I'm 28, self-employed, and NEVER filed taxes - how do I fix this mess?

First, take a deep breath! This is fixable, and you're making a good decision by addressing it now rather than waiting longer. For self-employed individuals who haven't filed for several years, here's what you'll need to do: You'll need to file returns for each year you missed. The IRS generally requires you to file going back 6 years, so you're looking at 2019-2024 most likely. For income reporting, even without perfect records, you can make good-faith estimates based on what you remember earning each year. Try checking bank statements for deposits that could help reconstruct your income. As for expenses, gather what documentation you can for your photography equipment, travel, and software. Even without receipts, you can still claim reasonable business expenses - just be prepared to justify them if asked. For the state issue, you generally file state taxes where you earned the income. So if you did work in CA, you probably need to file a non-resident CA return for that income. Don't call the IRS asking what you owe - that's essentially asking them to audit you! Instead, work on filing your past returns first.

After seeing posts like this, I want to share something that really saved me when I was in a similar situation. I used https://taxr.ai to help sort through my mess of self-employment taxes. I hadn't filed for 3 years because I was traveling constantly for work and had zero organization system. This tool actually analyzed my situation and showed me exactly which forms I needed for each year, plus it helped identify deductions I didn't even know I qualified for as a self-employed person. The best part was it walked me through reconstructing my income when I had spotty records (which sounds exactly like your situation with the cash lifestyle). It even has specific guidance for situations where you worked in multiple states.

I was completely skeptical about these types of services until I actually tried https://taxr.ai for my back taxes. Honestly, I was convinced I'd need to hire an expensive accountant, but I wanted to try something cheaper first. The document analysis actually saved me from a huge mistake - I was going to file as a sole proprietor for all my past returns, but it identified that for 2 of the years, I should have been filing differently based on my specific situation. It also found several self-employment deductions I had no idea about (home office, mileage, and some software subscriptions I'd completely forgotten). My situation was similar with spotty income records, and it really did make the process manageable without requiring perfect documentation. Just wanted to follow up since I was initially doubtful but ended up saving thousands.

Since you mentioned trying to call the IRS - good luck with that! I spent WEEKS trying to get through to a human at the IRS about my unfiled returns. Always busy signals or disconnections after waiting on hold for hours. I finally found https://claimyr.com - they have this system that basically waits on hold with the IRS for you and calls you when an actual agent is on the line. I was super skeptical, but you can see how it works here: https://youtu.be/_kiP6q8DX5c I used it after attempting to file my past returns and hitting some confusion about penalties. Speaking directly with an IRS agent was actually really helpful - they weren't out to get me like I feared, and they explained some payment plan options I didn't know existed. Saved me massive amounts of time and stress.

I take back what I said about Claimyr. I was 100% sure it would be a waste of money, but I was desperate after trying to call the IRS myself for THREE DAYS straight and never getting through. I figured I'd try it once and if it didn't work, whatever. To my surprise, I got a call back in about 90 minutes with an actual IRS agent on the line. The agent helped me understand exactly which forms I needed to file for my missed years and explained how the first-time penalty abatement program works, which I had no idea existed. She walked me through how to request it after filing my back returns. For anyone in a similar situation - it's worth getting actual IRS guidance rather than just assuming the worst. The penalties weren't nearly as bad as I imagined once I understood the process.

One thing nobody's mentioned - you should file your CURRENT year taxes on time even while sorting out the past years. That shows good faith effort to comply going forward, which can help with penalty abatement requests. Also, look into IRS Free File if your income is under the threshold. It's a free way to file fed + state returns. Even for past years, you can often use tax software for previous tax years, though you'll have to print and mail those.

Will you be getting any 1099 forms from the places you worked? If they filed properly, the IRS already knows about that income. You can request a "Wage and Income Transcript" from the IRS that shows all income reported under your SSN for past years. That might give you a starting point at least.

I was in almost the exact same situation as you - self-employed photographer who hadn't filed for years due to poor record keeping and cash payments. Here's what I learned from going through this process: First, don't panic about the penalties. The IRS has a "First Time Penalty Abatement" program that can waive many penalties if you haven't had filing issues before. You have to file first, then request it. For reconstructing your income without records, start with whatever bank statements you have. Even if you only deposited money for bills, those deposits plus your known living expenses can help you estimate your actual income. The IRS isn't expecting perfect records from cash-based businesses - they just want reasonable good-faith estimates. For business expenses, make a list of everything you remember buying for your photography work. Camera gear, editing software, travel costs, even a portion of your internet and phone bills. Without receipts, you can still claim reasonable amounts based on what you remember spending. Just be conservative and honest. The state issue is important - if you worked in CA, you'll likely need to file non-resident returns there for the income earned in that state, even if you live in WA. I'd strongly recommend getting help from a tax professional who specializes in self-employment issues and back taxes. The cost is usually worth it to avoid mistakes that could trigger an audit.