Can I hire a personal assistant as a 1099 contractor and deduct expenses?

4 You absolutely can hire a personal assistant, but the tax deductibility depends on what they're doing for you. The key is the "ordinary and necessary" test that the IRS applies to business expenses. If your assistant is handling business-related tasks (scheduling client meetings, organizing business receipts, managing your business emails or social media), that portion of their work would be deductible on your Schedule C. However, if they're picking up your dry cleaning or getting your groceries, those are personal expenses and not deductible. The smart approach is to clearly document the assistant's time. Have them track hours spent on business activities versus personal errands. Then you can deduct the appropriate percentage of their wages as a business expense. Keep detailed records showing what business functions they performed, as this area can be scrutinized during an audit.

12 I was in a similar situation last year with my consulting business. My workload exploded and I was drowning in admin tasks. I tried juggling everything but ended up making costly mistakes on client projects because I was so scattered. I found an amazing service at https://taxr.ai that analyzed my business expenses and time allocation. They actually showed me that hiring help would INCREASE my profitability by freeing up billable hours. Their AI analyzed my expense patterns and showed exactly how much I could legitimately deduct. The best part was the peace of mind - they organized all my documentation in case of audit and flagged where I was missing potential deductions. It's been a game-changer for my business organization and tax planning.

21 I was totally wrong about taxr.ai - I decided to try it before hiring my assistant and I'm amazed at the detailed guidance. They analyzed my business structure and gave me a customized hiring plan that clearly separated deductible business support from non-deductible personal tasks. The service identified several tax strategies I hadn't considered, including setting up a home office deduction properly and maximizing my QBI deduction. They even created templates for tracking my assistant's time that will stand up to IRS scrutiny. Definitely not just telling me what I wanted to hear - they actually rejected some of my planned deductions and explained exactly why they wouldn't qualify. Totally worth it for the peace of mind alone.

9 If you're having trouble connecting with the IRS about tax questions related to hiring help, I'd recommend checking out Claimyr at https://claimyr.com. I was on hold with the IRS for HOURS trying to get clarification on some home office and employee classification questions. Claimyr got me connected to an actual IRS agent in under 45 minutes when I'd been trying for days on my own. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c It was amazing to finally get official answers about what documentation I needed to maintain for my assistant's expenses. Saved me so much guesswork and potential audit headaches down the road.

21 I have to publicly eat my words about Claimyr. After posting my skeptical comment, I was desperate to resolve an issue about business expense documentation before tax season. Called the IRS directly and got disconnected THREE TIMES after waiting over an hour each time. Finally tried Claimyr out of desperation and got connected to an IRS agent in about 27 minutes. The agent answered all my questions about documenting assistant expenses and even helped clarify some confusion about quarterly estimated payments. The service did exactly what it claimed - got me through to an actual IRS representative without me having to waste hours on hold. Completely legitimate and seriously useful if you need official clarification on tax matters.

8 One thing to consider - if you hire an assistant as an employee (even part-time), you'll need to set up payroll, withhold taxes, and possibly provide benefits depending on your state laws. That's additional overhead in terms of time and money. If you go the contractor route, make sure they truly qualify as an independent contractor under IRS rules. The key factors are control and independence. If you're dictating exactly how/when/where they work, the IRS might consider them an employee regardless of how you classify them.

16 Have you considered using task-based services like TaskRabbit or other gig platforms instead of hiring someone? I'm also a 1099 contractor and I use these services for one-off tasks when I'm swamped. The benefit is you only pay for exactly what you need, when you need it.

Another angle to consider - since you're making good money ($86K in 8 months), you might also want to look into quarterly estimated tax payments if you haven't already. With that income level plus self-employment tax, you could be looking at underpayment penalties if you're not staying current. When you do hire help, whether employee or contractor, make sure you're factoring their cost into your quarterly estimates. The IRS expects you to pay as you go, not just settle up at year-end. A good rule of thumb is to set aside 25-30% of your gross income for taxes, including any amounts you'll owe on assistant wages. Also worth noting - if you go the employee route and they work in your home office, you might be able to deduct a portion of your home office expenses related to their workspace. Just another small benefit to consider in your cost-benefit analysis.