One thing nobody mentioned - make sure you're tracking your deadhead miles too (the miles driving back from a delivery when you don't have food in the car). Those miles are fully deductible for your DoorDash work! I made the mistake of only counting miles when I had food in the car my first year and missed out on almost 40% of my potential deduction. For your 1099 work, it's any mile driven for business purposes, including getting back to a hotspot area.

I'm a newer delivery driver and this whole thread has been incredibly helpful! I had no idea about the W-2 vs 1099 distinction for mileage deductions. I've been driving for a local pizza place (W-2) for about 6 months and just started with Uber Eats on weekends. Reading through everyone's experiences, it sounds like I need to completely separate my tracking - no deductions for the pizza place miles, but full business mileage deduction for Uber Eats including those return trips I never thought to track. One question though - if I'm doing both jobs in the same shift (like finishing my pizza place shift then immediately going online for Uber Eats), how do I handle the transition? Is the drive from the pizza place to my first Uber pickup considered business mileage for the 1099 work? Also want to echo what others said about asking for higher reimbursement from employers. My pizza place only pays 40 cents per mile and after reading Connor's success story, I'm definitely going to have that conversation with my manager!

An important detail that nobody has mentioned yet - when your company recalculates the Annual Lease Value, make sure they use the REDUCED value for the ENTIRE calendar year, not just from the point they make the correction. My company initially only applied the new lower value from July onward (when I brought it to their attention) but the IRS rules clearly state the redetermination applies for the whole year. Had to have another conversation with payroll to get them to apply it retroactively to January. Also worth noting - if you're still with the same employer and using the same car in 4 more years, you'll get ANOTHER recalculation at the 8-year mark. The value keeps stepping down as the car ages.

Great question about leased vehicles! Yes, the 4-year recalculation rule absolutely applies to employer-provided leased vehicles too. The IRS doesn't distinguish between owned and leased vehicles for Annual Lease Value calculations - what matters is that you're receiving the personal use of a company vehicle as a fringe benefit. Your employer should still recalculate the Annual Lease Value based on the current fair market value of the specific vehicle you're driving, even though they don't own it. The fact that it shows up on your W-2 confirms they're treating it as a taxable fringe benefit under the ALV method. The recalculation should reflect what that particular car (with its current mileage, condition, and age) would be worth if you were to purchase it today, not the original lease value or what the company pays in lease payments. This often results in significant savings since leased vehicles typically depreciate just like owned vehicles. Make sure your HR/payroll team understands this applies to leased vehicles - some companies mistakenly think the lease situation changes the rules, but it doesn't according to IRS Publication 15-B.

Quick tip from someone who's been filing Schedule C for small amounts of side income for years - don't stress too much about the business code. I literally used the wrong code for 3 years straight (I picked something that sounded close enough) and the IRS never batted an eye. As long as your income and expenses are reported accurately, the code is more for statistical purposes than anything that will affect your tax liability.

I went through this exact same situation last year with my wife's consulting work. She received a 1099-NEC for about $1,800 and we were equally confused about all the Schedule C requirements. Here's what I learned: Yes, you absolutely need to file Schedule C, but you can keep it simple. For the business activity, just put "Speaking Services" or "Educational Speaking." The business code 711510 (Independent Artists, Writers & Performers) that someone mentioned earlier is perfect for this situation. For accounting method, choose "Cash" since he got paid when he received the money. Business start date would be when he gave his first presentation. Most of the other fields you can answer "No" or "N/A" if they don't apply. The one thing I wish I had known earlier - definitely track any expenses related to these speaking engagements. Travel costs, materials he bought or printed for the presentations, even mileage to the venues. We missed out on probably $200-300 in legitimate deductions because we didn't keep good records. Also, yes, he'll owe self-employment tax (about 15.3%) on the net profit, but if you have expenses to deduct, that reduces the amount subject to SE tax. The good news is $2,025 isn't a huge amount, so even with SE tax, it shouldn't be a massive hit to your refund.

11 I'm in the same boat with Fidelity! Did anyone actually try calling Vanguard the old-fashioned way? What number did you use? The main customer service line has kept me on hold for ages.

I've been dealing with a similar issue with my Schwab account - turns out there can be several reasons why tax forms don't show up online even when they should. One thing that helped me was checking if there were any unresolved account issues or if I had any pending transactions that might be holding up form generation. Also, if you had any dividend reinvestments or automatic investments during the year, sometimes those can complicate the form processing timeline. Vanguard might be waiting for final cost basis adjustments before releasing your forms. I'd definitely recommend calling that tax support line someone mentioned - the regular customer service reps often don't have access to the same information as the tax document specialists. When you do call, have your account number ready and ask specifically about "form generation status" rather than just asking about missing forms.

Does anyone know if there's a way to see what your tax bill might be before getting all the official forms? I've got a similar situation but want to start budgeting for what I'll owe.

Just wanted to add something that might help ease your anxiety - the IRS has a "safe harbor" rule that protects you from underpayment penalties if you pay at least 100% of last year's tax liability (or 110% if your prior year AGI was over $150k). So even if you end up owing a decent amount on your capital gains, as long as your withholdings from your regular job or other estimated payments cover what you owed in 2022, you won't get hit with penalties. Your tax preparer will check this when you meet in February. The key thing is you realized these gains in December 2023, so they're part of your 2023 return. You have until April 15, 2024 to pay without any late payment issues. Try not to stress too much about it!