I use TaxJar for my online shop (about $60k/year in sales). It's definitely an expense but saves me tons of time. The automated filing feature is worth every penny during tax season. I tried doing it manually for the first year and spent entire weekends just on sales tax returns.

If you're just starting out, might be overkill. I use a spreadsheet to track sales by state, and only file in 3 states currently. Once you hit 5+ states, the software becomes more worth it. A middle ground could be using something like taxr.ai to monitor your nexus thresholds, then switching to automated filing software once you have multiple state obligations.

Ugh, seriously?? I didn't even know there was a difference! My shopping cart on my website just has a flat tax rate setting. Sounds like I need to look into tax calculation plugins. Does anyone know if Shopify handles this automatically or do I need additional apps?

Shopify has basic tax calculation built in, but it's not perfect for complex situations. They automatically calculate rates based on customer address, but if you need more sophisticated rules (like product-specific exemptions or detailed nexus settings), you might want a tax app like TaxJar or Avalara's integration. The basic Shopify tax settings work fine for most small sellers though!

This is really helpful! I definitely have some expenses I could deduct. Do I need receipts for everything? Some of my expenses were paid in cash and I'm not sure if I kept all the receipts.

You should have documentation for everything you deduct, but it doesn't necessarily have to be receipts. Bank/credit card statements can work too. For cash purchases without receipts, keep a detailed log going forward (date, amount, business purpose). The IRS is more likely to scrutinize cash expenses without documentation. For mileage, you need a log of business trips (dates, destinations, purpose, miles). For home office, measure the dedicated space and calculate what percentage of your home it represents. You can use the simplified method ($5 per square foot up to 300 sq ft) which requires less record-keeping.

Business expenses are WAY better because they reduce both income tax AND self-employment tax (15.3%). Traditional IRA only reduces income tax. If you're low income, most of your tax bill is probably self-employment tax anyway.

Thanks for this info! I'm new to the hair business (just got licensed last year). Question - can you deduct the cost of your own haircuts/color since we have to look good for clients? And what about clothes you wear to work?

Unfortunately, you cannot deduct the cost of your own haircuts/color even though we need to look good for clients. The IRS considers these personal expenses, not business expenses, even for hairstylists. It's frustrating but that's how they interpret the tax code. As for work clothes, you can only deduct clothing that is not suitable for everyday wear. For most hairstylists, our work clothes can be worn outside of work, so they're usually not deductible. However, if you have to buy specific uniforms with salon logos or specialized protective clothing that you wouldn't wear elsewhere, those may qualify as deductible expenses.

I got audited 2 years ago and they did question my health insurance deduction! But I had all my premium statements and proof of payment, and I was fine. The key is documentation - keep records showing you paid the premiums and that those payments match what you deducted. Don't be afraid to take legitimate deductions!

Thank you for mentioning estimated tax penalties - I hadn't even thought about that! Do you know what percentage of my total tax liability I need to have covered through withholding/payments to avoid the penalty? Also, is the mortgage interest deduction still worth it with the higher standard deduction? We pay about $1,300/month in mortgage interest.

Generally, you need to have paid at least 90% of your current year tax liability or 100% of last year's tax liability (110% if your AGI was over $150,000) through withholding and estimated payments to avoid the penalty. Since you mentioned both employment and business income, you'll want to calculate this carefully. With the mortgage interest, it depends on your total itemized deductions. At $1,300/month, that's $15,600 annually. For 2024, the standard deduction for married filing jointly is $29,200. So unless your other itemizable deductions (state/local taxes up to $10,000, charitable contributions, etc.) push you over that threshold, the mortgage interest alone won't make itemizing worthwhile. But if you're close to that threshold, making strategic charitable donations could tip you over to where itemizing makes sense.

This is a legitimate strategy called "income timing" or "income shifting" - IF you're using cash basis accounting (which most small businesses do). You can delay sending December invoices until January to recognize that income in the next tax year. Just make sure you're consistent with your accounting method. The flip side is also true - you can accelerate deductions by making business purchases before December 31st rather than waiting until January. Just ensure whatever you purchase is actually needed for your business and isn't just spending money to save on taxes (which rarely makes financial sense).

Do you know what happens if you don't file the 709 form? Are there penalties? I gave my sister about $30k last year for medical bills and had no idea I needed to file anything since I'm nowhere near that lifetime limit.

There can definitely be penalties for not filing Form 709 when required, even if no tax is due. The standard penalty is 5% of the tax owed per month, up to 25%. But since you likely don't owe any actual tax (just needed to file the form), the penalty might be minimal or potentially zero if you can show reasonable cause. For your specific situation with your sister, you might actually qualify for a medical expense exception. Payments made directly to medical providers on someone else's behalf are exempt from gift tax and don't require filing. But if you gave the money directly to your sister who then paid the bills, that's technically a reportable gift. I'd recommend speaking with a tax professional about filing a late 709 to get compliant.

Thank you for this clear breakdown! I was definitely mixing up the different concepts. So if I understand correctly, I can give gifts to anyone (younger, older, same age) and use my lifetime exemption, but there are extra rules if the person is much younger than me (like grandchildren)?

Exactly right! Your lifetime gift tax exemption ($12.92 million in 2023) applies to all taxable gifts regardless of the recipient's age. You can give to your spouse, sibling, friend, or anyone else and it works the same way for basic gift tax purposes. The generation-skipping transfer (GST) tax is an additional layer that only applies to gifts to people who are at least 37.5 years younger than you (or in a defined generational category like grandchildren). These transfers are potentially subject to both regular gift tax and GST tax, but there's a separate GST exemption amount (currently also $12.92 million) to offset this additional tax. This was designed to prevent wealthy families from skipping tax by bypassing a generation.