Mailande is a modern-day renaissance woman and champion for the power of creativity. As she uses her talents to help mission-driven organizations communicate their stories, she also seeks to use her own creative risks as a catalyst for helping others do the things that make them come alive.
She’s been a source of inspiration to people around the world through her work as a mentor, teacher, illustrator, singer, entrepreneur, and keynote speaker.
What are different ways you’re working to change the world?
The way I think about it is in concentric circles.
It starts with my direct client work, which is the inner circle. I’m a writer, I’m an illustrator, I make websites, and I have a few other projects that I’m working on in parallel. I mainly work with nonprofits, social enterprises, individual creative people, and small businesses. The center of all of it is using my love of words and images, alongside my background in communications, to help people tell their stories. That’s my core profession.
As a writer, I’m part of Briteweb, an amazing digital and branding agency that specializes in working with social impact organizations. My projects so far have mainly engaged philanthropy advisors and impact investing firms. My job is to tell their story, online and off—whether that involves reimagining their website, helping them rebrand, or helping them with specific longform pieces. Working with one specific client recently has given me the opportunity to speak with incredible people working on issues that range from indigenous land rights to lowering homicide rates for men of color. It’s so inspiring. I love that I get to think about how to convey the meaning of their work to others who could become champions for them.
As a website creator, I typically work with small businesses or individuals to develop an online presence that can help them find clients and build community around their work. Helping them tell their stories, both visually and verbally, is satisfying stuff. My target audience can’t afford a giant agency, so I can collaborate with them to make something sophisticated, affordable, and easy to use.
As an illustrator, I largely make custom work for clients—everything from handwritten and hand-drawn poems to wedding invitation suites.
In the next circle, my work gets more experimental. Over the last few years, I started drawing again—that’s something I did all the time as a kid, but I’d let it fade as I headed into adulthood. In 2015, I started making tiny drawings on the back of my grad school business cards (which I dubbed #TheBizcardProject), and otherwise drawing on things that weren’t really meant to be drawn on (better known as #MailandeDrawsOnThings), and sharing my work on Instagram. Doing all of that started as an exercise in helping me escape perfectionism, which is a challenge for me, but it’s what really kickstarted my career as an illustrator. But even when my experiments didn’t lead to paid work, they did give me an avenue for taking risks with my own time and creativity. My hope was to help other people connect with their own ability to take their own risks and explore the things that bring them joy, that make them unique.
“I feel really strongly that both creativity and risk are key parts of the joy of being human.”
I think that when we tap into the things that only we can see in our minds and make them real, there is an incredible, unique satisfaction that comes with that. The problem is that when we’re three, this is totally acceptable—but once we hit school, we’re told to color inside the lines, and to make things they way they’re supposed to be made. Our ability to keep that vibrant space in our minds, to keep it flowing and free, starts to get shut down. We’re asked (and coerced) to be like everyone else.
The second circle of my work, this experimental circle, involves actively pushing against that. I encourage people to ask themselves: what can you look at and see as an unusual canvas? How can you think of those things that your brain comes up with in swirls of color or sounds—whether it’s architecture or a political campaign or a community service project—and let that stuff swish around, coalesce, and live somewhere in a way that has never been seen before? We can all do that: imagine and translate and create.
We get asked to disregard that energy and do what other people are already doing. I’m trying to push against that publicly and encourage other people to do the same. We expect that if we do something weird, or say something different, we’ll be sanctioned in some way. It’s always a social risk to do something before anyone tells you that it’s okay. But so much of the fear we feel around that risk is completely manufactured.
For example, one of the things that made me laugh during The Bizcard Project was that I had rules: I had to make one drawing every day; I had to draw in pen, so I couldn’t sketch first; if I screwed up, I couldn’t start over; and I had to post it on the internet. There are a couple of drawings that I shared with people that I can’t stand—some line isn’t lined up right or I hate the way the colors turned out—but I made myself post them anyways.
You know who else complained about the stuff that drove me crazy? Literally nobody, ever.
Our fears about how people will react are often so much more intense than anything than anything that will really actually happen. But also, if someone doesn’t like it . . . who cares? It really doesn’t matter. Tons of artists and thinkers have talked about the power of connecting with a small, specific audience, rather trying to please everyone and their mother. You really just need to find the handful of people who truly get what you’re about.
Obviously, when I make things, I want people to like my work. But if they don’t, that’s okay. You have to get into the mindset of hearing all feedback as something you can take or leave. Different people have different biases and opinions. You’re going to be different than the next person, and that’s okay.
So, what is the 3rd concentric circle?
It’s what has grown in the last couple of years, kind of by accident. Once I started engaging in this creative work, people started asking me to talk about it. That led to the beginning of a path that involves speaking, teaching, and running workshops. With each of those components, I’m trying to help other people open themselves to taking risks and explore what that means to them in a more direct way.
I’ve spoken at Duke University, East Carolina University, CreativeMornings, and TEDxDurham, all of which explored these themes in different contexts. I also taught design thinking in Cuba, which is still really connected to this. I was helping teenagers understand how to learn and stretch their comfort zones in a new place, taking risks all the time. It was exciting to see them interpret what they were seeing and develop solutions to some of the problems they observed.
