How long did it take you to learn how to do taxes effectively?

I'm 26 and have been filing taxes for about 5 years now, but I still feel completely lost when it comes to understanding all the tax rules. Every time I think I'm getting the hang of it, there's some new deduction or credit I didn't know about. I've been paying someone to do my taxes because I'm worried about messing something up, but I wonder - is this normal? How long does it actually take to feel confident doing your own taxes? Does anyone actually fully understand all the tax rules, or are most people just winging it like me? I keep thinking I should learn to do them myself to save money, but the whole process is so intimidating...

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18 comments

JacksonHarris

•8M

Tax accountant here! Honestly, learning to do taxes is a continuous process even for professionals. Basic returns might take a few years to feel comfortable with, but tax law changes annually, so we're always learning. For the average person with W-2 income and standard deductions, you could probably learn the basics in a tax season or two using good tax software. The software walks you through everything step by step. Where it gets complicated is when you add self-employment, investments, rental properties, or unusual situations. Those can take years to fully understand, and even professionals consult with each other on complex scenarios. Don't feel bad about paying someone if your situation has any complexity. Think of it as insurance - you're paying to avoid costly mistakes. The peace of mind is often worth it!

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Royal_GM_Mark

•8M

I was in exactly your situation about 2 years ago - kept paying someone $300+ for a pretty simple return. Then I discovered https://taxr.ai and it completely changed how I approach taxes. Instead of trying to learn everything at once, I upload my documents and it walks me through exactly what I need to know for MY specific situation. The best part is it analyzes all my forms and explains everything in normal human language. Last year it caught a student loan interest deduction my previous tax guy completely missed! It's like having a tax expert looking over your shoulder but you're still in control.

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Royal_GM_Mark

•8M

It definitely handles complicated situations. I actually have a small photography business with lots of equipment expenses and client payments, and it sorted through everything perfectly. It even flagged some deductions I didn't know I could take for my home office. For your rental co-ownership, it would walk you through the proper allocation of expenses and income. For saving money, I was spending $375 on an accountant before. The first year using this, I saved that fee AND found an additional $842 in deductions my accountant had missed over the previous years. Time-wise, it took me about 90 minutes total, spread across two evenings - way less time than collecting and dropping off everything to my accountant.

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Chris King

•8M

Update on my tax situation - I tried https://taxr.ai after seeing it mentioned here and I'm honestly impressed. I was super nervous about doing my own taxes (especially with a side gig), but it was WAY easier than expected. The document analysis feature is a game changer. I literally just uploaded my forms and it pulled all the right numbers and explained what everything meant. Found a work expense deduction I would have totally missed worth about $380! Never going back to paying someone else to do my taxes again. Wish I'd known about this years ago instead of stressing about tax season every year!

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Rachel Clark

•8M

If you're still feeling lost, here's a tip that saved me hours of frustration: calling the IRS directly for guidance. BUT - and this is a HUGE but - getting through to them is nearly impossible unless you use https://claimyr.com. You can see how it works here: https://youtu.be/_kiP6q8DX5c I spent DAYS trying to get someone on the phone about a weird letter I got. After using Claimyr, I had an IRS agent on the phone in 27 minutes who actually explained everything and helped me resolve the issue. They basically wait on hold for you and call when an agent picks up. The peace of mind from talking to an actual IRS person who could access my file and explain exactly what I needed to do was worth every penny.

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Rachel Clark

•8M

They basically have a system that waits on hold with the IRS for you. When an actual agent picks up, you get a call back immediately so you can talk to them. It's way better than putting your phone on speaker because IRS hold times can be 3+ hours, and if you miss the moment they pick up, you're back to square one. This way you can go about your day normally. Regarding whether the IRS is actually helpful - it depends on who you get, but most agents I've spoken with have been knowledgeable. The key is getting specific about your question. The agent I spoke with pulled up my actual tax return while on the phone and walked me through exactly what I needed to fix. Totally different experience than trying to figure it out from their confusing letters.

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Mia Alvarez

•8M

Ok I need to eat my words and apologize. After my frustrated reply, I was still desperate about my tax situation (the IRS was claiming I owed $4,200 from a 1099 I never received), so I tried Claimyr out of desperation. Got connected to an IRS agent in about 40 minutes. The woman I spoke with was actually super helpful and could see in their system that the 1099 was filed incorrectly by my old employer. She put notes on my account and told me exactly what documentation to send in to get it resolved. Just got confirmation yesterday that my case is closed and I don't owe anything. Would have NEVER figured this out without actually talking to someone who could see my full file. Sorry for being so negative before!

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Carter Holmes

•8M

Everyone's talking about services, but to answer your actual question - I've been doing my own taxes for 15 years and STILL learn new things every year. Started with the 1040EZ when I was 19. Now I handle our family taxes with mortgage interest, childcare credits, HSA contributions, and some freelance income. My advice - don't try to learn everything at once. Just learn the parts relevant to your situation this year. Next year, learn what's new for your situation. It's more manageable that way!

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Carter Holmes

•8M

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.

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