How many times a year do I need to pay taxes? What are the deadlines? Worried I'll go to jail if I miss a payment (tax newbie here)

Omg thank you so much, I've been seriously panicking! So when you say "what you've already paid through withholdings" - that's what shows up on my pay stub where it says federal tax, state tax, etc? So I've actually been paying my taxes all along without realizing it? Also, what's this W-2 form? Is that something I need to get or fill out?

Yes, exactly! Those line items on your pay stub labeled federal tax, state tax, Social Security, Medicare - those are all your tax payments being automatically withheld and sent to the government. You've been paying taxes all along with every paycheck. A W-2 is a form your employer will send you by the end of January each year. It summarizes all the income you earned and all the taxes that were withheld during the previous year. You don't need to request it - your employer is legally required to provide it. You'll use this form when you file your tax return in April. It has all the information you need to complete your tax filing.

Does it work if you have more complicated stuff like side gig income? I do regular W-2 work but also make money selling stuff on Etsy, and I have no idea how to handle that part.

How does this actually work? Is it just another tax software thing that asks you a million questions, or is it something different? I'm tired of spending hours trying to figure out if I'm doing my taxes right.

It works great with side gig income! It explains how to report your Etsy sales, what expenses you can deduct, and how to handle estimated quarterly payments if you need to make them. It can analyze 1099 forms from platforms like Etsy and explain exactly what you need to report. This is different from regular tax software. You upload your tax documents (or even take photos of them), and it analyzes everything to explain what you're looking at and what you need to do. It's more like having someone review your situation and guide you rather than just filling in boxes on a form. Saved me so much time compared to trying to Google everything myself.

Seriously? I thought it was impossible to get through to the IRS. My dad spent like 6 hours on hold last year and then got disconnected. How much does this cost?

This sounds like a scam. There's no way to "skip the line" with government agencies. You just have to wait on hold like everyone else.

It's definitely a lifesaver during tax season when wait times are insane. It doesn't let you "skip" the line exactly - it uses technology to navigate the IRS phone system and waits on hold for you, then calls you once an agent is actually on the line. That's how it saves you from sitting there listening to hold music for hours. They don't claim to have any special relationship with the IRS - it's just a really smart system that handles the waiting part so you don't have to. I was skeptical too until I tried it and was talking to an actual IRS representative while my friend who called directly was still on hold.

Thank you for breaking it down so simply! So just to double check, since I'm only working this regular job where they take taxes out of my paycheck, I really just need to worry about filing my return by April 15th each year? And then I use the W-2 form my work sends me to do that?

Exactly right! Since you have a regular job with taxes being withheld from each paycheck, you only need to file once a year by April 15th. Your employer will send you the W-2 form you need (usually by end of January), and you'll use that information to file your return. The whole process is pretty straightforward for most employees. You can use free tax filing software if your situation is simple, which it sounds like it is. The software will walk you through entering the information from your W-2 and ask some basic questions to make sure you get any credits or deductions you qualify for.

VITA was awesome when I first started working! The volunteers are usually retired accountants or tax professionals who really know their stuff. Just make sure to book early because appointments fill up fast in March and April.

This sounds perfect for me! I'll definitely look into VITA - having someone walk me through it the first time would be so helpful. Thanks for letting me know about this option!