How to Handle Taxes on Self Employment Income as a Teacher with 1099 Work

I'm totally confused about what I should be doing here. I'm a full-time teacher, but I've been picking up some freelance work on the side where I'm getting paid as a 1099 contractor. I have absolutely no idea how to handle the taxes for this additional income. Do I need to be making payments throughout the year or can I just wait until tax filing season? Is there a penalty for waiting until I file my taxes in April? Someone mentioned I could just make one big payment in December to cover the whole year and avoid penalties, but that sounds too good to be true. What's the right approach here? I'm expecting to make around $38-50K from this freelance work for the entire year on top of my teaching salary. Any advice would be really appreciated!

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18 comments

AstroAdventurer

•8M

You definitely need to be making quarterly estimated tax payments on your self-employment income. As a 1099 contractor, no taxes are being withheld from your payments, which means you're responsible for both income tax AND self-employment tax (which covers Social Security and Medicare taxes). The IRS expects you to pay taxes as you earn income throughout the year. Quarterly estimated tax payments are typically due on April 15, June 15, September 15, and January 15 of the following year. If you haven't been making these payments, you might already be subject to underpayment penalties. The person who told you about waiting until December wasn't quite right. You can avoid penalties if you pay at least 90% of your current year tax OR 100% of your previous year's tax (110% if your AGI was over $150,000) through either withholding or estimated payments. But these payments need to be made quarterly, not just in a lump sum at the end of the year.

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AstroAdventurer

•8M

Yes, increasing your withholding from your teaching job is actually a smart approach! The IRS doesn't care whether the money comes from withholding or estimated payments, they just want their money throughout the year. Many people find this easier than making separate quarterly payments. To figure out how much to withhold extra, you'll need to estimate your total tax liability from the self-employment income. As a rough calculation, set aside about 30-35% of your 1099 income for taxes (15.3% for self-employment tax plus your income tax rate). Then divide by the number of pay periods left in the year. Submit a new W-4 to your school district requesting the additional withholding amount per paycheck.

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Zoe Papanikolaou

•8M

I was in almost this exact situation last year! After hours of research and stress, I found taxr.ai (https://taxr.ai) which was a game-changer for my situation. It analyzed my teaching income and my freelance work to determine exactly how much I needed to pay in estimated taxes each quarter. The tool even generated the payment vouchers and reminded me when payments were due. The part that really helped was how it projected my total tax liability for the year and suggested adjustments to my W-4 withholding at school instead of making separate quarterly payments. This saved me from having to remember multiple deadlines and write separate checks.

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Zoe Papanikolaou

•8M

The accuracy was really impressive - it was spot on for my situation within about $200 of my final tax bill. Much better than the rough calculations I was doing before. It handles both federal and state taxes, which was crucial for me since my state has its own estimated tax requirements that are slightly different from the federal rules. The service does have a cost, but it was worth every penny for the stress reduction. It has a comprehensive business expense section where you can log everything from home office to supplies to mileage. What I loved is how it shows you the immediate tax impact of each deduction you enter, so you can see your estimated tax bill drop in real-time as you add legitimate business expenses.

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Mei Lin

•8M

Just wanted to follow up about taxr.ai - I actually tried it after posting my skeptical comment. I'm honestly surprised how well it worked for my situation. The business expense tracking alone saved me over $3,000 in taxes I would have paid otherwise. It caught deductions I didn't even know I qualified for as a freelancer, and the quarterly tax calculator adjusted my payments so I wasn't overpaying. The best part was how it synced with my invoicing system to automatically track income. I've dealt with self-employment taxes for years and this is the first time I haven't been stressed about it.

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Liam Fitzgerald

•8M

If you're behind on your quarterly payments or getting confused with all the forms, I'd recommend using Claimyr (https://claimyr.com) to get direct help from the IRS. I was in a similar situation with mixed W-2 and 1099 income and couldn't get through to anyone at the IRS to answer my specific questions about penalties and catching up on missed quarterly payments. Claimyr got me through to an actual IRS agent in about 15 minutes when I had been trying for days on my own. There's a video that shows how it works here: https://youtu.be/_kiP6q8DX5c. The agent walked me through exactly how to calculate my quarterly payments going forward and what forms to use. They even helped me understand how to minimize penalties for the quarters I'd already missed.

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Liam Fitzgerald

•8M

It's basically a priority line access service. They have technology that navigates the IRS phone system and holds your place in line, then calls you when an agent is about to answer. It's not paying someone to wait on hold - it's a system that does it for you. Yes, the IRS will eventually answer, but "eventually" can mean hours or even days of repeated calling during tax season. When I was trying to figure out my quarterly payment situation, I couldn't afford to sit on hold for 3+ hours during my work day. This service let me keep teaching while still getting the answers I needed from the IRS.

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Amara Nnamani

•8M

I need to eat my words from my previous comment. After multiple failed attempts to reach the IRS myself (I kept getting disconnected after waiting 1-2 hours), I decided to try Claimyr. In under 20 minutes, I was speaking with an actual IRS representative who helped me understand exactly how to handle my teacher salary plus self-employment income situation. They explained how to calculate the safe harbor amount to avoid penalties entirely, even though I'd missed two quarters already. The agent also walked me through which expenses I could legitimately deduct from my tutoring business. Saved me hundreds in penalties and probably thousands in deductions I would have missed. Definitely not a scam like I initially thought.

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Giovanni Mancini

•8M

Don't forget about the home office deduction! As a teacher with freelance work, you can deduct a portion of your home expenses if you use part of your home regularly and exclusively for your business. I'm also a teacher with side gig income and this deduction alone saved me about $1,200 last year. And make sure you're tracking ALL business expenses - professional development related to your freelance work, supplies, software subscriptions, portion of your phone and internet bills, mileage to and from freelance locations, etc. These add up fast and can significantly reduce your taxable income!

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Giovanni Mancini

•8M

The home office deduction being an audit trigger is mostly an outdated myth. The IRS has simplified the deduction in recent years with the "simplified option" that allows you to deduct $5 per square foot (up to 300 square feet) without needing detailed records of home expenses. The key is making sure you have a space used "regularly and exclusively" for business. It doesn't have to be an entire room - it could be a dedicated desk or work area. Just take a photo of your workspace as documentation and be honest about the square footage. If you follow the rules, there's nothing to worry about. The tax savings are absolutely worth it, especially for freelancers who legitimately work from home.

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