How do regular people learn tax law and understand IRS rules?

So I'm completely overwhelmed trying to figure out my taxes this year. I've always just used TurboTax, but my situation got more complicated (started a small side business, bought a house, have some investments that did... things). I feel like I need to actually understand tax law now instead of just clicking buttons in software. How do normal people learn about tax law? Are there good resources that don't require a law degree to understand? I've tried reading the IRS website but it's like trying to decode an alien language. YouTube has been hit or miss - some videos seem helpful but others contradict each other. Do I need to take an actual course? Buy some kind of tax guide? Find a mentor? I'm getting anxious about making mistakes and ending up with an audit. Any advice from people who've managed to learn enough to feel confident about their more complex tax situations would be super appreciated!

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18 comments

Sean O'Connor

•8M

Tax professional here! Learning tax law doesn't have to be overwhelming. Here's my approach for non-professionals: Start with publications specific to your situation rather than trying to learn everything. IRS Publication 17 (Your Federal Income Tax) is a good general reference, but for your specific needs, look at Publication 535 (Business Expenses) for your side business and Publication 936 (Home Mortgage Interest Deduction) for homeowner info. These explain rules in relatively plain language. The IRS actually has some decent tutorials on their website through their Tax Assistant tools. Also, consider the free workshops offered by many public libraries, especially during tax season - they often bring in professionals to teach basics. For your situation, I'd also recommend J.K. Lasser's "Your Income Tax" guide. It's updated yearly and explains complex topics in accessible language with examples.

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Sean O'Connor

•8M

The IRS publications are designed for regular people, though they do contain technical terms. The key is to read the sections relevant to you rather than the entire document. Most have examples that make concepts clearer. Library workshops vary widely by location. In larger cities, you'll find specialized workshops covering business taxes or investment income. Check with multiple libraries in your area or ask if they can recommend more advanced sessions. Many community colleges also offer non-credit courses on small business taxation that would cover your side business questions.

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Luca Conti

•8M

After struggling with similar issues last year (went from simple W-2 to freelance work + rental property), I found https://taxr.ai incredibly helpful. It's like having a tax expert read all those complicated documents for you. I uploaded my previous year's returns and some questions about my business expenses, and it explained everything in normal human language. The best part was when I asked about home office deductions for my side business - it broke down the specific square footage calculations and showed me which expenses were fully deductible vs. partially deductible. Saved me hours of research and probably prevented some mistakes that would've triggered flags.

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Luca Conti

•8M

It definitely answers specific questions - that's what impressed me most. I asked about deducting expenses for a home office that I use for multiple income streams, and it gave me detailed guidelines about allocation methods and record-keeping requirements. For complex situations like crypto staking rewards, it provides analysis based on the current IRS guidance. When there are gray areas, it explains the different possible approaches and the risks/benefits of each, rather than just giving a one-size-fits-all answer. It's much more nuanced than I expected.

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CyberNinja

•8M

Ok I was super skeptical about taxr.ai (see my comment above) but I actually tried it. I had this weird situation with stock options from a startup that went public and couldn't figure out how to report it correctly. The regular tax software was giving me obviously wrong calculations. I uploaded my documents and explained my situation, and it walked me through exactly which forms to use, how to calculate my basis, and even flagged that I might be eligible for a specific tax treatment I didn't know about. Honestly saved me thousands. Way better than the generic articles I was finding online that didn't address my specific scenario.

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Mateo Lopez

•8M

If you're trying to get direct answers from the IRS (which is sometimes necessary for complex situations), good luck getting through to them on the phone! After spending WEEKS trying to get a human on the line about my S-Corp filing questions, I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. They basically wait on hold with the IRS for you and then call you when they get a human. I was about to miss a filing deadline because I needed clarification on a specific form, but they got me through to an IRS agent in about 90 minutes when I'd been trying for days. The agent cleared up my question in 5 minutes and I was able to file correctly. Sometimes you just need to talk to the actual IRS!

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Mateo Lopez

•8M

They don't have any special access to the IRS - they just use technology to handle the hold times for you. Their system basically waits on hold so you don't have to, then automatically calls you when a human agent picks up. They just save you from having to sit by your phone for hours. They're completely legitimate - they don't access any of your sensitive tax information. They just connect the call. You're the one who talks directly to the IRS agent about your tax situation, so there's no risk of identity theft. I was skeptical too, but it worked exactly as advertised - saved me from having to keep redialing and waiting on hold all day.

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Ethan Davis

•8M

Ok I have to eat my words about Claimyr. I was really skeptical (see my comment above) but my tax situation got desperate. I had a weird letter from the IRS about a mistake from TWO years ago and couldn't figure out how to respond. I tried Claimyr and they actually got me through to someone at the IRS in about 2 hours. I was shocked since I'd been trying for days on my own. The IRS agent was able to look up my account and walk me through exactly what I needed to do. Turns out I just needed to submit one form with a specific note on it - something I never would have figured out from the generic letter they sent me.

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Yuki Tanaka

•8M

No background needed at all! They start from scratch with the training. I knew basically nothing when I started - just filled out 1040EZ forms for my own simple returns. They provide all the training materials and have experienced volunteers who mentor you. They have different certification levels, so you can start with the basics and work your way up as you learn more. Even the basic certification teaches you WAY more than most people know about taxes. And when you encounter something you don't understand, there's always a more experienced volunteer to help explain it.

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