Oh that's a really good point I hadn't considered! I did have some taxes taken out of my paychecks that year. Do you know if I'd still be able to get that money back even though it's been a few years?

Yes, you can still get that money back! For 2018 returns, you have until April 15, 2022 to file and claim any refund owed to you. After that date, any unclaimed refund becomes property of the Treasury. If you're due a refund, there's actually no penalty for filing late. The penalties only apply when you owe taxes. So this might be a win-win - you comply with the IRS request and potentially get some money back at the same time.

Also worth noting that if you had self-employment income over $400, you're required to file too, even if your total income is below the standard threshold. Made that mistake my first year doing gig work.

Thanks for mentioning this. I asked her and surprisingly, she says she's never received any notices from the IRS questioning her filing status. Which seems weird to me? Wouldn't they automatically catch that we're married but filing differently?

The IRS system isn't as automated and efficient as people think. They have matching programs that flag obvious discrepancies like reported income not matching W-2s, but filing status verification is more complex and often requires human review. The IRS is severely understaffed and underfunded, so many issues that should be caught slip through. This doesn't mean you're in the clear though - they can still discover it during a random audit or if another issue triggers a review of her returns. The fact that she hasn't received notices yet is actually pretty common, but doesn't mean it won't become a problem later.

This is crucial. If you've been claiming the same dependents on your return while she's also claiming them as HOH, that's definitely going to raise red flags for the IRS.

24 H&R Block's software isn't any better. I switched to them thinking they'd handle it correctly and had the same issue. I think the problem is that they don't have a specific input field for the amount already reported as income on your W-2.

18 Thanks for sharing that about H&R Block. I was considering switching to them next year but maybe that's not the solution. I wonder if the more expensive tax prep options like a CPA would handle this correctly. Seems ridiculous that we have to jump through all these hoops for something that should be straightforward.

Thanks for sharing your experience. What kinds of deductions did they find that you weren't aware of? I'm trying to get a sense of whether I'm missing major opportunities by using TurboTax.

My CPA found several deductions I had missed completely. The biggest was properly documenting home office expenses since I occasionally work from home - this included a portion of utilities, internet, and even some home maintenance costs that I never would have thought to deduct. They also helped me properly categorize some of my investment expenses and found that some financial advisory fees I was paying were partially deductible. For your specific situation, they might find ways to optimize your stock grant taxation or identify deductions related to your attempted business venture that go beyond just the direct ad costs. A good CPA doesn't just file forms - they look at your whole financial picture and find optimization opportunities. The first year with mine, she saved me about $3,200 compared to what I would have paid using TurboTax, which more than covered her fee.

I've tried both and honestly they're pretty similar for stock stuff. The real difference comes with having someone who can give you planning advice BEFORE tax time. Software just helps you report what already happened, not optimize for the future.

That's a fair point about the planning aspect. I guess my experience was that H&R Block's interface specifically for stock grants and basis tracking was more intuitive than TurboTax, but you're absolutely right that neither one provides forward-looking strategic advice. For someone with the OP's income level, getting that proactive guidance could definitely be worth the CPA cost, especially with the mix of salary, stock grants, and trading activity. I still use software myself, but I'm also not dealing with $110K in stock gains!

This! I switched to an S-Corp last year and it saved me about $4k in self-employment taxes. Just make sure your salary is "reasonable" for your industry or the IRS might get suspicious. Also, you'll need to run actual payroll which adds some complexity and costs.

That's exactly right. The key is finding the sweet spot where the tax savings outweigh the additional costs and complexity. For my web development business, I waited until I was consistently making about $60k before making the switch. The "reasonable salary" part is crucial - you can't just pay yourself $1 and take everything else as distributions. I researched industry standards for my area and skill level, then documented why my salary was reasonable. Having this documentation is important if you're ever questioned. Also worth mentioning that with an S-Corp, you'll need to separate your personal and business finances completely, run payroll (usually through a service), and file more complex tax returns. There's software that helps with this, but it's definitely more work than a sole proprietorship.

I vaguely remember seeing something about this when I was researching, but wasn't sure if it applied to me since my income is relatively low. Does it work for all self-employed people or are there specific requirements? How complicated is it to calculate?