One thing no one's mentioned yet - if you're planning to ever move to the US in the future, getting tax compliant now is SUPER important. My cousin ignored his US filing requirements for years while living in Asia, then tried to move back to the States and had major issues getting a mortgage, credit cards, etc. because he had no US tax history or credit score. Also, while the Streamlined procedures are great, they can change or end at any time. The IRS could decide tomorrow to make the requirements stricter. I wouldn't wait.

I'm dealing with a very similar situation right now! I'm a 35-year-old dual US/German citizen who has lived in Berlin my entire adult life and only recently discovered I was supposed to be filing US taxes. Like you, I never had an SSN and was completely in the dark about these requirements. Here's what I've learned from my research and initial steps: 1. **Don't ignore it** - I know it's tempting (especially seeing your brother's approach), but this problem doesn't go away and can get much worse over time. 2. **SSN application is straightforward** - I got mine at the US consulate in Frankfurt last month. Just needed my birth certificate, passport, and proof of identity. The whole appointment took maybe 30 minutes. 3. **Focus on the Streamlined procedures** - This seems to be the gold standard for people in our situation. My tax advisor confirmed that most people like us end up owing little to nothing after foreign tax credits. 4. **Get professional help** - I initially tried to figure this out myself but quickly realized the complexity was beyond what I could handle alone. A good expat tax specialist is worth every penny. The hardest part for me was overcoming the initial panic and paralysis. Once I started taking concrete steps, it became much more manageable. Your music career income situation might be more complex than my regular employment, but the basic framework is the same. Feel free to reach out if you want to compare notes as we both work through this process!

What tax software are people using for old returns like 2021? Can you still use TurboTax or H&R Block for prior years? I'm in a similar situation and not sure which option is best.

I went through this exact same situation with my 2020 return! The panic is real but you're actually in a much better position than you think. Since you're owed a refund, you have zero penalties to worry about. One thing I wish someone had told me earlier - gather ALL your documents first before you start filing. I made the mistake of starting with just my W-2 and then realized I was missing my 1099-MISC from that side gig income you mentioned. It delayed everything by weeks. For your $3,800 side gig income, you'll definitely need to file a Schedule C if it was freelance/contractor work, and don't forget about potential business deductions you might have had that year - home office, supplies, mileage, etc. Those can really add up and increase your refund. Also, double-check your bank records from 2021-2022 to see if you made any estimated tax payments that you might have forgotten about. I found I had made a small quarterly payment that I completely forgot about, which added another $400 to my refund. The whole process took me about 6 weeks from filing to receiving my refund, but that included the time I spent tracking down missing documents. You've got this!

Just wanted to add something important - make sure you track your business expenses! That $2600 isn't all taxable if you spent money to earn it. Did you buy any equipment? Software subscriptions? These can be deducted from your income before calculating taxes. I made about $3000 last year from my Etsy shop, but after deducting all my supplies and shipping costs, my taxable income was only about $1800. That saved me a decent amount on self-employment taxes.

I'm in a similar boat - made around $1,800 from tutoring other kids in my neighborhood and now I'm panicking about taxes. Reading through all these responses has been super helpful though! One thing I want to add is that you should definitely keep good records going forward. I wish I had tracked my expenses better from the start. Things like if you had to buy any coding books, pay for software licenses, or even gas money driving to meet clients - these could all potentially be business deductions. Also, don't beat yourself up about not knowing this stuff. Most adults don't understand taxes either! The important thing is you're asking the right questions now and taking care of it properly. Better to file late than never file at all, but you still have plenty of time before the April deadline. Good luck with everything - sounds like you've got some solid options with the tax software people have recommended here.

Just to add a bit more info - there's one other tax benefit you should know about with HSAs when you're contributing out of pocket. When you contribute through payroll deductions, you also avoid FICA taxes (Social Security and Medicare taxes) on those contributions, which is about 7.65%. BUT when you contribute directly to your HSA, you still get the income tax deduction, but you don't get the FICA tax savings. So there is a slight reduction in tax benefits when contributing outside of payroll, though the income tax deduction is usually the bigger benefit anyway. Something to be aware of, but definitely not a reason to stop contributing!

Make sure you keep track of when you're contributing! For 2024, you can actually contribute up until the tax filing deadline in April 2025. But if you start a new job in a few months and get a different health plan that's not HSA-eligible, you'll need to prorate your contribution limit based on the number of months you were eligible. The IRS uses the "last-month rule" where if you're eligible on Dec 1, you can contribute the full annual amount, but you need to remain eligible through the end of the following year (testing period). Otherwise, you'd need to calculate your limit as 1/12 of the annual limit for each month you had eligible coverage.

I switched from a national chain ($800) to a local CPA ($500) for my S-Corp and got much better service. The national chains use a business model based on volume and standardized processes, while local CPAs can be more flexible with pricing for simple returns. Look for a small local firm that specializes in small businesses. Be upfront about your situation - tell them you have everything organized and just need the final tax prep. Many will offer tiered pricing based on complexity.

As a small business owner who's been through this exact situation, I can relate to your frustration with the pricing. What really opened my eyes was when I asked my tax preparer for a detailed breakdown of their process. Turns out they spend about 20 minutes on data entry but another 90 minutes on review, verification, and compliance checks I never considered. The real value isn't just in the data entry - it's in catching potential issues before they become IRS problems. Last year my preparer caught that I was misclassifying some expenses that could have triggered an audit. They also identified a depreciation error from two years back that saved me from having to amend multiple returns. That said, $750-$1200 does seem steep for a straightforward S-Corp. I'd recommend getting quotes from 2-3 local CPAs who specialize in small businesses. Many will give you a phone consultation to understand your situation and provide a more accurate quote. You might find someone who charges $400-600 for the same quality of work, especially if you emphasize how organized your records are. The key is finding someone who values efficiency and is willing to price accordingly when a client makes their job easier.