What initially inspired you to go down this path?
The truthful answer to this question is a sad one. While I was in business school, I lost three grandmothers and a young cousin in the span of two years. My cousin was 24. It was awful. It sounds cliché, but after seeing my family rocked like that, I realized I could die at any time. I started asking, what about my brothers? What about my parents? What about my friends? What about me? What if I only have two years to live and I spend them in a job that leaves me burned out and sad all the time? I don’t want to downplay that sometimes being able to work at all is a privilege, for a lot of people. I am aware I’m lucky to be able to ask these questions.
But I felt that as long as I could try to envision my ideal life and make it real, I was going to try. Part of it was just wanting to spend that unknown amount of time in the best way that I could. In a way that made me able to shine a light on important things, and to live with intention and joy.
Honestly, when I was in grad school, I went through a short period of depression. I would wake up, get in the car, put my hands on the steering wheel, start crying, and then go back to bed. I knew that that was not how I wanted to experience my life. Thankfully, it didn’t last for a very long time, but it was signal to me that part of the way I was thinking about my future wasn’t jiving with what I knew to be true for me. No matter what, I told myself, it’s not worth it for life to feel like this every day. I have to fix this before I do anything else. I learned about managing stress, nutrition, exercise, and tons of other factors in order to take care of this one body I have—which includes the mind and heart. It’s my number one priority. I can’t do all of the things that are important to me if I don’t do that first.
What are the biggest obstacles you’ve had to overcome thus far? You seem to have so much put together, but I’m guessing the road hasn’t been perfect.
Other than the challenges we’ve talked about so far, I’m lucky enough to have a life that’s relatively free of hardship. However, there a couple of systemic things that have been a little tricky.
One of them is that the American economy is not set up for self-employed people. I pay a larger burden of taxes than people who are traditionally employed, my health insurance is awful, and I don’t enjoy most of the benefits built by society to support workers. I’m excited to think that there might be shifts in that. In Durham, for example, the Freelance League of North Carolina is thinking about policy questions to better support freelance workers. Roughly 35% of Americans participate in some type of freelance work. That’s a significant number, and we really don’t have the structures to support them. Plenty of people stay in a 9-to-5 job they hate because they can’t afford to lose their health insurance. That’s depressing. It doesn’t make companies or their managers get more efficient, or make them better at mentorship in order to hold onto their talent. It’s basically holding people hostage for stuff that shouldn’t be the determinant of what you’re doing with your life. It’s so frustrating to me.
Also, so many women are freelancers because this country has shamefully inadequate maternity policies. It’s a disaster, and it causes so many women so much trouble when navigating their career path.
The lack of resources at the outset of starting my company was also scary. There are so many logistical considerations and tax implications that were surprising. I felt as though I had to ask “How do I deal with this weird unexpected thing?” every three seconds. It’s a lot. And that’s where building a network of other artists and creative entrepreneurs has been key for me. Also, it’s worth saying that none of this would have been possible without my commitment to relationships. My best opportunities have come from people I’ve known for 10+ years. 100% of my work has been found through word-of-mouth connections. Going into every relationship, I think, “How can I help you? Can we build something together? If not me, who do I know that could move something forward for you?” Many times, the opportunity to collaborate might not come around until five years later, but we’re still building a foundation of trust and support that will serve us well at any point. That’s so important as an independent worker.
It’s hard to figure these things out. It’s hard to forgo the benefit packages—I actually tell people that I don’t want to know about their company benefits, because I don’t want to compare them to mine (or the lack thereof). But I do try to think of it in the lens of the perks I’ve created for myself: I can take off on a meditation retreat if I want to, I can go see my mom for a week and not have to be back at the office, I can work in a forest or by the ocean or in a taxi in Kyrgyzstan. When I feel jealous of someone else’s gourmet corporate cafeteria, I focus on the things I can create specifically for me. That comparison is hard. Frankly, I also know that basically everyone I went to school with makes more money than me. I’m still building my creative practice. I know I will continue to grow income and inspire others. But that doesn’t mean that it’s not hard.
It’s also led to a bunch of unexpected richness. For example, I’ve discovered a love of cooking because eating out all the time isn’t great for my budget. I have such a great time with it. I’ll just sit at my kitchen table and read cookbooks for fun, flagging new recipes and getting super stoked about it. I might not have discovered the stress relief inherent in cooking, let alone the sacredness of nourishing myself, without the financial incentive to cook and eat at home.
Many people think that working at a company is safer, but the truth is that your company can fire you at any moment for any reason. I’m not ever going to fire myself. I value my employment. Recognizing and honoring my own intrinsic value is exciting.
Also, knowing I have the room to pivot or expand my expertise if I want to is empowering. I’ve been growing an offering around helping people de-clutter, which brings me (and them) a ton of joy. Giving myself the freedom to explore new kinds of work is important to me, and it would be a lot harder if I didn’t have control over my daily schedule the way I do. That’s not to say people with 9-to-5’s can’t have a side hustle! It just adds another layer of challenge, for sure.
