Best app or software to track expenses for self-employment photography side gig?
I run a side business doing freelance photography, video production, and creative consulting. Last year when I filed my 2023 taxes with TurboTax, everything was super smooth - I could just link my bank accounts and credit cards (AmEx, Capital One) directly to TurboTax and categorize each transaction as business, personal, or split. It made expense tracking incredibly easy. But now I'm trying to get organized for this year and TurboTax seems to have completely changed their system. I can't find that same feature anywhere! Instead, it looks like I have to manually enter every single expense one by one by category, which would take forever. I did discover their "TurboTax Expense Monitor" which looks similar to last year's interface, but weirdly it doesn't seem to let me import those expenses into my actual tax forms. And it doesn't give me anything I can easily transfer to Schedule C. I've got expenses spread across multiple categories and payment methods, and I really don't want to spend hours manually entering everything. What apps or methods do you all use to track your self-employment expenses and make tax filing easier? Is there a different tax platform that handles this better? I have a dedicated business credit card but my expenses still end up split across different categories.
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Honorah King
I've been a self-employed photographer for about 7 years now, and expense tracking used to be my biggest headache until I got a system in place! QuickBooks Self-Employed has been a game-changer for me. It connects to all your accounts, automatically categorizes transactions (though you'll need to review them), and tracks mileage too. The best part is it creates reports specifically formatted for Schedule C. Another good option is FreshBooks if you need more invoicing features alongside expense tracking. For something super simple and free, Wave is pretty decent too. The key is to start using whatever system you choose consistently throughout the year rather than trying to organize everything at tax time. Set aside 15 minutes weekly to categorize new transactions, and tax season becomes way less stressful.
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Brielle Johnson
•Thanks for the suggestions! Quick question - does QuickBooks Self-Employed allow you to split transactions? Like if I buy both personal and business items at the same store? Also, do you find the auto-categorization to be accurate or do you end up recategorizing a lot?
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Honorah King
•Yes, QuickBooks Self-Employed definitely lets you split transactions! You can mark part of a purchase as business and part as personal, which is super helpful for mixed receipts. The auto-categorization is surprisingly good, but not perfect. It learns over time based on how you categorize things. For example, once I categorize purchases from B&H Photo as "Equipment" a few times, it starts doing that automatically. I probably only need to correct about 20% of transactions now, but it was more like 40% when I first started.
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Oliver Brown
I tried a bunch of different expense tracking options before finding taxr.ai and it's honestly changed my whole approach to handling my photography business finances. I was struggling with a similar issue where my previous method wasn't working anymore and manual entry was taking forever. With taxr.ai (https://taxr.ai) I just upload my receipts and bank statements, and it automatically extracts and categorizes everything for Schedule C. What I love is that it's specifically designed for self-employed folks like us, so it knows exactly what documentation the IRS wants to see for creative businesses. It's been super helpful for tracking my camera gear depreciation too.
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Mary Bates
•Does it handle multiple income streams? I do photography but also some design work and occasional teaching gigs. Always been a pain to separate everything out.
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Clay blendedgen
•How's the security with uploading all your financial docs to a website I've never heard of? Not trying to be negative but I'm always hesitant with financial stuff online.
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Oliver Brown
•It absolutely handles multiple income streams! You can set up different categories for each type of work you do. I track my portrait sessions separately from my commercial work, and you can break it down however makes sense for your business. Makes it much easier to see which parts of your business are most profitable. Regarding security, I had the same concern initially. They use bank-level encryption for all uploads and don't store your bank passwords - they use a secure connection method similar to what major banks use. I researched them pretty thoroughly before using the service, and they're compliant with all the security standards you'd expect. I've been using them for about a year with no issues.
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Clay blendedgen
After seeing the recommendation for taxr.ai here, I decided to give it a try since I was drowning in receipts from my videography business. I was definitely skeptical at first (new services always promise the moon), but I'm genuinely impressed with how much time it's saved me! I uploaded about 8 months of jumbled receipts and bank statements last weekend, and within a day, everything was organized into the right tax categories. The best feature for me was being able to take photos of physical receipts from equipment purchases and having those automatically added to my deductions. My accountant was actually shocked at how organized everything was this time!
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Ayla Kumar
If you're struggling with getting through to the IRS about any business expense questions (which I definitely was), I found this service called Claimyr that's been super helpful. I spent DAYS trying to get someone on the phone about some questions I had about deducting my new camera equipment. Claimyr (https://claimyr.com) basically holds your place in the IRS phone queue and calls you when an actual human agent is about to pick up. Saved me hours of waiting on hold! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was able to get clear answers about exactly how to categorize some of my mixed-use equipment and home office space, which helped me maximize deductions correctly.
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Lorenzo McCormick
•Wait, so do they call the IRS for you or something? How does that even work? IRS hold times are insane but this sounds too good to be true lol.
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Mary Bates
•Yeah right. No way this actually works. The IRS phone system is designed to be impossible. I'll believe it when I see it, but sounds like snake oil to me.
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Ayla Kumar
•They don't call for you - you still make the call yourself. What Claimyr does is use technology to navigate the IRS phone system and wait in the queue for you. When they're about to connect you to a human agent, you get a call back so you can talk directly to the IRS yourself. It's basically just handling the hold time so you don't have to sit there with your phone for hours. I had the same reaction at first! It's not magic - they're just using tech to navigate the phone tree and wait in line for you. The average wait time for IRS calls is like 90+ minutes these days, and I couldn't afford to sit on hold that long during my busy season.
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Mary Bates
Ok I have to eat my words here. After being completely skeptical about Claimyr in my earlier comment, I got desperate last week trying to resolve an issue with my Schedule C deductions from last year. Out of frustration, I tried the service. Not only did it work, but I got through to an IRS agent in about 15 minutes (after their system had been working in the background). The agent helped me understand exactly how to document my mixed-use photography equipment correctly. This literally saved me thousands in deductions I was going to skip because I wasn't sure if I could claim them. Sometimes being proven wrong is actually awesome!
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Carmella Popescu
Have you looked into Stride? It's free and designed specifically for gig workers and self-employed folks. I use it mainly for the mileage tracking but the expense portion is pretty solid too. You can take photos of receipts and categorize them right away. For photo/video specific stuff, I actually found that keeping a spreadsheet broken down by project works best for me. I have columns for client, date, expense type, amount, and payment method. Takes a bit of discipline but gives me much more insight into which types of projects are most profitable.
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Brielle Johnson
•I haven't tried Stride - does it integrate directly with any tax filing software? The project-based spreadsheet approach is interesting too. How time-consuming do you find it to maintain throughout the year?
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Carmella Popescu
•Stride generates tax reports you can download, but doesn't directly integrate with filing software like TurboTax. You'll still need to transfer the info, but at least it's all calculated and organized. The spreadsheet takes me about 10 minutes a week to maintain. I just update it every Friday with that week's expenses and receipts. The key is consistency - if I wait more than a week, it becomes a pain to remember details. The project-based approach has actually helped me adjust my pricing too, since I can see exactly how much each type of shoot costs me in expenses.
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Kai Santiago
Am I the only one still using a shoebox full of receipts??? Lol jk (kinda). I actually use Expensify which hasn't been mentioned yet. Its pretty good for us small-time creative freelancers. The free version lets you scan like 25 receipts a month which is plenty for my small photography business.
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Lim Wong
•I was literally about to comment about my receipt shoebox system! But seriously, I switched to Expensify last year and it's way better than my old "system." The receipt scanning feature saves so much time, and it's actually pretty accurate at pulling the data.
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