Would this still work if both jobs have widely different pay? My main job is about $75k but my weekend job only brings in like $9k. I'm worried about being in different tax brackets.

Yes, it still works with different pay levels! The important thing is to calculate based on your highest marginal tax bracket when combining all income. At $75k for your main job, you're already in the 22% federal bracket (assuming single filing status). The additional $9k from your weekend job would also be taxed at 22% federally. So you'd take $9,000 × 0.22 = $1,980 in additional tax for the year. Then divide that by your remaining pay periods to get the per-paycheck additional withholding amount. Just remember this is a simplified approach. If you're close to moving into a higher bracket with the combined income, you might want to use the IRS calculator for more precision.

This is a really good point. Does the social security cap apply per employer or across all your jobs combined? I work three part-time jobs and I'm nowhere near the cap with any single one.

I actually tried that first! We used Workday, but my login stopped working shortly after I left the company. I called about getting it reactivated but that just led me back to the same HR department that never answers. Frustrating because I know the W-2 is probably sitting right there in the system.

That's unfortunately pretty common - companies often disable access but don't communicate how former employees should get their tax documents. One thing you could try is reaching out to your former manager or even colleagues still at the company. Sometimes they can put internal pressure on HR that gets better results than calling from the outside. If that doesn't work, a former coworker might be able to tell you who specifically in HR handles tax documents, so you could email them directly instead of calling the general HR line. Large companies often have dedicated tax specialists who are separate from the regular HR team.

This actually worked for me last year! I filed a complaint with my state labor board and they contacted my former employer. Got my W-2 within a week after months of trying on my own.

What about the tax debt situation? Would an accountant help navigate that better than tax software?

For the tax debt situation specifically, an accountant can provide strategic advice, but they don't have any special access to the IRS. They'd likely advise you to contact the IRS directly to set up a payment plan or explore settlement options. A tax professional might be able to help determine if any of the debt can be addressed through penalty abatement requests or other relief programs. They can also advise on whether filing jointly or separately makes more sense given the outstanding debt. But for actually resolving the debt, you'll still need to work directly with the IRS one way or another.

The marriage penalty isn't as bad as it used to be after the 2017 tax changes, but it can still hit high earners. At their income level (over $400k combined), they could definitely face some penalty. I'd suggest looking at the actual tax brackets for 2024 and calculating both ways. Don't just assume joint is better!

Did you end up owing a lot more? I'm worried about making mistakes too. Did the IRS charge you penalties or just the additional tax?

Nope, unfortunately dual-status returns still can't be e-filed. I tried with both TurboTax and H&R Block last year, and both required paper filing. It's one of those weird IRS limitations that they haven't updated yet. Make sure you send it certified mail so you have proof of delivery!

I didn't even think about quarterly taxes! We haven't been paying anything throughout the year. Is it too late to fix this for last year? And how do we figure out how much to pay each quarter going forward?

It's too late to fix last year's quarterly payments now, but you can avoid penalties going forward by starting them this year. For most resellers, you need to pay estimated taxes if you expect to owe $1,000+ at tax time. For calculating the amount, you can either pay 100% of last year's tax liability divided into four payments (the "safe harbor" method), or 90% of what you expect to owe this year. I personally set aside 30% of my net profit each month and make payments on the quarterly due dates (April 15, June 15, September 15, and January 15). There's a form called 1040-ES that helps with calculations, or your tax software should have an estimated tax calculator. Start now and you'll avoid the shock next tax season!

And sales tax! If you're selling online, the marketplace might collect it for you (like eBay or Amazon) but if you sell directly you might need to collect and remit sales tax depending on your state and sales volume. That tripped me up my first year.