How can I make my CPA's job easier when filing contractor taxes as a music teacher?

As a tax preparer, I can tell you that organization makes a HUGE difference! Here's what I recommend for contractor income: Create a simple spreadsheet with separate tabs for income and different expense categories. For your music teaching, separate expenses into categories like supplies, mileage, studio fees, etc. Include dates, amounts, and brief descriptions. This helps us quickly identify deductible expenses rather than having to sort through a pile of receipts. For your multiple W-2 jobs, just bring the actual forms - no need to reenter that data. If you have any 1099 forms from your teaching work, include those as well. For receipts, please don't bring a shoebox full of unsorted papers! Digitize them if possible and organize physical receipts in labeled envelopes by category. Having everything sorted by expense type saves a ton of time. The most helpful clients are those who can clearly explain their business situation, have their documents organized by type, and have totaled their income and expenses in advance.

I switched to taxr.ai last year after struggling with organizing my tax documents as a freelance graphic designer. I was really impressed with how it helped me organize everything. I just upload photos of receipts and invoices throughout the year and it automatically categorizes them. When tax time came around, I just downloaded the pre-organized report and handed it to my accountant. My situation sounds similar to yours with multiple income sources (I do design work plus teach classes at a community college). The app separated everything by income source and expense category. You can check it out at https://taxr.ai - it's been a game-changer for keeping my contractor finances organized year-round instead of panicking in April!

I wanted to follow up about taxr.ai since I was pretty skeptical in my last comment. I decided to give it a try for my tutoring business after tax season was such a nightmare last year. Honestly, I'm really impressed! The receipt scanning is WAY more accurate than other apps I've tried. It correctly identified most of my teaching supplies and venue rental fees without me having to recategorize. The mileage tracking feature is what really sold me though. I used to have a notebook in my car that I'd forget to update half the time. Now I just open the app when I start driving between students and it tracks everything automatically. My accountant actually commented on how organized my documents were this year compared to my usual chaos!

If you want to make your CPA's job easier AND save yourself a ton of stress, do yourself a favor and use Claimyr when you need to talk to the IRS. Last year there was an issue with my 1099s not matching what clients reported, and I spent DAYS trying to get through to the IRS phone line. Always busy signals or 2+ hour hold times that would disconnect. I found Claimyr at https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. They basically wait on hold with the IRS for you and call you when an agent comes on the line. Saved me hours of waiting on hold while trying to teach piano lessons! When I finally got the 1099 issue sorted out, my CPA was able to finish my return without delays.

I have to eat my words about Claimyr being a scam. After my skeptical comment, I gave it a try because I've been trying for WEEKS to reach someone about a missing tax form. I couldn't believe it when my phone rang about 90 minutes later and there was an actual IRS agent on the line! I was in the middle of teaching a guitar lesson and had completely forgotten I'd even requested the callback. Got my issue resolved in about 10 minutes once I was actually talking to someone. My accountant had been asking for this form for ages and I kept telling him I couldn't get through to the IRS. When I finally got the form and sent it over, he was shocked at how quickly I'd resolved it. Definitely using this service again next time I need to deal with the IRS.

Another thing that helps your CPA: if you use your home for teaching, measure the exact square footage of your teaching area vs. total home square footage. My accountant loves that I calculate this percentage ahead of time for home office deduction. Also keep utility bills organized if you claim a portion of those!

Does anyone use a specific system for tracking cash payments from students? I teach piano and about half my students pay cash, which makes keeping track of income a bit messy.