Thea Kennedy is an award-winning, multi-disciplinary art director, and designer with a primary focus on art direction, design and content creation for the digital space. She has broad online and offline experience in luxury goods, home, fashion, beauty industries, and is now breaking into the tech industry. Thea is also a member of our Creative Lady Directory!

We are absolutely loving her insights regarding the differences in work flow between full and part-time freelance work, and really appreciating the wisdom she shares around things that are important to have in place before you make a big cross country move.

Tell me about your path to becoming a freelance art director and designer.

I got my first break with a job in the Global Marketing Department at Ralph Lauren. I designed printed materials for product, presentation and training internally. These included mainly books, posters, and brochures.

During this time people started to reach out to me with freelance projects. I would take anything on that I had time for. Annual reports, logo’s, wedding invitations, magazines, packaging and so on. I didn’t realize it at the time, but balancing freelance work with full-time corporate design work was a great education in project management. When I began to move on to more senior roles in my corporate life, it felt like a natural transition. I already knew how to manage my time, set expectations, work within tight timeframes, and manage up. I also could clearly communicate with non-creatives, thanks to all my freelance clients.

After being solely a print designer for about five years, I decided I wanted to transition into the digital space. Mainly for practical reasons, but I also was enamored with the idea of the impermanence of digital design

A friend from grad school had just gotten an Art Director job at a start-up called One Kings Lane, and he asked me if I wanted to work for him. I thought it was the perfect opportunity to dip my toes into the waters of the online design world. And it was great to work with a friend, who would be patient with me as I learned how to design in the digital space.

We were the first two hires in the creative department, so we built everything from the ground up. Templates, templates and more templates, along with evolving the branding look and feel. Ironically, because it was a start-up in the tech space, I was one of the only people who knew how to design for print, so I ended up doing all the print stuff too.

I then went on to consult as BaubleBar’s first art director. My focus was tightening up and strengthening their existing branding, as well as working on the UX for key areas of sale on their site.

From there I went to Bumble and bumble, my first job exclusively focused on digital design. As my work experience expanded to heavily digital design, I noticed that the social space was often neglected, and it seemed like such a huge miss. Creatively, it was a place that could be taken less seriously and you could have more fun with! (A Creative’s dream!) This was in 2012, when most people in corporate leadership positions didn’t quite realize the power of social media. I made a point to always create a social component to each campaign we launched while I was there.

Around this same time, my own social presence had blown up, and I started getting paid to do partnerships and collaborations with brands I admired. I also started my blog around this time.

A few years after that, I went on to philosophy skincare, as their Digital Art Director. Things by then had really shifted, and I remember during the interview, everyone seemed more interested in asking me about social media. I realized then, that it might be perhaps possible, to be an art director just for social media….

Throughout all these jobs, I was still freelancing non-stop on the side. I was also getting pretty burned out. I decided to take a risk, quit my job at philosophy, and see if it would be possible to freelance full-time instead. The day I quit my job I got an offer to work with the Creative Director at a new fashion start-up called Spring. And I could work remotely… It seemed like the stars had aligned. My only request was that I work 4 days a week, so I could dedicate one solid day to my own work.

I did full-time freelance work for about a year and a half- working for Spring, West Elm, and Chloe + Isabel, along with a handful of entrepreneurs and small business who needed help with branding.

Then an opportunity came along that lured me back into corporate world… an offer to be Design Director at Bobbi Brown Cosmetics, focusing specifically on Social Media. It seemed like too perfect of a fit to turn down…I had to take a chance and go back into the corporate world.

In the beginning, how did you attract your first good clients?

Almost all my freelance clients have been from referrals, or from people who follow me online, and are familiar with my aesthetic.

Do you have any tips for being your most productive?

My tips for being your most productive are two-fold:

1. If you’re a freelancer who has a full-time job, I recommend really planning your time and creating a schedule for yourself that works best for your lifestyle, and acknowledging any roadblocks that could potentially happen along the way.

For example: I find it really challenging working every night after work on freelance projects, so I try to create a schedule from the start that is mindful of that. I like to work in large chunks of time, over the weekends. So, when I send a project schedule to a client, I usually note that I will have work for them to review Tuesday (giving myself a day buffer to look at the work I’ve done over the weekend with fresh eyes). Tuesdays are great, because it usually takes clients 1-3 days to respond, so then I’ll collect all feedback by the end of the week, and then can proceed with revisions over the weekend.

For this reason, I also seldom take on rush jobs, because I can’t work on a compressed timeline for a freelance job, and work full-time during the day. I know I won’t produce good work.

2.If you’re a full-time freelancer:

When I’m working full-time as a freelancer, I’ve found it hugely beneficial to create a very strict schedule and routine for myself. I wake up early- usually between 5:45 AM-6:30, and I hit the gym. Then I like to do Morning Pages, drink my coffee, make myself breakfast, and do a ten-minute meditation before I start my day. Usually, my workday starts around 10 AM.

All my projects have detailed timelines broken out by day, so I know every morning what I need to focus on. I prefer to take on a few large projects at a time, instead of lots of little ones, so this helps immensely too with my day to day schedule. I only do small one-off projects for clients I’ve worked with in the past and have good relationships with.

I try to stick to an 8-hour work day, although of course that’s not always possible. When I’m working from home, I like to light candles and dim the lights about half an hour before my workday is over. If I’m not already listening to music, I’ll put on a favorite album too. This helps calm my brain a bit, and get ready to unwind. I think it’s important to leave the mental stress of work behind, especially if you’re working from home, and don’t have a physical space to leave behind.

