Dribbbling with Anna Hurley

Tristan Almario
Closer&Closer
Published in
5 min readJul 11, 2020

Written by Anna Hurley

So you’re a freelance artist looking to attract clients. Or, you’re not a freelance artist, but you’re interested and curious about what freelance life entails. Or, you’re just a creative wanting to share your work with the world. I think all of those places are great places to be. I’ve been in all of those places, and have learned a thing or two about how to move between them, and I’d love to share some of that with all of you.

My name is Anna Hurley, and at the start of 2020, I went from being an in house illustrator at Asana to a full-time freelance illustrator. Transitioning into being 100% freelance was hard, but not for the reasons I originally expected.

Going from having consistent work and paychecks to having no idea when the next paycheck will come is an extremely scary leap to make.

But during my transition, I realized the thing holding me back was just that: the mental hurdle that is fear. In the years before I switched, I was constantly telling myself I couldn’t do it, using any excuse from “I don’t know how to buy my own healthcare” to “I can’t do my own bookkeeping.” Once I quit my in house job, however, I realized all of these things were 100% doable, and they were only mental hurdles that had been keeping me from what I wanted to be doing all along. The hurdles I had seen weren’t actually there, they were something I had made up in my head to keep me from pushing myself past where I felt secure.

I would say that’s the biggest step you need to take when moving into the freelance space, or when moving into anything new and unknown, is getting over those mental hurdles.

Once I realized that all the barriers were in my head, I focused on trying to get my work out there on tools like Dribbble and Instagram. And this is where I learned another important lesson: consistency and repetition are key. I first started posting on Dribbble around 10 years ago after graduating from college, when it was still pretty new. Since I had just finished college, I was worried I would fall out of practice with my art, and I wanted a way that I could keep drawing every day and staying consistent. So, I started posting random doodles on Dribbble almost every day. I posted whatever I wanted, and my main mentality was that I just wanted to share my work with people.

I didn’t go into it thinking, “I’m going to get so many clients from this!” I truly just wanted to get my work out there and keep myself consistent and repetitive, and after 10 years of doing that, it’s paying off.

Instagram is the other main social media platform I use for my art. If I’m being honest, I probably use Instagram even more consistently than I do Dribbble, for a couple of reasons. First, I just find it so engaging and immediate. It’s so quick and easy to pick up your phone and post, and within seconds the post is flooded with comments and feedback. It’s also great for following your favorite artists and getting that daily inspiration fix. Of course, it has its problems, but it really is a great way to gain exposure for your art while also getting inspiration. I think that’s why I love Instagram so much, it keeps me in study mode.

There’s not enough emphasis on the act of studying within the design world. Everyone’s always telling you to practice, practice, practice, but I believe studying is just as important.

Looking at a piece of art that you like and asking yourself what you like about it is one of the best steps you can take in developing your personal style.

Being introspective, learning to determine what you like and why you like it, and then figuring out how to incorporate those elements into your work is crucial to evolving your style and growing as an artist.

All of this just goes to show, there is no formula for successfully gaining exposure. I believe you just need to find the platform that you enjoy the most because that is the one that you’ll be the most consistent and repetitive on. Make sure it’s one where you feel inspired because you should always be studying in order to further develop your personal style. And most importantly, make sure you’re not allowing those mental hurdles to stop you from delving into your next big growth experience, whether that’s picking up more freelance work, taking on a new job, or just furthering yourself as an artist.

About Anna Hurley:

Anna Hurley spends most of her time drawing things for fun and profit. She’s specialized in branding for companies large and small as well as packaging design and has designed a plethora of printed paraphernalia throughout her career. She can usually be found eating the free samples in the cheese aisle.

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