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Something nobody's mentioned yet - you might want to look into making an estimated tax payment for the current year too. If you're still doing freelance work, you could end up in the same situation next year with owing taxes. The IRS has a system where you're supposed to pay taxes quarterly if you have income that doesn't have taxes withheld. The due dates are April 15, June 15, Sept 15, and Jan 15 of the following year. It helps avoid a big bill and potential underpayment penalties at tax time.
I didn't even think about that! Do I need to be making quarterly payments on freelance income going forward? How do I figure out how much to pay?
Yes, if you expect to owe $1,000 or more in taxes at filing time, you should be making quarterly estimated payments. The easiest way to calculate is to take about 30% of your freelance income (that covers both income tax and self-employment tax for most people) and pay that amount quarterly. You can make these payments online through the IRS Direct Pay system or through the EFTPS (Electronic Federal Tax Payment System). There's also Form 1040-ES which has worksheets to calculate a more precise amount if you want to be more accurate. Setting aside money from each freelance payment into a separate savings account specifically for taxes is also a good habit to start.
Don't forget about state taxes too! If you owe federal taxes on that unreported income, you probably also need to file a state amendment and pay additional state taxes. The process varies by state but is usually similar to the federal amendment.
This is super important! I once amended my federal return but forgot to do my state amendment. Ended up getting a notice with penalties a year later. Each state has different forms for amendments - some call it a "corrected return" instead.
Is there any penalty for not filing if you're due a refund? My cousin didn't file in 2023 but she definitely had tax withheld from her paychecks that she should get back.
No penalty if the IRS owes YOU money! But your cousin only has 3 years to claim that refund or she loses it forever. So she has until April 2027 to file her 2023 return and get that money back. The IRS is totally happy to keep your refund if you don't ask for it back in time!
One thing to consider - if your daughter qualified for any tax credits in 2023 like the American Opportunity Credit for college expenses, filing late could mean missing out on those. Some credits have specific filing deadlines separate from the refund deadline.
She did start college in fall 2023, so this is really good to know. We paid about $3,500 out of pocket after her scholarships. I'll make sure we look into that credit when filing her prior year tax return. Thank you!
Just wanted to add that you should keep good records of all your Roth IRA contributions over the years. I learned this the hard way! The financial institutions don't track your basis for you, and if you ever get audited, the burden is on you to prove those were contributions coming out, not earnings. I recommend creating a simple spreadsheet with dates, amounts, and which tax year each contribution was for. Keep copies of your account statements showing the contributions too. This makes it super easy if you ever need to withdraw or if there's any question about what portion of your Roth is contributions vs. earnings.
That's really good advice. I think I have most of my contribution records in old emails, but should I also request official documentation from my financial institution to be safe?
Absolutely get official documentation if you can. Year-end statements are great because they often summarize annual contributions. Some institutions also provide specific tax forms or contribution confirmations. If they offer any kind of contribution history report, definitely request that. Email confirmations are good supplementary evidence, but official statements directly from the institution carry more weight if there's ever a question. The more documentation you have, the better, especially for older contributions that might be harder to verify years later.
Has anyone tried just calling the financial institution directly? Sometimes these 1099-R coding issues are just simple mistakes they can fix by issuing a corrected form. My brother had this happen last year with Fidelity and they sent him a corrected 1099-R with the right code within a week.
I tried that with Vanguard last year and they refused to change the code. They said their policy is to use code 1 for all early distributions and it's up to the taxpayer to claim any exceptions on their tax return. Super annoying but apparently common practice.
Don't forget that if you're deducting Facebook marketing, you should also track conversions so you can prove the business purpose if audited. I track each lead that comes from Facebook and how many convert to clients. My tax guy says this helps establish that the ads are "ordinary and necessary" because I can show they actually generate business. I keep a spreadsheet showing cost per lead and cost per client acquisition from each marketing channel.
How detailed do you get with tracking? Do you need to show specific clients that came from specific ads? I'm not very organized with this stuff.
You don't need to get super granular with connecting specific clients to specific ad campaigns, but having general data is helpful. I use Facebook's conversion tracking pixel on my website and then keep a simple spreadsheet that shows monthly ad spend, number of leads generated, and clients that resulted. The key is showing that your marketing expenses have a legitimate business purpose and aren't personal. Even basic tracking is better than nothing. When I started, I just asked new clients "how did you find me?" and kept notes. Now I use more sophisticated tools, but both approaches work for establishing the business connection.
I'm a bit confused... I'm also a realtor spending about $900-1200/month on Facebook. Does anyone know if we need to keep the actual ad creatives as documentation or just the receipts from Facebook? My ads change every couple weeks.
The receipts are most important, but I also take screenshots of my active campaigns and save them in a folder. My accountant said receipts prove the expense, but screenshots of the ads help prove they were for business if questioned.
Natalie Wang
Just an extra tip - if you've been using FreeTaxUSA for multiple years, you can actually go back and look at your 2019 Schedule A to see exactly how much state income tax you deducted. Look at line 5a. This will help you understand how much of your refund might be taxable. Also remember that if you didn't receive any tax benefit from the deduction (like if you were close to the standard deduction amount), then the refund isn't taxable. The worksheet helps figure this out.
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Noah Torres
ā¢Where do you find old returns in FreeTaxUSA? I've been using them for years but never figured out how to see my past filings.
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Natalie Wang
ā¢You need to log into your FreeTaxUSA account, and on the main dashboard there should be a section called "Prior Year Returns" or "Tax Return History." Click on that and you'll see all the years you've filed with them. Select 2019, and you can view or download the full PDF of that return. If you downloaded and saved your returns each year, you can also just open the PDF directly from your computer. The Schedule A is usually around page 11-13 of the complete return.
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Samantha Hall
Is this 1099G thing only an issue if your state refund is large? I got like $340 back from state taxes for 2019 but never received a 1099G. Should I be worried??
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Ryan Young
ā¢States are required to issue 1099-Gs for all refunds they send, but sometimes they don't if the amount is very small. $340 is actually right around the threshold where some states might not bother. Technically you're still supposed to report it if you itemized that year, but realistically the tax impact would be very minimal.
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