I hadn't thought about checking for residual distributions. That's a great point! Do you know if the broker would have sent any notification about this, or would I need to call them specifically to ask?

They typically send a notification, but these can easily get missed, especially if they went to an old email address or got filtered as spam. I'd definitely recommend calling your broker directly and asking if there were any final distributions related to the company. Sometimes these distributions are very small (like pennies per share) but they still affect your tax basis. Also, ask if they have any record of the exact date the shares became worthless in their system. Brokers often have this information officially recorded, which can be very helpful for tax documentation.

This is a really important point. I've seen people miscalculate their basis on ESPP shares all the time. The Form 3922 should show the FMV and the actual purchase price, right? So you can figure out what the discount was?

Does this also work with retirement account withholding? I take distributions from my IRA and could potentially increase the withholding there instead of making estimated payments.

Yes, it absolutely works with retirement account withholding too! Any federal income tax withholding (from W-2 wages, retirement distributions, etc.) is treated as if it occurred evenly throughout the year, regardless of when it actually happened. So increasing your IRA distribution withholding late in the year is a perfectly valid strategy to make up for estimated payment shortfalls. It's especially useful if you realize in November or December that you're going to owe more than expected.

Thank you for clarifying this! I was looking at the wrong line on my previous return. Looks like I need to pay about $2,400 more than I thought to hit the safe harbor. Better to know now than get hit with penalties later!

Wait really? The mileage deduction is that much? I never tracked my miles but I was doing Doordash like 4 nights a week for about 8 months. How would I even calculate that now after so much time has passed?

You can create a reasonable estimate based on your delivery history. Most delivery apps keep a record of your deliveries - try to get that data from Doordash if you can. If that's not possible, make a good faith estimate. Calculate your average deliveries per shift, estimate miles per delivery (including driving to pickup locations), and multiply by your working days. Document how you arrived at this estimate in case of questions. For 4 nights a week for 8 months, you're looking at roughly 128 working days. Even at a conservative 30 miles per shift, that's 3,840 miles or about $2,150 in deductions! Just be honest but thorough - this could significantly reduce what you owe.

Good point about state taxes. One thing to add - some cities also have local income taxes that apply to self-employment income. I found out the hard way after getting a notice from my city tax department a year after dealing with the IRS!

I've been using Justworks for my C Corp for about 2 years now. It definitely simplifies the admin side but doesn't really address the tax optimization between multiple income sources. You still need a good accountant for that part. The PEO basically just handles compliance, payroll processing, and can get you better benefits options than you'd have as a tiny company.

This is actually a really good point. I've used fiscal year planning with my S-Corp (mine runs Feb-Jan) and it gives me an extra month to make strategic decisions before the personal tax year ends.

I hadn't thought about the fiscal year angle at all. My C Corp is currently on a calendar year but I'm wondering if it would be worth changing that. Would it complicate my accounting too much to have different fiscal years?

How long should we actually keep inheritance paperwork? I'm drowning in statements and forms from my mom's estate from last year.

Keep the original basis documentation (showing what your dad paid for investments) permanently, or at least until several years after you've sold the inherited assets. The step-up in basis rules are critical for calculating capital gains tax when you eventually sell. For the tax returns themselves and supporting documentation, the standard is to keep them for at least 7 years, but for inheritance matters I personally keep everything indefinitely. The IRS has no time limit for auditing returns where they suspect substantial underreporting, and inheritance situations are unfortunately common triggers for those kinds of reviews.

I used them last year for my mom's estate and it was a complete disaster. The regular preparer had NO IDEA how to handle the inherited IRA distributions and I ended up having to go to a CPA to fix everything. Cost me way more in the end.