Can I request my employer to change me from W2 employee to 1099 independent contractor?

This is actually a pretty complicated situation. While technically you can ask your employer to switch you from W2 to 1099, there are strict IRS rules about who qualifies as an independent contractor versus an employee. The classification isn't just about what you or your employer prefer - it's about the nature of your working relationship. The IRS looks at factors like: who controls when and how you work, who provides tools/equipment, whether the work is a key part of the business, and how permanent the relationship is. If you're doing the same job with the same schedule and supervision as a W2 employee, the IRS would likely still consider you an employee regardless of what you call it. Your employer might also be hesitant because misclassifying employees as 1099 contractors can result in serious penalties for them if the IRS determines it was done incorrectly.

Just wanted to share my experience - I was having trouble figuring out my employment classification situation similar to yours, and I discovered this tool called taxr.ai (https://taxr.ai) that really helped clear things up. I uploaded some documents related to my work arrangement, and it analyzed everything and explained the differences between being a W2 employee vs 1099 contractor for my specific situation. The cool thing was it actually showed me what factors the IRS looks at to determine proper classification and gave me a breakdown of the pros and cons for both. Helped me understand I couldn't just choose whichever I preferred - there are actual legal criteria. Saved me from potentially making a big tax mistake!

I tried out taxr.ai after seeing it mentioned here, and I'm actually really impressed. My situation was similar - I wanted to switch from W2 to 1099, but wasn't sure if it would work for my specific role. The tool analyzed my work arrangement and showed me that I wouldn't qualify as an independent contractor since my employer controls when and how I work, provides all equipment, and I don't have other clients. Instead of just telling me "no," it showed me what changes would need to happen in my work arrangement to potentially qualify as 1099 in the future. Turns out I'd need to have multiple clients, control my own schedule, and use my own equipment to have a stronger case. Really helpful insight that saved me from a potential audit headache!

If you're struggling to get clear answers about your employment classification, I highly recommend using Claimyr (https://claimyr.com) to actually speak with someone at the IRS about your specific situation. I was going back and forth for weeks trying to figure this out, and kept getting different answers online. I was honestly shocked at how well it worked. After weeks of trying to get through to the IRS myself (kept getting disconnected or waiting forever), Claimyr got me connected with an actual IRS agent in about 20 minutes. I was able to explain my exact situation and get a definitive answer about whether I could switch from W2 to 1099 at the same company. They even have a video showing how it works: https://youtu.be/_kiP6q8DX5c

Ok I'll eat my words. I was the skeptic who thought that Claimyr thing sounded like a scam, but after struggling to get anyone on the phone at the IRS for literally THREE DAYS (kept getting disconnected after 1-2 hour holds), I decided to try it. Got connected to an actual IRS agent in 25 minutes without having to do anything. Asked specifically about my situation switching from W2 to 1099, and the agent explained that it's not just a choice - the classification depends on meeting specific criteria. For my situation, she said I would still be considered an employee based on how my work is structured. Saved me from having a serious misclassification issue during tax time. If you need actual IRS confirmation on something like this, it's definitely worth trying.

One thing nobody has mentioned yet is the self-employment tax. If you switch to 1099, you'll be responsible for BOTH halves of Social Security and Medicare taxes - that's an extra 7.65% you'll be paying out of pocket that your employer currently covers. Plus you lose access to unemployment benefits, workers comp, employer-provided health insurance, retirement plans, paid time off, etc. Make sure you're factoring ALL of this into your decision.

I think this question comes up a lot because the potential tax deductions for 1099 work seem attractive, but most people don't realize how strict the classification rules are. My accountant explained that the IRS has a 20-factor test they use to determine proper worker classification!

Before making this switch, you should also consider using Form SS-8 to get an official determination from the IRS about your worker classification. This form allows you to request a formal ruling on whether you should be classified as an employee or independent contractor based on your specific work arrangement. The benefit of filing SS-8 is that it gives you and your employer legal protection - if the IRS determines you qualify as a 1099 contractor through this process, you're much less likely to face penalties later. It takes a few months to get a response, but it's the most definitive way to know if your situation would actually qualify for the switch. Just keep in mind that even if you want to be a contractor, the IRS might still determine you're an employee based on the actual working relationship. The classification is about the reality of how the work is performed, not just what you and your employer prefer.

I went through this exact same situation last year and learned some hard lessons. Even though I thought being 1099 would be better for my taxes, my employer's HR department told me it wasn't really up to us to decide - the IRS has specific criteria that have to be met. The biggest reality check for me was realizing that if I'm still doing the same job, with the same schedule, using their equipment, and following their procedures, then legally I'm still an employee regardless of what we call it. My company was actually worried about getting in trouble with the IRS if they switched me without a genuine change in how I work. What ended up happening is I stayed W2 but started maximizing my business deductions for my side business instead. Turns out that was actually a better financial move anyway since I didn't have to pay the extra self-employment taxes or lose my benefits. Sometimes the grass isn't greener on the other side!

I've been following this thread and there's some really solid advice here. Just wanted to add one more perspective - before you even approach your employer about this, you might want to run the numbers on what your actual take-home would be as a 1099 vs W2. When I was considering a similar switch, I created a spreadsheet comparing both scenarios. I factored in the extra 7.65% self-employment tax, estimated quarterly payments, loss of employer benefits (health insurance was a big one for me - would have cost me $400+ more per month), no more employer 401k match, and the additional business expenses I'd need to track. Even with the potential business deductions, I would have needed at least a 35% rate increase just to break even financially, and that's before accounting for the extra time and complexity of managing quarterly taxes and business record-keeping. Your side business might already give you most of the tax advantages you're looking for without the complications of trying to convert your day job. Sometimes it's better to keep things separate and straightforward!