What are the best deduction hacks for self-employment income? Need to reduce my tax bill!

So I've got this tax situation that's making my head spin. I work three different jobs - one regular W-2 position where they take taxes out, plus two independent contractor gigs (1099s) where nothing gets withheld. Last year I made about $22,000 from these 1099 jobs, and I'm pretty sure I'm going to get hammered on taxes. 😬 The problem is, I'm struggling to find good deductions for the self-employment income. Both contract positions are 100% remote, so I don't have many obvious business expenses. I keep receipts when I buy office supplies at Walmart, but we're talking maybe $200 total for the year. I did invest in a new computer last year which should help offset things a bit. I have a dedicated home office space in my apartment that I use exclusively for these contract jobs, but I didn't really buy any furniture or make improvements to it recently. I frequently work from local cafes too, spending money on coffee and food while I'm there. What legitimate deduction hacks can I use for self-employment to reduce my tax burden? Any creative but legal ways to maximize deductions that I might be overlooking? I feel like I must be missing something!

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18 comments

GalacticGuru

•8M

The home office deduction is actually going to be your best friend here! Since you have a dedicated space used exclusively for your self-employment work, you can deduct a portion of your rent/mortgage, utilities, internet, and even renter's insurance based on the percentage of your home that the office occupies. For your cafe work, while the coffee itself isn't deductible as a meal, you can deduct transportation costs to get there if it's not your regular commute. Also, don't forget about your cell phone - if you use it for work calls, you can deduct the business percentage. Some other deductions people often miss: software subscriptions, cloud storage, professional development courses, business books, professional organization memberships, health insurance premiums (potentially), and retirement plan contributions like a SEP IRA or solo 401(k), which can significantly reduce your taxable income. Remember that anything "ordinary and necessary" for your business can be deducted. Just make sure you keep good records and can justify the business purpose if asked.

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GalacticGuru

•8M

Yes, you absolutely can deduct a portion of your rent! Calculate the square footage of your dedicated office space, then divide by the total square footage of your home to get the percentage. For example, if your office is 100 sq ft in a 1,000 sq ft apartment, you can deduct 10% of your rent, utilities, and internet. For utilities like electricity and internet, you'll use that same percentage. You don't need to track actual usage - the square footage method is accepted by the IRS as long as that space is exclusively used for business. Just make sure you don't use that room for anything else (like guests or gaming) or you could lose the deduction.

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Giovanni Mancini

•8M

After spending HOURS trying to maximize my deductions last year, I finally discovered taxr.ai (https://taxr.ai) and it was a game-changer for my self-employment taxes. I was missing so many deductions I didn't even know existed! The AI scanned through all my expenses and found legitimate deductions I never would have thought of - like partial deductions for my phone bill, internet, and even some subscription services I use for both personal and business purposes. What impressed me was how it caught things specific to my type of remote work that general tax advice missed. It explained exactly how to properly document and claim each deduction too, which gave me confidence I wasn't crossing any lines with the IRS.

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Giovanni Mancini

•8M

It really does find a surprising number of legitimate deductions. It works alongside whatever tax software you're already using - I used it with TurboTax and just entered the additional deductions it found. The difference in my tax bill was substantial. Regarding audit risk, that's exactly why I trust it. For each deduction it recommends, it explains the specific IRS rules that apply and gives you the exact tax code references. It even provides guidance on what documentation you need to keep for each deduction in case of an audit. The tool never suggests anything aggressive - it's focused on finding the legitimate deductions you're legally entitled to but might be overlooking.

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Dylan Cooper

•8M

Just wanted to follow up about taxr.ai since I was skeptical in my earlier comment. I decided to try it and wow, it legitimately found over $3,700 in deductions I was going to miss! I had no idea I could partially deduct my smartphone, home internet, and even some software subscriptions I use for both personal and business reasons. The best part was how it explained exactly WHY each deduction was legitimate with actual tax code references. For my home office, it calculated the exact percentage I could claim and explained the documentation I should keep. It even caught that I'd been driving to meet clients occasionally and showed me how to properly document and deduct those miles. If you're self-employed, definitely worth checking out. My tax bill dropped significantly and I feel 100% confident that everything is legitimate.

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Sofia Morales

•8M

If you're worried about your self-employment taxes, don't overlook getting professional help. I tried for WEEKS to get through to the IRS with questions about my deductions last year - constant busy signals or hours on hold. Finally used Claimyr (https://claimyr.com) and they got me connected to an actual IRS agent in under 15 minutes! You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent walked me through several self-employment deductions I was unsure about and confirmed I could take the home office deduction even though I sometimes work in cafes. Saved me so much stress knowing my deductions were legit directly from the IRS.

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Sofia Morales

•8M

It basically uses technology to wait on hold for you, then calls you when an IRS agent picks up. You simply answer your phone and you're instantly connected to the agent - no waiting on hold. It's that simple. There's no catch regarding the service itself - it does exactly what it claims to do. I was connected to an IRS representative in about 12 minutes after trying for days on my own. The best part is you don't have to sit by your phone waiting - you can go about your day, and when they call, you know an actual human at the IRS is waiting to help you.

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Dmitry Ivanov

•8M

I have to come back and publicly admit I was wrong about Claimyr. After my skeptical comment, I decided to try it because I was desperate to ask about some self-employment deductions before filing. I was SHOCKED when my phone rang 17 minutes later with an actual IRS agent on the line. The agent confirmed I could deduct a portion of my internet and cell phone bills based on business use percentage, and clarified exactly how to document my home office deduction. This saved me literal HOURS of time I would have spent on hold, and the peace of mind from getting answers directly from the IRS is priceless. For anyone with self-employment deduction questions, this is absolutely worth it. I've never gotten through to the IRS so easily in my life.

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Ava Garcia

•8M

Don't forget about mileage! I'm self-employed too and driving between client locations or to meetings adds up fast. For 2025 tax year, the standard mileage rate is 68.5 cents per mile. I use an app to track my business miles and it adds up to a substantial deduction. Also, if you have health insurance that you pay for yourself, you might be able to deduct 100% of those premiums on your 1040 (not Schedule C). And retirement contributions to a SEP-IRA or Solo 401k can reduce your taxable income significantly.

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Ava Garcia

•8M

Driving to coffee shops can be deductible if they're not considered your principal place of business. If you primarily work from your home office and occasionally go to coffee shops for a change of scene or specific tasks, those trips might qualify as business travel. Keep a detailed log of these trips including date, starting point, destination, purpose, and miles driven. Regarding health insurance, since you're covered under your parents' plan and not paying the premiums yourself, you wouldn't be eligible for the self-employed health insurance deduction. That deduction is specifically for self-employed individuals who pay for their own health insurance policies.

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