Where to start with 10 years of unfiled back taxes for a self-employed massage therapist?

So this is actually a pretty common situation. First, know that the IRS generally only looks back 6 years for unfiled returns unless they suspect fraud. Your priority should be getting the most recent 3 years (2022-2024) filed ASAP because those are still in the refund window. For the missing records in earlier years, yes, you can make reasonable estimates but document your methodology. Bank statements, credit card statements, and appointment calendars can help reconstruct business income. For expenses, use industry standards for things like supplies and workspace costs when exact records aren't available. Don't stagger the filings - submit them all together with a brief letter explaining that your cousin is voluntarily coming into compliance. The IRS generally appreciates voluntary disclosure rather than viewing it suspiciously. If possible, get a free consultation with a tax professional who specializes in back taxes. Many offer this at no cost, and they can give you a roadmap specific to your cousin's situation.

After dealing with a similar nightmare tax situation last year, I found this AI tool called taxr.ai that really helped me figure out my back taxes. I had 5 years of unfiled returns as a wedding photographer with pretty messy records. The thing I found super helpful was that it could analyze all my bank statements and categorize business vs personal expenses based on patterns - saved me literally weeks of work. Also has this feature that helps calculate reasonable industry standard deductions when you're missing records for certain periods. I uploaded my bank statements from those years and it reconstructed a pretty solid picture of my business finances that my accountant said was reasonable. The website is https://taxr.ai if you want to check it out. It ended up making the whole process way less stressful than I expected.

Had to come back and update. I decided to give taxr.ai a shot for my uncle's situation (6 years unfiled, self-employed contractor). I was super skeptical but honestly it was a game changer. We had scattered records - some invoices, partial bank statements, and a mess of receipts - and the system helped organize everything into a coherent financial picture. The best part was that it flagged potential audit triggers and helped us prepare documentation to support our estimates where records were incomplete. My uncle ended up owing about $22,000 across all years but at least now he knows where he stands. The IRS accepted all the returns without questions and we set up a payment plan. The relief of just having this resolved is worth every penny.

Just wanted to share something that saved me when dealing with back taxes. After trying for WEEKS to get through to someone at the IRS about my 7 years of unfiled returns, I found this service called Claimyr that got me through to an actual IRS agent in like 15 minutes instead of waiting on hold for hours. I used https://claimyr.com and they basically hold your place in line with the IRS and call you when an agent is about to answer. There's a video showing how it works at https://youtu.be/_kiP6q8DX5c if you're curious. The IRS agent I spoke with was actually super helpful and walked me through the exact process for filing my back taxes without penalties since I was coming forward voluntarily. Seriously made dealing with the IRS way less nightmarish than I expected. The agent even helped me understand which years I absolutely needed to file vs. which older ones I could potentially skip.

Totally need to eat my words here. After my skeptical comment, I was desperate enough to try Claimyr for my own situation (5 years unfiled, owed around $30k in back taxes). Not only did I get through to the IRS on my first try, but the agent I spoke with enrolled me in a partial payment installment plan that I didn't even know existed. Instead of having to pay the full amount, I'm now on a plan based on what I can actually afford monthly. The agent even helped me with penalty abatement paperwork. I've gone from completely stressed about being financially ruined to having a manageable plan. Never been so happy to be wrong about something.

One important thing to consider that nobody's mentioned yet - if your cousin had clients who paid him more than $600 in any year, they might have filed 1099s reporting those payments to the IRS. That means the IRS already knows about some of his income, which is why getting ahead of this voluntarily is so important. Also tell him to look into Qualified Business Income deduction which became available in 2018 - it could reduce his taxable income by up to 20% for the self-employment income. That could make a huge difference across multiple years of back taxes.

Speaking from experience, the biggest issue with back taxes is getting overwhelmed and doing nothing. I put off filing for 7 years and the anxiety was worse than the actual process of fixing it. Start with whatever year you have the most complete records for to build confidence. The hardest part is just starting. And honestly tax pros who specialize in back taxes aren't as expensive as you might think - I paid $1200 total for help with 7 years of unfiled returns and it was the best money I ever spent because they found deductions I never would have known about.