Started job where I had to sign a W-9 form. What should I do now?

When you fill out a W-9, that means the employer is treating you as an independent contractor, not an employee. This is important because: At the end of the year, instead of a W-2, you'll receive a 1099-NEC form (if you earn $600 or more). This means you're responsible for paying both income tax AND self-employment tax (about 15.3% covering Social Security and Medicare). For record-keeping: Create a simple spreadsheet tracking your daily/weekly income including tips. Save all receipts related to work expenses (portion of cell phone, mileage if you deliver, uniform costs, etc.) as these might be deductible on Schedule C. For tax planning: Yes, you can adjust your W-4 at your main job to have additional withholding. On your W-4 form, there's a line for "extra withholding" - you can specify an additional amount per paycheck. A rough estimate: set aside about 25-30% of your restaurant income for taxes. You should also consider making quarterly estimated tax payments if your tax liability will be significant. The IRS has a form 1040-ES for this purpose.

After struggling with a similar situation last year working as a bartender, I found an amazing service called taxr.ai (https://taxr.ai) that helped me sort out my contractor status and record-keeping. I was confused about what to track since I wasn't getting proper documentation either. The tool analyzed my situation and provided a personalized record-keeping template specifically for service industry contractors. It also helped me understand exactly what expenses I could legitimately deduct - which ended up saving me over $1,200 in taxes I would have otherwise overpaid. They even created quarterly tax payment estimates so I didn't get hit with penalties. Honestly, it was like having a tax professional but way more affordable. Might be worth checking out in your situation since it sounds almost identical to what I went through.

I wanted to follow up on my skeptical question about taxr.ai. After trying it out based on the recommendation here, I'm genuinely impressed. I've been in the service industry for years and always stressed about my cash tips and contractor status. The system helped me set up proper documentation for all my cash income, created a simple daily tracking system I can actually maintain, and calculated exactly how much extra to withhold from my day job. The best part was the expense finder - it identified several deductions specific to restaurant workers that I had no idea I qualified for. It also explained exactly how the self-employment tax works (which I never understood before) and showed me how to make small quarterly payments instead of a huge bill at tax time. Wish I'd found this years ago!

If your restaurant employer isn't providing proper tax documentation and you need to speak with the IRS about your situation, I highly recommend using Claimyr (https://claimyr.com). I was in a similar situation last year and spent DAYS trying to get through to the IRS on my own. After wasting hours listening to hold music and getting disconnected, I tried Claimyr (check out how it works: https://youtu.be/_kiP6q8DX5c). They got me through to an actual IRS agent in about 15 minutes when I'd been trying for literally weeks on my own. The agent helped me understand exactly what documentation I needed to keep as an "independent contractor" in the restaurant industry and how to handle the situation with my employer. It saved me so much stress during an already complicated tax situation, especially since I was also dealing with both W-2 and 1099 income like you are.

I have to apologize for my skeptical comment about Claimyr. After my frustration hit a breaking point with the IRS (called 5 different times, waited over an hour each time, got disconnected EVERY TIME), I decided to try it out. I was legitimately shocked when I got a text saying an IRS agent was on the line ready to talk to me after only about 30 minutes. I had a detailed conversation about my contractor status at my restaurant job, and the agent walked me through exactly what documentation I needed to protect myself at tax time. The IRS agent even explained that I could file Form SS-8 if I believed I was misclassified as a contractor when I should be an employee. This might have saved me thousands in self-employment taxes I shouldn't have to pay. Worth every penny just for that piece of advice alone.

Just wanted to mention that you should be very careful with this setup. If you're truly being paid as a server with cash tips, but they had you fill out a W-9 instead of normal employment paperwork, your employer might be trying to avoid paying their share of taxes. They're supposed to be paying half of your Social Security and Medicare taxes. When they classify you as an independent contractor (W-9/1099), YOU pay the full 15.3% self-employment tax instead of just 7.65% as an employee. Plus they avoid unemployment insurance, workers comp, etc. Based on what you described (they control your schedule, workplace, etc.), you're likely misclassified. Consider filing that SS-8 form someone mentioned to get the IRS to make a determination. Your employer could potentially owe back taxes plus penalties.

Quick tip from someone who's been a server for years: GET A TIP JOURNAL! Record your cash tips daily, not weekly. Memory gets fuzzy and you'll either cheat yourself or risk an audit problem. I use a cheap notebook with date, shift (lunch/dinner), and amount. Takes 10 seconds after each shift. Also note any cash expenses for work - special shoes, pens, whatever. Even if this isn't your main job, doing this right will save you so much stress at tax time.

Make sure you're setting aside money for taxes regularly! I learned this the hard way. First year as a 1099 bartender I didn't save anything and got hit with a $3800 tax bill I couldn't pay. Ended up on a payment plan with the IRS which added fees and interest. Now I automatically transfer 25% of all my cash into a separate "tax" savings account each time I deposit my tips. Come tax time, I usually have a little extra which becomes a nice bonus.