What has been your greatest struggle as a freelancer so far?

I often find myself too busy with projects to take a step back and think of big-picture goals for my business, and for myself as a designer. I need to start doing that more.

What is your favorite thing about freelance?

My years of freelancing and balancing a full-time job have taught me so many lessons, some expected and some unexpected, and I’m really grateful for that.

Working full-time as a freelancer, I love the freedom, especially creating my own schedule and my own ways of doing things.

After 13 years in Brooklyn you made the move back to CA. How are you feeling about that transition? Do you have any recommendations for ladies who may be feeling a similar pull?

The transition has been a lot more challenging than I could have imagined. Besides the fact that the industry in California vs. New York is like night and day, culturally, California and New York might as well be different countries. Everything is different here. The pace is different. The way people interview out here is different. The work itself is extremely different. The skill set expectations are slightly different. The hierarchy is different. In New York, creative leads. In California, tech leads.

My general recommendation for any creative ladies who might want to make the move out west - try and line something up before you get here. The industry is much slower out here than it is in New York. I wasn’t expecting that, and I was pretty thrown off. However, if you’d like to pick up and move out here on a whim, like I did, just be prepared. Save a lot of money, and be patient. Things always have a way of working out in the end.

With the recent move in mind, how do you continue to attract your ideal clients?

When I moved from the East Coast, I also had a career pivot in mind. Less fashion and beauty work, more work focused on branding, innovation, and technology. Situating myself in the heart of Silicon Valley, I hoped the work would just come to me… and it did!

The first thing I did when I moved to California was sign up for a desk at a local WeWork. I did this mainly to keep up a routine, because at the time I was living out of a suitcase, and I hadn’t even decided what city I was going to officially relocate too! This ended up being hugely beneficial to my freelance career, which I wasn’t expecting! My first client I met at WeWork. He and his wife had just started a company together, and I did their branding. They were a dream to work with, and they will always have a special place in my heart, as my first California clients.

I also reached out to all my creative friends out here. It just so happened, that my friend’s husband, also an Art Director, had recently gone from corporate life to freelance as well, and he needed help on a large-scale branding project he was working on. He asked if I would like to help out, and I jumped at the chance. Over the years, he and I have spent countless hours’ nerd-ing out over typography and our design hero’s, and it felt so good to partner with someone who was just as passionate as I was.

But, after I few months, I realized that I actually didn’t want to work on my own. I wanted to build up a new network, a California network. And because I was not just relocating, but also wanting to change industries, it made the most sense to me to seek out work within a large company. I felt like I needed to understand the system and the culture of the tech world.

So, currently I’m doing contract work at Apple, as well as maintaining my own clients on the side.

Can you tell us a bit about your decision to start Design Quixotic? Additionally, how has this outlet and community informed your design work?

I am somewhat of a reluctant blogger, I usually would rather be designing. But, after I amassed nearly 2 million followers on Pinterest through sharing my daily design inspirations, I decided to expand that into the blog format. The blog for me is very personal, and really, it’s a way to stay connected and always search out inspiring or interesting things.

Having a large online following is an amazing way to get a pulse on what people respond to visually. While it hasn’t dictated my work, I feel confident going in specific visual directions, and it’s a great way to convince clients of definitive visual directions I’d like to explore. I can say, I’ve seen a lot of responses to X style, this is what’s on-trend currently- let’s explore it! Or, the opposite. I’ve seen this style online for a few years, it’s sort of at the end of its cycle, but X trend I’m starting to see people really respond to. I think this year it’s going to blow up. Having that kind of immediate access to what people like is incredible.

Do you have any tips for dealing with the nitty-gritty business details?

Despite the scariness of things like accounting, invoicing and contracts, these are the MOST important things! Take them seriously, and don’t avoid them. If you feel overwhelmed, get help. Hire an accountant, hire a lawyer to help write up a few different variations of contracts that you foresee needing. Make sure that you are legally protected before you start any project.

Also, don’t forget that your own branding and aesthetic should carry over to these less-glamorous facets of your business as well! Your contract, invoice, and project timeline will be the first things that your clients will see from you, so make a good first impression. Take some time with the design, and refresh it every few years, as you would with your website, media kit, and so on.

How do you whet your creative appetite?

I go to museums, galleries, lectures, concerts, plays and miscellaneous design events as much as possible. It’s important to stay connected with your passion. I also have a weakness for art and design books.

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Right now, my work-life balance is pretty out of whack. Hopefully I can change that soon. I have dreams of having hobbies and free time again. I hate being a workaholic.

Do you have any music, podcast, or book recommendations that you'd like to share?

For the past couple of years, I fell into a deep creative funk. I felt like I lost my inspiration and drive. It was really scary actually. The only way I knew how to cope with this, was through reading about creativity, (I find books really comforting). I have a short list for you!

The Artist's Way, by Julia Cameron

This book was given as a gift to me in college, I re-read it whenever I’m going through a tough time, and it always helps! I still do the Morning Pages ritual, and it really helps ground me - even if it’s just stream of consciousness ramblings. In fact - even better if it is!

The War of Art: Break Through the Blocks & Win Your Inner Creative Battles, by Steven Pressfield

The Creative Habit: Learn It and Use It for Life, by Twyla Tharp

Daily Rituals: How Artists Work, by Mason Currey

The 3 greatest attributes you need to be a freelance creative are:

Courage, Faith, Determination.

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