This is a really good point about new skills vs improving current skills. How can you tell the difference though? If the conference has some sessions on topics I currently work with and some on areas I want to expand into, how would the IRS view that?

The key distinction is whether the education maintains/improves skills in your current business versus qualifying you for a completely new profession. If you're already in the field and attending sessions that expand your knowledge within that same general area, that's usually deductible even if it covers some new aspects. For example, if you're a marketing consultant attending a digital marketing conference that includes some sessions on emerging platforms you haven't worked with yet, that's still improving skills in your current profession. The IRS is mainly concerned with preventing people from deducting education that represents a career change (like a real estate agent deducting law school tuition).

Good point about tax brackets! I did this last December - prepaid about $3,000 in business expenses that weren't due until January because I had an unusually high income year and wanted to reduce my 2024 tax bill.

Do you know if there's a penalty for not having paid this originally? I'm in a similar situation with PFML benefits from 2022 and worried about penalties and interest on top of the taxes.

There's usually an underpayment penalty plus interest that accrues from the original due date of the return. However, you might qualify for penalty abatement if this is your first time having an issue with the IRS and you have a clean compliance history for the previous 3 years. The IRS calls this "First Time Abatement" and it's relatively easy to get if you qualify. You'd still owe the tax and interest, but they can remove the penalties. You have to specifically request this though - they won't automatically give it to you.

I successfully contested mine. The key was proving the premiums were paid post-tax. I submitted a letter from my employer's HR department confirming the PFML premiums were deducted after taxes, copies of my paystubs showing the deductions, and my W-2 showing the full wages were reported (indicating no pre-tax deductions for PFML). I also included the relevant IRS guidance on taxability of disability benefits based on premium payment method. It took about 8 weeks, but they reversed the determination.

Thanks for the detailed info! Did you mail in all these documents or were you able to handle it electronically? And did you need to use any specific IRS forms for the response?

This is blowing my mind. So if the tax bracket changes at say $50,000, and I make $51,000, only that extra $1,000 gets taxed at the higher rate? Not my entire income? Why doesn't anyone explain this clearly??

Exactly! You've got it right. If the bracket changes at $50,000 and you make $51,000, only that extra $1,000 gets taxed at the higher rate. Your first $50,000 is still taxed at the lower rates. It's one of the biggest tax misconceptions out there. I think it doesn't get explained clearly because even some managers and HR people don't understand it fully. I've heard countless stories of people afraid to take raises or overtime because they thought they'd lose money. The truth is, earning more money will always result in taking home more money (even after the tax increase on that portion).

TurboTax is probably the most user-friendly for beginners. It basically interviews you and explains tax concepts as you go. It costs more than some others, but the guidance is helpful when you're just starting out. FreeTaxUSA is a good cheaper option if your taxes are simple.

But why would they reduce my income to zero though? Wouldn't they just hit me with penalties for not making enough quarterly payments? I did make some estimated payments but probably not enough.

You're right - they typically just assess penalties rather than reclassifying the income completely. This sounds more like either an error in processing or a mismatch in reported income. The zero income modification is unusual and definitely warrants investigation. When you contact them, specifically ask if this is related to Form 1099 mismatches or if they're questioning the nature of your business itself. Sometimes they'll reclassify business activity as a "hobby" if you've reported losses for several years, but reducing legitimate income to zero is different.

This is good advice. CP2000 specifically is an income verification notice that compares what you reported against what was reported to the IRS by others. Each notice type has specific response requirements.

1 That's good to know! If my cost basis is missing, can I just use the price I remember paying or do I need actual documentation?

5 You really need documentation to support your cost basis if it's missing from your 1099-B. The IRS can question unsupported numbers during an audit. If you absolutely can't find records, you should make a good faith effort to reconstruct the cost basis using historical price data from when you purchased the securities. Some brokerages have historical price lookup tools, or you can use financial websites that show historical prices. Just make sure to keep notes on how you determined each cost basis amount in case you need to explain your methodology later. Documenting your research process shows you made a reasonable effort to comply with tax requirements.

12 Really? That seems excessive. What about losses? Can those offset other income or do they only offset capital gains?