Thank you for this info! I'll definitely check the affordability calculation. My 1095-C shows coverage was offered starting in April, but my 1095-A covers January through December. So it sounds like I might need to repay premium tax credits just for April-December? The numbers on my tax return seem higher than that though.

You've got it right - you would only need to repay premium tax credits for the months when affordable employer coverage was available (potentially April through December in your case). If your tax software or calculation is showing a higher repayment amount, it might be incorrectly assuming you were ineligible for the entire year. Form 8962 (Premium Tax Credit form) allows you to do a month-by-month calculation. Make sure you're completing Part IV of that form correctly to allocate by month rather than using the annual calculation. This is a common area where tax software can get things wrong if the information isn't entered precisely.

Form 8965 isn't used anymore for tax years after 2019. The individual mandate penalty is $0 now at the federal level (though some states still have their own penalties). You're thinking of the old system. The issue here isn't about avoiding a penalty but about whether they have to repay premium tax credits they received.

What kind of background did you need to get hired at a tech company? Did you need technology experience or just strong sales tax knowledge? I'm interested in making a similar move.

Strong sales tax knowledge was definitely the priority, but familiarity with how software and digital goods are taxed across different jurisdictions was key. I had worked with several SaaS clients at my previous firm, which gave me relevant experience. Having some understanding of how technology companies operate is helpful, but they're mainly looking for someone who can navigate the extremely complicated tax treatment of digital products. Each state has different rules for how they tax software, subscription services, implementation fees, etc. If you can become an expert in that niche, tech companies will be very interested. Start by researching the specific tax rules for digital products in major states like California, New York, and Texas to build your knowledge base.

This is really interesting! What kind of technical skills would I need to develop to go down this path? I have basic SQL knowledge but haven't done much beyond that. Is there a particular certification or training program you'd recommend?

You don't need to be a programmer, but understanding how ERP systems work is essential. Focus on learning the basics of major platforms like SAP, Oracle, or NetSuite. SQL is definitely useful for data manipulation and reporting. Avalara and Vertex both offer certification programs for their solutions, which are a good place to start. Try to get involved in any tax technology projects at your current company, even if it's just helping with requirements gathering or testing. The key is to demonstrate that you understand both the tax implications and how they translate to system requirements. Most of the specific technical skills can be learned on the job, but showing interest and basic aptitude will get your foot in the door.

Do you track miles driving to your first pickup? I heard different things about whether that's deductible or not.

Yes, I do track miles to my first pickup, but there's some nuance here. If you're driving from home directly to your first delivery pickup, the IRS technically considers that a non-deductible commute. However, if you first drive to a "regular place of business" (like a specific area where you regularly start deliveries) and then to your first pickup, those miles can be deductible. The key is consistency and documentation. I have a designated "staging area" where I officially start work, which allows me to deduct more miles. Many tax professionals have different interpretations of this rule for gig workers, so it's something to discuss with a tax pro familiar with independent contractor rules.

I used it last year and it was OK but not great. It asks good questions about deductions but I still felt like I might be missing things. This year I'm trying FreeTaxUSA which is cheaper and handles self-employment pretty well from what I've heard.

Oh wow I had no idea about this! I definitely had over $10k in my Korean bank accounts... is there a deadline for this form too? Is it the same as the regular tax deadline?

The FBAR deadline is technically April 15th (same as tax day), but there's an automatic extension to October 15th - you don't need to request it. File it as soon as you can though! It's filed electronically through the FinCEN BSA e-filing system, not with your tax return to the IRS. I'd also check if you need to file Form 8938 (Statement of Foreign Financial Assets) with your tax return if your foreign accounts exceeded certain thresholds. The requirements are different than FBAR and it goes with your tax return, not separately.

I think the 2024 FEIE amount is actually $126,500, but your point still stands! Also, make sure you file Form 2555 to claim it.

What about bank statements? Should I bring those too? I have most of my Amazon expense receipts saved but I'm not sure what else they might want to see related to my finances.

Yes, definitely bring your bank statements, especially ones showing your business expenses. The Revenue Officer will want to understand your complete financial picture. Bank statements help verify both your income sources and your expenses. Having those statements also helps with credibility - it shows you're being transparent and cooperative. Focus on the last 3 months at minimum, but if you have statements going back through the unfiled tax periods, those would be valuable to bring as well.

Valid point! I got a scam IRS letter once that looked super official. Real Revenue Officers will also have a badge and ID they can show you. And they never demand immediate payment during the first meeting.