Have you considered looking for a new job? Any company that messes up your pay and then drags their feet fixing it doesn't deserve your loyalty. Just sayin' 🤷‍♂️

This is definitely frustrating, but you're absolutely right to push back! Your employer made the mistake with your W-4, so they should fix it properly. Altering your W-2 could create tax complications for you down the road. I'd recommend being persistent - document everything in writing, reference the IRS guidelines others have mentioned, and don't accept "20-30 weeks" as reasonable. They have payroll systems that can handle corrections much faster than that. Keep escalating up the chain if needed - this is your hard-earned money we're talking about!

The community college near me offers free tax preparation through their accounting program! Students get real-world experience and you get free tax help - even with self-employment income! I'm SO ANGRY that the IRS and tax prep companies don't advertise these options more widely!!! Check your local community colleges, universities with accounting programs, or even law schools. Many have IRS-certified volunteer programs that can handle self-employment returns at no cost. You deserve access to free filing regardless of your income source!

I wish I had seen this thread earlier this tax season! As someone who just started freelance consulting work, I fell into the exact same trap - spent three weekends trying different "free" platforms only to hit paywall after paywall once I mentioned my 1099-NEC income. What's really frustrating is that the IRS's own Free File page makes it sound like there are plenty of options, but when you actually try to use them, it's a different story entirely. I ended up using Cash App Taxes based on a recommendation from another forum, and honestly, it worked better than I expected. The interface was clean, it walked me through all the Schedule C stuff without trying to upsell me, and both my federal and state returns were actually free. My only advice is to gather ALL your business receipts and expense documentation before you start - having everything organized made the process so much smoother. Thanks for sharing your experience - it's reassuring to know others have navigated this successfully!

One thing nobody has mentioned is that Missouri has some specific state-level considerations for S-corps that differ from some other states. I'm a MO agent too, and our state taxes S-corps a bit differently than sole props. Make sure whoever you work with is familiar with MO specifically. Also, did your CPA mention anything about how the 20% QBI deduction factors into this decision? That's another big piece of the S-corp vs LLC analysis that might affect your choice.

Great point about Missouri-specific considerations! The QBI deduction interaction is crucial and often overlooked. For S-corps, the QBI deduction applies to your business income MINUS the W-2 wages you pay yourself. So if you're paying yourself a high salary (like that 70% some CPAs recommend), you're reducing the income eligible for the 20% QBI deduction. This creates an interesting balance - you want your salary high enough to avoid IRS scrutiny but not so high that you lose significant QBI benefits. In many cases, this actually supports the 50-60% salary range that others have mentioned here. Missouri also doesn't conform to federal S-corp elections automatically, so you need to make a separate state election. Plus MO has that franchise tax for S-corps that LLCs don't pay. These state-level costs should definitely factor into your breakeven analysis. I'd recommend running the numbers with both federal AND Missouri tax implications included. The total picture might be different than just looking at federal savings alone.

@Liam McGuire - I just went through this exact decision process last month! The combination of student debt stress and stock grant confusion is rough, but you can definitely figure this out. Here's my practical approach: First, don't panic about the 30-day deadline - you still have time to get the right information. Email your HR team TODAY asking for: 1) The current 409A valuation per share, 2) Your exact number of shares, 3) Your exercise/strike price (if any), and 4) Whether this is an ISO, NSO, or RSU grant (the tax treatment differs slightly). While you're waiting for those numbers, think about your risk tolerance. Filing 83(b) is essentially making a bet that your company will grow significantly over the next 4 years. If you're at a very early-stage startup with lots of growth potential, it usually makes sense. If you're at a more mature company that's already highly valued, the benefits are smaller. Given your $42k in student loans, I'd suggest calculating what that immediate tax hit would mean for your monthly budget. If it's going to stress you out financially or delay your loan payments, that's a real cost to factor in too. Sometimes the peace of mind from better cash flow is worth more than potential tax savings. One last thing - if you decide to file, make sure you send it certified mail and keep copies. The IRS is strict about the 30-day deadline and proper filing procedures. Don't let a paperwork mistake invalidate your election!

@Liam McGuire - As someone who works in equity compensation at a tech company, I see employees struggle with this decision all the time. The good news is that your situation (early career, student debt, first stock grant) is actually pretty common and manageable. Here's what I tell everyone: the 83(b) decision comes down to three key factors - current valuation, growth expectations, and your personal cash flow. Since you mentioned this is part of a promotion package, I'm guessing your company values talent retention and likely has decent growth prospects. The student loan concern is totally valid, but remember that you're not committing to monthly payments - this would be a one-time tax event that you'd handle during your regular tax filing. If the current 409A valuation is low (which it often is for earlier-stage companies), your immediate tax hit might be surprisingly small - maybe $500-2000 depending on your grant size and company stage. My recommendation: Get those specific numbers from your finance team this week, then run a simple calculation. If the immediate tax cost is less than what you'd pay in student loan interest over 2-3 months, and you believe in your company's growth potential, filing 83(b) usually makes financial sense. Don't let fear of the unknown drive this decision - get the real numbers and then you can make an informed choice. You've got this!

A quick tip if you do take this job - I make a deduction worksheet for all 1099 work. Track mileage between work sites (not commuting), any supplies you buy, portion of phone/internet if you use them for work, professional subscriptions, software, etc. Keep ALL receipts, take photos of them with your phone right away (they fade!). Also track any home office space if you do some work from home.

Just wanted to add another perspective here - I was in almost the exact same situation last year (required to work in their office, set schedule, but given a W9). After doing some research, I decided to take the job but immediately started documenting everything that showed I was really an employee, not a contractor. Things like: emails about required work hours, office policies I had to follow, equipment they provided, training materials, etc. After 6 months, I filed Form SS-8 with the IRS to get an official determination on my classification. The IRS ruled I was misclassified as a contractor and should have been an employee. Long story short - I got a refund for the extra self-employment taxes I paid, and my employer had to reclassify me and pay their portion of payroll taxes going forward. It was a bit of a process but totally worth it financially. If you take this job, document everything that shows they control how, when, and where you work. It could save you thousands later if you need to challenge the classification.