That's really good advice about documenting my attempts to get the W2! I've been asking them verbally every week but haven't put anything in writing. I'll send an email today and keep a copy. I didn't know about checking the IRS website for electronically filed W2s. I'll definitely create an account and check that out. Would it show up there even if the restaurant owners are new to filing this paperwork? Maybe they submitted it correctly to the IRS but just didn't know they needed to give me a copy?

Yes, documenting your requests in writing is crucial. Save copies of your emails or get a receipt for any certified mail you send. This protects you by showing you made good-faith efforts to get your W2 properly. If they did file electronically with the IRS, it should eventually show up in your wage and income transcript, but there can be delays, especially during tax season. New business owners might indeed have filed correctly with the IRS but not realized they need to provide copies to employees. That happens more often than you'd think. The transcript approach is worth checking, but it might not show recent filings immediately - sometimes it takes weeks or even months for newly filed information to appear in your transcript.

Good point! When I had this problem in Michigan, I just attached a copy of the federal 4852 to my state return with an explanation letter. But my friend in California had to fill out a separate state form.

That's interesting! My vintage business will be expanding to sell some digital patterns soon. Do you know if downloadable sewing patterns would be taxable in Colorado? Or would they count as a non-taxable service?

Digital products in Colorado are generally taxable if they're considered "tangible personal property" in electronic form - like downloaded patterns, designs, etc. However, custom design work or services are usually exempt. For your sewing patterns, they would likely be considered taxable digital goods in Colorado since they're standardized products rather than custom services. But other states vary wildly on digital taxation - some exempt all digital products while others tax everything. The rules change constantly too, which makes compliance a huge headache for businesses like ours.

I've been using TaxJar for about 2 years and it's decent but not perfect. It sometimes gets special district taxes wrong in Colorado which then requires manual adjustments. If you're only selling in a few states it might be overkill. Avalara is more comprehensive but also more expensive.

1 Is that actually legal though? Everything I've read says you have to do the quarterly thing if you have self-employment income. I really don't want to mess this up and get hit with penalties.

22 It's absolutely legal. The IRS doesn't care HOW you pay your taxes as long as you pay enough throughout the year. The law requires you to pay taxes as you earn income, but doesn't specify whether that has to be through estimated payments or withholding. If your W-2 job withholds enough to cover both your regular income AND your self-employment income, you're fulfilling the requirement. You're still paying "as you go" - just through increased withholding rather than separate quarterly payments. Many tax professionals actually recommend this approach if your self-employment income is relatively small compared to your W-2 income.

5 TurboTax Self-Employed does have a feature for estimated tax payments, but honestly it's pretty basic. It gives you the bare minimum calculation without optimizing for your specific situation. I used it last year and still ended up overpaying by about $800.

Do you know if the IRS is still experiencing those huge processing delays like they were last year? I'm worried my late return will go into some kind of backlog and take forever to process.

The processing delays have improved somewhat compared to last year, but they're still working through backlogs. E-filing is definitely your best bet for faster processing - paper returns are still facing significant delays. I've noticed that returns claiming certain credits seem to face longer processing times, especially Earned Income Tax Credit or Additional Child Tax Credit. If your return is straightforward, you should see faster processing even filing late.

This is super important advice. I learned this the hard way a few years ago when I delayed filing because I couldn't pay. Ended up with much bigger penalties than if I'd just filed and set up a payment plan right away.

I'm fairly certain mine are all after-tax since I'm paying directly from my personal bank account each month. But is there a way to verify this for sure? The premiums went up significantly after retirement compared to when I was working.

The significant increase you're seeing is common. While employed, employers often subsidize a large portion of premiums or you may have been paying with pre-tax dollars through a Section 125 cafeteria plan. In retirement, you're typically paying the full premium with no subsidy. You can verify by requesting a benefits statement from your former employer or the plan administrator. They should be able to confirm that your payments are being made with after-tax dollars. The statement from them would also serve as excellent documentation for your tax records in case of an audit.

This! Standard deduction for 2024 is $14,600 for single filers and $29,200 for married filing jointly. Make sure itemizing actually benefits you before going through all this documentation hassle.