Make sure you keep copies of EVERYTHING. The IRS lost my amendment twice last year smh

Check your transcripts every week. Sometimes they update there before the Where's My Amended Return tool shows anything

One thing that might help ease your stress - the IRS is generally more interested in getting you back into compliance than in punishing you. They see situations like yours all the time, especially after the chaos of the past few years. When you're gathering documents, don't forget about things like state tax refunds you might have received (those can be taxable income), unemployment benefits, or any side gig income from apps like Uber, DoorDash, etc. These smaller income sources are easy to forget but can add up. Also, if you moved during those years, make sure you're filing in the correct states. Some states have no income tax, others do, and you might owe taxes in multiple states depending on when you moved and where you worked. The key is just to start. Pick one year (I'd suggest 2020 since it's the oldest) and focus on getting all the documents together for just that year first. Once you see how the process works for one year, the others will feel much more manageable. You've got this!

I went through something very similar a few years back - hadn't filed 2018-2020 due to job changes and personal issues. The anxiety was honestly the worst part! Here's what worked for me: Start by requesting your wage and income transcripts from the IRS website (irs.gov/individuals/get-transcript). This will show you exactly what income the IRS has on record for each year, which helps you identify any missing documents and gives you a baseline to work from. One thing that really helped my peace of mind was calling the IRS Taxpayer Advocate Service (1-877-777-4778). They're specifically there to help people in situations like yours get back on track. They can't do the filing for you, but they can explain your options and help you understand what to expect in terms of penalties. Don't beat yourself up about this - life happens, and you're taking the right steps now. The IRS would much rather have you file late than not at all. Focus on getting organized first, then tackle one year at a time. You'll feel so much better once you start making progress!

Has anyone had success just checking the "Exempt" box in Workday for a paycheck or two? I'm considering this but not sure of consequences...

I completely understand your frustration with the new W-4 form! I went through the exact same thing last year and felt like I needed a degree in tax law just to adjust my withholding. Here's what worked for me: The quickest way to increase your take-home pay temporarily is to use Step 4(b) "Other Deductions." In Workday, this might be labeled as "Additional Deductions" or something similar. You can enter a dollar amount here that reduces your taxable income for withholding purposes. A rough rule of thumb: if you're in the 22% tax bracket and want an extra $200 per paycheck, you'd enter about $4,500-$5,000 in deductions (this assumes biweekly pay). The system will withhold less tax because it thinks you have more deductions coming. Just remember to change it back after a few paychecks! I set a calendar reminder because it's easy to forget. Also keep in mind you're just borrowing from your future tax refund - you'll still owe the same total tax for the year. The Workday interface is definitely confusing compared to the actual IRS form, but once you find that deductions field, it should do what you need.

I made this exact mistake my first two years in business and it ended up triggering a letter from the IRS. They have reports from payment processors about how much you processed, so if there's a big discrepancy they'll notice. Better to do it right and avoid the headache!

This is such a helpful thread! I've been making the same mistake with my freelance graphic design business. I use Stripe and have been only reporting the net amounts that hit my bank account. Reading through all these responses, it's clear I need to start reporting the gross amounts on line 1 and then deducting the Stripe fees separately. I'm actually relieved to learn that even though I've been doing it wrong, my net taxable income probably hasn't been too far off since I wasn't claiming the processing fee deductions either. Going to dig up my Stripe annual statements and see if I can figure out the correct numbers for this year's filing. Thanks everyone for sharing your experiences - makes me feel less alone in being confused about this stuff!

One thing nobody's mentioned yet - make sure both you and your wife update your W-4 forms with your employers. After I got married, we both kept our "Single" withholding status and got hit with a $3200 tax bill at filing time! The withholding tables are different for married people, and if you're both working, you might need to withhold at the "Married but withhold at higher Single rate" or add additional withholding.

Hey don't forget about potentially adjusting your retirement contributions too. My husband and I discovered that when we got married and started filing jointly, we could leverage our income difference to max out his 401k and IRAs differently than before. Ended up saving us about $4,200 in taxes while building retirement faster.