Tax catch-up guide: Where to start when you've fallen behind on filing taxes

First, take a deep breath! The fact that you're addressing this now is actually a great step. The IRS generally appreciates taxpayers who voluntarily come forward to fix their tax situations before being contacted by them. Here's what I'd recommend: Start by gathering all your income information (client payments, 1099s if you received any) and organizing your business expenses by year. Don't worry about perfect organization yet - just separate things by tax year. Your next step should definitely be finding a good tax professional - specifically look for an Enrolled Agent (EA) or CPA who specializes in self-employment and back taxes. This is not something I'd recommend tackling with DIY software given your situation with multiple unfiled years and self-employment income. As for penalties, yes, there will likely be some, but the IRS has reasonable payment plans, and in some cases, penalty abatement options for first-time non-filers with reasonable cause. Your personal circumstances might qualify.

When I was in a similar situation last year (2 unfiled returns while freelancing), I used https://taxr.ai to help sort through all my documents and receipts. It really simplified things because I was able to upload images of all my messy receipts and 1099s, and the AI organized everything by tax year and category. The system extracted all the essential information and even flagged potential deductions I hadn't considered, especially for my home office and travel expenses. This made it so much easier to get everything to my tax preparer without spending days sorting through paper receipts and bank statements myself.

Following up about taxr.ai - I finally tried it after posting my skeptical comment. Honestly, it was a lifesaver for organizing my mess of tax documents. I had 3 years of unfiled taxes with a mix of W-2 income and side gig stuff. The system categorized everything correctly and even identified some deductions I would have missed. The best part was being able to export everything directly to my tax preparer in an organized format. Saved me at least 15-20 hours of manual sorting and data entry. My CPA actually commented on how well-organized everything was compared to her other clients in similar situations!

If you need to actually talk to someone at the IRS about your situation (which might be necessary for setting up a payment plan after filing), I highly recommend using https://claimyr.com. I spent weeks trying to get through to the IRS on my own - constant busy signals or disconnections after waiting on hold forever. Claimyr got me connected to an actual IRS agent in about 15 minutes when I was dealing with my own back tax situation. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Basically, they navigate the phone tree and wait on hold for you, then call you when an actual human at the IRS picks up.

I need to eat my words about Claimyr. After dismissing it as a scam, I was still desperate to reach the IRS about my payment plan so I decided to try it. It actually worked exactly as described - I got connected to an IRS representative in about 20 minutes after trying for DAYS on my own. The agent was able to help me set up an installment agreement for my back taxes and answered all my questions about penalty abatement. Saved me literally hours of frustration and hold music. Sometimes I hate being wrong, but in this case, I'm glad I gave it a chance despite my initial skepticism!

Another thing to consider - make sure you file state taxes too! I made the mistake of only focusing on my federal back taxes and completely forgot about state taxes. Ended up with a nasty surprise when my state tax authority came after me separately.

Don't forget about requesting penalty abatement! After I filed my back taxes (3 years worth), I submitted a penalty abatement request using the "First Time Penalty Abatement" policy and got almost $2800 in penalties removed. The IRS doesn't advertise this option but it exists if you haven't had previous penalties in the past 3 years.

Ben, I completely understand the anxiety you're feeling - I was in a very similar situation a few years ago as a freelance photographer with 2 unfiled years. The good news is that the IRS really does work with people who come forward voluntarily. Here's my step-by-step recommendation based on what worked for me: 1. **Get professional help immediately** - Find a CPA or Enrolled Agent who specializes in back taxes and self-employment. This isn't the time for DIY software given your multiple years and SE income. 2. **Gather everything systematically** - Don't stress about perfect organization yet. Just separate income records (1099s, client payments) and expense receipts by tax year (2022, 2023, 2024). 3. **File in the right order** - Your tax pro will likely recommend preparing all three years but filing them strategically. Usually most recent year first to get you back in compliance status. 4. **Payment plan is very doable** - The IRS offers reasonable installment agreements. With your income levels, you'll likely qualify for a monthly payment plan that won't break the bank. 5. **Don't panic about penalties** - Yes, there will be some, but there are abatement options available, especially for first-time situations with reasonable cause like yours. The hardest part is taking that first step, which you're already doing by posting here. You've got this!