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Just my 2 cents - for contract income of only $4800 in a quarter, you might not actually need to make estimated payments depending on your overall tax situation. There's a safe harbor provision where you won't face penalties if: 1) You'll owe less than $1,000 in tax for the year after withholding 2) You pay at least 90% of this year's tax through withholding/est. payments 3) You pay 100% of last year's tax (110% if higher income) If you have a regular job with withholding that covers your tax liability from last year, you might be fine!
Oh wow, this is really helpful info! I do have a full-time job with regular withholding that more than covered my tax liability last year. Does that mean I might not even need to worry about this missed payment? How would I figure out if I'm covered by this safe harbor thing?
You're likely in good shape then! If your W-2 withholding from your regular job will cover at least 100% of what your total tax liability was last year, you should qualify for the safe harbor provision and avoid any penalties. To verify this, look at your last year's tax return (Form 1040) and find the "total tax" line (line 24 on recent returns). Then check your projected W-2 withholding for this year - if it will be equal to or greater than last year's total tax, you're covered by the safe harbor rule. Many people with side gigs and regular employment fall into this category and don't actually need to make quarterly payments despite having untaxed income on the side.
One thing nobody mentioned is that you should update your address with the IRS ASAP! You can do this by filing Form 8822. It's super important because even if you don't owe penalties now, you definitely want any future IRS correspondence going to the right place!
You can also update your address with the USPS and they will forward your mail, including IRS notices. I did this when I moved and it worked fine.
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Another approach to consider: you might want to pay slightly more than the calculated amount for your estimated taxes. I max out the 24% bracket too, and I always add an extra 5% to my estimated payments as a buffer. This helps in case of any calculation errors and prevents surprises. Also, don't forget that you can adjust your payments throughout the year. If your income situation changes, you can modify your remaining estimated payments accordingly.
That's a good suggestion about adding a buffer. I hadn't considered that. How do you handle the timing of your Roth conversions throughout the year? Do you do them all at once, or spread them out quarterly to match when you're making the estimated payments?
I spread my conversions throughout the year rather than doing them all at once. This gives me more control and helps with cash flow since I'm making estimated tax payments quarterly anyway. I usually do slightly larger conversions in the first half of the year, especially if the market is down. This gives those converted amounts more time to potentially grow tax-free in the Roth. By December, I have a clearer picture of my exact tax situation and can make a final conversion that precisely hits my target bracket maximum.
Has anyone been using tax software to calculate these estimated payments? I tried using last year's TurboTax to estimate my 2025 taxes for Roth conversions, but it keeps giving me errors about tax year mismatches.
Most tax software isn't designed for future year planning like this. I've had good luck with Excel spreadsheets that you can update with the new tax brackets each year. The IRS usually announces inflation adjustments for the upcoming year around October/November.
Thanks for confirming what I suspected! The tax software just isn't built for this kind of forward planning. I guess I'll need to build my own spreadsheet or look into some of the dedicated retirement planning tools mentioned in this thread.
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I use a super simple formula for estimating my take-home pay as a freelancer. Take gross income, subtract business expenses to get net profit. Set aside 15.3% of that for self-employment tax, then another 15-25% for income tax (depending on your bracket). What's left is roughly your take-home. So for your friend making $75k: - Let's say $10k in business expenses - Net profit = $65k - SE tax = ~$10k (15.3%) - Income tax = ~$10-16k (15-25%) - Take-home = ~$39-45k This isn't perfect but gives you a ballpark. I always set aside 30% of every check I get into a separate tax account to be safe.
Thanks for this breakdown! But what about the tax deductions for health insurance premiums and retirement contributions? I've heard those can make a big difference for self-employed folks.
Good point! Self-employed health insurance premiums are generally deductible "above the line" which means they reduce your adjusted gross income. Same with retirement contributions to SEP IRAs, Solo 401(k)s, etc. So if your friend pays $6,000 annually for health insurance and puts $10,000 into a SEP IRA, that could reduce their taxable income by $16,000, which would save roughly $4,000-5,000 in income taxes depending on their bracket. That would increase their take-home by the same amount.
Has anyone found a good app for tracking self-employment income and expenses that also estimates your quarterly tax payments? I've tried a few but they're either too complicated or don't calculate taxes accurately.
I've been using QuickBooks Self-Employed for about 2 years now. It automatically tracks mileage, lets you categorize expenses, and calculates your quarterly tax payments. It's not perfect (sometimes categorizes things wrong), but it's been pretty close on the tax estimates.
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Don't forget to look into the Fresh Start program with the IRS. If you've been incarcerated and have no assets, you might qualify for Currently Not Collectible status which would put your tax debt on hold. Also, tax debts over 10 years old can sometimes be uncollectible due to the statute of limitations. I went through something similar after 4 years inside. The key is to stay in communication with the IRS - that's the biggest mistake people make. Once you get your transcripts, you might also qualify for innocent spouse relief if some of these taxes stem from a former partner.
Thanks for this info! When you say "stay in communication" with the IRS - what's the best way to do that? Should I be calling them regularly or sending letters? I worry about saying the wrong thing or making my situation worse.
The best way to stay in communication is to respond to every notice they send you, even if it's just to say you're working on gathering information. Phone calls are good for quick questions, but always follow up with something in writing when dealing with actual tax issues or disputes. Don't worry too much about saying the wrong thing. The IRS deals with people in your situation all the time. Be honest about your incarceration, your current financial situation, and your willingness to resolve the issue. They actually have programs specifically designed for people with hardships, but you have to be proactive in requesting them.
One more thing - if you were working in any prison work programs during your incarceration, that income might be taxable depending on the program type. Most prison work doesn't generate W-2s, but some work release or industry programs do. Check if you have any legitimate income from those sources before disputing everything. When I got out, I had both fraudulent income reports AND legitimate ones from my work release program in the last 8 months of my sentence.
This is so important! My cousin disputed ALL income on his transcripts after incarceration and ended up creating more problems because he actually did have legit income from a work program that partnered with a private company. They had withheld taxes and everything.
Zoe Kyriakidou
Does anyone know if there's a specific CRA guidance document on this? I remember seeing something a while back about expenses that are "ordinarily" personal but can be business expenses in certain contexts.
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Jamal Brown
•I believe what you're thinking of is Interpretation Bulletin IT-518R. It talks about food, beverage, and entertainment expenses. The CRA distinguishes between expenses incurred for entertainment purposes (50% limit) and those that are part of your income-earning process (potentially 100% deductible).
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Mei Zhang
One thing to consider - if they're getting free meals or discounted pricing in exchange for the content creation, that creates another tax wrinkle. That would technically be barter income and needs to be reported as revenue, which offsets some of the deduction benefit. I've seen this trip up a lot of content creators who don't realize that "free" products or services received in exchange for promotion are technically taxable income at fair market value.
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