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Questions to Ask Yourself Before Going Full-Time Freelance

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March 5, 2018 | Tags: , , , , , , , ,

When you’re considering quitting your job to start a freelance career, I recommend asking yourself these questions. (First, take my freelance writing online course to learn how to become a successful freelancer before taking the plunge.)

  1. Am I just unhappy with my job?

Before I created this freelance writing e-course on Teachable, friends would often ask me for freelance writing tips and how to freelance on the side or how to leave their jobs to become freelance writers. I’d mentor them and share my advice and time (for free) and then when I’d check in later to see how freelancing was going, they realized what they really wanted to do was change jobs.

Don’t quit your full-time position and announce to the world that you’re going to freelance full-time from home if you haven’t made any money freelancing yet.

It’s a fun, lucrative career but freelancing is not for everyone. Spend time examining whether you really want to freelance, or,  if you just need a new job, a different boss, or a shorter commute. Get tips on how to freelance when you have a full-time job.

  1. How much money do I have in savings?

Remember, it may take a few months for you to get paychecks in. That’s because once you have assignments approved, you’ll submit an invoice after the piece is finalized. Some clients pay within 30 to 45 days. Others take a few months. (Think about that: If you worked every day at your job for a month and didn’t see that pay for months. That’s occasionally what it’s like for freelance writers.) If you have a lot of personal debt, I’d recommend freelance writing on the side while working your full-time job to pay that down first so you don’t have that weighing over your head while working as a full-time freelancer. Read more of my finance tips for freelancers here.

  1. What will I do about health insurance?

In this gig economy, determining what a freelancer will do about health insurance is an important question. I joined Freelancer’s Union and get my health insurance through them. People ask how much freelancers pay for health insurance all the time so I’ll let you know right here. I pay approximately $450 a month for my very, very basic health insurance. That’s just for me and it’s a no-frills plan. If I’m trying to make at least $75/hour as a freelancer, that means six hours of my month are just for basic health insurance. That’s a lot. To me, it’s still worth it to have coverage and to work for myself. But, you need to think about this and factor it in. There are other health insurance options out there and plans vary by state so do your research in this area to estimate how much you’ll need to pay for health insurance each month.

  1. Am I disciplined?

When I tell people that I’m a freelance writer, people often tell me that they could never do this because they would just slack off if they worked at home. Believe me, I’m not super disciplined all the time—and I’m writing this blog while watching ‘The Rachael Ray Show’—but you need to be able to focus intently and put your butt in the chair to find new clients, write articles, and get work done. Some days it’s harder than others to accomplish tasks when you don’t have a boss looking over your shoulder. Find out how many hours freelancers work each week.

  1. Am I organized?

Or even “Can I become organized if I’m not right now?” I have a few Google docs dedicated to tracking my article assignments, due dates, how much I’m making on that assignment, and invoices out. Some people dedicate a certain day of the week to doing admin work and tracking down payments, or following up on article ideas. Being organized is a very helpful skill when you’re freelance writing. (Here are the skills you need in order to make six figures freelancing.) There are also invoice tracking programs for small businesses and entrepreneurs for sending and tracking invoices. You could hire a virtual assistant to help you as well. Once freelancers start juggling multiple clients, having a system in place will help you keep your cool when your workload gets busy.

  1. Will I become a hermit?

Okay, this won’t necessarily happen, but freelancing and working for yourself as an entrepreneur can be quite lonely. It’s important to schedule activities with friends and freelancers, former coworkers, and potential clients that get you out of the house. You might even find that having an online community to chat with and bounce ideas off of is beneficial.

In my freelance writing online course, I show you how to become a successful freelance writer, someone who can make a living writing, or do other freelance work as a side hustle. But, I don’t tell students that they should quit their jobs right after taking my freelance writing e-course. Becoming a successful, full-time freelance writer is possible–but it isn’t the best fit for everyone. That’s why I want you to make money from home by freelancing on the side at first. Build up your business and then….take the plunge to becoming a successful full-time freelance writer! Check out my course or contact me about one-on-one freelance coaching to help you reach your freelance goals.


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