Women Who Work: CEO and Designer Jess Freeman

You’ve seen her all over from Glamour and the Rising Tide Society to Belong Magazine and the Savvy Community. Jess Freeman of

Jess Creatives

is a graphic and web designer running her own brand. How does she do it? Let’s find out!

How did you make the leap to your current role?

I began doing freelance design during college, and that continued to grow after I graduated and began working in the corporate world. I did a lot of personal design projects, began blogging and started using social media to network and market my business. Eventually, I built up enough of a client base to quit my day job and go full-time!

When you were a kid, what did you want to be when you grew up?

For the longest time, I wanted to be a teacher, because that’s what my mom did. There were a few years that I thought about being a nurse – but then, realized I hated math and science! I decided in high school that I wanted to pursue design.

What was your first job ever? Did it help you in your current role?

My first job ever was baking monster-sized cookies for our city pool (who would re-sell them to kids). This truly was an entrepreneurial job that taught me a lot about time management and handling clients. I remember that one summer, the pool manager didn’t want to me as much for my cookies – and rather than taking less money, I said no and lost that job. While it wasn’t great to lose my job, I learned about charging what you’re worth! (And, thankfully found another job in town.)

What made you want to start your business?

What or who inspired you to do so? I kind of fell into freelancing during college, but the more and more that I worked with my own clients, the more I realized I didn’t like designing at my day jobs. I wanted the freedom of my own schedule, and the freedom to choose my projects. I don’t have any entrepreneurs in my family, so there wasn’t any one particular person that inspired me to pursue this, but there were a few online entrepreneurs that I began following online, that were so inspiring!

What does your job entail? How do you explain what you do to others?

I’m a graphic and web designer, and I help service-based entrepreneurs create a brand that shines. I design a variety of projects, but most often, I’m working on logos and websites for other business owners! 

How long have you been doing this?

I’ve been running Jess Creatives for six years, but full-time for three!

What is a day for you like? What is your routine?

The only consistent routine in my life is getting up at 4:30 every day. After my husband and I workout, we come home to eat breakfast and watch the news. (Don’t we sound old?!) I start work a few hours later, but then the daily stuff always varies on client projects, videos that need to be recorded, etc.  

How do you end your work day?

I usually write down a few notes in my planner about things to work on first thing, any calls or emails that need to happen – just some reminders so that my brain can halfway turn off for a few hours. Once my husband comes home from work, we’ll eat dinner and then just hang out for the rest of the evening.

How did you go about starting your business? What were some of your initial steps that you took?

After college is when I really began to actively try to grow my business. One of the best things I ever did was start blogging! Many of those first blogs weren’t great, but we all have to start somewhere. Getting in the habit of consistently producing content was great for educating potential clients, and increasing my brand visibility.

What are your biggest responsibilities as an entrepreneur/freelancer?

My biggest responsibility is with each of my clients – I hold their brands in my hand. There is enormous power in elevating the look of your brand and your online presence, that could change the direction of their business.

What has been the hardest part of your transition?

Right after I quit my day job, I made a big announcement, posted everywhere, and emailed all of my past clients. Many of those past clients responded with projects – and soon I was trying to juggle 13 clients at one time. I didn’t have a system set-up for a waiting list at the time, which made that first month really overwhelming!

What has been the easiest part of your transition?

Since I already had clients on board, I didn’t have to chase clients. One of my biggest recommendations to new freelancers is to try and have some repeat clients on board before transitioning to running your business full-time. Even if those clients can’t sustain your entire business, having at least a few will make your life less chaotic.

What keeps you motivated?

As cliche as it sounds, I truly love what I do, and love helping others. I’m always trying to get better at what I do, and with the variety of projects and clients that I have, I feel like that’s always happening!

How do you define success now?

For me, success is having clients who finally resonate with their brand after working with me. Whenever you are proud of your brand and online presence, I believe you market yourself better and put out your best work!

 How do you prevent burn out?

I work really hard to set firm boundaries. I focus during the day, to get all of my work done by the time my husband comes home. In the evenings, I rarely work – and take off the weekends to just rest, have fun, and spend time with my husband and friends. I also don’t take on too many projects at once, even if it means making a little less money.

What do you think is the most important characteristic to have for someone who wants to take a similar career route to yours?

I think entrepreneurs have to be able to take action and follow through. There are many people out there who have great ideas or great intentions – but that gets you nowhere. I believe the best entrepreneurs and business owners are those who implement new ideas, even if it means possibly failing.

What do you wish you knew before starting out on your own path?

I wish I had known more about finding your ideal clients, how to “target” them more, and help them the best. I didn’t know much about niching down, and was too afraid – but now I know it can actually help you be more successful and visible! 

Did anyone help you in developing your own business or side business?

My husband provided a lot of moral support and insight. He’s not a businessman, but I don’t know that I would be where I am today without his support. There have been times that I’ve wanted to quit, that I’ve doubted myself, or that I’ve struggled – and he’s been there to help push me through.  

Do you have a work idol? Is there a working woman or man out there that you admire?

One of my mentors is Heather Crabtree – I admire her so much for how she has grown her business and community. I also am a huge fan of Gary Vaynerchuk, because of his no-nonsense attitude towards business and entrepreneurship.

What is your favorite thing about the industry you work in?

I love that design is always changing, as it keeps my life interesting! There are design trends, and new design tools and practices. What I’m designing today will probably be different a year or two from now.

What are some tools that you can live without?

First, Adobe Creative Cloud – because it’s literally how I do all of my designing. It is a paid tool, and pretty expensive if you are not a designer, but I love it. Then, Wave would be my next favorite tool. Wave is what I use for my invoicing and it’s so simple, especially for recurring invoices. Last, I’d have to say TubeBuddy, which is a browser extension. With TubeBuddy, you can do all sorts of research for your YouTube videos, as well as get lots of analytics!

What do you have on your desk or working space right now?

Just the usual – my planner, an array of post-it notes, Sharpie pens, and a can of Diet Dr. Pepper. I have a pretty large desk, so I have some other things, but they’re further ‘back’ on my desk, so these are just what’s riiiiight under my hands.

What do you want other women in similar situations to know about your chosen career path?

It’s not going to be easy, especially when it comes to dealing with your insecurities. People say that when you get married, your insecurities and flaws become more obvious, and I think the same can be said for small business owners. But, the more you face this head on and deal with it, instead of trying to avoid, the more you will grow as a person.

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Wendy Vazquez