As a fellow newcomer to the US tax system, I completely understand your confusion! I went through something similar when I first arrived. One thing that really helped me was understanding that the W-4 is just an estimate for withholding - you're not locked into anything. Since you're both working and newly married, I'd recommend: 1. Both select "Married filing jointly" on your W-4s 2. Make sure to check the "Multiple Jobs or Spouse Works" box in Step 2 on both forms 3. Consider using the IRS withholding calculator at irs.gov to get a more precise estimate For dependents, put 0 unless you have children or other qualifying dependents. Health insurance coverage doesn't make you dependents of each other. The good news is that when you file your actual tax return next year, you can choose the filing status that works best for you (likely married filing jointly), regardless of what you put on your W-4s. The W-4 is just to help get your withholding close to what you'll owe. Don't stress too much - you can always adjust your W-4 later if needed once you see how your first few paychecks look!

Welcome to the US tax system! As someone who also navigated this as a new immigrant, I totally get the confusion. The key thing to remember is that your W-4 and actual tax filing are separate decisions. For your W-4 forms, since you're legally married and both working: 1. Select "Married filing jointly" in Step 1 2. Definitely check the "Multiple Jobs or Spouse Works" box in Step 2 - this is crucial to avoid underwithholding 3. Put 0 for dependents unless you have children The immigration status piece that @Sophie Duck mentioned is really important. If you arrived recently, look into whether you qualify as a resident alien for tax purposes and consider the First-Year Choice election if you don't meet the substantial presence test yet. One practical tip: keep your first few pay stubs and use the IRS withholding calculator online after a month or two to see if you need to adjust. Since your wife is changing jobs in August anyway, that's a perfect time to fine-tune the W-4 based on what you've learned. Don't worry about getting it perfect immediately - you can always adjust as you go!

This thread has been incredibly helpful for understanding the HSA tax situation as a self-employed person! I'm a freelance software developer who's been self-employed for about 8 months, and like many others here, I had no idea about the FICA tax implications of HSA contributions. I've been contributing $4,300 annually to my individual HSA, thinking I was being smart about taxes, but now I realize I'm paying about $658 extra in self-employment taxes (15.3% × $4,300) compared to what I would have paid as a traditional employee. That's a pretty significant "penalty" for being self-employed that nobody talks about! The solo 401k strategy everyone's discussing is definitely something I need to implement. I had my priorities completely backwards - maxing out HSA first instead of prioritizing retirement accounts that actually reduce self-employment taxes. It's one of those things that seems obvious once you understand the mechanics, but the marketing around HSAs being "triple tax-advantaged" really doesn't mention this crucial distinction for self-employed folks. I'm curious - for those who have restructured their approach to prioritize solo 401k contributions first, have you noticed any other tax planning opportunities that became clearer once you started thinking about self-employment taxes more strategically? I feel like I'm probably missing other optimization strategies too. Thanks to everyone who shared real numbers and experiences. This kind of practical advice is worth its weight in gold!

This discussion has been incredibly eye-opening! As a freelance photographer who's been self-employed for about a year, I completely fell into the same trap as everyone else here - prioritizing HSA contributions thinking they were universally the best tax move. I'm contributing about $4,300 annually to my individual HSA, which means I'm paying roughly $658 in extra self-employment taxes that I wouldn't pay as a traditional employee. That's almost two months of my health insurance premiums! It's frustrating to discover this "hidden penalty" for being self-employed, especially since no one mentions it when discussing HSA benefits. The solo 401k strategy that keeps coming up in this thread is definitely my next priority. I had it completely backwards - funding my HSA before maximizing retirement accounts that actually reduce self-employment taxes. @Makayla Shoemaker's point about the QBI deduction and other self-employment tax strategies is also really helpful for thinking about the bigger picture. What strikes me most about this conversation is how the "triple tax-advantaged" marketing around HSAs really doesn't tell the whole story for self-employed folks. We're missing that third advantage (FICA savings) that makes HSAs so attractive for traditional employees. It's one of those nuances that can cost us hundreds or thousands annually if we don't understand it. Thanks to everyone who shared real numbers and experiences - this is exactly the kind of practical guidance that makes the difference between stumbling through self-employment taxes and actually optimizing them!

