Thank you SO much for pointing this out! I hadn't even thought about my son potentially checking the wrong box. Did that delay your refund significantly? And is there anything else I should warn him about on his return?

Yes, it delayed our refunds by about 3 months and we had to submit additional documentation proving I provided more than half his support. Super frustrating! Also make sure he understands he won't get certain credits like the recovery rebate credit or earned income credit that are only for independent filers. My son was confused because TurboTax initially calculated a bigger refund before he marked himself as a dependent. The software correctly adjusted it, but he thought he was doing something wrong because the refund amount dropped.

I used FreeTaxUSA for both my return and my son's last year. It asks really clear questions about dependent status and was completely free for his simple return. For mine it was only $15 for state filing. TurboTax wanted to charge us for deluxe versions for both returns which was unnecessary.

This is brilliant advice about the 15-minute chunks. I've been completely avoiding my tax situation because it feels too overwhelming. Breaking it down like this might actually help me start tackling it. Do you think it's better to start with organizing documents first or jumping straight into the payment plan applications?

I definitely recommend starting with organizing your documents first. Gather everything you have - tax returns, notices from the IRS, pay stubs, bank statements, bills, etc. Just having everything in one place reduces the mental load significantly. Once you have your documents organized, then use a 15-minute session to read through any notices carefully and make notes about what you need to do next. This makes the payment plan application process much smoother because you'll have all the information readily available when filling out forms or talking to representatives.

The tea ritual sounds helpful but where do you find these VITA people? Are they only available during tax season or can you talk to them year-round for planning purposes?

Did you use any specific resources to learn? I'm trying to get better but don't know where to start besides random YouTube videos.

I started with the IRS's own guides which are surprisingly readable for most basic topics. Their interactive tax assistant on irs.gov is helpful for specific questions. For learning tax concepts more broadly, I actually found the "dummy" books useful when I was starting out - "Taxes For Dummies" explains things in plain language. The J.K. Lasser tax guides are good too if you want something more comprehensive. These days, I learn a lot from r/tax and r/personalfinance on Reddit. People post specific scenarios that help me understand new situations before I encounter them myself. And don't underestimate the value of the help sections in tax software - they're written to explain things simply.

First time always takes longest! My first return took me forever too. This year (my 4th time) took about 45 minutes. It gets WAY faster once you know what documents you need and understand the basic flow.

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 this breakdown! Would you recommend getting a consultation just for the first year of marriage to understand any new strategies, or is this something we should plan to do annually going forward?

I'd recommend a consultation for the first year of marriage to understand the new strategies and options available to you as a married couple. After that initial consultation, you can assess whether the accountant provided enough value to continue annually. Many clients find that an every-other-year check-in with an accountant is a good compromise - they get periodic professional review while handling the more straightforward years themselves. Given both your high incomes, there may be ongoing tax planning opportunities that make annual meetings worthwhile, but this is something you can determine after that first consultation.

This is such an underrated comment. I spent 8 hours doing my taxes last year with similar income to OP, and all to save maybe $400 on an accountant? That's a terrible hourly rate for my weekend time!