Words of empowerment can be life-changing. Sometimes they come from others sharing their experiences and wisdom, and sometimes they have to come from ourselves to finally overcome the negative self-talk within. These words are crucial because everywhere we look, there are people telling us to change direction and that we’re going to fail if we don’t conform. Andrea Pippins has done things the way she felt the world wanted her to, and then learned to do them the way she felt was best for her. Andrea’s experiences in overcoming obstacles, fear and seasons without work have all taught her to value her creative vision above all and to center her work around it.
Andrea is an artist, illustrator and author. Her newest book, Becoming Me: A Work in Progress: Color, Journal & Brainstorm Your Way to a Creative Life releases today! Read her interview after the jump for her inspiring work process and business values. Then go pick up a copy of her book and doodle your way to developing your own creative vision for your work. –Lauren
Why did you decide to start your own thing, versus work for someone else?
Working for myself is something I wanted to do for a long time but didn’t have the courage to do until recently. My background is in graphic design, so I had been working for several companies, like Hallmark Cards and TV Land/Nick@Nite, before moving on to teaching design courses full-time as an assistant professor. While teaching, I was also doing a lot of freelance work on the side, like art commissions, branding, and illustration. Both full-time and freelance [work] were fulfilling in very different ways. In one job I got to work with amazing colleagues and young people, and in the other I had total freedom over my creative endeavors. But then it got a little crazy.
Because I was still teaching, my schedule was very intense with trying to manage both workloads. I was exhausted and finally realized doing both was not sustainable. So in 2014 I made the decision to take that leap and work for myself full-time.
Can you remember when you first learned about your field of work? How did you discover what it was, and how did you know it was what you wanted to do?
Unofficially, I didn’t really know about graphic design until I saw Halle Berry playing the role of Angela in the film Boomerang. Angela was an art director and artist, and it was my first time seeing a woman of color doing that kind of work. It blew me away, even if it was fiction. But it wasn’t until I started applying for schools that I really learned about careers in graphic design, or what was called commercial art or graphic art at that time.
Honestly, I was a kid who loved art, someone who loved to create but had very little knowledge about what I could do with those skills. I had never taken an art class (until my senior year in high school), had never been to art camp or had any real opportunity to develop my artistic skills. But somehow I knew I needed to work in a field that would allow me to be creative while having a steady income. And it seemed that graphic design would do just that.
What was the best piece of business advice you were given when you were starting off?
The best advice I received when I first started out was from a professor who taught my senior portfolio class. He told us to show our portfolio to anyone who was willing to look. Meaning, regardless of whether that person is hiring, reach out and ask if they can give you some constructive feedback about your work. After graduating, I moved to New York on a whim and took his advice to heart. I emailed, cold-called, and met with any creative director, designer, or art director who was willing to take a little time out of their day to look at my portfolio.
I lugged that huge portfolio case all over Manhattan and some parts of Brooklyn every day I was off from my part-time design job. There was a huge bruise on the side of my leg from that portfolio hitting it as I walked up and down the subway stairs. It was my badge of honor from pounding the pavement.
That experience was tough but great. It allowed me to practice presenting my work and make professional connections, all while learning the city. Eventually, all that portfolio lugging and dropping-off led to a full-time gig at TV Land/Nick@Nite. It took a year before that happened, but by then I had built up a ton of confidence and character (and buff arms), thanks to that awesome advice. I wasn’t afraid to introduce myself to anyone.
What was the most difficult part of starting your business?
The most difficult thing in starting my business was making the decision to leave my full-time job and committing to my work as a full-time freelancer. It was so hard and scary. But I knew deep down I had to take that chance. I don’t recommend this part: I didn’t have any savings or any real plan, but at my core I knew it was something I needed to do. Fortunately, I was offered my first book deal a month after my last day of work.
Can you name the biggest lesson you’ve learned in running a business?
There are two really big lessons I’ve learned. First that it is super important to have a vision for my work. My business began organically, and in the beginning I accepted freelance opportunities as they came, not really thinking too much about whether it was the right fit. I said “yes” a lot to build my portfolio. Which, in essence, is necessary to gain experience and to help determine what you do and don’t like. But I’ve learned it’s important to be clear about the type of work I want to do: work that is in-line with my values and represents who I am as an illustrator/artist. Without those guidelines, it is very easy to get caught up in a rabbit hole of projects that don’t align with who you are. And that can be bad for your portfolio, your integrity, and your motivation.
The work you create attracts more of that kind of work. So when you have a vision for your work and the trajectory of your business, it gives you clarity, and the ease and confidence to say “no” to something that doesn’t align with what you want to do.
Which leads me to the second-biggest lesson: giving myself permission to say “no.” I am always so incredibly grateful for every opportunity that comes my way. But I have to remind myself that for now, I am a one-woman show and I can only do so much. Looking to that vision I have for my business, which is written down in my journal, to see if an opportunity fits has become the perfect system to help me decide whether I should say “yes” or “no.”
Can you name a moment of failure in your business experience that you learned from or that helped you improve your business or the way you work?
OMG, I’ve learned so much from the mistakes I’ve made! When I finished grad school, my plan was to work for myself, and if it didn’t pan out I would look for a full-time teaching job. It was the first time I’d actually pursued the idea of freelancing full-time. During that time, my blog, Fly, was doing really well. My audience was growing, the blog was generating income, and it was also working as a great way to attract more freelance opportunities.
