This is super informative! I had no idea about the "Wealth Squad" - is this something regular people with side businesses need to worry about? Or is it more for super wealthy individuals? Like what's the threshold where they start getting interested?

The Wealth Squad typically focuses on individuals with income or assets over $10 million, so most regular people with side businesses wouldn't be on their radar specifically. However, anyone with unusual income patterns can still trigger standard IRS compliance flags. For more typical side businesses, it's the regular IRS examination divisions that might notice discrepancies. The important thing is maintaining good records that show the source of your income and legitimate business expenses. Unexplained deposits or lifestyle expenses that don't match reported income are what typically trigger closer examination, regardless of income level.

True about shell companies! I work in banking and you wouldn't believe how sophisticated some fraud schemes are. But even with elaborate setups, people eventually slip up. Either they can't resist flaunting wealth or they make a reporting mistake. That's usually how they get caught.

Thanks for bringing this up! I checked my paystubs and they definitely show federal and state tax withholding, so I should be getting a W-2. They were taking out Social Security and Medicare too. I'm thinking maybe they just don't have my current address since I moved shortly after leaving? But still, they should've responded to my emails asking about it. So frustrating.

That's good you confirmed they were withholding taxes! In that case, they're definitely required to provide a W-2. The address issue could definitely be part of the problem - sometimes companies just mail them to the last address they have on file. You might want to check if your former employer used a third-party payroll service like ADP, Paychex, or Gusto. If they did, you might be able to create an account directly with that service and access your W-2 electronically. Many of my past employers used these services, and I could get my tax forms even years later by logging into those platforms.

This actually works surprisingly well! When my husband's former employer was ignoring his requests, he physically went to their HR office. Amazing how quickly they produced his W-2 when he was standing right in front of them. Sometimes the old-school direct approach is still the most effective.

Do you know if California requires a separate extension filing?

California automatically grants you the same extension as federal (6 months) without requiring a separate form - but ONLY if you don't owe additional tax. If you do owe CA tax, you need to file Form FTB 3519 and make a payment by the original due date to avoid penalties. New York also gives an automatic extension matching the federal timeframe. Texas doesn't have state income tax so no worries there. Most states follow federal extensions but there are definitely exceptions, so always double-check your specific state's requirements.

TaxAct tried to charge me last year when I went to submit the extension. Did you actually get through the whole process for free?

That's really interesting - I didn't realize I could challenge my classification. The owner did control my schedule completely and I used his truck, not my own vehicle. Does filing the SS-8 cause problems with filing my current return, or can I still go ahead and file using the income as self-employment while the SS-8 is being processed?

You can absolutely file your current return while the SS-8 is being processed. In fact, you can file Form 8919 "Uncollected Social Security and Medicare Tax on Wages" along with your return if you believe you were misclassified. Use code G in column C which indicates you filed Form SS-8 but haven't received a determination. This approach allows you to only pay the employee portion of Social Security and Medicare taxes (7.65%) instead of the full self-employment tax rate (15.3%). If the IRS later determines you were correctly classified as an independent contractor, you may need to pay the difference, but if they determine you were misclassified, you've already filed correctly.

Having a contract is definitely helpful, but even text messages or emails discussing pay rates and work arrangements can serve as evidence of the working relationship. The IRS understands that not all independent contractor relationships have formal paperwork.

Do you have a template for this spreadsheet you could share? I'm doing freelance work for the first time this year and I'm trying to get organized before tax season.

I don't have a template to share but it's pretty simple to create. I just use columns for: Client Name, Project Description, Date Paid, Amount, Payment Method, W-9 Submitted (Y/N), 1099 Expected (Y/N), and 1099 Received (Y/N). I also have a separate tab for business expenses with columns for: Date, Vendor, Description, Amount, Payment Method, and Category (like "Software," "Equipment," etc). Nothing fancy but it keeps everything organized when it's time to do taxes.

Technically you're supposed to report all income, even small amounts. But realistically the IRS is more concerned with larger amounts. You should definitely start reporting your income going forward though. The IRS has been increasing focus on gig/freelance work.