VENTING - I can't take doing taxes anymore, ready to quit...?

I've been preparing my own taxes for the past 6 years and I'm at my breaking point. This tax season has been a NIGHTMARE. I just spent 14 hours this weekend trying to figure out all these new tax forms because I started freelancing on the side while keeping my full-time job. The Schedule C is driving me insane, and I'm not even sure if I'm tracking my business expenses correctly. My income jumped to about $78,500 this year ($62,000 from my W-2 job and about $16,500 from freelance work), and I'm terrified I'm going to mess something up with the self-employment taxes. I didn't do quarterly payments because I didn't realize I needed to, and now I'm panicking about penalties. I've looked at hiring a tax professional, but the quotes I'm getting are $400-500! That's a huge chunk of my potential refund. Has anyone else hit this wall where you're just ready to throw your hands up and quit doing your own taxes? Is it worth paying someone just for the peace of mind? I'm seriously considering just using one of those tax prep services instead of trying to figure it all out myself.

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19 comments

Malik Jackson

•8M

I feel your pain! That transition from W-2 only to adding self-employment income is a huge learning curve. The good news is that once you figure it out this year, next year will be much easier. For your Schedule C, the main thing is to be organized with your business expenses - categorize everything clearly (software, office supplies, professional development, etc.) and keep all receipts. For self-employment taxes, yes, you should be making quarterly estimated payments, but the penalty for not doing so your first year usually isn't too bad. At your income level ($78,500 total with $16,500 freelance), getting professional help might actually save you money. A good tax preparer will find deductions you might miss and help you set up a system for next year's estimated payments. Think of the $400-500 as not just paying for tax prep but also for education and peace of mind.

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Malik Jackson

•8M

A good rule of thumb is to set aside about 30% of your freelance income for taxes (covers both income tax and self-employment tax). You can make quarterly payments through the IRS Direct Pay system based on what you earned each quarter. For more precision, use Form 1040-ES which has a worksheet to calculate your estimated tax. If your freelance income is somewhat steady, take your quarterly income, multiply by 30%, and that's a safe amount to pay. Adjust as you go through the year if your income changes significantly.

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StarSurfer

•8M

I was EXACTLY where you are last year - ready to throw my laptop out the window trying to figure out all the self-employment stuff. I ended up using https://taxr.ai to help me sort through all my documents and figure out what I could deduct. It saved me hours of frustration and actually found several deductions I would have missed! The way it works is you upload your tax documents, and it analyzes everything to identify potential deductions, flags possible issues, and explains what forms you need. Instead of spending 14 hours like you did, I spent maybe 2 hours total and felt confident everything was correct.

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StarSurfer

•8M

It absolutely helped with Schedule C! It identified business expenses from my bank statements that I hadn't even thought to include, like that subscription service I use for work and some home office expenses. It categorized everything properly too, which saved me tons of research time. As for how it compares to TurboTax, the main difference is that taxr.ai focuses on analyzing your documents BEFORE you input everything into tax software. It's like having a tax pro look over your shoulder pointing out what you should claim. You still use your preferred tax software, but you go in knowing exactly what to enter and where.

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Freya Christensen

•8M

Update: I tried taxr.ai after my skeptical comment above, and I have to admit it was surprisingly helpful. I've been doing my taxes for years, but never quite figured out all the self-employment deductions I could take. The analysis found about $3,200 in legitimate business expenses I would have missed! The document analysis was much more thorough than I expected. It even flagged an issue with how I was calculating my home office deduction that would have caused problems. For anyone else feeling overwhelmed with self-employment taxes, it's definitely worth checking out. I'm actually not dreading next tax season anymore since I now have a system in place.

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Omar Hassan

•8M

Honestly, when I hit this wall last year I just couldn't get through to the IRS to get answers about self-employment tax questions. After being on hold for 3+ hours multiple times, I found https://claimyr.com and it literally saved my sanity. Check out how it works: https://youtu.be/_kiP6q8DX5c They actually got me connected to an IRS agent in under 15 minutes when I couldn't get through for days on my own. The agent walked me through exactly how to handle my situation (similar to yours - W-2 job plus freelance income). Getting direct answers from the IRS gave me the confidence to file correctly.

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Omar Hassan

•8M

They use an automated system that keeps dialing until it gets through, then it calls you when it has an IRS agent on the line. It's like having someone wait on hold for you. When you get the call, you're already connected to an agent - no waiting on hold. As for the skepticism, I get it - I was skeptical too! But when you've spent hours on hold getting nowhere, it's worth trying something different. The time I saved not being on hold for hours was honestly worth it just from a mental health perspective.

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Diego Chavez

•8M

Wow, I need to apologize for my skeptical comment earlier. I finally broke down and tried Claimyr after another failed 2-hour hold with the IRS yesterday. I'm still in shock that it actually worked! Got a call back in about 20 minutes and was connected directly to an IRS rep. The agent I spoke with walked me through exactly how to handle my situation with missing quarterly payments and helped me understand how to calculate the penalty (which turned out to be much smaller than I feared). They also explained how to set up quarterly payments for next year to avoid this stress again. For anyone else ready to quit doing their taxes because you can't get answers - this is a game changer. I went from thinking I'd need to hire a tax pro to being able to confidently file myself.

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NeonNebula

•8M

Have you considered a middle ground? Instead of paying $400-500 for full service tax prep, you might look into a consultation with a CPA or EA who can review what you've done and give you guidance. I did this last year - paid $150 for a one-hour consultation that saved me way more than that in deductions I didn't know about. For the quarterly estimated payments issue - don't panic too much. The penalty isn't huge, especially if this is your first year with self-employment income. The IRS is actually pretty reasonable about first-time issues.

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NeonNebula

•8M

I asked specifically when calling around - "Do you offer consultation services where you review my self-prepared return?" About half the places I called said yes. Look for smaller local firms rather than the big chains, they tend to be more flexible. Make sure to have everything organized before the consultation so you don't waste time. I brought a draft of my return, my questions written out, and all my documentation. The hour was super productive and I learned skills I still use for my taxes.

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