Life Admin✓ Follow-up at 8 weeks2,450 views
I'm behind on my taxes and I'm terrified of the IRS
A tax catch-up plan covering filing back taxes, finding affordable help, setting up payment plans, and preventing future tax anxiety.
📊
Follow-Up Result
8 weeks laterFiled 2 years of back taxes and set up a payment plan with no penalties
The Problem
I haven't filed my taxes in two years. It started because I was confused about freelance income and then the anxiety snowballed. Now I'm terrified the IRS is going to come after me. I have a shoebox of receipts, no idea what I owe, and I can't afford an accountant. Every time I think about it, I panic and avoid it for another month. The longer I wait, the worse it gets.
The Plan
Week 1-2: Stop Avoiding and Start Gathering
Take a deep breath: the IRS would rather you file late than not at all. They're more lenient than you think, especially if you come to them first
Gather everything: W-2s, 1099s, receipts, bank statements. If you're missing W-2s, you can request transcripts from the IRS for free
If your income is under $79,000, you can use IRS Free File — completely free tax preparation software
If your situation is complex (freelance, multiple states), look into VITA (Volunteer Income Tax Assistance) — free tax prep by trained volunteers
File the most recent year first, then work backward — getting current is the priority
Week 3-4: File and Set Up a Plan
If you owe money, file anyway — the penalty for not filing is 10x worse than the penalty for not paying
Request a payment plan (installment agreement) online at IRS.gov — you can pay in monthly installments
For future years: set aside 25-30% of freelance income for taxes as you earn it — put it in a separate savings account
Consider quarterly estimated tax payments to avoid a big bill at year-end
Set a calendar reminder for tax season: gather documents in January, file by March, done
Resources
IRS Free File — free tax preparation for income under $79,000
VITA locations — find free tax prep help at irs.treasury.gov/freetaxprep
IRS payment plans — set up installment agreements at IRS.gov
r/tax — community advice on tax situations
Follow-Up Result
8 weeks in: I filed both years of back taxes using IRS Free File. Turns out I was owed a refund for one year and owed $1,800 for the other. Set up a payment plan for $150/month with no additional penalties because I filed voluntarily. The whole process took two weekends. The anxiety of avoiding it was 100x worse than actually doing it. I've set up a separate savings account where 25% of my freelance income goes automatically for taxes. I also found a VITA volunteer who helped me understand deductions I'd been missing. Filing next year's taxes on time will be the first time in three years and I'm weirdly looking forward to it.Know someone with this problem?
Share this solution. They get $5 off their first plan.