One thing nobody mentioned yet - you might need to pay quarterly estimated taxes if you expect to owe more than $1,000 in taxes for the year. This is especially important for self-employment since you don't have an employer withholding taxes. Self-employment tax is about 15.3% on top of regular income tax, which catches a lot of first-timers by surprise. Google "1040-ES" for the forms you need.

Hey Giovanni! I was in a similar situation when I started my photography side hustle in college. Here's what I wish someone had told me upfront: You're absolutely right to want to handle this yourself - it's actually pretty straightforward once you understand the basics. Even if you only make a few hundred dollars, you should report it. The good news is that as a student, you likely won't owe much in actual taxes, but you will need to pay self-employment tax (about 15.3%) on any profit over $400. Here's my simplified checklist for you: 1. Keep detailed records of ALL payments (screenshots work fine) 2. Track any business expenses (phone bill, props, etc.) 3. You'll file Schedule C with your regular tax return 4. If you make over $1,000 profit, start making quarterly payments to avoid penalties The payment app thing is confusing - they'll send you a 1099-K if you receive over $600, but you need to report everything regardless of whether you get that form. Pro tip: Open a separate bank account just for this income if possible. Makes tracking everything so much easier come tax time. You got this! 💪

I'm really confused by all this ERTC amendment stuff... My CPA told me the reduction should only be for the refundable portion, not the nonrefundable part. But now I'm reading conflicting advice here. Does anyone have an actual IRS reference that clarifies this?

I went through this exact same situation with my S-Corp last year and can confirm what others have said - you need to reduce wage expenses by the FULL ERTC amount (both refundable and nonrefundable portions), excluding any interest received. The key thing to remember is that the ERTC is essentially the government reimbursing you for wages you paid, so you can't also deduct those same wages as a business expense. It would be double-dipping. For your $87k in 2020 and $112k in 2021 refunds, make sure you separate out any interest portion before calculating the wage expense reduction. The interest is taxable income but doesn't affect the wage deduction adjustment. One heads up - this will create a significant increase in your pass-through income, which means additional personal tax liability when you amend your 1040s. With amounts that large, you might want to consider making estimated payments to avoid underpayment penalties. The amendment process can take several months, so plan accordingly for the cash flow impact.

My accountant always tells me to focus on the "ordinary and necessary" test for business expenses rather than just the timing. If this conference is ordinary and necessary for your business type, the IRS is less likely to question it regardless of when you deduct it. Just make sure you have good documentation showing how it relates to your business - things like the conference agenda, notes you took, business cards you collected, etc. This has saved me multiple times during reviews.

This is exactly the kind of timing question that trips up so many small business owners! The key thing to remember is that for most small businesses using cash accounting, you generally deduct expenses in the year you both pay for them AND receive the economic benefit. Since your conference is in September 2025 and you're not paying until then, that's clearly a 2025 deduction. Even if you had prepaid in 2024, the IRS could still argue the economic performance doesn't occur until you actually attend the conference. One thing I'd add to the great advice already given - consider keeping a simple spreadsheet of planned business expenses like this so you can do better tax planning for next year. Knowing you'll have that conference deduction in 2025 might influence other timing decisions you make with income and expenses. Also, don't forget that if you travel for the conference, those travel expenses (flights, hotels, 50% of meals) are also deductible business expenses for the same tax year as the conference itself.

Another option is to just estimate the Dec 31 value of your Traditional IRA. If you converted most/all of it, just put $0 or whatever small amount was left. If the actual 5498 shows a different amount when you get it in May, you can always file an amended return if the difference is significant. In my experience though, for most conversions, the difference won't materially affect your tax situation enough to warrant an amendment.

Pro tip: Call your brokerage and ask for the Dec 31 value over the phone. They can tell you even if the 5498 hasn't been issued yet. I did this with Vanguard last year for exactly the same situation and they gave me the info in 2 minutes!

Has anyone here tried just using a dedicated business vehicle vs trying to split personal/business miles? I'm thinking about just buying a separate truck just for my construction business to avoid all this logging headache.

For tracking mileage with that much driving, I'd strongly recommend getting a GPS-based mileage app like MileIQ or TripLog. They automatically detect when you start and stop driving, so you just need to swipe to categorize each trip as business or personal. Way easier than manual logs when you're hitting 10+ stops per day. One tip I learned the hard way - start tracking from day one of your business operations, even before you officially launch. The IRS wants contemporaneous records, and trying to recreate months of mileage later is a nightmare. Also, since you're looking at such high mileage (50-100k annually), the standard mileage rate will almost certainly be your best bet. At current rates, that's potentially $33,500-$67,000 in deductions annually. Just remember you have to choose your method in the first year you use the vehicle for business - you can't switch from actual expenses to standard mileage later. Good luck with the new business! The mileage tracking becomes second nature after a few weeks.