Thanks for the tip about checking that box on the W-4! I didn't know there was a specific option for multiple jobs. Does this mean I should check this box on both job W-4s or just the second one?

You should only check the multiple jobs box on one of your W-4 forms, not both. If you check it on both, you'll likely have too much withheld and end up with a large refund (which means you're giving the government an interest-free loan all year). For the most accurate withholding, I'd recommend using the IRS Withholding Estimator on their website. It lets you enter info from both jobs and will tell you exactly how to fill out both W-4 forms for the perfect withholding amount.

Did you find that working that many hours was worth it financially? After taxes, did you still come out way ahead? Wondering if killing myself with 70-hour weeks would actually leave me with much after Uncle Sam takes his cut.

But they did withhold Social Security and Medicare - just not federal income tax. Does Form 8919 still apply in my situation?

You're right - Form 8919 wouldn't apply in your situation since your employer did properly withhold Social Security and Medicare taxes. I misunderstood your original post. For federal income tax withholding issues, there unfortunately isn't an equivalent form. Since you correctly filled out your W-4, this is definitely the employer's mistake, but as others have mentioned, the IRS still considers the tax liability yours. Your best options are still to speak with management about potential compensation and set up a payment plan with the IRS for any amount you can't pay immediately.

This! I had a similar situation and got the penalties removed. You still have to pay the base tax but it saved me a few hundred in penalties. The IRS form to request this is pretty straightforward.

That's a great tip about insurance discounts! I hadn't even thought about that angle. Do you remember what documentation you needed to provide to your insurance company to get the discount?

I just needed to provide a copy of the installation certificate and proof of purchase. They sent an adjuster out to verify it was properly installed and connected to our natural gas line. The whole process was pretty simple - took about 2 weeks to get approved and the discount was applied to my next bill. Some companies might also want to see that it's been inspected by your local municipality, so make sure you have those permits in order too.

That's correct! If the primary purpose of the generator is to power medically necessary equipment, it can potentially qualify as a medical expense deduction. You'd need documentation from a doctor stating the medical necessity, and the expense would need to exceed 7.5% of your AGI when combined with other medical expenses. My mother has a similar situation with her CPAP machine and was able to deduct part of her generator purchase.

I've filed with Form 8960 for the past three years and haven't been audited. It's not a red flag by itself - lots of people pay NIIT. What matters more is large discrepancies between what you report and what the IRS already knows from your 1099s and other information returns. Just make sure all your investment income is properly reported, and the Form 8960 calculations are correct. And yes, put the amount from line 21 on Schedule 2, Part II, line 11 as everyone has said.

Thanks for the reassurance! That's helpful to know it's not automatically going to trigger extra scrutiny. I'll make sure all my 1099s match up with what I report.

This is such a good point! I was using the free version of [tax software] and kept looking for Form 8960 but couldn't find it anywhere. Ended up having to upgrade to the "premium" version which cost $70 more just to access this one form. Feels like a scam but I guess that's how they make their money.

This is so incredibly helpful and encouraging! I've been worried that my deafness would be a major obstacle, but you've made me see how it could actually be structured as an advantage. Would you mind sharing what transcription app you use for those video calls? And did you mention your hearing status upfront in your marketing or just your communication preferences?

I use Otter.ai for most transcription needs - it works really well for video calls and integrates with Zoom. I've also had good experiences with Microsoft's transcription tools which are built into Teams if your clients prefer that platform. I don't explicitly mention being hard of hearing in my initial marketing materials. Instead, I focus on the benefits of my communication style - "comprehensive written documentation," "efficient digital workflows," and "secure client portal communications." However, I am open about it once I'm in direct communication with potential clients. I frame it positively: "I've developed a streamlined communication system that ensures nothing gets missed and all advice is documented for your records." Most clients actually appreciate this approach, especially when they realize they can send questions at 10pm and get a thoughtful written response instead of playing phone tag.

Do most self-employed CPAs offer payment plans for clients? I'm wondering if that's something I should build into my business model from the start.