Has anyone tried using the IRS Tax Withholding Estimator? It helped me figure out my withholding issues last year.

This is a really common issue for tipped employees, and you're smart to be thinking ahead about potential tax liability. The inconsistent withholding happens because your paycheck amount varies so much with tips - when tips are high, there's often not enough in your actual hourly wages to cover all the required withholdings. One thing that might help is talking to your payroll person about adjusting your W-4 to have an additional flat amount withheld each pay period, regardless of your tip income. You could also consider opening a separate savings account specifically for taxes and automatically transferring a percentage of your weekly earnings there. Keep detailed records of all your tip income too - you'll need accurate numbers for tax filing, and it'll help you calculate how much you should be setting aside. Generally, putting away 20-25% of your total income (wages + tips) for taxes is a safe bet for most servers.

I'm dealing with this exact same issue right now and honestly, this thread has been a lifesaver! I set up my single-member LLC mid-year and have been so confused about how to handle the tax filing with mixed 1099s. What really clicked for me after reading everyone's responses is understanding that even though I have an LLC and EIN, the IRS still sees my business income as personal income because it's a "disregarded entity." So whether my 1099s show my SSN or EIN doesn't actually change my tax liability at all. I was getting ready to pay an accountant hundreds of dollars just to confirm what I should enter in TurboTax, but now I feel confident moving forward with entering everything in the business section like everyone suggested. Going to definitely send my clients updated W-9s with my EIN for next year though - the privacy and business credit benefits make total sense. Thanks to everyone who shared their experiences! It's so reassuring to know this is a common situation and not something to stress about.

I just wanted to add my perspective as someone who's been through this multiple times with different LLCs. The confusion you're experiencing is totally normal - the relationship between LLC structure and tax filing can be really counterintuitive at first. One thing that might help is thinking of it this way: your LLC is like a legal "wrapper" around your business activities, but for tax purposes, the IRS basically looks right through that wrapper and sees your business income as personal income. That's why they call it a "disregarded entity." So when TurboTax asks for your business information and you enter your LLC name and EIN, you're just providing organizational details. The actual income reporting works the same whether your 1099s have your SSN or EIN - it all flows to the same place on your tax return. I'd also suggest keeping a simple spreadsheet of your 1099s showing which ones came with which identifier. It's not required, but it's helpful for your own records and gives you peace of mind if any questions come up later. You're definitely on the right track though!

Great question! I went through this exact same situation last year. Here's what I learned: You're right to be confused - it's not intuitive at first. For income tax purposes, yes, you calculate based on your TOTAL income (W2 + freelance) to determine your tax bracket. But here's the key part everyone gets mixed up on: The 15.3% self-employment tax is ONLY applied to your freelance income, not your total income. And you're not double-paying Social Security/Medicare - at your W2 job, you and your employer each pay 7.65%, which adds up to the same 15.3%. When freelancing, you're essentially both employer and employee. One important detail: there's a Social Security wage cap ($160,200 for 2023). Once your combined W2 + freelance income hits that cap, you stop owing the Social Security portion (12.4%) but still owe Medicare (2.9%) on all earnings. For quarterly payments, I calculate: (Expected freelance profit × 15.3%) + (freelance profit × my marginal tax rate). Then I subtract what my W2 job already withholds to avoid overpaying. Start simple with tracking everything and setting aside about 25-30% of freelance income. You can always adjust once you see how your first year plays out!

One thing that really helped me when I was figuring this out was understanding that you can actually adjust your W2 withholding to cover some of your self-employment taxes! If you don't want to deal with quarterly payments, you can fill out a new W-4 at your day job and have them withhold extra federal tax from each paycheck. Just calculate your expected self-employment tax liability for the year, divide by the number of pay periods remaining, and add that amount to your withholding. This approach is especially nice because W2 withholding is treated as if it was paid evenly throughout the year, even if you increase it later in the year. Quarterly payments have to be made on time or you could face penalties. Just make sure you're still tracking your business expenses properly since those reduce your self-employment tax base. And remember you can deduct half of your self-employment tax as an "above the line" deduction on your 1040 - it's like getting back some of the "employer" portion you paid!

I went through this exact same situation with my freelance business EIN last year! The mistake is super common - the IRS application can be confusing about employee intentions. I'd recommend calling the IRS Business & Specialty Tax Line first (800-829-4933) as others mentioned, but if you can't get through after a few tries, the written request route works great too. I sent a simple letter explaining the error and got it resolved in about 4 weeks. The key thing is to act on this soon - don't let it sit like some people do. The IRS is actually pretty reasonable about fixing these application errors, especially when you're proactive about it. Once it's corrected, you'll get peace of mind knowing you won't have to deal with those quarterly employment forms you don't need.

I had this same issue with my single-member LLC about 6 months ago! The good news is you definitely don't need to get a new EIN - that would actually create more complications down the road. What worked best for me was calling the IRS Business & Specialty Tax Line (800-829-4933) early in the morning, around 7-8 AM. The wait times are usually shorter then. When you get through, just explain that you made an error on your EIN application by indicating you would have employees when you don't, and ask them to update your filing requirements to remove Forms 940 and 941. The representative will ask for your EIN, business name, and some basic verification info. They can make the change right there on the call - it literally takes about 5 minutes once you're connected. Make sure to ask them to send you a confirmation letter showing the updated requirements for your records. One tip: have your EIN confirmation letter handy when you call, as they might reference the original application details. The whole process was way easier than I expected, and now I only have to worry about my regular business tax returns instead of those quarterly employment forms I never needed in the first place!

As a newcomer to this community, I'm finding this discussion incredibly helpful! I'm in a very similar situation with my insurance provider's portal being down for maintenance. What I'm taking away from all the advice here is that for those of us with employer-sponsored health insurance who had continuous coverage all year, we can confidently proceed with filing our taxes without the physical 1095-B form. The consensus seems to be that this form is primarily for record-keeping rather than submission with your return. I particularly appreciate the suggestion about contacting your employer's HR/benefits department for written confirmation of coverage dates - that's such a practical backup solution I hadn't considered! It's reassuring to hear from multiple people who've successfully filed without the form and had no issues. For anyone else dealing with this frustration, it sounds like the key is just being able to accurately confirm you had qualifying health coverage for all 12 months. Don't let insurance website technical difficulties delay your tax filing - especially if you're expecting a refund!

As a newcomer to this community, I want to thank everyone for this incredibly informative discussion! I'm dealing with the exact same issue - my insurance provider's website has been "under maintenance" for over three weeks now, right when I need my 1095-B form most. Reading through all the responses here has been so reassuring. The key points I'm taking away are: 1) The 1095-B is primarily for record-keeping, not submission with your tax return 2) If you had continuous employer-sponsored coverage all year, you can accurately answer the coverage questions without the physical form 3) Contacting your employer's HR/benefits department for written confirmation is a great backup strategy 4) Keeping documentation like paystubs (showing premium deductions) and insurance cards provides good backup records It's frustrating how common these website issues seem to be during tax season when we need these documents most! But it's clear from everyone's experiences that we don't need to let technical difficulties delay our tax filing. I'm going to follow the advice here and move forward with filing this week rather than waiting indefinitely for my insurance company to fix their portal. Thanks to everyone who shared their experiences - this community is such a valuable resource for navigating these everyday bureaucratic headaches!