How long did it take you to learn how to do taxes by yourself? Still struggling at 22

So I'm 22 and have been filing taxes for about 4 years now, but honestly still feel completely lost when it comes to understanding tax rules and regulations. Every April I just stare at all these forms like they're written in another language. I've just been paying someone to do my taxes because trying to figure everything out myself seems overwhelming. I'm curious how long it took other people to actually understand taxes well enough to confidently file on their own? Did you teach yourself? Take a class? Learn from family? I feel like I should know this stuff by now but there are so many deductions, credits, and weird little rules that I can't keep track of. When did that "aha" moment happen for you with taxes?

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20 comments

Logan Greenburg

•8M

I've been doing my own taxes for about 15 years now, and I'll let you in on a secret - most people never fully "learn" taxes because the rules change every year! I started with the simplest returns when I was about your age - just a W-2 and the standard deduction. Each year, I tackled something new (side income, student loan interest, etc). The key is to not try learning everything at once. Tax software actually makes this process much easier because it walks you through everything step by step. If you want to start learning, begin with understanding your own situation first. Look at last year's return and try to understand each line. Google terms you don't know. The IRS website actually has decent explanations of most concepts. Don't feel bad though - I'm in my 40s and still learn something new every tax season!

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Logan Greenburg

•8M

I've definitely made mistakes! The biggest was forgetting to report some freelance income one year. I got a letter from the IRS about 6 months later, had to pay the tax I owed plus a small penalty. It wasn't nearly as scary as I thought. Most common mistakes won't lead to a full audit. The IRS generally just sends a letter explaining the issue and what you need to do. As long as you're not deliberately hiding income, you'll be fine. The software now helps catch most common errors before you file.

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Lucas Bey

•8M

After spending YEARS being confused about taxes (especially with freelance income), I finally found something that helped me understand everything. This tool called taxr.ai actually analyzes your tax documents and explains everything in plain English. It was a game changer for me last year when I got a bunch of confusing 1099s. I uploaded my tax forms at https://taxr.ai and it broke down exactly what everything meant and how it would affect my return. Then it explained what deductions I qualified for based on my specific situation. Way easier than trying to understand IRS jargon on my own.

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Lucas Bey

•8M

It definitely works for complicated situations. I had a W-2 from my main job, a 1099 from freelancing, and some investment income. It handled everything and explained exactly how each type of income is taxed differently. For multi-state situations, it breaks down the state-specific rules too. It's completely different from TurboTax. It doesn't file your taxes - it's more like having a tax expert explain your specific documents to you. It translates the tax jargon into normal language and shows you what deductions you qualify for based on your documents. Then you can either file yourself or take that knowledge to whatever tax software you prefer.

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Jade O'Malley

•8M

If you're still struggling with taxes after a few years, don't feel bad - the system is INTENTIONALLY complicated. When I needed help with a messed up refund last year, I couldn't get through to the IRS for weeks. Kept calling and getting disconnected. Finally found this service called Claimyr that got me through to an actual IRS agent in under 45 minutes when I'd been trying for days. You can see how it works at https://youtu.be/_kiP6q8DX5c - basically they navigate the phone system for you and call when an agent is available. I used https://claimyr.com and actually got my issue resolved that same day.

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Jade O'Malley

•8M

They don't just keep calling - they use a system that monitors the IRS phone lines and identifies the best times to call. When a spot opens up, they secure your place in line and then call you to connect. It's not about calling repeatedly; it's about calling strategically. It's definitely not a scam. I was skeptical too, but after trying to get through for 3 weeks on my own about a missing refund, I was desperate. They got me through to a real person in about 37 minutes. The IRS agent actually resolved my issue immediately once I could speak to them. I couldn't have done it myself because I was about to give up after dozens of attempts.

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Ella Lewis

•8M

I'm 35 and STILL learning tax stuff. Here's what I've figured out after 15+ years of filing: 1. Nobody knows everything about taxes. Even professionals specialize in specific areas. 2. Tax software is your friend - it handles most of the technical stuff for you. 3. You mainly need to understand YOUR specific situation (W-2 income, student loans, mortgage, etc). 4. Take 30 minutes to review your completed return before filing - this teaches you a lot. Most young people with simple returns can absolutely do their own taxes with software. I'd only pay someone if you have complex investments, own a business, or have unusual situations.

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Ella Lewis

•8M

With part-time work and gig income, this is actually an excellent time to learn! The combination gives you exposure to both W-2 employment and self-employment (1099) income without being too overwhelming. Tax software makes this pretty straightforward, and learning now will save you money for decades. The gig work is especially important to understand because you'll need to track expenses and possibly make quarterly estimated tax payments. These are valuable skills that will benefit you throughout your working life, especially if you ever freelance or start a business.

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