start freelancing

What to Consider Before You Quit Your Day Job and Start Freelancing

JessieStarting a Business 3 Comments

It started as a joke. After a rough day juggling blog articles and social media calendars in my marketing agency job, I leaned over to my friend. “I swear, I’m half tempted to just get out and go freelance.” He chuckled knowingly, and the conversation moved on.

I didn’t give it much thought. But the next day, I found myself making the same joke. This time it wasn’t as funny.

It was time to make a change. Turning in my notice was, frankly, one of the hardest interpersonal interactions of my life. I second-guessed myself the whole time and felt horrible for leaving my coworkers to fight through the work on their own. What kept me going was the knowledge that I had considered the decision from every angle, and it felt like the right choice.

And it WAS the right choice. That first run at freelancing gave me a taste of freedom and eventually led to an exciting opportunity to run marketing at another company. Now, having made the decision to freelance twice, I can confidently say I’ve learned a thing or two about what you need to consider before taking the leap.

Here are the most important questions to ask yourself before turning in that resignation letter.

Are you an expert in a topic?

This might put a damper on things if you’re hoping to jump into a new career. The reality is that before you start freelancing, you need to have expertise from DOING. You don’t need to know everything, but you do need to know enough to be able to get results for your clients. And unfortunately, a college degree alone probably isn’t enough.

Now, that isn’t to say that it hasn’t been done before. Freelancing is an unregulated industry, and plenty of people jump in after reading a book or taking a course on how to do the work. But while you might be able to turn out something usable, a few books or an e-course can’t prepare you for the times when the client asks why you chose to do this over that. Becoming an expert takes time, and I strongly believe that you need the deep understanding from experience in order to build a stable business.

The first time I started freelancing, I specialized in content writing. I had an English degree, sure, but I also had been writing blog articles for two years at a marketing agency, so I knew what worked and what didn’t. People around me confirmed my skill in that area. I was confident that I could craft articles that would perform well.

Now, if you don’t have expertise in a topic, don’t give up—go get it. You could go after an entry level job in your desired industry to get some mentorship and see how it’s actually done. If you have been researching the topic for a while, you could offer the service at a deep discount to test out your actual abilities. Once you have proof (for yourself and potential clients) that you can get results, you’re ready to go big time.

Can you make freelancing your side hustle?

If possible, try getting at least a client or two before you quit. Go through the whole process of finding them, pitching them, and setting up with an agreement. This will give you an idea of what it’s like to actually run a freelancing business, and will help you start building a freelance portfolio.

I’ll be honest—moonlighting like this can be a little miserable. You lose a lot of nights and weekends. This is how most freelancers start, though, and it helps you begin establishing an income.

It takes commitment. It takes sacrifice. But you are the only one who can make changes in your career, so it’s time to roll up your sleeves.

How long can you go without an income?

Even if you build up a healthy side hustle while you’re still working full-time, you’ll probably be making a bit less than you’re used to. And of course, if you jump in without any side hustle at all, expect to go without work for a while as you figure everything out.

What do your monthly expenses look like? Do you have a healthy savings account that could cover them for a few months, or a partner you can lean on while you get things going?

Do an analysis of the past 3 months to see where your money goes. Use that to build a monthly budget.

Starting a freelancing business is so much more enjoyable when you aren’t desperate for the next check. You’ll also be in a better position to win the right clients instead of clinging to any measly job that comes your way.

Finally, give yourself as much time as possible to get your feet under you. Cut back on spending as much as you can to build up a buffer. And when that first check finally comes, don’t immediately revert to your old spending habits. Your income will be more sporadic, so it’s important to create a modest budget and stick to it until you have a good idea of what kind of income you can earn.

Are you ready to learn a TON about how to run a business?

In a job, you focus on your specialty all day. Writers write. Designers design. Developers code.

As a freelancer, though, plan on spending much less time on your specialty area—at least, at first. Expect that at least half of your time will be spent on courting clients, working on your website, networking, writing proposals, hunting down invoices, and all the other less-than-exciting stuff.

I found it immensely helpful when I first started out to research how other freelancers are doing all of this (and I’ve since written about my client intake process, which should be helpful). The business side is the hard part. Client management takes good communication and organization skills. You are the expert now, the professional. You have to act like it. Make the time to research good client management techniques.

How thick is your skin?

I’ve always hated this question because it implies that only thick-skinned folks who don’t give an F can succeed. I’d like to take a more nuanced approach.

Here’s a confession: I don’t have a thick skin. I consider myself a pretty empathetic person, which on one hand makes it easy for me to put myself in the target audience’s shoes and churn out some great copy. On the other hand, though, it has made me question my abilities and my people skills at times when I should have stayed focused on my purpose.

But while I don’t have a thick skin, I do have a strong support system. Getting your business off the ground can also a highly emotional experience. It’s stressful to wonder where your next check is coming from, and there’s a lot of potential for fear in making big business decisions. I’ve been very fortunate in that the people closest to me are extremely supportive in my career decisions. When I’m feeling down about losing a project or fearful of the future, they’re there to boost me back up.

This isn’t just freelancing advice. It’s life advice. The bottom line is that you need a way to hold onto confidence, even when things look bleak. This starts on the inside, but if you need to build a stronger support system, get out there and welcome some great people into your life.

Most people think that when you do a good job, you grow in confidence. And while that is partially true, it can work the other way around too: The more confidence you build in yourself, the better you’ll perform.

I’ll tell you something, creating a business is like raising a kid—everyone feels qualified to give you advice on how you should do it. It’s usually well-meant, and even helpful sometimes. But at the end of the day, you’re the one who has to live with your decisions. Have the gut strength to make them for yourself.

To end this somewhat meandering thought on a practical note, I’ve found it extremely helpful to constantly learn through entrepreneur-focused podcasts, and interact with fellow business owners through Facebook groups. These two avenues deepen my knowledge, give me perspective, and connect me with others who are doing the same work I’m doing. They help me have a thick skin when I need it because I’m armed with and understanding of what’s normal in my industry.

So then, finally, speaking of connecting with others…

What to Consider Before You Quit Your Day Job and Start Freelancing | Jessie Lewis


What contacts do you have?

My first freelancing gig came through a referral from a coworker. He knew my work, and he put me in touch with another freelancer who needed some extra help. It was a huge leg up, and I am eternally grateful to have been able to start out my business that way.

Chances are, you know someone too who could lead you to your first client. Make it known in your social circles that you’re freelancing, and be clear about what your services are. If you know someone who knows a lot of other people, consider reaching out personally (but professionally!) and putting a bug in their ear. You never know what might come back.


Freelancers, what have I missed?

I’m just one person. What do YOU think is most important to consider before starting a freelancing business? Leave your thoughts in the comments!

Photo by Cathryn Lavery on Unsplash

Comments 3

    1. Post
  1. I love this! I think another thing I would add is finding a mentor. My mentors have been a bedrock in my business. It’s falls into having a support network, but I think finding a mentor is a more deliberate process.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.