This is such an encouraging thread to read! As someone who's been considering a career change, hearing about the different tools and approaches available now makes tax preparation seem more accessible than I initially thought. @Sophia Rodriguez - your background sounds really solid for this field. One thing I'd add is that you might want to consider getting some hands-on experience with different tax software platforms during your preparation phase. Each one has its quirks and learning curve. The suggestions about AI tools like taxr.ai and services like Claimyr are fascinating - it sounds like technology is really changing how tax professionals can serve their clients more effectively. When I was looking for a tax preparer last year, I would have been impressed if someone could resolve IRS issues quickly instead of the usual "we'll send a letter and wait 6-8 weeks" approach. Your idea about specializing in immigrant families is brilliant. There's definitely a need for preparers who understand the specific concerns and complexities that come with different visa statuses and documentation requirements. That personal understanding you have could be incredibly valuable to that community.

This is such a comprehensive discussion! As someone who's been through the process of starting a tax preparation side hustle, I wanted to add a few practical considerations that might help. First, Sophia, your background is excellent for this field. The combination of bookkeeping knowledge and family tax experience gives you a solid foundation. I'd recommend starting with the IRS Volunteer Income Tax Assistance (VITA) program - it's free training and gives you hands-on experience with real returns under supervision. Regarding software, I started with TaxSlayer Pro for smaller practices - it's affordable and user-friendly for beginners. Drake Tax is another good option as you grow. Don't feel pressured to jump into the most expensive platforms right away. One thing I wish someone had told me: liability insurance is non-negotiable, but also consider getting an Employer Identification Number (EIN) and setting up a separate business bank account from day one. It makes tax season organization so much easier and looks professional to clients. The seasonal intensity everyone mentioned is real, but there are ways to smooth it out. I do tax planning consultations and amendment work during the off-season, which helps maintain client relationships year-round. Your bookkeeping background could also complement this nicely. Good luck with whatever you decide!

I'm confused about something - if the government knows ur making illegal money isn't that just admitting to a crime?? like if i put $50,000 in "other income" and I don't have a job, isn't that basically telling them im doing something illegal?

This is such an important topic that I think gets overlooked. I've been dealing with a similar situation where I had some cash income from freelance work that wasn't reported by the clients (they paid under the table). I was terrified about how to handle it properly. What I learned from talking to a tax professional is that the key is being proactive about reporting ALL income, even if the source might raise questions. Like others mentioned, you can use broad categories without getting into specifics that might be self-incriminating. The bigger risk is trying to hide income entirely - that's where people get into serious trouble with tax evasion charges. The IRS has gotten very good at detecting unreported income through data matching and lifestyle audits. It's much better to report everything and deal with any questions that come up than to try to fly under the radar. One thing I'd add is that if you're in this situation, it's really worth consulting with both a tax attorney and a CPA who understand these issues. The consultation fee is nothing compared to the potential consequences of handling it wrong.

Don't forget that the self-employed health insurance deduction is an adjustment to income (above-the-line) rather than an itemized deduction or business expense. You don't actually claim it on Schedule C! It goes on Schedule 1, Line 17.

Great discussion here! I went through this exact transition two years ago and can confirm that ACA marketplace plans definitely qualify for the self-employed health insurance deduction. The key thing that helped me was understanding that COBRA isn't considered "employer-subsidized" since you're paying 102% of the premium cost. One practical tip: if you're starting self-employment mid-year like I did, make sure to keep detailed records of when your self-employment actually began versus when you left your corporate job. There might be a gap between leaving your job and officially starting your consulting business, and you can only deduct premiums for the months you were actually self-employed. Also worth noting - if you're expecting variable income in your first year of freelancing, consider whether you might qualify for Premium Tax Credits on the marketplace. Even if you don't think you'll qualify based on your corporate salary, your actual self-employment income might be lower than expected, especially in year one when you're building your client base. The math usually works out better with an ACA plan + the self-employed deduction versus COBRA, but definitely run the numbers for your specific situation!

Has anyone tried entering these as "Other Itemized Deductions" in TurboTax? I think I did this last year with some professional courses but now I'm worried I might have done it wrong...

I'm dealing with a similar situation but wanted to add another perspective that might help. My wife is a CPA and she always reminds clients that the documentation is just as important as the deduction itself. Even if you find a way to deduct these Udemy courses (through a side business or employer reimbursement), make sure you keep detailed records of: - Course receipts and payment confirmations - Course syllabi or descriptions showing job relevance - Any certificates of completion - Documentation of how the skills apply to current work duties The IRS is particularly scrutinous of education expenses because they're often claimed incorrectly. If you do end up with a legitimate deduction path, having bulletproof documentation will save you headaches if you're ever questioned about it. Also, for future courses, consider platforms that partner with accredited institutions. Some online course providers now offer college credit options that would qualify for education credits, even if they cost a bit more upfront.

11 When I first started my business, I made the mistake of just applying 15.3% directly to all my earnings and ended up overpaying by quite a bit! The 0.9235 factor is actually a benefit for us self-employed folks. Quick tip: Don't forget that after calculating your SE tax, you also get to deduct HALF of that amount from your income for calculating your income tax. That's another benefit most people miss! It's on Schedule 1 of your 1040.

The confusion around the 0.9235 multiplier is totally understandable! I had the same question when I first started freelancing. Think of it this way: when you're a regular employee, your employer pays half of your Social Security and Medicare taxes (7.65%) and you pay the other half (7.65%). As self-employed, you're both the employee AND the employer, so you owe the full 15.3%. But here's the key part - employees effectively get a "discount" because their employer's portion (7.65%) is tax-deductible to the business. The 0.9235 factor essentially gives you that same advantage by reducing the income subject to SE tax, which mathematically works out to be equivalent to making half of your SE tax deductible. So instead of paying 15.3% on your full income (which would be unfair compared to employees), you pay 15.3% on 92.35% of your income, resulting in an effective rate of about 14.13%. It's actually designed to keep things fair between employees and self-employed individuals!