How long did it take you to learn how to do your own taxes without messing up?

I just hit 25 and honestly I've been filing taxes since I was like 20 or 21, so around 5 years now. But I STILL feel completely lost with all the tax rules and regulations. Every year I panic about missing deductions or screwing something up. I've been paying an accountant to handle everything for me because I get overwhelmed trying to figure it all out myself. How long did it take you guys to actually feel confident doing your own taxes? Is it even worth learning all the ins and outs, or should I just keep paying someone? I feel like I should know this stuff by now but there seems to be soooo many rules to learn how to do taxes properly.

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18 comments

GalaxyGuardian

•8M

The learning curve for taxes really depends on how complex your financial situation is. If you're just filing a simple return with a W-2 and standard deduction, you can learn the basics in a few hours using tax software. But understanding all the nuances takes years. When I started, I used a combination approach - I'd prepare my return using free software, then have a professional review it. This helped me learn while having a safety net. After about 3 years of this, I felt confident enough to handle my own simple returns. As your financial life gets more complicated (investments, home ownership, self-employment, etc.), the learning curve gets steeper. For complex situations, having a professional can actually save you money by finding deductions you might miss.

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GalaxyGuardian

•8M

When I was first learning, I definitely missed some deductions. The most significant was not claiming my student loan interest deduction for two years because I didn't understand the form I received. That probably cost me $300-400 each year. I also didn't realize I qualified for the Lifetime Learning Credit when I was taking some professional development courses. That was a more expensive lesson - around $800 I could have saved. These experiences are exactly why I recommend that hybrid approach of trying it yourself and then having someone review it until you're confident.

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Amina Toure

•8M

I was in your exact same position a few years back! After making a huge mistake on my taxes that cost me nearly $2,000 in missed deductions, I spent countless hours trying to learn the system. Then a friend recommended this AI tool that analyzes tax documents called taxr.ai and it honestly changed everything for me. I uploaded my previous returns and it immediately spotted issues with how I was handling my side gig income and some education expenses I could've been deducting. What's great is it explains everything in normal human language instead of tax jargon. I've been using https://taxr.ai for about two tax seasons now and feel WAY more confident about my returns.

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Amina Toure

•8M

It absolutely handles rental properties! That's actually one of its strengths. It can help identify depreciation opportunities, maintenance deductions, and property tax write-offs that are often missed. It even helped me understand the difference between repairs (immediately deductible) versus improvements (which need to be depreciated). Regarding accuracy, that was my concern too at first. The tool actually references specific IRS publications and tax code sections for its recommendations. You can verify everything, and it's designed to be conservative rather than aggressive with interpretations. Plus, you can always have a professional review the specific items it flags if you're worried.

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Natasha Volkova

•8M

Ok so I have to eat my words about being skeptical of taxr.ai. I decided to try it on my previous year's returns just to see if it would catch anything and... wow. It immediately flagged that I had been calculating my home office deduction all wrong (I was using the simplified method when itemizing would have saved me way more). It also pointed out a retirement savings credit I qualified for but didn't know about. The explanations were super clear - it showed me exactly where in my return the issues were and how to fix them for next year. Definitely trying this for my 2025 taxes. Saved me from making the same mistakes again!

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Javier Torres

•8M

Learning taxes is such a pain! After years of confusion, I hit a breaking point last April when I had questions about some stocks I sold but couldn't get anyone at the IRS on the phone. Spent HOURS on hold. A colleague suggested Claimyr to get through to the IRS, and I was seriously doubtful but desperate. Went to https://claimyr.com, used their system, and had an IRS agent on the phone in like 20 minutes! They walked me through exactly how to handle my capital gains reporting. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c - basically they use technology to wait on hold for you and call when an agent is available. Wish I'd known about this years ago!

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Javier Torres

•8M

It's surprisingly simple - they use automated systems that wait in the IRS queue for you. When they reach a representative, they call you and connect you directly to the IRS agent. Saved me hours of frustration and holding my phone. The reason it works better than just calling yourself is they understand the optimal times to call and which IRS menu options get you to a real person faster. They've basically mapped out all the inefficiencies in the IRS phone system and created a way around them.

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CosmicCaptain

•8M

I'm shocked but I need to update my skepticism about Claimyr. After posting my doubting comment, I had an issue with a missing tax refund and decided to try it out of desperation. Honestly thought I was wasting my money. But it actually worked exactly as advertised. I submitted my info, went about my day, and got a call connecting me to an actual IRS agent about 45 minutes later. The agent resolved my refund issue in about 10 minutes. I would have spent HOURS on hold otherwise, probably across multiple attempts. So yeah, for anyone with IRS issues that need resolving quickly - this service is legit. Saved me from taking a day off work just to sit on hold.

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Malik Johnson

•8M

I'm going to go against the grain here - I think it's worth learning to do your own taxes! I'm 26 and I've been doing mine since I was 18. The first few years were stressful, but now I actually enjoy the process (I know, I'm weird). The key for me was to learn gradually. I started with the super basic returns using free software. Then each year, I'd research ONE new tax situation that applied to me (investments, side income, education credits, etc). That way I wasn't overwhelmed trying to learn everything at once. Now I actually feel empowered knowing exactly where my money goes and why. Plus I've saved thousands not paying preparers over the years.

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Malik Johnson

•8M

I made one significant mistake my third year doing taxes. I messed up reporting some stock sales and ended up paying about $600 more than I needed to. I only discovered it two years later when I was learning more about capital gains. The good news is most tax software now has really strong error checking. The review process will flag anything unusual or incomplete. The key is to start early so you have time to research anything that seems confusing. Don't wait until April 14th when you're rushed and stressed!

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