My biggest mistake was not fully understanding what that meant. At that time I had done a blogging project with the Gap and artwork for a limited-edition series of Converse shoes for Free People, which were both amazing projects, but for some reason it didn’t click for me that the reason that work was coming to me was because of the work I was sharing on my blog. Instead of posting more work, sharing more of my process and more about my experiences, I was producing content about what other women were doing. Let me just say, I absolutely love highlighting the work of others. It’s inspiring, and supporting other women who are pursuing their creative passions feeds me. But I completely forgot that I too was a woman looking to create for a living. What I know now but didn’t realize then was that my blog, and the other social media platforms to come soon after, was an extension my portfolio.
Not realizing this then kept me from actively promoting and getting my work out there as one should when they are trying to get more work. So eventually the freelance opportunities slowed down and I had to face the reality that I had to look for a full-time job. When I couldn’t find one, I had to move back home with my mom. It was a really rough time for me.
But I needed that lesson because it taught me to be more strategic about how I connected with my audience and how to attract more work. Looking back, the framework was there, but there was no vision, no plan, and I wasn’t consistent with promoting what I could do as a designer/illustrator.
If you were magically given three more hours per day, what would you do with them?
I would definitely spend those three hours making art for the sake of making art, because it’s a form of meditation for me. It relaxes me. Or just chatting over a bottle of prosecco with my guy.
What has been the biggest sacrifice you’ve made in starting your business?
I love spending time with friends, being social and just hanging out. But between my business, my art, making time for myself, and nurturing a new romantic relationship, I’ve had to really prioritize my time. Which means minimizing a lot of social activities like coffee dates, dinners, and happy hour gatherings. Sometimes it’s really hard to say “no,” but sometimes one has to.
Can you name your greatest success (or something you’re most proud of) in your business experiences?
I am most proud of taking that leap of faith to work for myself full-time. I did it at a time when I was really trying to be better about listening to my gut. So far it’s working out really well.
I also want to add that not being afraid to ask for more money when negotiating a contract or rate with a client is something I am super proud of. Over the years I’ve had to learn the importance of valuing my myself and the work I do. I’m always fair in negotiations, and I’ve gotten to a place where I feel confident enough to ask for what I think my talents, skills, and time are worth.
What business books/resources (if any) would you recommend to someone starting a creative business of their own?
Lately I have been really focused on approaching my business from a place that really speaks to my heart. I just finished The War of Art by Steven Pressfield and loved it. I think I may need to read it again. It’s perfect for amateur artists trying to establish themselves as professionals and for working through the creative blocks, or resistance, we always experience. From a financial standpoint I REALLY love The Law of Divine Compensation by Marianne Williamson. I’m reading it for the third time. It helped changed my perspective about money and how I earn it.
Art Inc. by Lisa Congdon is also great.
Has failing at something or quitting ever led to success for you? If so, walk us through that.
That time when I had to move back home and rethink my path was a time when I felt like I had failed, but it led to success. Although my initial plan was to go back to school to get my MFA so I could teach on the college level, I was really apprehensive about it — deep down I wanted to be an entrepreneur. But teaching was a necessary stepping-stone for me. It forced me to get organized, and more comfortable with public speaking, and clear about my own creative process. Teaching gave me access to people and resources that are really only available in academia and allowed me to build a different kind of network through mentorship and collaboration with young people (it’s super-important to connect with advanced people, peers, AND new talent). Their work, their enthusiasm about design, and their dedication is so inspiring. Seeing them create got me excited about creating. Teaching has led me to become an author and has given me the confidence to teach workshops and do speaking engagements. It was the bridge I needed to feel comfortable enough to go out on my own.
In your opinion, what are the top three things people should consider before starting their own business?
The first thing is their intentions. We have to ask ourselves “why?” Why are we pursuing this business and what is the goal? Everyone has their own unique source of motivation, but it’s really important to dig deep and determine why you are doing this thing. And this question can be for anything — relationships; a project, too. When the intention comes from a place of being needy, selfish, or anxious, you may succeed, but you won’t feel that great in the end. When it’s from a place of genuine interest, fulfilling a need to make the world better or to simply bring joy, then we are in turn filled with joy. What you put out comes back, so be careful with your intentions.
Next I would say one should ask if this “thing” should be a business or a hobby. Both are great, but running a business is work, and if you really love that thing (insert: knitting sweaters, baking cookies, painting murals, etc.) because it makes you relaxed and happy, consider whether you want to keep it that way or if it makes sense to turn it into something bigger. Sometimes when you become dependent on that thing you love for income, it can turn you off from it. So be sure you want it to be a business, or consider parts of it as a business and keeping other part of it just for you. For example, I love drawing and making prints. But because I teach, do speaking engagements, write books, and do freelance illustrations and design, I’m not dependent on making art as my sole source of income. Having those other sources allows me to do whatever I want for my art prints.
And finally, consider that at least in the beginning you will have to wear multiple hats in addition to being the brain behind the business. For many, it’s not ideal but often necessary when starting from scratch. The benefit of this is that when it’s time to hire someone to do it you will know exactly what to ask for, and you will not take those tasks for granted.
What’s the first app, website, or thing you open/do in the morning?
The first thing I open in the morning is my journal or idea book, which also holds my vision board. I try to make time to write a little something before I start my day. I can’t say it happens every morning, but when I am able to, it really feels great. It’s a time to document my first thoughts of the day, record a weird dream, or make a note of how I’d like to see the day progress.
What’s the hardest thing about being your own boss that isn’t obvious?
I don’t know if this is obvious, but it’s really hard for me to design for myself. Whether it’s designing a new look for my blog, my portfolio site, or printed promotional materials, I’m either too critical or not critical enough, and then procrastination takes over. It is such a struggle. And when I do finally like something, I like it for a week and then I’m ready to redesign again. It’s a blessing and burden. As a designer, you can design for yourself, but you also put a lot of pressure on yourself to create something that fully reflects you, which is almost impossible, and it can be paralyzing.