Don't forget about the Qualified Business Income deduction! As a sole proprietor, you can deduct up to 20% of your net business income. So if you make $10k from DoorDash after expenses, you could potentially deduct another $2k from your taxable income. It's automatic for most people under certain income thresholds.

One thing that really helped me when I started DoorDashing was setting up a simple spreadsheet to track everything weekly. I log my total earnings, miles driven, gas expenses, and any other costs like phone accessories or hot bags. For quarterly payments - since you're making decent money ($7,200 in 4 months), you'll probably want to either increase your W-2 withholding or make estimated payments. A rough rule of thumb is to set aside about 25-30% of your net DoorDash income for taxes (including self-employment tax). So on that $7,200, maybe put $1,800-2,100 aside. The self-employment tax is the big surprise for most new gig workers - it's about 15.3% on your net earnings, which covers Social Security and Medicare taxes that would normally be split with an employer. But the good news is you can deduct half of that self-employment tax on your return!

Thanks for all the helpful responses everyone! I'm feeling much more confident about this now. Just to make sure I understand the process correctly: 1. Make the two credit card payments first (through approved payment processors) 2. Wait 1-2 days for them to process and show up in my IRS account 3. Use Direct Pay for the remaining balance One follow-up question - when I'm making the credit card payments, do I need to specify which tax form they're for? I filed a 1040 with a Schedule C, so I want to make sure the payments get applied to the right place. Also, is there a way to check online that all my payments have been properly applied before the deadline? The reward calculation definitely makes sense for my situation since I'm working toward a signup bonus on one card and have a 2% cashback card for the other payment. Even with the processing fees, I'll come out ahead.

Just wanted to chime in with my recent experience doing exactly this! I had a $6,200 tax bill last month and used two credit card payments of $2,000 each, then paid the remaining $2,200 through Direct Pay. A few practical tips from my experience: - Make sure you're using the official IRS-approved payment processors for credit cards (PayUSAtax, Pay1040, or Official Payments). Don't use any third-party sites that aren't listed on the IRS website. - Keep your browser open and take screenshots of each confirmation page immediately. I learned this after my first payment confirmation email got delayed by several hours. - The Direct Pay system is really user-friendly and will show you your updated balance after the credit card payments post, which took about 36 hours in my case. One thing I wish I'd known ahead of time - if you have a business checking account, you can also use that for Direct Pay as an additional option if needed. Might be helpful if you hit any daily limits on your personal account. The whole process was much smoother than I expected, and getting those credit card rewards definitely made the convenience fees worth it!

Just wanted to add another perspective on this - I went through the exact same confusion with my NQSO sale last year. The key thing that helped me understand it was thinking of it as two separate transactions that happen to be reported on different forms: 1) The "exercise" transaction: You paid $20K to buy stock worth $92K. The $72K difference is compensation income (goes on W-2). 2) The "sale" transaction: You sold stock with a basis of $92K (your $20K cost + $72K already-taxed income) for $92K in proceeds. When you think of it this way, it makes sense that there's essentially no capital gain or loss on the sale - you're just converting already-taxed compensation income into cash. The tricky part is that most employers don't adjust the cost basis on the 1099-B to reflect the W-2 income, so you have to do it manually when filing. This is super common with NQSOs, so don't worry - you're not missing anything obvious, the reporting is just confusing by design!

Just wanted to share my experience since I went through this exact same situation with NQSOs last year! The confusion you're experiencing is totally normal - the way stock options are reported across multiple forms is genuinely confusing. You're absolutely right to be concerned about double taxation, but the good news is that once you make the proper adjustments, you won't pay tax twice on the same income. Here's what I learned: The $72K that shows up on your W-2 represents the "bargain element" - essentially the difference between what the stock was worth when you exercised ($92K worth of stock) and what you paid to exercise the options ($20K). This gets treated as regular compensation income. The 1099-B is reporting the stock sale, but the cost basis needs to be adjusted to reflect that you already paid tax on $72K of that value through your W-2. So your true cost basis for tax purposes should be $92K ($20K you paid + $72K already taxed), not just the $20K shown on the form. When you file, you'll likely need to use Form 8949 to make this basis adjustment. Most tax software will guide you through this when you indicate you have stock compensation income. The end result should be little to no capital gain or loss from the actual sale, since you sold immediately after exercising. Don't stress too much - this is a very common situation and the IRS sees these adjustments all the time with employee stock options!