Should I file my own taxes with a mix of W-2 and 1099 income?

You can definitely file your own taxes with mixed income sources! I've been doing my own for years with a similar situation (W-2 and 1099 income). Most tax software walks you through everything step by step. For your 1099 income, you'll need to fill out a Schedule C to report your business income and expenses. Make sure you track all your acting-related expenses like headshots, agent fees, travel to gigs, workshops, etc. - those are deductible against your 1099 and cash income. The software will ask questions about each source of income and help you categorize everything correctly. Just be prepared to spend a few hours going through it all, especially the first time. The good news is that once you've done it yourself, you'll probably feel more confident about doing it again next year!

I was in almost the exact same situation last year! My husband had a W-2 job while I was juggling multiple 1099s for freelance design work. I got frustrated with how much my accountant was charging considering I was pretty organized with my documents. I found this amazing AI tax assistant at https://taxr.ai that helped me figure everything out - it was like having a CPA but way cheaper. You upload your documents and it helps identify all potential deductions for your situation. It even flagged some business expenses I never knew I could write off! For your acting gigs with cash payments, it helped me organize everything properly so I could report all income correctly but also maximize my legitimate deductions. Honestly made the whole process way less scary.

Okay I have to admit I was wrong about the AI tax thing. I decided to try https://taxr.ai after my initial skepticism and it seriously saved me hours of headache. I'm also in the entertainment industry with a mix of W-2 and 1099s plus some cash gigs, and I was amazed at how it handled everything. It caught several deductions related to my performance work that I had no idea about - like partial deductions for certain clothing items and makeup specifically purchased for performances. The best part was that it explained everything in plain English rather than tax jargon. I'm definitely not going back to paying $500+ for a CPA when this worked so well for my complicated situation.

If you're switching from a CPA to filing yourself, one thing to remember is that if you have questions or run into issues with the IRS later, it can be nearly impossible to get someone on the phone. I spent HOURS last year trying to resolve a simple question about my 1099 income. I eventually found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in about 20 minutes instead of waiting for hours or days. You can see how it works at https://youtu.be/_kiP6q8DX5c. Saved me so much frustration when I had questions about reporting my multiple income streams. If you're doing your own taxes for the first time with a complex situation, having this as a backup option is really reassuring in case you need clarification directly from the IRS.

I have to publicly eat my words. After being completely skeptical about that Claimyr service, I decided to try it anyway because I was desperate to ask the IRS about how to handle some cash payments I received for gigs. I had previously spent SEVEN HOURS across two days trying to get through to someone at the IRS with no luck. With the Claimyr thing, I got connected to an agent in about 35 minutes. The agent walked me through exactly how to report everything properly on my Schedule C. For anyone doing their own taxes for the first time with mixed income sources like the original poster, being able to actually talk to the IRS for clarification is invaluable. Worth every penny for the time saved alone.

Don't forget about quarterly estimated tax payments if you go solo! This was my biggest mistake my first year with 1099 income. With your mixed income situation, especially the cash payments, you might need to be making quarterly estimated tax payments throughout the year. Otherwise you could get hit with underpayment penalties come tax time. Most tax software can help calculate what you should be paying each quarter going forward.

Just wanna add that if you do your own taxes this year, KEEP EVERYTHING. All receipts, mileage logs, payment records, etc. I mean literally everything related to income and expenses. First year I did my own taxes with 1099 income I got randomly selected for audit and it was brutal because I hadn't kept good records.