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Meet Meagan O’Brien

Today we’d like to introduce you to Meagan O’Brien.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
I can’t remember a time in my childhood before me taking a pencil to paper and drawing.

Growing up in upstate NY in an old farmhouse in the suburbs, my family told me I would sit in a corner for hours and draw. I would illustrate stories, or copy the art from VHS Disney movies, and later I would draw everything I saw in the room including the people. I liked the challenge of capturing a moment in time.

Coming of age in the early 00’s I was exposed to tons of new technology. I fooled around with the first versions of Photoshop and Illustrator, had a blog before they were called “blogs”, messed around with HTML/CSS code, and got a MySpace as soon as it was available. Yet entering college I was determined to be an illustrator, and not get mixed up by becoming a graphic designer. Then I took my first design class sophomore year and I was hooked. Although I graduated with a BFA in graphic design from Alfred University, my senior thesis project was where I created the social artwork of Portrait for a Story (, a project I still continue today.

When I graduated college in 2008 and moved to the Boston area the country was just entering the recession. I remember frantically applying for jobs and taking the first salaried position offered to me as a designer at an invitation and card company. Despite my youthful naivety, I knew after three months it was the wrong job for me, but I would be there for two more years before I felt like I could quit and begin freelancing.

The choice to freelance came slowly and with a lot of help! Over those two years living in Somerville, MA I met a few other freelancers through vending at ArtsUnion craft fairs ( and attending lectures and potlucks at local organizations like Sprout ( The connections I would make offered me my first freelance illustration projects, one of them turning into the successful children’s app abcWOW, while another became my part-time summer gig as an event coordinator.

In this time I picked up skills to design and develop websites built in WordPress and my business grew. I also volunteered for the Boston Dyke March ( and Boston Free Radio ( which opened the doors to more networking, freelancing, and even teaching jobs.

Almost a decade later, I have maintained most of those original clients and added dozens of others. The majority of my clients found me by word of mouth, or from when I volunteered my time (not in a design capacity!) at various organizations.

Right now I am at the most exciting moment of my professional career to date. I’ve chosen to abandon the many hats I used to wear, like web developer and event coordinator, to focus primarily on design, illustration and animation.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
People often say to me “it must be great to be your own boss!”, and perhaps they think I role out of bed and get to be creative all day. I wish. Being your own boss actually means wearing all the hats of a normal business. You are CEO, sales, accounting, human resources, marketing, customer service, and sometimes you even fit into design!

Most of these skills didn’t come naturally to me, and I had to do a lot of research, ask friends questions, and sometimes hire people to get the work done. Even though I have now built a good basic structure for my business I am always tweaking for better efficiency and looking to automate my processes. Time management, knowing how to motivate yourself, and self-discipline is the only ways to survive. One of the most difficult things I’m facing now is writing contracts and pricing my work.

Directing my business towards primary illustration is coming with a new set of challenges around licensing. In the past, many clients have asked me to do an illustration-based project, like a poster design, and then used that art on a t-shirt or as a bus station and without my knowledge. Currently, I am working on licensing language to prevent that and am connecting with a lawyer who can review my work to make sure I’m protecting myself.

We’d love to hear more about your business.
With over ten years of experience working in the design industry the reason, I remain a freelancer is because I love what I do. Every client excites me with their project, and whether it’s a small job or large ongoing work I’m ready to dive in. My best work is done when I’m being challenged, under a deadline, and have the ability to really collaborate and communicate with the client.

Having formerly worked at jobs in marketing, web development, and television I have a stronger understanding of our growing social media landscape that allows me to push my designs. I specialize in illustration, branding, animation and storytelling which helps me create unique, playful identities for clients. Specifically, I am most known for my graphic and illustrated posters which have been hung in Somerville, Cambridge, Malden, Arlington and Chelsea.

I am also pulling from my experiences running Portrait for a Story to offer a new service I’m calling “visual documentation”. The service includes using different artistic mediums, from drawing to video animation, to capture the most important stories in people’s lives. The idea is along the lines of someone live painting at a wedding, but instead of a finished painting, you receive an audio adventure documenting a special moment.

As far as I know, this kind of service hasn’t officially existed before, and I’m excited to offer it to people to help capture their lives!

What role has luck (good luck or bad luck) played in your life and business?
Luck is a tricky subject! After all, we make our own choices, we’re drawn to the right or the wrong people, and maybe we happen to be in the right place at the right time and that leads to the right thing. However, many things we consider to be “lucky” in life are things we have no control over. What some might see as ‘’luck’ often is ‘privilege’.

I am privileged and have had certain opportunities simply because I was born in the United States, am white, grew up around technology, and if I ever was in real financial trouble I have a family that is able to step in and helps me. It was easier for me to become a freelance graphic designer because of all these structural systems that I was lucky enough to be born into.

That being said, I suppose you could say I’m unlucky to live in a world that still generally favors men. The wage gap affects all jobs, including freelancing! There are many things I haven’t had control over and that has impacted where I am today. However, I can’t imagine any luck would change my desire to observe and sketch the world around me. Some things are just meant to be.

Contact Info:

  • Website:
  • Phone: 781-987-4217
  • Email:
  • Instagram: @meaganobrien
  • Facebook: meaganaok

Image Credit:
Jess Barnthouse, Bess Paupeck

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