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One thing to watch out for with multiple jobs in the same year: Social Security tax withholding. Each employer will withhold 6.2% for Social Security up to the annual wage base limit ($147,000 in 2022), but they don't know what another employer already withheld. If your combined income from both jobs exceeds the wage base limit, you might have excess Social Security tax withheld. The good news is you'll get this back when you file your return. Just something to be aware of when looking at your YTD totals.
Oh that's really interesting and not something I had considered! My combined income won't be anywhere near that limit this year, but good to know for the future. Are there any other deductions that might work this way when you have multiple employers?
Medicare withholding is different - there's no wage base limit for the standard 1.45% Medicare tax, so that continues regardless of how much you earn. However, there is an Additional Medicare Tax of 0.9% that kicks in when your income exceeds $200,000, which can also be overwithheld with multiple employers since each employer starts withholding this when your wages with them exceed $200,000. State unemployment insurance contributions might also have wage bases that work similarly to Social Security, where you could have excess withholding with multiple employers. This varies by state though, so you'd need to check your specific state's rules.
I recommend getting an account on the IRS website to track your withholding. You can see what each employer has reported for your quarterly tax payments. Super helpful when you've had multiple jobs!
I've heard about this but haven't tried it. Is it the same as creating an account on irs.gov? Is it easy to set up? I've had three W-2 jobs this year plus some freelance work and I'm worried about keeping track of everything.
One thing nobody's mentioned yet is contacting your Congressional representative's office. I had a nightmare situation with the IRS last year that dragged on for 8 months with no resolution despite sending in documentation multiple times. I finally contacted my Congressman's office and explained the situation. They have staff specifically dedicated to helping constituents with federal agency issues. I filled out a privacy release form, and within THREE WEEKS, the IRS had processed my documentation and resolved the issue. Congressional offices have special channels to IRS Taxpayer Advocate offices that can cut through red tape. Don't underestimate how effective this approach can be when you've tried everything else!
That's a great suggestion I hadn't thought of! Did you just call your representative's local office? Was there a specific person or department you asked for? I'm willing to try anything at this point.
Yes, I called my rep's local district office (not their DC office). Just ask to speak with the caseworker who handles IRS issues. Every congressional office has staff dedicated to constituent services. They'll email you a privacy release form that you need to sign and return, which gives them permission to inquire about your case. Make sure you provide them with copies of all the correspondence you've had with the IRS so far, including your notice numbers and any reference numbers. The magic happens because congressional inquiries go to a special unit at the IRS that is much more responsive than regular channels. They have to provide updates to congressional offices, so things suddenly start moving much faster.
Has anyone tried using the IRS's online account features to resolve these types of issues? I set up an online account on IRS.gov recently and was shocked to find I could see all my notices, tax records, and even upload documents directly through the portal rather than mailing them. I'm wondering if uploading documents this way is more reliable than sending them through the mail where they seem to get lost in the void.
I've used the online account system and while it's good for viewing your tax records and making payments, I found the document upload feature to be hit or miss. I uploaded documentation for an issue similar to OP's, and there was no confirmation that anyone had reviewed it or that it was attached to my case. I ended up having to mail in physical copies anyway after calling and finding out the uploaded documents weren't associated with my specific case/notice. The system needs a lot of improvement.
Thanks for sharing your experience. That's disappointing to hear. I was hoping the online system would be more efficient, but sounds like it has the same problems as mailing documents. Did you at least get some kind of upload confirmation when you submitted the documents, or was it completely unclear if they were received at all?
One thing nobody's mentioned yet - if your employer offers a Flexible Spending Account (FSA) for healthcare, you can use that to pay for therapy with pre-tax dollars, which is even better than taking the deduction in many cases. My therapist doesn't take insurance either but gives me a superbill that I submit to my FSA for reimbursement. The advantage is you don't have to worry about the 7.5% AGI threshold with an FSA. The downside is the use-it-or-lose-it aspect and the lower contribution limits compared to itemizing deductions.
Does the FSA administrator ever question therapy expenses or ask for details beyond the superbill? I'm private about my mental health treatment.
