Has anyone used the W-4 Tax Withholding Estimator on the IRS website? I'm in a similar situation and wondering if it's worth the trouble of filling it out.

I went through this exact same situation when I switched from a $48k job to a $95k position in March last year. What really helped me understand what was happening was looking at my pay stub breakdown more carefully. Your new employer is definitely withholding as if you'll make the full $102k for the entire year - they have no way of knowing about your previous income unless you specifically account for it on your W-4. Since you only started in February, you'll actually earn about 11/12 of that $102k plus whatever you made in January at your old job. This means your actual annual income will be significantly less than what your current employer is using for withholding calculations, so you should expect a decent refund. In my case, I got back about $1,800 more than I expected because of this overwithholding situation. If you want to be more precise, you can use the IRS withholding estimator or update your W-4 to account for your actual projected annual income from both jobs combined. But honestly, if you're planning to use that refund for something specific like a down payment, the overwithholding might work in your favor as a forced savings plan.

One thing to consider is that if you do owe taxes, you'll pay at your ordinary income tax rate, not capital gains rates. I surrendered a policy last year and was surprised by the tax bill since I'm in the 32% bracket. Might affect your decision if you're in a high tax bracket.

This is a great question and I can see you've gotten some solid advice already! Just wanted to add a few practical considerations from someone who went through this recently. First, definitely request that premium history statement from your insurance company as others mentioned - you'll need it for accurate tax calculations. When I did this, I was pleasantly surprised to find that the total premiums paid over the decades were actually close to the surrender value, so my tax hit was minimal. Second, timing matters. If you're expecting a bonus or other income that might push you into a higher bracket this year, you might want to consider whether surrendering in January of next year could save you on taxes. Also, don't overlook the potential for quarterly estimated tax payments if the taxable portion is significant. The IRS expects you to pay taxes on this income during the year it occurs, not just when you file your return. One last thought - if you do decide to go the surrender route, make sure you understand any surrender charges the policy might have. Some whole life policies have surrender periods that could reduce your cash value, though after 30+ years this is less likely to be an issue. Good luck with whatever you decide!

Your in the same boat as me! My preparer messed up everything and ghosted me. Been waiting 6 months for my refund now because of 'verification' 😤

This is exactly why I always double-check everything before leaving the tax office! Those kinds of errors can definitely cause delays - the IRS computer systems flag mismatches between names and SSNs automatically. You should definitely push back harder on the preparer to fix this. They have a responsibility to correct their mistakes, and "the IRS already accepted it" doesn't mean the errors won't cause problems later. Document everything in case you need to file a complaint with their licensing board.

Has anyone used TurboTax to figure this out? I'm in a similar situation and the software is confusing me.

Just wanted to add some clarity based on my experience as a tax preparer - the key issue here is understanding what "keeping up a home" means for HOH purposes. The IRS defines this as paying more than half the cost of rent, mortgage interest, real estate taxes, insurance on the home, repairs, utilities, and food eaten in the home. Since you're paying 65% of these household maintenance costs, you definitely qualify for HOH with your son as your dependent. However, your girlfriend would need to show she pays more than half of these same household costs to qualify for HOH with your daughter. This is where it gets tricky - you can't both be paying more than half of the same expenses. The child-specific expenses your girlfriend pays (daycare, clothing, medical) are important for determining who can claim the child as a dependent, but they don't count toward the "keeping up a home" test for HOH status. My recommendation: You claim HOH, and your girlfriend should probably file as Single (assuming she can't demonstrate paying more than half of household maintenance costs). You'll both still claim your respective children as dependents and get those tax benefits. Consider consulting a tax professional to review your specific numbers - this is one of those situations where the details really matter for compliance.

Has anyone tried just asking the client to pay in 2024? I had something similar and just explained to my client how it would simplify my taxes. They were fine moving up the payment by a couple weeks. Business expenses crossing years is annoying for everyone, not just you!

I've been dealing with this exact scenario for years as a freelance consultant. The key thing to remember is that your business expense and the reimbursement are separate events for tax purposes. Deduct the $750 expense on your 2024 return when you paid it - this is correct regardless of when you get reimbursed. For 2025, the reimbursement isn't taxable income because it's returning money you already spent from your own pocket. One tip that's helped me: I always send clients a year-end summary of any unreimbursed expenses from that tax year. This creates a paper trail showing the expense was legitimate and business-related, which is helpful if the IRS ever questions it. Plus it sometimes motivates clients to pay faster when they see the total amount outstanding! The accounting can get messy if you have multiple clients and cross-year expenses, but the tax treatment itself is straightforward once you understand the principle.