I've tried both! The box is simpler but less accurate. The worksheet was more accurate for us BUT you need to redo it if your income changes at all during the year. We both got raises mid-year and ended up owing $800 because we didn't update our W-4s.

I'd definitely recommend adjusting yours first since you're the higher earner - that way you can see the immediate impact on your paychecks and get a feel for whether you're on the right track. From my experience, making changes to both W-4s simultaneously can make it really hard to tell which adjustment is causing what effect. Start with yours, give it 2-3 pay periods to see how it looks, and then fine-tune your husband's if needed. Also, just a heads up - if either of you gets performance bonuses or other variable income throughout the year, you might need to revisit this. Bonuses can throw off your withholding calculations pretty significantly!

TurboTax is still overpriced compared to other options. FreeTaxUSA would have done the same return for about $15 federal + $15 state. Same forms, same everything.

You're probably right. I went with TurboTax out of familiarity since I've used it before, but will definitely check out FreeTaxUSA next year. Even at $89 I saved nearly $180 compared to H&R Block, but saving another $60+ would be even better. I think a lot of these tax prep businesses rely on people not knowing the alternatives or being afraid to file themselves. After doing it myself, I realized it wasn't nearly as complicated as they made it seem.

This is really helpful advice! I'm in a similar boat - got quoted $280 at H&R Block for a W-2 plus some Uber driving income. I had no idea there were free options that could handle Schedule C and SE forms. Quick question - when you mention trying the free software first just to see what forms are needed, can you actually go through the whole process without filing and then use that information elsewhere? I'm nervous about starting something and accidentally submitting it. Also, for someone who's never filed with 1099 income before, are there any common mistakes I should watch out for when doing it myself? I don't want to mess something up and end up owing penalties later.

That's really helpful to know! Did you use a tax professional or did you file yourself? I'm in the same boat but nervous about doing it wrong.

This is really reassuring to hear from someone who's actually been through this exact situation! I'm in a similar spot with health issues taking priority over work right now. Just to clarify - when you resumed filing and claimed those losses, did you need any special documentation beyond your old Schedule D? I'm wondering if I should also keep my brokerage statements from the year I realized the losses, just in case the IRS wants to see the original transaction details.

I need to jump in here because this suggestion could lead to audit trouble. The IRS is very clear that expenses must be allocated properly between different activities. You can't take expenses that are clearly related to your W2 job and artificially assign them to a side business just to get a deduction. If you have a legitimate side business, then yes, you can deduct expenses that are actually for that business. But creating a side business just to deduct W2 expenses, or improperly allocating W2 job expenses to a side business, could be considered tax fraud.

Sorry, I should have been clearer. I wasn't suggesting creating a fake business or misallocating expenses! I meant that if OP already has a legitimate side business, some expenses that benefit both activities (like a cell phone used for both) could have the appropriate portion allocated to the side business. Many salespeople I know do have side gigs like consulting or training, and properly allocating shared expenses is totally legitimate. But you're absolutely right that you can't just make up a business or improperly allocate expenses that are purely for your W2 job.

This is really helpful advice, especially the point about tracking everything even though we can't deduct it federally right now. I hadn't thought about the 2026 expiration date - that gives me hope that this situation might improve in a couple years. The education credits angle is interesting too. Some of those sales training courses I mentioned taking were pretty expensive, so if they could qualify for education credits instead of business deductions, that might actually work out better. Do you know if there are specific requirements for training to qualify as education credits for someone who's already working in sales? Also, I'm curious about your experience approaching your sales manager about expense reimbursement. What kind of expenses were they most willing to cover, and how did you frame the conversation? I'm worried about seeming like I'm complaining about costs or asking for special treatment.

Great question about the education credits! For sales training to qualify for education credits, it generally needs to either maintain or improve skills required in your current job, or meet requirements of your employer/law for keeping your job. The tricky part is that it can't be training that qualifies you for a new trade or business. Since you're already working in sales, courses that enhance your existing sales skills (like advanced negotiation, customer relationship management, or industry-specific product training) have a good chance of qualifying. Keep all documentation showing the course content relates directly to your current role. For the expense reimbursement conversation, I framed it as an investment in my performance rather than asking for help with costs. I prepared a simple proposal showing how certain expenses (client entertainment, training, professional subscriptions) directly contributed to my sales results. I used specific examples like "the sales methodology course I took helped me close X additional deals worth $Y in commissions to the dealership." Most sales managers understand that top performers need tools and training to stay competitive. The key is connecting your expenses to measurable business results and presenting it as a win-win rather than just asking for money back.

I did! I got a $300 bill reduced to $75 by calmly pointing out that we'd never discussed rates for phone consultations and that I'd have chosen email (which was covered in my package) had I known. I basically said "I value your expertise and am happy to pay for it, but I need transparency about costs upfront so I can make informed decisions." They were actually pretty reasonable once I framed it that way.

This is excellent advice about documentation and setting clear expectations going forward. I'm actually dealing with something similar right now and wondering - when you had that conversation about establishing billing guidelines, did you put the new agreement in writing? I'm worried about having another "he said/she said" situation down the road if we just discuss it verbally.

Absolutely get it in writing! I learned this the hard way from my first surprise billing incident. After our conversation, I followed up with an email summarizing what we discussed: "Just to confirm our conversation today, going forward you'll notify me if any question will require billable time beyond what's included in our annual service, and your rate for additional consultations is $X per hour with Y minimum billing increment." Then I asked them to reply confirming the terms. This way there's a clear paper trail and no room for misunderstandings later. It actually made our working relationship much better because we both knew exactly what to expect.