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The 6 Steps I Took to Quit My Job and Start Freelancing

Jessie Authentic Business Leave a Comment

A few months ago, I wrote about what I’d hypothetically do if I were to start freelancing again.

Well, far from the hypothetical, I’ve quit my job and I am, indeed, starting up my own business again.

Making that kind of decision is never easy, so today I want to share the process I went through to gain the confidence to head this direction, and ensure this decision is a success. To all you tired folks on your morning commute who dream of being self-employed, this one’s for you.

Step 1: Try on every pair of slippers until you find the ones that fit just right

The first time I started freelancing, I jumped in with only a vague idea of what I wanted to do. I figured I’d figure it out as I went, build my parachute on the way down, so to speak. But without a clear direction, I quickly found myself doing the exact work I was doing as an employee—except now I had zero social life and was making less money.

Naturally, I quit and went back to full-time employment.

This time around, I knew that I had to get really, really clear on what my job would look like if I was going to make this career change work.

So, I made a list of everything I was interested in and had been interested in from childhood. Full transparency here, options like zookeeper and tour guide were definitely on the table.

I then began systematically trying out new experiences while I was still in a job and had the financial means to do so. I dove into sewing and design, wondering if I had a future in starting a clothing line. I tried out yoga and took a pole dancing class to see if I just needed more exercise and self expression (conclusion: I am way too weak for pole dancing. Those girls are STRONG).

The bottom line? Do stuff. Don’t sit around dreaming! You have to try things out if you want to get real answers.


Best decision ever: I bought a Moleskine (ugh, you guys, I get the hype now) and used it as my dumping ground for all thoughts related to my someday business. I used it for dreaming about what my life would look like, what kinds of products I’d create, and how I felt about all of these new experiences I was trying on for size. It has been the hands-down best way to keep my thoughts organized and get to a place where I could look back on everything and understand the big picture before making The Big Decision to start freelancing.

I’ll be honest with you. This time of experimentation was really tough. Not only time-wise trying to fit in activities after work, but also emotionally. It’s disheartening when you try so many different options, only to find that every direction you try is the wrong one. But keep going. The next step will become clear the further you go.

Finding my direction

I finally realized that instead of learning an entirely new skillset (sewing, zookeeping, pole dancing, etc.), it would make much more sense to build off of my current skill set (writing and marketing).

This is likely true for you as well. What are you good at? What kinds of experiences have you had that can help guide this next step?

Maybe you’re in clothing retail and getting burnt out. Who could benefit from your knowledge? Could you give fashion advice as a personal stylist? Or maybe you learned a ton about managing retail teams, which you could share with smaller businesses as a consultant?

That’s not to say you can’t switch gears entirely to, say, design or writing. Go for it! Just take some time to build up that skill set before you hand in your resignation. Create a portfolio of your work that you can show to potential clients. Make yourself into a specialist. Decide exactly what you want to do, and get the credibility to do it.

Step 3: Decide who you want to work with

There are thousands of businesses who could use your services. But that doesn’t mean you should go after all of them.

There’s this great saying in the business community: If you try to appeal to everyone, you end up appealing to no one (more on that here). In other words, you have to get really clear on what kind of people you want to work with so you can create services and messaging just for them. If you think “My customers are any businesses that needs help with their marketing,” those business owners will be left wondering: “Wait, is this actually for me?”

You have to get clear on your target audience so you can call them out and let them know you have the perfect solution for them.

I settled on freelancers and entrepreneurs as my target audience. Both groups are trying to start a business from scratch, and I am such a huge supporter of those who are trying to make a big difference in their career and move beyond the 9-to-5. You guys are my tribe, and when you take the leap, I want to help you reach the other side successfully!

Step 4: Before you start freelancing, test out your business idea

At this point, I had a business idea that I felt really good about: Helping freelancers and entrepreneurs craft their brands and write their websites. Progress! But before going for it, I needed to see if I would actually enjoy the work, and more importantly—if I was any good at it.

Here’s what I did:

First, I found a Facebook group with freelancers in my area. After a few days of contributing to the group and making my name known, I shared a link to a page on my website where I explained the situation. I shared how I wanted to try out consulting, so I was opening up three coaching spots for individuals who would get to work with me for six weeks. At the bottom was a link to a questionnaire application. Then, I sat back and waited for responses.

I’m going to pause right here and say: Normally, I would definitely recommend charging for your time. Your time is valuable and you need to treat it as such. In this scenario, though, I needed specifically to see if this was something I loved doing enough that I’d do it for free.

Out of six or so people who applied, I chose three who seemed most eager and were in a place in their business I knew I could help. It was a big commitment, and but this process gave me the confidence to finally turn in my resignation.

Step 5: Define and price your services

The big step: Setting prices.

A lot of freelancers aren’t sure how on earth to charge for their work. So, they put it off, and then go with whatever feels right for a given project.


Instead, set very clear pricing ahead of time (check out my article on setting your freelance prices). List out each service you offer and how much you’ll charge for it, and what will cause variance in pricing. For example, it’s totally okay to charge more because you know the project will take a lot of specialized research, or less if it requires skills you haven’t honed yet. Just have a formalized system so that when you are speaking with a client, you can state your number clearly and confidently.

For my business, I created a dynamic Excel sheet that detailed the project, expected time commitment, and price. I even included information on how many of each project I expected to win each month, and if their total would add up to my income goal.

You can use this Excel file for yourself. Grab my template here!

Step 6: Create your website

I don’t care if you’re a deep sea fisherman or a corner store owner—if you have a business, you need a website.

WordPress (hosted WordPress, not and Squarespace are the easiest options for creating a beautiful, functional website. However, they do have a learning curve if you’re not familiar with them. Set aside a good amount of time to get your site up and running. (Not sure which one to use? Read my review on WordPress vs. Squarespace.)

My website is built on the WordPress platform, and I host with GoDaddy. I’ve also invested in a WordPress theme called X Theme, which gives me a lot of control over the design with only basic coding knowledge.

The 6 Steps I Took to Quit My Job and Start Freelancing | Jessie Lewis


Take the next step

These are the steps I took. Yours may be different. Don’t be afraid to follow what feels right to you. The truth is you’ve got this lovely little internal voice that always knows what the right next step is, and the more you listen to it, the stronger it gets. Keep your eyes focused on what your heart knows it wants, and continue fleshing out those whispers of an idea. That kind of definition brings confidence, and with confidence comes action.


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