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Tax tips 2024: Remote executive assistants


Kirk Pepi


May 6, 2024



read time

4 mins

an illustration of dollar bills pouring out of a laptop screen toward the viewer. the computer is white against a light blue background.

Virtual and freelance executive assistants have lots to think about during tax season. Feel no fear; we're here to break things down for you.

Table of Contents

  • 1. 1099 101

  • 2. Reduce your tax bill

  • 3. General tax hacks for remote executive assistants

  • 4. Make tax season less stressful

  • 1. 1099 101
  • 2. Reduce your tax bill
  • 3. General tax hacks for remote executive assistants
  • 4. Make tax season less stressful

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Working remotely as an executive assistant is a liberating experience, right? No more morning commutes or disappointing lunches in the office cafeteria. You can even spend all day in your pajamas – unless you have a Zoom call, of course!

Being a virtual assistant is less stressful than going to the office – until it's time to file your taxes. Many self-employed professionals struggle to calculate what they owe Uncle Sam, don't know what 1099 form they'll receive or what deductions and credits to claim. 

Let's clear up the confusion once and for all. 

1099 101

Some virtual assistants, like Waylon Smithers, work for just one executive – imagine dealing with multiple Mr. Burnses! If they were contractors or freelancers, filing taxes would be a piece of cake. They'd make quarterly payments based on their projected income and then, at the end of the tax year, report information on a 1099-NEC from their company on their tax return – or more specifically, Schedule C (Form 1040). 

Other executive assistants – and perhaps you're one of them – work for two, three or even more organizations simultaneously. In these situations, you'll receive 1099-NECs from different companies every January if you earned more than $600 in the previous year. You'll need to make sure the numbers on those forms are correct before calculating your annual earnings. 

To confuse matters further, you might not even get a 1099-NEC if paid for your services through PayPal, Stripe or a similar platform. Instead, you'll receive a 1099-K – but only if you receive over $20,000 in funds from 200 or more transactions. Made less than that amount? You'll have to work out your annual earnings yourself. 

View and download different 1099 templates on our website so you know what to expect when you receive one.

Reduce your tax bill

Credits and deductions lower your tax liability, but which ones can you claim as a remote executive assistant? It all depends on your situation and outgoings in the previous tax year. 

Deductions you might be able to claim include:

  • the home office deduction if you use a specific part of your home for your job 
  • work-related travel costs
  • purchases of office supplies, like a computer, printer and stationery 
  • internet and phone costs in your business
  • any health insurance premiums you pay

Unlike traditional employees, you'll need to pay self-employment tax on your earnings, which covers Social Security and Medicare. However, you can deduct half of the amount you owe on your return, which could reduce your bill considerably. 

Common credits you might be entitled to:

  • saver's credit – which might lower your tax liability if you contributed to a retirement plan in the previous tax year.

Lifetime Learning Credit and American Opportunity Credit – which can also lower your bill if you paid for certain types of education in the last tax year.

General tax hacks for remote executive assistants

We said it before, and we'll say it again: filing taxes as a remote worker can be seriously complicated! So, work with an expert if your situation is particularly complex. Tax filing might be super simple if you're a sole proprietor, but you might need a helping hand or two if you have a different business structure, such as an LLC or S-corp. 

Also, be wary of quarterly estimated taxes. The IRS expects you to make payments for any tax not subject to federal withholding in January, April, June and September based on how much you think you'll owe the government at the end of the year. Get this wrong, and the IRS could slap you with a nasty underpayment penalty after you file your return. Ouch. 

Finally, always keep records of your earnings and transactions throughout the tax year, just in case the IRS wants to see them. Audits are rare, but they can happen! 

Make tax season less stressful

Tax doesn't have to be taxing, but it almost always is. To reduce stress, familiarize yourself with the different 1099 forms, know what deductions and credits you can claim and understand how quarterly estimated payments work. You'll thank yourself when it's time to fill in your return. 

Oh, and if you need to sign documents from business partners, accountants and other people during tax season, a good eSignature tool can help!

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