Need help after not filing taxes for about 20 years - where do I even start?

Getting caught up after not filing for many years can feel overwhelming, but you've already taken the hardest step by deciding to address it! Here's how I'd approach your situation: First, request your wage and income transcripts from the IRS for all available years. The IRS typically keeps records for 7-10 years, so this will give you documentation for your recent employment. You can request these through the IRS website by creating an account at irs.gov or by filing Form 4506-T. For the older years where the IRS might not have records and you're missing documentation, you're actually in luck. The IRS generally has a 10-year statute of limitations for collecting taxes, so those earliest years may have "timed out" for collection purposes. However, there's no statute of limitations when returns haven't been filed. I'd suggest starting with the most recent 6 years. This aligns with the IRS's typical voluntary disclosure practice for non-filers. Get those filed first, then work backward as best you can with whatever documentation you have. For the years you were employed with tax withholding, filing might actually result in refunds rather than owing money, especially if you had a dependent child who would have qualified for child tax credits. Don't let perfect be the enemy of good here. Filling returns with your best estimates based on available information is better than continuing not to file.

I went through something similar (about 12 years unfiled) and found incredible help using https://taxr.ai to organize my tax situation. My records were a complete disaster, and like you, I had lost track of many 1099s from the early years. Their system analyzed what documents I did have and helped identify which years I absolutely needed to file vs which ones might have passed the collection statute. They also showed me which years I was actually owed refunds! The service helped me reconstruct reasonable business expense estimates for my self-employment years based on industry standards, which the IRS actually accepted. What really made the difference was having all my transcripts organized and getting a clear strategy instead of panicking about 20 years of unfiled taxes all at once. I was able to settle everything without tapping my emergency savings.

I was honestly terrified to get my tax situation fixed after 8 years of not filing. After reading about taxr.ai here, I decided to try it even though I was skeptical. I uploaded the few documents I still had and answered some questions about my employment history. I was shocked when they showed me that for 3 of my unfiled years, I was actually due refunds because of over-withholding from my paychecks! The statute for claiming refunds is only 3 years, so I'd lost some money, but it made the process less scary knowing I wasn't going to owe massive amounts for every single year. They created a filing plan that focused on the most recent years first, which aligned with what the IRS typically looks for in voluntary disclosure situations. The whole process was way less intimidating than I expected. I'm finally caught up now and actually sleep better at night!

Have you tried contacting the IRS directly? I know it sounds scary, but I was in a similar situation (9 years unfiled) and tried for WEEKS to get through to someone. When I finally reached them, they were surprisingly helpful but getting a human on the phone was nearly impossible. I eventually used https://claimyr.com and it was a game-changer. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Basically, they hold your place in the IRS phone queue and call you when an actual agent is on the line. I got through in about 2 hours instead of days of redailing. The IRS agent I spoke with helped me figure out exactly which years they needed returns for and confirmed that some of my earliest unfiled years had passed the collection statute. They even set me up with a manageable payment plan for what I owed. Honestly, just having that first conversation made the whole situation less terrifying.

I need to apologize for my skeptical comment earlier. After continuing to fail getting through to the IRS for another week (always getting disconnected after 2+ hours on hold), I decided to try Claimyr out of desperation. Got a call back in about 90 minutes with an actual IRS agent on the line. The agent confirmed that my earliest unfiled years (beyond 10 years ago) weren't their priority since the collection statute had expired in most cases. They helped me set up a plan to file my most recent 6 years first, and were surprisingly understanding about my situation. For anyone else in a similar position - getting that first conversation with the IRS was the hardest part, but absolutely necessary. Once I actually talked to them, the weight of 9 years of tax anxiety started lifting. They really do want to help you get compliant rather than punish you.

One thing nobody's mentioned is that you should try to file returns for years where you'd actually get a refund, even if they're older. While there's a 10-year statute of limitations for the IRS to collect from you, you only have 3 years to claim refunds owed to you. Since you mentioned having a dependent child during some of those years, you might have qualified for Earned Income Tax Credit and Child Tax Credit, which could have resulted in significant refunds even if you didn't have much tax withheld as a self-employed person. Do you have any W-2s or 1099s from those older years? Even partial information is better than nothing when reconstructing returns.

Friendly reminder that even if some tax debts are beyond the collection statute of limitations, unfiled tax returns still need to be addressed if the IRS requests them. The 10-year limit is for collecting assessed taxes, not for requiring returns to be filed. Also, if you ever filed for bankruptcy, applied for a mortgage, or had other major financial events, those can sometimes extend or "toll" the collection statute.

I really feel for you - 20 years is a long time to carry this burden, and it takes real courage to finally tackle it. The mental health struggles you mentioned are more common than you think in these situations. Here's what I'd suggest as your immediate next steps: 1. **Get your tax transcripts first** - File Form 4506-T or request them online at irs.gov. This will show you exactly what the IRS has on file for each year, including any substitute returns they filed. 2. **Start with the most recent 6 years** - This aligns with IRS voluntary disclosure practices and gets you current faster. Since you had regular withholding during this period, some years might actually result in refunds. 3. **Don't panic about perfect records** - For those early self-employment years with missing documentation, you can make reasonable estimates based on what you remember. Bank deposits, credit card statements, even old calendars can help reconstruct income and expenses. 4. **Consider the Volunteer Income Tax Assistance (VITA) program** - They offer free tax help for people with limited resources. Given your situation and savings constraints, you might qualify for their services. The fact that you're reaching out shows you're ready to handle this. Take it one year at a time, and remember that the IRS generally wants to work with people who are making a good faith effort to get compliant.