22 You can file without the actual W2 by using Form 4852 (Substitute for Form W2). You'll need your last paystub to estimate your earnings and withholdings. BUT you should only do this after trying to get your W2 from your employer and then contacting the IRS for help. The downside is your refund might be delayed while the IRS verifies your information. If your estimates are significantly off from what your employer reports, you might need to file an amended return later.

5 Thanks for the info! I'll try contacting my employer one more time tomorrow, and if that doesn't work, I'll try the IRS route before using Form 4852. Hopefully I can still get my refund relatively soon - I hate how one missing form can mess up everything!

1 Oh! I didn't think of that! We did use some online system for viewing our paystubs. I'll try logging in tonight to see if I can access it. Hopefully my account is still active even though I don't work there anymore. That would be such an easy solution!

Thank you for this suggestion! I didn't even think about exemptions. Do I need to apply for these or are they automatic? Our county website is pretty awful and hard to navigate.

You almost always need to apply for exemptions - they're rarely automatic. Most homestead exemptions require an application within the first year or two of occupancy. Your county's tax assessor's office should have the forms, even if their website is terrible. It's worth calling them directly or visiting in person since these exemptions can save you significant money every year. Some counties also have partial exemptions for energy-efficient new construction, so ask about that too if your home has any green features. Don't wait on this - many exemptions have filing deadlines that, if missed, mean you'll have to wait until next tax year.

This is such an important point! I'm in Illinois and our property taxes are always paid in arrears. Made for a very confusing first year in our new build because the tax bills didn't match what we expected.

I'm actually not sure! In the first service I think I just followed the prompts about having received a 1099-MISC and entered the numbers. In the second one I might have categorized it differently without realizing. That could explain the difference. Do you know if mediation work should be considered self-employment income or something else?

Mediation work reported on a 1099-MISC should typically be treated as self-employment income, which means you'd need to pay self-employment tax on it (an additional 15.3% covering both employer and employee portions of Social Security and Medicare). If one service is calculating it as self-employment income and the other isn't, that would explain a big difference. The service showing you owe money is probably calculating it correctly with self-employment tax, while the other might be missing that. Check box 7 on your 1099-MISC - if there's an amount there for "Nonemployee compensation," that's definitely self-employment income.

Second this advice about the local tax preparer. Online services have improved but they're still not perfect with state-specific regulations. I found a small local accounting office that reviewed my self-prepared return for $65 and found several errors that would have cost me hundreds.

Do you use a special app for tracking receipts? I have a small Etsy shop and I'm terrible at keeping track of all the little supply purchases and shipping costs.

I use a combination of tools that work well together. For receipts, I use an app called Expensify - you just snap a photo of each receipt immediately and it extracts all the important data. Then I export everything quarterly to a spreadsheet for my records. The key is making it a habit to immediately capture every receipt the moment you get it. For mileage tracking, MileIQ has been a game-changer. It runs in the background on your phone and automatically detects when you're driving. After each trip, you just swipe right for business or left for personal. Super easy and has detailed reports for tax time. The peace of mind from knowing everything is properly tracked is honestly worth even more than the tax savings!

I've heard this before but I'm actually the opposite - I LIKE getting a big refund because I'm terrible at saving. It's like a forced savings account for me that turns into a nice vacation fund each spring. Would you really recommend changing to smaller refunds for everyone?

Wouldn't insurance be a cheaper solution than maintaining multiple LLCs though? Like getting a good general liability policy plus specific riders for the higher-risk activities?

You raise an excellent point about insurance. A comprehensive liability insurance policy with specific riders for higher-risk activities is often a more cost-effective solution than maintaining multiple LLCs with separate filing fees, registered agent fees, and accounting costs. The ideal approach for many entrepreneurs is a combination: one well-structured LLC with proper internal bookkeeping to track each business activity separately, plus tailored insurance coverage that addresses the specific risks of each business type. This gives you both liability protection and tax efficiency without the administrative burden of multiple entities.

Do you use accounting software to track everything? I'm trying to figure out if I need separate QuickBooks accounts or if there's a way to tag transactions by business type within one account.