Jessica shares how she knew it was time to leave her day job to focus on her business. If you’re considering a similar move, there’s a lot you can learn from her story.

Jessica, tell us a little bit about yourself and your background.

I currently live in Dallas, Texas. I am a lettering artist, illustrator, and graphic designer. Lettering and illustration used to be my hobbies, but now they’re my career.

I received my degree in architecture from Texas A&M University, but getting a degree in architecture is really tough. After I graduated, I wasn't 100% sure it was something I wanted to pursue—it's not something that's as easy as getting your degree, and I couldn’t see myself doing it for the rest of my life.

Part of the curriculum for an architecture degree is taking a course in graphic design, and it was one area of architecture where I felt like I was actually really good at what I was doing. Although people might not think so initially, there’s some overlap between architecture and graphic design. You learn a lot of the same design principles; you just apply them differently. In architecture, you're applying them to three-dimensional space and the way that people experience it. With graphic design, you're applying these same principles to visual communication of an idea or concept.

After I graduated, I started doing graphic design projects on the side and would compete in design contests online. I basically taught myself and used the Internet to learn more about graphic design on my own timeline. Eventually I got my first job as a graphic designer in 2011, and I worked in the industry for 10 years before starting my business full-time.

When did you make the transition to being a self-employed artist? How did you know you were ready to make that jump?

Although I had dabbled in it before, I picked up lettering again in 2016 just for fun. After a couple of years and a lot of practice, I was like, “You know what? I think I'm actually really good at this.” Around this time, I started meeting people through Instagram that did lettering for a living, and I thought, “If they could get paid to do this, I could get paid to do this, too.”

So in 2019, I started my illustration business on the side as a creative outlet from my 9-5 job. I just felt like what I was doing at my daytime job wasn't cutting it for me creatively, and I started to feel burned-out.

Then the company I was working for went through a merger in the middle of 2020, and things started changing. It became difficult for me to run my side business when so much of my energy was being taken by a job that I didn’t find fulfilling. I knew that was the time to leave; it felt right in the moment. I felt that if I could just dive into my business and give it 100%, I could do it. I knew I could make enough money to stand on my own. At that point, I had already set up my business structure, I had clients coming in, and the timing was right.

What are your favorite and least favorite parts about working for yourself?

I think the most challenging thing is when there are quiet times in your business and things aren’t coming in as quickly as they usually do. Even if you know it’s coming, it’s not fun. It can be pretty demoralizing. I usually find myself asking “Are people not seeing my work? Am I not spending time in the right spaces?” Knowing that there’s going to be a time where you’re low on work and having to simultaneously deal with all the doubts, thoughts, and emotions that come along with that can be the hardest part.

My favorite part is being able to take on work that I’m really passionate about and saying no to projects that don’t serve me or feel right. I've always wanted to do book covers, and I had the opportunity to do my first book cover this year, which came out of nowhere. I always dreamed of having my design on a book cover, and it's happening. That wouldn't happen if I had stayed at my job and maybe dabbled in this or did it as a hobby; I wouldn't have had the time to put my work out there for the right people to see it.

Where do you see yourself and your business 5 years from now?

I’m not a huge fan of these questions, and I’ll tell you why. In general, I like to have a loose plan—a plan with room. I try not to project that far out because I want to be open to possibilities. I want a compass of where I’m headed, but not a map.

That being said, I definitely have some dream projects I would love to accomplish someday—teach a course, write a book, create a home collection, and work with certain brands I love. As important as it is to plan ahead in your business, I think it’s just as important to take time to dream big so you can keep those things in mind as you move forward. You never know when you’ll meet the exact right person who can make one of your seemingly distant dreams into a reality!

For now, I'm loving my business. I only see good things coming for me in the future. I think that there's a specific type of challenge that I thrive on being an entrepreneur. You take on so many roles when you run your own business—it’s never boring for me. I work so much more now than I did in my full-time job, but the work is so much more rewarding.

What advice do you have for others that are looking to start their own creative business?

Even though it’s difficult, try taking it on as a side hustle before jumping into it full-time. That was a good trial run for me to see what it was like to run my own business and to imagine what my life would look like. I know it can be difficult for other people, but if you can do it, I do recommend doing it on the side of something that keeps you financially stable.

If that’s not possible, my recommendation is to do your homework and be really resourceful. There are so many people out there that are willing to help you if you just ask. You'd be surprised how much free advice and free information you can find out there. For example, I often reach out to other artists I know through Instagram to ask about how they price their projects if I’m feeling stuck. As long as you approach the conversation with good intentions, people will be more than happy to answer your questions.

How did you hear about Stride?

I heard about Stride through Dribbble, which is a website for graphic designers, illustrators, and web designers to share their work with their peers and get feedback. I remember hearing about Stride a few years ago on Dribbble’s site and how Stride can help people find health insurance, and I remember thinking, “Wow, that’s really cool.” One of my biggest concerns leaving my full-time job was wondering how to find and pay for health insurance. When it was time for me to leave my full-time job to start my lettering business, I remembered Stride and headed there to find health insurance.

My experience with Stride has been phenomenal. Everything on the website is explained in plain English and is straightforward and professional, but not condescending. Everything is explained to you in a way that makes sense. Things like health insurance can be so stressful and draining to plan for, and Stride makes the process so easy and approachable.

Thanks for sharing your story with the Stride community, Jessica! You can see more of Jessica’s work on her Instagram, Twitter, and her website.

Meet the graphic designer who turned her side hustle into full-time work