Thanks for this suggestion! I looked it up and there's actually a VITA site at my local library this weekend. Do you know if I need to bring anything specific with me? I have my W-2 and ID but not sure what else they might need.

Definitely bring your photo ID, social security card (or a document with your SSN), all tax documents (W-2s, 1099s, etc.), and last year's tax return if you have one. Also bring your bank account info (routing and account numbers) for direct deposit of your refund. They usually prefer if you make an appointment, so call ahead if possible. Some sites also require you to fill out an intake form before your visit to save time. Most locations can file both federal and state returns for you, and they double-check everything to make sure you're getting all the credits you qualify for.

Be careful with TurboTax "Free" Edition! They often upsell you halfway through the process. I switched to FreeTaxUSA after getting charged $40 for state filing with TurboTax when they advertised it as free.

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?

That's a great idea about the union resources! I didn't even think about instrument insurance being deductible. I've actually been paying like $30/month to insure my guitars but never thought about that as a tax thing. Do I need to be a full-time musician for lessons to count as professional development?

You don't need to be a full-time musician for lessons to potentially qualify as professional development. The key factor is whether the training maintains or improves skills needed in your current work - even if that work is part-time or supplemental income. The IRS looks at whether the expense directly relates to your existing music business, not how many hours you put into it. For example, if you're already getting paid for guitar performances and you take advanced lessons to improve those specific performance skills, that could be deductible. However, if you decided to learn an entirely new instrument that you don't currently use in your paid gigs, that might be considered preparation for a new career and wouldn't qualify.

How do you calculate the percentage though? Like I use Spotify all day every day, some for gig research and some for personal listening. Seems impossible to track accurately.

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.