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Sharing my favorite tax meme: "Tax Season is just finding out if you sent the government the right amount of your money that they already took from your paycheck all year." š I feel this in my soul right now as I'm digging through receipts.
That's painfully accurate! My personal favorite is "Why is the 1040-EZ form 36 pages long? NOTHING about taxes is EZ!
Hahaha that one hits too close to home! I've been sending that exact meme to everyone. My other favorite is the one with the dog sitting in the burning room saying "This is fine" but photoshopped with tax forms all around š
Serious question - does anyone else find that tax memes are actually educational sometimes? I learned what a W-9 was from a joke about freelancers, and now I understand Schedule C better from all the self-employment memes floating around.
YES! I literally learned about quarterly estimated payments from a meme that was like "When you realize April, June, September and January are actually quarterly" with a shocked face. My accountant was impressed I even knew about them for my side gig.
As someone who worked for a tax resolution firm, I want to add something important: look into the IRS Fresh Start Program. It's designed specifically for people with significant back taxes. Depending on your current financial situation, you might qualify for an Offer in Compromise (settling for less than you owe), Currently Not Collectible status (temporary pause on collections), or a manageable payment plan. Also - this is crucial - if you had years where you made under the filing threshold, you might not even need to file for those years. But you'll need to verify that with a professional who can look at your specific situation. Good luck! Taking the first step is always the hardest part.
Thank you so much for mentioning the Fresh Start Program. I had no idea that existed. Do you think I should try to figure out which years I actually need to file before contacting them? Or should I just reach out and see what they say I need to do?
I'd recommend getting an understanding of your situation first before contacting them about Fresh Start. Request your tax transcripts for the past 6-10 years - this will show what income information the IRS already has on file for you. That way you'll be prepared for the conversation. As for which years to file, generally focus on the last 6 years as a priority. For years where your income was below the filing threshold (around $12,950 for 2022 as a single filer, but it varies by year and filing status), you might not technically be required to file - but there could be exceptions if you were self-employed or had certain other situations.
One thing nobody's mentioned yet - if your income really was under $25k for most of these years, you might actually be due refunds for some years rather than owing money! I had a friend in a similar situation who didn't file for 7 years, and when he finally did his taxes, he was owed refunds for 4 of those years. Just be aware that you can only claim refunds for the past 3 years (so 2022, 2023, and 2024 for this year's filing season). Any refunds for earlier years are lost forever, but you still need to file those returns if required.
You can file for FREE using the IRS Free File program partners if your income is under $73,000. No need to pay TurboTax for basic credits like the Saver's Credit! Go to irs.gov/freefile and you can access truly free tax filing software that handles all these credits without charging you.
Every time I try to use the IRS Free File options, I get partway through and then they tell me my situation is "too complicated" and try to upsell me. Does this actually work for claiming credits like the Retirement one?
Yes, it absolutely works for claiming the Retirement Savings Contribution Credit! The key is to start directly from the IRS.gov/freefile page rather than going to the tax company's main website. The versions of tax software available through the official IRS Free File program are different from the "free" versions advertised on the companies' own websites - they include all forms needed for most credits and deductions without upselling. Just make sure your income is under the threshold (currently $73,000) to qualify.
Check your W-2 box 12! I had the same thing happen and realized my employer had been putting a small amount into a retirement plan automatically. Look for codes like D, E or G in box 12 of your W-2. If there's a value there, you might actually qualify for the credit!
Just wanted to add that I'm an independent contractor in executive protection, and I've gone through this exact issue. The key distinction the IRS makes is whether the training is maintaining existing skills versus acquiring new skills. Maintaining existing skills you already use in your current profession is more likely deductible. Acquiring new skills to expand your expertise often isn't. My specialized Krav Maga training was denied as a deduction because I couldn't prove it was "ordinary and necessary" for my specific security contracts, even though it seemed logical to me.
What about uniforms and equipment? I'm guessing my security uniform is deductible but what about boots, flashlights and that kind of stuff?
Uniforms are typically deductible if they're required for your job and not suitable for everyday wear. So generic black pants probably wouldn't qualify, but a shirt with a security company logo would. Equipment like flashlights, specialized boots, and other gear is generally deductible if it's specifically required for your security work and not something you'd use outside of work. Keep all receipts and document how each item is used specifically for work purposes. Small items under $200 can often be fully deducted in the year purchased, while more expensive equipment might need to be depreciated over several years.
has anyone here used TurboTax for this kind of deduction? do they have any specific guidance for security professionals? i'm trying to decide which tax software to use this year and wanna make sure it covers these industry-specific deductions.
I used TurboTax Self-Employed last year for my security consulting business. It does have some industry-specific questions but honestly wasn't great for the more nuanced deductions. It asked about standard business expenses but didn't really guide me through the professional development stuff. I ended up upgrading to their Live service to talk to a tax expert about my martial arts training.
Riya Sharma
Just wanted to share that many H&R Block and some Jackson Hewitt offices are Certifying Acceptance Agents who can handle the ITIN application right there when they prepare your taxes. They verify your original documents on the spot so you don't have to mail anything to the IRS. We did this for my mother-in-law last year and it was SO much less stressful than sending her Philippine passport through the mail. It cost a bit extra but the peace of mind was worth it.
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Santiago Diaz
ā¢Do they speed up the actual processing time though? Or just help with the document verification part?
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Riya Sharma
ā¢They don't speed up the IRS processing time once it's submitted, but they eliminate the extra time your documents would spend in transit to and from the IRS. They also help prevent errors that could cause delays or rejection. In our case, the tax preparer caught that we had the wrong type of visa documentation before submission, which definitely would have caused issues. Overall, our total wait time was about 9 weeks from submission to receiving the ITIN, which seemed faster than friends who mailed everything themselves.
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Millie Long
WARNING! Be careful with who prepares your W-7. My cousin used some "tax preparer" from Facebook who charged $200 to handle her husband's ITIN application, and it was rejected TWICE because they filled out Section 6 completely wrong. Wasted 5 months and had to pay penalties for late filing! The IRS is super picky about the W-7 form. Make sure whoever helps you is actually qualified. Ask specifically about their experience with ITINs, not just general tax preparation.
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KaiEsmeralda
ā¢This happened to my neighbor too! They used some random preparer and later found out the person wasn't even a legitimate Certifying Acceptance Agent. So many scammers target immigrants specifically :
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