Thanks for the recommendation! I've heard good things about TaxAct from a coworker too. Did you find their interface easy to use? I'm not super tax-savvy and need something that explains things clearly.

Their interface is pretty straightforward and they explain tax concepts in plain English. They use a question-based approach that helps catch things like HSA contributions without you needing to know which specific forms are required. The help sections are quite clear with examples, and if you get stuck, they have decent customer support through chat. For someone who isn't tax-savvy, they offer good guidance without overwhelming you with jargon. Their review system also catches common errors before you file.

FreeTaxUSA is such an underrated option. Been using them for 4 years now and they handle everything correctly including my rental property and side business. None of the upselling garbage that TurboTax does either.

Would I have to pay taxes on the conversion from after-tax to Roth though? I'm confused about how this is different from just doing a backdoor Roth IRA.

You only pay taxes on the growth between the time you make the after-tax contribution and when you convert it to Roth. If you convert frequently (some plans even allow automatic conversions), this tax amount is minimal. The main difference from a backdoor Roth IRA is the amount you can contribute. A backdoor Roth IRA is limited to $7,000 per year (2025 limit for those under 50). With the mega backdoor Roth, you could potentially contribute up to around $43,500 more (the exact amount depends on your plan and the total annual 401k limit of $70,000 for 2025 minus your regular contributions and employer match).

Great point about the flexibility! But don't you lose a lot to taxes on dividends and capital gains compared to Roth growth that's completely tax-free?

Can you explain more about how to document this? Like what kind of proof would you need to show the IRS that your education is "ordinary and necessary" for your business? I'm taking some digital marketing courses and want to deduct them for my Etsy shop.

Documentation is crucial. I keep a business education folder with: course descriptions/syllabi highlighting specific skills taught, a written explanation connecting each course to specific aspects of my current business operations, evidence that these skills are industry standards (like professional association recommendations), and a log tracking how I've implemented these skills in my business. For your digital marketing courses and Etsy shop, save the course descriptions, then create a document explaining how each marketing technique directly applies to growing your existing Etsy business. Track your marketing metrics before and after implementing what you learn to show business purpose. If similar businesses commonly use these marketing techniques, note that as evidence that the education is "ordinary" in your field.

That's a really good point about credits vs deductions! I think business expense deductions don't have the same caps as education credits though? At least that was my understanding. Can you take BOTH the business education deduction AND education credits for the same expenses?

But what happens if the amount the company reports paying you (if they filed anything before going bankrupt) doesn't match what you report? Could that trigger an audit?

That's a good question. If there's a discrepancy, it potentially could raise a flag in the IRS system. However, if you're reporting based on your actual income records (bank deposits, etc.), you're still doing the right thing. If the company reported incorrectly before going bankrupt, that's their mistake, not yours. Just make sure you have documentation of all the income you received - bank statements, invoices, contracts, emails confirming payments. If you're ever questioned, you can show you reported based on your actual earnings. The IRS is generally understanding when you can show you made a good-faith effort to report accurately.

CA resident here too. The Franchise Tax Board definitely wants documentation, but I found they accepted my own records (invoices + bank statements) when I couldn't get a 1099 from a client who went out of business. I included a brief statement explaining the situation with my filing.

I've heard about EFTPS but am confused about the setup process. Does it link directly to your bank account? And does it automatically calculate how much you should pay each quarter or do you still need to figure that out yourself?

Yes, you link it directly to your bank account during the setup process. It's a government system that lets you schedule and make federal tax payments online. It doesn't calculate your estimated payment amounts for you - you'll still need to determine that yourself based on your income projections. But it does give you an immediate confirmation number when you make a payment, which is super helpful for record-keeping. You can also view your payment history anytime, which makes it easier to verify that your payments were received if you get duplicate notices.

That's a good point. I've seen people get confused between different IRS notices because they all look so similar with that same intimidating letterhead! The details really matter.