What advice do you have for people that want to change the world or pursue their passion?
I have a few ideas:
First, pay attention to how you spend your happiest free time. We hear so often that we should follow our passions, and so many people ask “But what if I don’t know what my passion is?” That’s totally fine! I usually suggest that people look at what they do when there’s no directive, when they’re free to choose how they spend their time. What are you doing? What are you reading about? What makes you really, really excited? Are you reading about payday lending policies? Are you reading about music production? I don’t believe that everyone needs to quit their job and follow something else full-time, but there’s always room to incorporate more of what you love into your life. If you’re not suited for independent creative work, fine! You can define a creative project for yourself. You can write a cookbook or start a blog about some niche subject or start drawings things because you feel like it, and because being a human can be fun. And who knows what might happen? One of my favorite books is “They Can’t Kill Us Until They Kill Us” by Hanif Aburraqib, who says that when he wrote it, he “just wanted some folks in Columbus to read it.” He really overshot that goal, but even if he hadn’t, the point was to make the work. So maybe you make something just for you, but five other people are totally inspired by it. Awesome! Or maybe you write an essay and share it with five people, but then it gets published on a blog and then an independent newspaper and a magazine. It’s all possible.
So, what moves you? What makes your heart get a little bigger? What experiences? What topics? What songs? What memories? They will give you threads to explore.
Second, whatever you’re doing doesn’t have to be one passion with a capital P. One of the reasons I started decluttering is that I started obsessively reading about minimalism—blogs, books, everything. I’ll never be someone who lives in a few white rooms with four carefully curated objects in them. I’m too visual. I like having things, but I want to be intentional about what they are. Reading more led me to start working on my own processes. I started doing frequent edits of my own life.
That got me curious about bringing other people into it. I read about the 30-Day Minimalism Game and decided to go for it. You give away one thing on the first day, two on the second, etc., and by the time you’re done, you’ve cleared out hundreds of objects. I recruited a crew of random friends to do it with me—everyone from my college French professor to a friend I’d met once at a wedding. We texted pictures to each other every day of our little piles of things before we sent them off to find better lives elsewhere. From there, I did a decluttering pilot project with a friend’s closet, which helped me identify where I could improve my process. Watching the weight lifted off of his shoulders was incredible, and I was so thrilled to be a part of it. But decluttering isn’t what I love to do most in the world, and it doesn’t have to be. I just love it in general. That’s why I just encourage people to follow their curiosity. It takes the pressure off of you in terms of finding the One Big Thing.
Third, surround yourself with people that challenge you and help you grow. Find people that you can talk to about your dreams. Let them stay on the lookout for ways that you can stretch yourself.
We haven’t talked about this yet, but I’m also a singer. It’s probably the scariest thing that I do, because it’s the most emotional thing I do. I’ve also been doing it for the longest. When it works, it’s the most wonderful feeling in the entire world. But I often let myself off the hook with it, because it demands a lot of me. And that’s intimidating.
A while back, I ran into a curator friend, Angel, who puts on amazing community events. By the end of our conversation, she mandated that I’d be putting on a one-woman show at a local cafe. It’s something I’d never done before. I said yes, because you don’t say no to Angel, but later, I wondered what I’d been thinking.
It ended up being one of the most powerful music performances I’ve ever done. We transformed the show into an ensemble performance, inviting friends and collaborators to come play and sing with me in support of immigrant and refugee rights organizations after Trump’s first travel ban. I would have never seen the potential in myself to lead something like that, but Angel saw it. It was her ability to see that potential that led to the opportunities we created together.
It’s been said that each of us is the sum total of the five people we spend the most time with. Who are those people in your life? How do they make you feel? Do they make you complacent or sad or beautiful or ambitious? And are those emotions what you want to be feeling?
If not, what can you do to find new people to be around? It may mean that you start fresh at a new meetup group, or just start doing things you love and looking around at who’s there with you. The world is so big! If you haven’t found your people yet, it doesn’t meant they aren’t there.
The last piece of advice is to create blank space. For a long time, my life was hilariously overscheduled. Every moment of my day was spoken for.
Over time, I’ve discovered that in order to do anything difficult— from working out an emotional issue to creating something brilliant— I need unstructured space. Americans have such an overextended work culture that it’s considered normal to spend all of your time thinking about your one job, to the complete detriment of everything else. So if you have to get up early to think about your startup idea, or miss out on happy hour to write your novel, do it. Show the things you love that they’re important to you.
There’s a quote by writer Annie Dillard: “How we spend our days is, of course, how we spend our lives.” I think about that every day. Of course, we all have to go to the dentist and pay taxes and wait in line for boring things and go through all kinds of difficulties. But, to the extent that you can, how can you create joy in your own life? Your joy, not something that’s dictated by anyone else? How can you make things that harness your own light? How can you share them with other people, so that they can bask in the glow for a little while? Give yourself the time and space to explore what that might look like for you. I promise that you’ll be changed by the process.
