I've been dealing with RSU taxation for several years now, and one thing that really helped me was understanding that the IRS treats RSU vesting as a taxable event regardless of whether you sell the shares or not. Your situation looks pretty standard - the $56,150.60 should appear as supplemental wages on your W-2 (often in Box 14 or combined with your regular wages in Box 1). The key is making sure your tax software or preparer knows that this income was already taxed when calculating your capital gains/losses. For future reference, some brokers offer better RSU tax reporting than others. If you're planning to stay with your current employer and continue receiving RSUs, it might be worth asking HR if they can switch to a broker that provides clearer tax documentation. I switched from E*Trade to Schwab a few years ago and the difference in reporting quality was night and day. Also, consider setting aside cash for taxes on future RSU vestings rather than always selling shares to cover. If you believe in your company's stock, you can avoid the immediate sale and potential regret if the stock price goes up later. Just make sure you have enough liquid funds to cover the tax bill!

I've been through this exact RSU mess before! One thing that really helped me was requesting what's called a "supplemental 1099-B" from my broker specifically for RSU transactions. Some brokers will provide this if you ask directly - it shows the correct adjusted cost basis that accounts for the compensation income already reported on your W-2. If your broker won't provide that (sounds like they already said no), you'll need to manually adjust on Form 8949. The key is using code "B" in column (f) and writing something like "RSU - basis adjustment per Pub 525" in column (g). Then adjust the basis to reflect that you've already paid ordinary income tax on the full vesting value. For your 137 remaining shares, definitely keep good records showing your $255.23 per share basis. I use a simple note in my investment tracking that says "RSU vest 8/2024 - basis adjusted for W-2 income" so I don't forget years later when I sell. The most important thing is making sure your total tax burden is correct - you should only pay ordinary income tax once (at vesting) and then capital gains tax later (when you sell) on any appreciation above the vesting price.

Ive been dashing for 3 years now alongside my office job. Keep EVERY receipt - gas, phone chargers, hot bags, etc. The tax write offs make a HUGE difference. Also dont forget about the quarterly payments! I put reminders in my calander cause I forgot the first year and got hit with penalties.

Great question! I started doing Doordash last year while working my regular job and learned a lot through trial and error. Here's what I wish I knew from the start: You'll definitely want to track your mileage religiously - it's usually your biggest deduction. I use a simple notebook in my car and jot down my starting/ending odometer readings for each dash session. The standard mileage rate for 2024 is 67 cents per mile, which adds up fast! For the quarterly payments, you can also ask your regular employer to withhold extra taxes from your paycheck instead of making separate estimated payments. I had my HR department take an extra $150 per month from my regular job to cover the Doordash taxes - much easier than remembering quarterly deadlines. One tip: keep a separate envelope or folder for ALL your Doordash-related receipts. Car maintenance, phone accessories, insulated bags, even hand sanitizer you buy for deliveries. These small expenses add up and reduce your taxable income. And definitely set aside that 25-30% of earnings right away. I learned the hard way that it's much easier to save as you go than scramble to pay a big tax bill in April!

One aspect that hasn't been fully explored here is the impact on your business insurance and potential liability exposure. When I was considering mixing trading activities with my consulting practice, my business insurance agent pointed out that trading activities could significantly change my liability profile and potentially void certain professional liability coverages. Many professional liability policies for consulting services specifically exclude investment and trading activities. If you're providing risk assessment services to hedge funds AND actively trading, you might need additional E&O coverage or securities-related insurance that could be quite expensive. From a practical standpoint, I ended up forming a separate LLC (elected as S corp for tax purposes) specifically for trading after discovering that my existing professional liability insurance wouldn't cover any claims related to investment activities conducted through the same entity. The additional entity costs were actually less than the insurance premium adjustments would have been. Also worth noting - if you're working with institutional clients in your consulting business, some may have vendor agreements that restrict or prohibit trading activities within the same entity due to potential conflicts of interest. This could impact your existing consulting contracts. Have you checked with your current business insurance provider about how adding trading activities might affect your coverage?

As someone who recently navigated this exact situation, I can confirm that the separate entity approach, while not legally required, offers significant practical advantages beyond just tax considerations. I initially tried to mix trading with my existing consulting S corp and ran into several unexpected issues. First, my business banking relationships became complicated - some banks have different requirements and fees for accounts that handle securities trading versus standard business operations. Second, my bookkeeping software needed expensive add-ons to properly track and categorize the different types of income and expenses. The real eye-opener was during my first audit. Having mixed activities made the examination much more complex and time-consuming. The IRS examiner spent considerable time trying to understand which expenses were related to which activities, and I had to provide extensive documentation to support the business purpose of various transactions. What finally convinced me to separate was realizing that the administrative headaches were costing me more in time and stress than the additional entity fees. Now I have clean separation, clearer record-keeping, and much better sleep at night knowing that if one activity faces scrutiny, it won't impact the other. For what it's worth, the separate LLC elected as S corp has actually helped me establish better credibility with both trading counterparties and consulting clients, since each entity has a clear, focused business purpose.

I had a similar experience when I moved mid-tax season! USPS forwarding does work for W2s since they're First-Class Mail, but there can definitely be delays. What really saved me was setting up informed delivery with USPS - it shows you scanned images of mail that's coming to your address each day. That way you can track when your W2 is actually in transit and know if it gets stuck somewhere in the forwarding process. Also, if your old employer has a main corporate number, try calling that instead of your local office. Sometimes the corporate payroll department can handle address changes more efficiently than local HR, especially if your old location was disorganized like you mentioned. They usually have better systems in place for handling former employee requests. One last tip - keep records of when you set up mail forwarding and any communications with your employer about the address change. If you do need to contact the IRS later, having that documentation will speed up the process significantly.

One additional thing to consider - if you've already set up mail forwarding, you can also submit a "Change of Address" form (Form 8822) directly to the IRS. This ensures they have your current address on file, which can be helpful if there are any issues with your tax return processing or if you're due a refund. You can download it from irs.gov or mail in a handwritten note with your old address, new address, and SSN. This is separate from updating your address with your employer, but it's good to have both bases covered. The IRS form is particularly useful if you end up needing to contact them about missing tax documents later - they'll already have your current address in their system. Also, don't forget to update your address with your state tax agency if you moved to a different state. They often have separate requirements and deadlines for tax document delivery.

This is such a relief to read! I had no idea this was such a common issue with the IRS system. I've been dealing with tax stuff for the first time on my own and when something like this happens it's absolutely terrifying. Thank you all for sharing your experiences - it really helps newcomers like me understand that these glitches happen and aren't necessarily our fault. Definitely taking notes on screenshotting everything and keeping manual records. This community is incredibly helpful!

Same thing happened to me about 3 months ago! I was absolutely panicking when my approved payment plan just vanished from the portal. Called the IRS and waited on hold for like 90 minutes, but the rep confirmed it was still 100% active in their system. She explained that their online portal has frequent display issues and that approved agreements sometimes temporarily disappear from view but remain valid on the backend. Got my official confirmation letter about 10 days later. Definitely call to confirm for peace of mind, but based on everyone's experiences here, you're probably totally fine. The IRS website is honestly just terrible at showing real-time status updates. Keep making your payments according to the original schedule you agreed to!