Is Becoming a 1099 Independent Contractor Right For You?

November 8, 2023 | Virtual Agents | Blog


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Is 1099 independent contract agent right for me

We encounter many of the same questions when first getting to know someone new. 

“What’s your astrological sign?” 

“Are you more of a cat person or a dog person?” 

“What’s your go-to pizza topping?” 

 “Would you rather work as a W2 employee or as a 1099 independent contractor?” 

Okay, maybe that last question is a bit less common than the others. At least, with that specific phrasing.   

But this is still a question that most of us should periodically ask ourselves, regardless of our current career trajectory. Life has a habit of taking us in new and unexpected directions. Consequentially, our values and priorities can change depending on our new circumstances. 

Whether it be due to the arrival of a new child, an unexpected move to a different part of the country, or simply a desire to pivot and try something new, most of us will, at some point, reconsider what we want out of our careers.   

But what exactly is the difference between a W2 employee and an independent contractor? And how can you determine which role is currently best for you? 

Sometimes, the best way to answer a question is to ask even more questions. 

For example: 

  1. Which role sounds more appealing to you currently?

         a. Business owner 

         b. Employee 


  1. Which is more important to you personally?

         a. The ability to work from anywhere 

         b. An in-person office culture  


  1. How do you envision your current dream career?

         a. Multiple clients and revenue streams 

         b. Commitment to a single organization 


  1. Which do you personally find more productive?

         a. The ability to set my own schedule and create my own hours 

         b. A set, daily schedule (i.e. working 9-5)  


  1. Which model works better for your current lifestyle?

         a. The freedom to take time off time when needed 

         b. Scheduling vacation days and paid time off well in advance 


  1. Financially, which would currently be more beneficial to you?

         a. More income tax deductions 

         b. Employer healthcare and savings plans  


7. How do you feel about doing your own taxes generally?

a. Budgeting my own taxes is no big deal for me

     b. I prefer to have my taxes withdrawn from my paycheck


8. How do you feel about to-do lists?

     a. I am most productive making my own list

     b. I am most productive when my to-do list is written for me


9. What about benefit packages?

     a. I do not need benefits through my place of work

     b. I need benefit options through my place of work


  1. 10. Which do you currently value more?

         a. A healthy work-life balance 

         b. Working within a team 


If you answered “a” to most of these questions, congratulations! You might benefit from a career shift to an independent contractor. (Unless you’re already an independent contractor, in which case, nice choice going for exactly what you want!) 

In essence, 1099 independent contractors typically possess the freedom and mobility to develop their businesses, pursue multiple clients, work remotely, and set their own schedules. The most common 1099 independent contractors tend to be freelancers and consultants, as well as medical professionals, lawyers, and home service workers who own their firms. 

Successful independent contractors are self-starters and excellent time managers. They typically have the flexibility to decide when to work, whether that be a 9-5 schedule or just a few hours a day.  

If you answered “b” to most of these questions, then congratulations to you, too! Prioritizing the safety and security of W2 employment is a completely valid career choice.  W2 employees generally lack the ability to build their schedules around work, but they do typically receive more benefits and options for savings plans than their 1099 counterparts. 

W2 employees can also often expect the company they work for to provide them with the necessary equipment required for their job, while independent contractors are expected to provide their own. Unlike W2 employees, independent contractors are also expected to complete and pay their income taxes without support from an employer.  

But not every independent contractor is expected to figure it all out on their own. At Liveops, we strive to set independent contractors up for success. The freedom to build your schedule and provide services remotely, along with connection to a network of like-minded independent agents, and unparalleled access to world-renowned clients. 

Looking to jumpstart a new chapter of your career? Whether it be a side hustle or a main gig, click here to learn why self-employed independent contractors across the country choose to be a Liveops Independent Contractor agent. 


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Jordan Lurie

Jordan Lurie is a content writer focused on the business world, legislation, and the economy. He aims to help provide growing businesses with the insights and tools needed to succeed in a competitive marketplace.

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