This thread has been incredibly informative! I'm dealing with the same situation with my 15-year-old who's been helping with my online retail business - mostly product photography, inventory management, and packing orders. Based on everything I've read here, I'm definitely going to treat her as an employee rather than issuing a 1099. The tax advantages are compelling, especially the FICA exemption under 18 and the potential for her first $12,950 to be tax-free. One question I haven't seen addressed yet - how do you handle paying your child if your business income varies significantly month to month? Should I aim for consistent monthly payments regardless of business performance, or is it okay to pay them more during busy months when they work more hours? I want to make sure the payment structure looks legitimate to the IRS while also being practical for our seasonal business fluctuations. Also, has anyone dealt with setting up direct deposit for their teenager, or do most people just write checks from the business account? Thanks for all the great insights everyone has shared!

This has been such an educational thread! I'm in the exact same situation with my 17-year-old who's been helping with administrative tasks for my consulting business. Reading through everyone's experiences has really clarified the employee vs. contractor decision for me. What I found most valuable is learning about all the tax exemptions - the FICA exemption under 18 and FUTA exemption under 21 are huge savings I had no idea about. And the college financial aid considerations mentioned by @Yara Nassar are brilliant - I never thought about how student work income gets assessed differently than parent income on the FAFSA. One thing I'm curious about that I haven't seen mentioned - do any of you report this employment arrangement differently on your state taxes, or does it generally follow the same rules as federal? I'm in California and want to make sure I'm not missing any state-specific requirements for family employment. The documentation tips about timesheets and taking occasional photos of them working are really practical advice I'm definitely going to implement. Thanks everyone for sharing your real-world experiences with this!

Has anyone else noticed that tax software seems to be getting buggier every year? I used to never have these problems, but the last 3 years I've had weird glitches with multiple platforms. Is it just me???

I went through something very similar last year! You're absolutely right that you can switch to any other tax software since H&R Block never actually transmitted your return to the IRS. I ended up using FreeTaxUSA after my initial software had issues, and it worked perfectly. One tip that saved me a lot of headache - before you start with the new software, gather all your original tax documents (W-2s, 1099s, etc.) and enter everything manually instead of using any import features. Yes, it takes a bit longer, but after dealing with one import glitch, I didn't want to risk another one. Plus, manually entering gives you a chance to double-check all your numbers. The IRS won't have any record of your attempted filing with H&R Block, so you're completely in the clear to file fresh with whoever you choose. Good luck!

Has anyone used TurboTax for this situation? I'm in a similar spot with increasing income and decreasing refunds and wondering if the software can help me understand what's happening.

I've been through this exact same situation and it can be really frustrating! What you're experiencing is completely normal tax behavior, but I know it doesn't feel that way when you're used to getting larger refunds. Here's the key thing to understand: your refund isn't actually "shrinking" - what's happening is that you're getting your money throughout the year in your paychecks instead of as one lump sum refund. When you claim your children on your W4, you're essentially telling your employer "I have dependents, so withhold less tax from each paycheck because my final tax liability will be lower." The periods where they stopped withholding federal taxes entirely likely happened because your W4 indicated you'd have little to no tax liability based on your dependents and income at that time. But as your annual income grew, you ended up owing more than initially calculated. Here's what I'd recommend: use the IRS withholding calculator on their website (it's free!) to figure out exactly how much should be withheld based on your current income and family situation. You can then adjust your W4 accordingly - whether you want smaller paychecks with a bigger refund, or keep things as they are with more money in each paycheck. Remember, ideally you want to break even or get a small refund - that means you kept your money working for you all year instead of giving the government an interest-free loan!

Quick tip from someone who got audited: the IRS specifically flagged my high meal expenses compared to my business revenue. Now I follow the 5 W's rule - document Who, What, Where, When, and Why on every receipt. I snap a pic with my phone and use the notes feature to add this info right away.

I've been dealing with this exact same confusion as a freelance graphic designer! One thing that really helped me was creating a simple spreadsheet template for meal tracking. I include columns for date, amount, location, who I was with, business purpose, and a photo of the receipt. My accountant told me the biggest mistake people make is not being specific enough about the business purpose. Instead of writing "client meeting," I write "discussed Q1 marketing campaign with ABC Company - reviewed design concepts and timeline." The IRS wants to see that actual business was conducted, not just that you happened to eat with someone. Also learned the hard way that coffee meetings count too if you're discussing business! I was missing out on deducting all those Starbucks meetings with potential clients. Just make sure you're consistent with your documentation from day one.

I went through something similar when I had to backfile my 2019 taxes last year. One thing that really helped me was checking with my bank statements from 2018 - if you had direct deposit, you can often figure out your net pay amounts and work backwards. What I did was look at my December 2018 bank deposits and compare them to my gross wages on the IRS transcript. The difference between gross and net pay includes all withholdings - federal taxes, state taxes, FICA, and any other deductions like health insurance or 401k contributions. If you can find your final paystub from 2018 or even your January 2019 paystub (which often shows year-end totals), that would be ideal. But the bank statement method can at least give you a reality check on whether any estimates you get seem reasonable. Also, don't forget that your state might have had different withholding rules in 2018 compared to now - some states changed their tax laws after the federal tax reform that year. So if you do use estimation methods, make sure you're using 2018 tax tables and rates, not current ones.

I actually work in payroll and can share some insights that might help! One thing that often trips people up is that state withholding amounts can vary significantly based on when during the year you started or stopped working with an employer, even if your annual income was similar to other years. If you do end up having to estimate your state withholding, here's a more precise method: Look at your federal transcript to see exactly when your W-2 wages were earned throughout 2018 (the IRS transcript sometimes shows quarterly breakdowns). Then use your state's 2018 withholding tables with your actual filing status and allowances from that year. Also, many people don't realize that if you moved between states during 2018 or worked for multiple employers in different states, you might have state withholding from more than one state. Your IRS transcript won't show this breakdown, but it's something to consider when doing your calculations. One more tip - if you end up contacting your former employer and they're still in business, ask specifically for your "annual wage and tax statement" rather than just asking for your W-2. Sometimes HR departments have different filing systems, and using the official terminology can help them locate your records more quickly.