Thanks for this suggestion! I just emailed HR to ask if we have an accountable plan or any reimbursement program for home office equipment. I had no idea this was even an option. If they say no, should I try to convince them to start one? Is it complicated for employers to set up?

Definitely worth suggesting if they don't have one already! It's not particularly complicated for employers to set up - they just need to establish a formal policy for what expenses qualify and require reasonable documentation from employees (receipts, etc.). Many companies don't realize this is a win-win. You get your expenses covered tax-free, and they get a business expense deduction while providing a valuable benefit that helps with retention. With so many companies now permanently remote, more HR departments are implementing these programs. Just frame it as a competitive advantage for them in the current job market.

This is extremely risky advice. The IRS systems specifically flag home office deductions that don't align with self-employment income. Taking deductions you're not legally entitled to is tax fraud, regardless of whether you've been caught yet.

Do you know if there's a limit to how many conferences you can attend and deduct each year? I've gone to like 4 already this year and wondering if that looks suspicious.

There's no specific limit on the number of conferences you can attend and deduct. The key test is whether they're "ordinary and necessary" for your business. If you can justify why each conference provides value to your specific business operations, then multiple conferences can be legitimate. However, if the conferences all cover very similar content, or if some seem only tangentially related to your business, that might raise questions. The IRS might look more closely if the pattern suggests the conferences are primarily for personal enjoyment rather than business development. Quality documentation of the business purpose for each one becomes even more important when you attend multiple events.

Yes, you'd need to allocate. If you would have gotten a single hotel room anyway, you can deduct the full room cost. But their flight, their meals, and any increase in room cost for double occupancy wouldn't be deductible.

5 Wait, so heavier vehicles get better tax treatment? That seems backwards from an environmental perspective. Why would the tax code incentivize bigger vehicles?

14 Yes, vehicles over 6,000 pounds gross vehicle weight rating (GVWR) are classified as heavy SUVs, trucks, or vans for tax purposes and aren't subject to the same luxury auto depreciation limits. This was originally intended for businesses needing work trucks, but it created a loophole that benefits larger personal vehicles used for business. You're right that it seems environmentally backwards. It's one of those tax provisions that has unintended consequences. The luxury auto limits were created in the 1980s to prevent businesses from deducting expensive sports cars, but the weight exception has ended up incentivizing larger vehicles. Congress has discussed changing this in recent years, but nothing has changed yet.

19 This is super helpful, thanks! If the car has actually increased in value since I bought it (crazy used car market last couple years), I would still use my original purchase price, right?

Any app recommendations for tracking mileage? I've been using a paper log but it's a pain.

I personally use MileIQ, but there are several good ones like Everlance and Stride. The key is finding one that automatically detects drives and lets you easily classify them as business or personal. Make sure whatever app you choose lets you export detailed reports that include start/end locations, odometer readings, and business purpose. The app I mentioned even lets you add notes for each trip which is super helpful if you get questioned about specific drives later. Most have free versions that work fine if you don't drive tons of miles.

Thanks, you're right - I do get a 1099-NEC that includes everything (services + mileage all together). So based on what you're saying, I should be able to deduct the full mileage at the standard rate since I'm paying taxes on the entire amount, including what was meant as "reimbursement"?

Yes, that's exactly right. Since your 1099-NEC includes both your service payments and mileage reimbursements as one lump sum, the IRS considers it all taxable income. Therefore, you are absolutely entitled to deduct all your business mileage at the standard rate on your Schedule C. Just make sure your mileage log is detailed and accurate to support your deduction if you're ever questioned. Include dates, destinations, business purpose, and mileage for each trip.

Thanks for the reminder about Schedule SE! I actually did factor that in when I increased my withholding. I calculated roughly what I'd owe for both income tax and self-employment tax on the $18,500 and that's how I came up with the $320 per paycheck increase. Do you know if there's an easy way to check if I'm on track to meet the safe harbor requirement? I'm still a bit nervous about whether I've withheld enough.

You can use the IRS Withholding Estimator on their website. It will let you input both your W2 income/withholding and your 1099 income, then tell you if you're on track. Another simple approach is to look at your last paystub from 2024 and add up the federal withholding. Then add what you expect to have withheld for the rest of 2025 based on your current withholding rate. If that total is at least $16,300 (your tax from last year), you'll meet the safe harbor requirement.

But aren't you basically losing money by giving the government an interest-free loan? You could be investing that money throughout the year instead. I set calendar reminders for estimated payments and it's not that bad.