Don't forget podcasts as a supplement to books! "Planet Money" by NPR has several excellent episodes on taxation that might help spark your interest before diving into heavier books. Their episodes "Tax Hero" and "Paying for the Crime" are particularly good introductions to tax concepts. There's also the "Taxology" podcast which is surprisingly entertaining despite focusing exclusively on tax history and policy. I've found listening to these while commuting helps build background knowledge that makes the books easier to understand.

As someone who also struggled with the dry nature of tax topics, I found that starting with "The Power to Destroy: How the Antitax Movement Hijacked America" by Michael Graetz really opened my eyes to how taxation connects to broader American political culture. It reads more like political history than a tax book, but gave me the conceptual framework that made everything else click. Another approach that worked for me was reading "The Hidden Wealth of Nations" by Gabriel Zucman alongside some of the books mentioned here. It's about tax avoidance and offshore banking, but understanding how the wealthy navigate (or circumvent) the tax system actually helped me better appreciate why certain rules exist for regular taxpayers like us. One thing I'd suggest is not trying to tackle too many dense books at once. I made that mistake initially and got overwhelmed. Pick one that sounds most interesting based on the recommendations here, read it thoroughly, then move to the next. The context from each book builds on the others in ways that aren't obvious at first.

Quick question about all this - I'm just a dog walker who files Schedule C. My tax software is showing an option for "paying myself" - should I just ignore that completely and stick to owner draws?

This situation is unfortunately more common than it should be. I've seen several cases where tax preparers set up sole proprietors with payroll systems, often because they're using generic business software that assumes corporate structures. The $275 fee is definitely a red flag - proper business tax preparation requires understanding entity structures, and competent preparers charge appropriately for that expertise. Your instincts are absolutely correct here. Beyond the immediate tax issues others have mentioned, there's also a compliance nightmare brewing. If your client is running payroll, they're likely supposed to be filing quarterly 941 forms, making federal tax deposits, potentially dealing with state payroll requirements, etc. All of this creates unnecessary administrative burden and potential penalties for a structure that shouldn't exist. I'd strongly recommend your client consult with a qualified tax professional (CPA or EA) to clean this up. They'll need to decide whether to amend previous returns or just correct going forward, depending on the amounts involved and audit risk tolerance. The sooner this gets fixed, the better - especially before any IRS correspondence arrives. Your recommendation about either taking proper draws or electing S-Corp status is spot-on. The client needs to pick a lane and do it correctly.

Went through literally the EXACT same thing last year! We thought we filed through H&R Block but never submitted. Found out when applying for a car loan. We ended up going to a local CPA who charged us $275 to e-file our prior year return. Had it done in 2 days and got confirmation really quick. Mortgage companies usually just need proof you filed, not that everything is fully processed. Ask your mortgage broker exactly what they need to see - sometimes just the filing confirmation is enough to keep the loan moving.

I'm a tax preparer and see this situation fairly often. Dylan, you're absolutely right to be concerned about timing, but there are a few things that can work in your favor here. First, since you already completed everything in TurboTax, you have all your documentation organized. A tax professional can take that information and e-file your 2021 return immediately - we're not restricted by the same e-file dates that consumer software has for prior year returns. For a straightforward return like yours (sounds like W-2 income), you should expect to pay $200-350 for the service. Yes, it's more expensive than doing it yourself, but given your mortgage timeline, it's probably worth it. Here's what I'd recommend: Find a local CPA or enrolled agent (not a chain like H&R Block) who can e-file immediately. Ask them to provide you with a copy of the filed return and the e-file confirmation. Your mortgage lender will likely accept this as proof of filing while they wait for IRS processing. The penalties aren't as scary as they seem - you're looking at roughly 5% of your tax owed per month for failure to file (capped at 25%), plus 0.5% per month for failure to pay, plus interest. On $1,800, that's probably around $400-500 in total penalties and interest for being 3+ years late. Get this handled this week if possible. Your mortgage situation is salvageable, but time is definitely of the essence here.

make sure to check your WMR too sometimes it updates b4 transcripts

Congrats on finally getting your 846! That's such a relief after waiting since May 2024. The timeline definitely makes sense - your amended return was completed on 1/16 and now you have a DDD of 2/14, which is pretty typical processing time. You should definitely see that $4,872 hit your account on or around 2/14. The fact that it went from processing to 846 so quickly after completion is a really good sign. Hang in there, you're almost at the finish line! 🎉

Question about crypto tax reporting software - has anyone used TaxBit, CoinTracker, or Koinly for situations like this? I'm dealing with something similar from 2022 trades but have about 300+ transactions. Not looking forward to entering all that manually.

This is exactly why crypto tax situations can be so confusing! The IRS automated systems just see the gross transaction amounts from exchanges without the context of your actual cost basis. It's really common for people to get these notices even when they had losses. I'm glad to see from your update that everything got resolved! For anyone else dealing with similar issues, the key is having good documentation of your actual transactions showing the purchase prices, sale prices, and dates. The 1099 forms from exchanges often don't tell the complete story. One thing I learned from my own crypto tax issues is that it's worth reporting losses even if you think you don't need to - they can actually be beneficial for offsetting other gains or reducing ordinary income up to $3,000 per year. Plus it prevents these kinds of automated notices from the IRS in the first place.