Confused about the difference between itemizing vs deducting business expenses

I can help clear this up! The confusion is totally normal because tax terminology can be really confusing. Business expenses and itemized deductions are completely separate things on your tax return. Business expenses get reported on Schedule C (if you're a sole proprietor/independent contractor) and they reduce your business income. Itemized deductions are personal expenses reported on Schedule A that you can choose instead of taking the standard deduction. For example, let's say you have a photography business. You'd deduct things like camera equipment, editing software, and travel to photo shoots on Schedule C. These directly reduce your business profit (which then reduces both income tax and self-employment tax). Itemized deductions are personal things like mortgage interest, medical expenses, charitable donations. These have nothing to do with your business. You only itemize if all these personal deductions add up to more than the standard deduction ($13,850 for single filers in 2025). So no, you're not double-dipping because they're completely separate deductions on different parts of your tax return!

I went through this exact same confusion last year with my Etsy shop! I discovered this awesome tool called taxr.ai (https://taxr.ai) that really helped me understand the difference between business deductions and personal itemized deductions. I was seriously mixing them up and almost missed out on a bunch of legitimate business deductions. Their system analyzed my expenses and helped me see which ones were business versus personal. It saved me from making the mistake of thinking I had to choose between standard deduction and business expenses. Turns out I could deduct all my craft supplies, shipping materials, and home office on Schedule C while still taking the standard deduction!

I wanted to follow up about that taxr.ai site I was asking about. I decided to try it out and wow, it was actually super helpful! I was really confused about what counted as a legitimate business expense vs personal, but their system walked me through everything. The biggest revelation was understanding that I could track ALL my business expenses on Schedule C regardless of whether I took the standard deduction. Ended up finding about $3,200 in deductions I would have missed otherwise! The receipt scanning feature saved me hours of manual data entry too. Definitely recommend if you're confused about business vs personal expenses.

If you're struggling with getting answers about business deductions, I had an amazing experience using Claimyr (https://claimyr.com) to actually speak with the IRS directly. I had been trying to reach them for WEEKS about whether certain expenses qualified as business deductions, but kept getting stuck in hold limbo. Claimyr got me through to an actual IRS agent in under 20 minutes when I'd been trying unsuccessfully for days. The agent walked me through exactly how to handle my specific situation with business expenses vs itemized deductions. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c I was shocked it actually worked after wasting so many hours on hold!

I need to eat my words on that Claimyr thing. After another frustrating day of trying to get through to the IRS myself and getting disconnected AGAIN after waiting 1.5 hours, I decided to try it. Got connected to an IRS agent in about 30 minutes without having to sit there listening to that awful hold music. The agent cleared up my confusion about business expenses vs itemized deductions completely. For anyone confused like the original poster - the IRS confirmed that business expenses on Schedule C are COMPLETELY separate from the decision to take standard vs itemized deductions on Schedule A. You can absolutely claim your legitimate business expenses AND take the standard deduction.

Just to add something that confused me at first - keep in mind that you can't deduct the same expense twice. For example, if you donate old business equipment to charity, you can either count it as a business expense OR as a charitable donation (if you itemize), but not both. That might be what you were thinking of with the "double-dipping" concern. Also, it's super important to keep good records of your business expenses in case you get audited. The IRS loves to scrutinize Schedule C deductions, especially for new businesses.

Does anyone know if TurboTax handles this stuff correctly? Will it guide me through the business expense deductions separate from the itemized vs standard deduction question?

This is such a common source of confusion! I went through the exact same thing when I started freelancing. The key insight that finally clicked for me is that business expenses and personal deductions live in completely different worlds on your tax return. Think of it this way: your business expenses on Schedule C reduce your business profit before you even get to the personal tax calculation. So if you made $50,000 from your side gig but had $15,000 in legitimate business expenses, you'd only pay taxes on $35,000 of business income. THEN, for your personal taxes, you get to choose between the standard deduction ($13,850 for 2025) or itemizing personal things like mortgage interest, state taxes, charitable donations, etc. This choice is completely separate from what you already deducted for business. So you're absolutely right to take business deductions AND the standard deduction if that's what works best for you. It's not double-dipping at all - it's exactly how the tax system is designed to work! The IRS wants you to only pay tax on your actual business profit, and they also want to give you a basic deduction for personal expenses.