In my experience, the FSA administrator has never questioned my therapy expenses or asked for additional details. The superbill usually just lists the service code and amount without any specific details about what was discussed in therapy. It typically shows something generic like "psychotherapy services" or a CPT code. FSA administrators are also bound by privacy rules, so they can't share information about your specific medical treatments with your employer. I've been submitting therapy expenses to my FSA for three years now without any privacy concerns.
Has anyone successfully deducted online therapy costs? I've been using BetterHelp for my trauma therapy and wondering if the same rules apply since they send digital receipts.
Just a heads up - I work in the high-ticket sales industry too and saw a company get absolutely hammered for this exact issue last year. The IRS determined ALL their 1099 sales reps were actually employees and hit them with back taxes, penalties, and interest going back 3 years. The company tried to claim the reps had "independence" but the IRS didn't buy it because they: 1) Had to attend mandatory meetings 2) Were required to use company scripts 3) Had to work specific hours 4) Used company CRM and tools 5) Were subject to performance reviews Sound familiar? Several reps got significant tax refunds since they'd been paying the full self-employment tax when they should've only been paying the employee portion. The company ultimately had to lay off about 30% of staff to cover the penalties.
Do you know if the reps had to pay back any of the business deductions they'd claimed? I've been deducting home office, internet, phone, etc., as a 1099 and I'm worried if I get reclassified I'll owe a ton for those past deductions.
From what I understand, the reps didn't have to pay back deductions they had legitimately claimed while operating under the 1099 status. The IRS generally doesn't penalize workers in these situations since you were filing based on the classification given to you by the company. However, going forward after reclassification, they could no longer claim those business deductions as W-2 employees. That's definitely something to consider in your calculations - while you save on the employer portion of FICA taxes as a W-2, you lose those valuable business deductions. In some cases, especially if you have significant legitimate business expenses, remaining a 1099 might actually be more financially beneficial despite the higher self-employment tax.
Has anyone successfully negotiated higher pay when transitioning from 1099 to W-2? I'm making about $17k/month as a 1099 sales rep, and I've calculated that I'd need at least a 9% raise to break even after losing my business deductions if I become a W-2 employee.
Yes! I managed to negotiate a 12% increase in my commission rate when my company reclassified me from 1099 to W-2 last year. The key was coming prepared with exact numbers showing: 1) The taxes they'd now be paying (7.65% of your income) 2) The benefits costs they'd incur 3) The exact business deductions I'd be losing 4) Market rates for W-2 sales reps with my performance level I presented it as a business case rather than a demand. They actually appreciated the transparency and realized keeping top performers was worth the adjustment.
That's really helpful, thanks for the specific percentage figure and the breakdown of what to include in the negotiation. I'll definitely put together that kind of detailed analysis before approaching them. I'm curious though - did your overall take-home pay end up being higher, lower, or about the same after the transition? And did you notice any benefits to being W-2 beyond just the tax situation?
Sofia Perez
I went through this exact thing! What state are you in? In my case (NC), they wanted proof that I had made my quarterly payments because their system showed I claimed credit for them on my return but they had no record of receiving them. Turns out my accountant had mistyped my SSN on ONE of the quarterly payment vouchers so it got credited to someone else's account!
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Zoe Alexopoulos
ā¢I'm in Maryland. And wow, that's exactly what I'm worried about! I do my own taxes with software but I'm not the most organized person. Did you have to provide actual payment records or did they eventually find the payment with the wrong SSN?
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Sofia Perez
ā¢They eventually found the payment under the incorrect SSN, but it took about 3 weeks and I had to provide
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Dmitry Smirnov
This might sound silly but are you sure it's a legitimate letter? Scammers are getting more sophisticated with tax-related cons. Check the phone number on the letter against the official state tax department number on their website (not the one in the letter). My brother got a very official looking "state tax" letter that turned out to be completely fake.
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ElectricDreamer
ā¢THIS!!! I almost fell for something similar. The letter had all the right logos and everything. Called the actual department and they confirmed they hadn't sent anything. Scary how good these scams are getting.
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Zoe Alexopoulos
ā¢That's a good point! I checked and it does seem legitimate - has all the official letterhead and the return address matches what's on their official website. I also logged into my state tax account and there's a notice there too mentioning documentation needed. But thanks for the warning - probably saved someone else from falling for a scam!
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