Where to get free tax advice from professionals? Urgent contractor tax questions

As someone who's been self-employed for years, here's what you need to know: You're now responsible for both the employee AND employer portions of FICA taxes (Social Security and Medicare), which comes to about 15.3% of your earnings. Plus regular income tax on top of that. The IRS generally expects you to make quarterly estimated tax payments when you have income without withholding. The first quarter payment for 2025 would be due April 15th. If you wait until next year's filing deadline, you might face underpayment penalties. For free tax help, try the NYC Volunteer Income Tax Assistance (VITA) program - they help people who make under $60K. Also check out your local library as many host free tax workshops. The Taxpayer Advocate Service is another good resource for free guidance. Since you're now self-employed, you can deduct business expenses like home office (if you have dedicated space), research materials, equipment, professional subscriptions, and even health insurance premiums. Start tracking everything now!

I was in a similar situation last year with a consulting gig and was completely lost about taxes! I eventually found this AI tool called taxr.ai that actually saved me from a major headache. It analyzed my situation (independent contractor with lump sum payment) and explained exactly what I needed to do about quarterly payments and potential deductions. I just uploaded my previous tax returns and answered some questions about my new income, and it gave me personalized guidance including how much to set aside and when to pay. The best part was it found deductions specific to my situation I wouldn't have known about. Check out https://taxr.ai - they have a free assessment that might help you figure out your specific situation without having to track down an in-person appointment.

Just wanted to update that I tried taxr.ai after seeing it recommended here and it was seriously helpful! I was in a similar contractor situation (though teaching online courses) and wasn't sure how to handle the taxes. The analysis it gave me was surprisingly detailed - it showed exactly how much I needed to set aside for federal, NY state, AND NYC taxes, plus gave me a breakdown of all the deductions I qualify for as an independent contractor. It even generated a calendar with payment due dates and amounts so I wouldn't miss those quarterly deadlines. Definitely worth checking out if you're looking for free tax help. Way more specific than the general advice I was getting elsewhere.

If you need to actually TALK to someone at the IRS about your situation (which I highly recommend for first-time contractors), good luck getting through to them. I spent HOURS on hold last month trying to get clarification about my estimated payments. After the third failed attempt, a friend recommended Claimyr (https://claimyr.com), which basically holds your place in the IRS phone queue and calls you when an agent is actually available. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Totally changed my experience - I finally got through to someone who explained exactly what I needed to do as a new independent contractor. Since you're in a new tax situation with this contractor role, talking to an actual IRS agent might give you more peace of mind than just reading online.

I need to eat my words and apologize to Profile 18. After posting my skeptical comment, I was STILL struggling to get through to the IRS about my contractor situation (kept getting disconnected after 1+ hour holds), so I reluctantly tried Claimyr. It actually worked exactly as described. I got a call back in about 2 hours while I was just going about my day, and suddenly I was talking to an actual IRS agent who walked me through everything I needed to know about estimated payments. They answered all my questions about deductions for my specific situation too. The agent told me that Mondays and early mornings are when they get the most calls, which I never would have known. For anyone else struggling with contractor tax questions, actually talking to the IRS was way more helpful than trying to figure it out alone.

Don't forget to check if your school/university offers free tax advice! I was a research assistant during grad school and my university had free tax workshops specifically for students with stipends and research positions. They even had dedicated sessions for independent contractors vs. employees. Worth checking if yours has something similar!

One thing nobody mentioned - get a separate bank account for your business income and expenses! I learned this the hard way when I started freelancing. The IRS can be really picky about commingling personal and business finances. Also download a free expense tracking app now and start using it immediately. Take pictures of all receipts. You'll thank yourself next April when you're not trying to remember what every purchase was for.