty free including earnings. This assumes 2019 was truly your first-ever Roth IRA.

This is a really helpful discussion! I wanted to add one more consideration that might be relevant for your planning. Even though you'll be able to withdraw everything tax and penalty-free once you meet both the age and 5-year requirements, it's worth thinking about the timing strategically. Since Roth IRAs don't have required minimum distributions (RMDs) like traditional IRAs do, you might want to consider leaving the money invested longer if you don't immediately need it. The tax-free growth can continue indefinitely, and it's one of the best tax-advantaged accounts you can pass to heirs. Also, if you're planning any large withdrawals, consider spreading them across multiple tax years to avoid bumping yourself into higher tax brackets with other income - though this is more relevant if you have traditional IRA distributions or other taxable income in the same years. The flexibility of having penalty-free access is great peace of mind, but the longer you can let that money grow tax-free, the better!

Warning about the red ink forms - order them NOW from the IRS if you're going that route! I waited until January last year and they were completely out of stock. Ended up having to buy them at an office supply store for like $50 which was highway robbery but I was desperate. The IRS sends them for free but they run out every year during tax season.

I went through this exact same confusion last year! Here's what worked for me after making some mistakes: First, yes you absolutely need Form 1096 - it's like a cover sheet that tells the IRS "hey, I'm sending you these 1099 forms." You attach it to Copy A of your 1099-NEC when mailing to the IRS. For the red ink issue - if you're only dealing with one or two forms, honestly just order the official ones from the IRS website (they're free but take 7-10 days). If you need them faster, most FedEx Office locations carry the official red ink versions for about $3-4 per form. BUT here's what I wish someone had told me earlier: since you're dealing with attorney fees on a 1099-NEC, double-check that you actually owe more than $600 to this lawyer in the tax year. If it's under $600, you don't need to file the 1099-NEC at all (though you can still deduct the expense on your business taxes). Also, make sure you have the lawyer's correct TIN/SSN on the form - the IRS gets really cranky about mismatched taxpayer identification numbers. I learned that one the hard way! The electronic filing through FIRE is honestly easier once you get past the initial setup, but for just one form, paper might be simpler for a first-timer.

Has anyone had experience with e-filing a deceased taxpayer's return as a Personal Representative? I'm trying to avoid paper filing if possible, but I'm not sure if the major tax software programs properly handle this situation.

I'm currently going through this same situation with my father's estate. One thing I want to emphasize that hasn't been fully covered - keep detailed records of EVERYTHING you do as Personal Representative. The IRS may request documentation later, and having organized files will save you major headaches. Also, consider getting an EIN (Employer Identification Number) for the estate if there are any ongoing income-generating assets or if you expect the estate to remain open for an extended period. This separates estate income from the final 1040 and helps with record-keeping. For the signature issue specifically, I found it helpful to practice writing "John Doe, Personal Representative for [Deceased's Name], Estate" a few times before signing the actual return. The IRS wants clarity about who is signing and in what capacity.

I just want to add another option that helped me when I was in a similar situation - check if Goodwill uses a third-party tax document service like TaxSlayer or Paychex for W2 distribution. Some employers outsource their tax document delivery to these services. You can usually find this information by calling Goodwill's main HR line and asking specifically which service they use for W2 distribution. If they do use a third-party service, you might be able to access your W2 directly through that service's website using your SSN and some basic employment information. Also, if you're really pressed for time and can't reach anyone at Goodwill, remember that you can call the IRS Taxpayer Advocate Service at 1-877-777-4778. They're specifically designed to help taxpayers who are having problems that can't be resolved through normal IRS channels, including issues with employers not providing W2s. They're separate from regular IRS customer service and often more effective at getting results quickly. Don't panic - this happens to thousands of people every tax season and there are always solutions available!

I work in HR and wanted to add some additional context that might help. First, employers are legally required to mail W-2s by January 31st to employees' last known address. If you moved after leaving Goodwill and didn't update your address with them, that's likely why you haven't received it yet. Here's what I'd recommend in order of priority: 1) Call Goodwill's regional payroll department (not your local store) and provide your current address. They can often email you a digital copy immediately while sending a corrected one to your new address. 2) If you can't reach them by phone, send a written request via email or certified mail. Include your full name, SSN, dates of employment, and current address. This creates a paper trail showing you made reasonable efforts. 3) Check if you still have access to any employee portal or payroll system you used while employed there. The good news is that if you truly can't get your W-2 after reasonable efforts, the IRS won't penalize you for filing late as long as you can document your attempts. Keep records of all your contacts with Goodwill. If push comes to shove, you can file Form 4852 using your last paystub information, but it's always better to get the actual W-2 if possible to avoid potential discrepancies later.