June 25, 2023
When you’re considering quitting your job to start a freelance career, I recommend asking yourself these questions.
There are so many things to think about before you start freelancing full time and it’s important to ask yourself these money questions and freelance career questions before you put in your two weeks’ notice on a full-time job. You’ll want to think about how you’ll pay for insurance, what you’ll do to pay bills when freelance work is slow, as well as how you’ll cover freelance business expenses and how you’ll find freelance writing jobs.
(First, take my freelance writing online course to learn how to become a successful freelancer before taking the plunge.)
Here, important questions to ask before going freelance and giving this career path a shot.
Before I created a 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. (This freelancer FAQ will answer all of your questions.)
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.)
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 as a side hustle first 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.)
In this gig economy, determining what a freelancer will do about health insurance is an important question. When I was single and living on my own in NYC, I joined Freelancer’s Union and got 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 paid approximately $450 a month for my very, very basic health insurance.
That’s just for me and it’s a no-frills plan. When I was trying to make at least $75/hour as a freelancer, that meant at least six hours of my month were just for basic health insurance—even if I didn’t use it.
That’s a lot of money and time. That’s why one of the most important questions to ask before going freelance is about what you’ll do for health insurance—if you live in the U.S.
You need to think about this and factor it into your budget. 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. (Wait, how much money do magazine writers make?)
When I tell people that I’m a freelance writer, they 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—ask the dog who watches me visit the kitchen often—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.)
Or even “Can I become organized if I’m not right now?”
Organization is a skill you need to think critically about when you ask yourself important questions before going full-time freelance. 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. I’ve found that these apps for writers help boost my productivity and keep my freelance writing business organized.
(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 them keep their cool when their workload gets busy.
You might not become a hermit 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. Read this tweet on how going to an in-person event turned into a $2,000 freelance assignment.
You might even find that having an online community to chat with and bounce ideas off of is beneficial. (These freelance writing tips will help you hit your income goals.)
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 ask yourself these important questions before going freelance so you learn how to make money from home by freelancing on the side and getting experience.
Build up your business and then….take the plunge to become a successful full-time freelance writer!
If you’re still weighing your options about whether you should take your freelance side hustle to full-time status, get in touch about one-on-one freelance coaching to help you reach your freelance goals.
Tags: freelance, freelance course, freelance writer, freelance writing, freelance writing online course, freelance writing tips, freelancer, productivity, six figure income, time management, work at home, work from home, writing tips
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