Pretty When We Win: Maggie Tsao, Creative Director

Pretty When We Win is a series that seeks to reconceptualize pretty by draining it of its negative power. This first iteration highlights inspiring stories of entrepreneurs who identify as women; it hopes to encourage contemplation of the word pretty and explore how we use it in our daily lives.

I had the pleasure of meeting Maggie through Instagram, and we became fast friends. Maggie is a thoughtful artist who is kind as she is creative. Once I learned more about Maggie’s profession and business, it was a no-brainer to feature her in this series.

Tell us a little bit about yourself.

I’m a Creative Director and Designer by trade. Mainly in the Branding and Motion Graphics industry. I freelance as my own business corporation. When I’m not working, I’m devoting all my extracurricular time and energy into Tender Forms. It’s a YouTube channel and Instagram account of all things slow beauty and living related.

Please name a woman who inspires you and why.

Karyn Kusama. I’m not sure why she popped into mind. Obviously, there’s an endless list of women who inspire me, but I’ll just run with it. Kusama is an American film director. I’m a fan of her later films like “The Invitation” and “Destroyer.” I find her storytelling stripped down but incredibly bold. I think it’s because there’s so little happening (visually) in each scene that it allows it to breathe and even gives the empty space meaning. This makes her a master of holding tension and demanding attention. Is there a better woman to look up to?

What served as the impetus to start your business?

Get ready for storytime. It was 2013, and I had just lost my Dad to cancer (sorry, to start on a downer). But, it really lit a fire under my apathetic butt to chase after my dreams. Insert all the common sayings: if not now, when? Life’s too short, etc.

I was a Creative Director at Showtime (though they wouldn’t give me the official title, another sign of my lack of forcefulness). Still, all the projects I wanted to be working on were outsourced to other creative agencies and studios. So I put in my resignation and went freelance so I could start working for the places that did the work I wanted to do.

What is the hardest part of doing something on your own?

It is a completely different work environment. As a company employee at Showtime, things were very lax there. The only pressure applied was placed by myself and my own ambitions. The freelance world within these creative production agencies and studios was the opposite: super long hours, endless work. Plus, you have to set yourself apart to continue getting hired, so there was a competitive aspect too. Not to mention everything I had to do before going freelance. I didn’t have a portfolio since Showtime was only my second job right out of college, so I built myself a portfolio site. I had to find an accountant and get incorporated so I could legally work for the places on my list. Then, I had to set aside my introvert tendencies and do what I hated most: market myself and ask for jobs. And when the jobs started coming in, setting my rates, how to pay myself through my business, and taxes were perhaps the biggest headache. An essential tip for those wanting to incorporate: find yourself a great accountant.

What keeps you up at night?

Feeling like I haven’t done or pushed myself enough. I have an incredibly long mental list of all the projects I want to do, but there just isn’t enough time. When do you think cloning will finally be FDA and ethically approved?

What struggles have you encountered that you feel are unique to women entrepreneurs? What’s the toughest part of being a woman entrepreneur?

There are two main struggles: 1. getting paid equally to a male counterpart, and 2. being mistaken as emotional instead of a good leader. To me, the toughest part is not always being taken seriously. I hate that I’m saying this, but it’s true. There’s just an innate default setting for everyone (including women) to overlook other female entrepreneurs. Don’t get me wrong, it’s vastly improved. Still, there’s a stereotype that women are gentle, fragile, emotional, quiet, instead of strong, leader, decisive, expert.

What kind of weight does the word pretty carry for you? What does pretty mean to you?

I’m happy to report the term used to carry a lot of burdening weight and now doesn’t carry much at all. I grew up in a predominantly African-American and Latino-American community. In elementary school, I was the only Asian (Taiwanese, 1st generation American). In middle school, I was one of two. Because of this, my definition of “pretty” when I was young and most impressionable was what I saw in school, on television, and in magazines. In other words, I never felt pretty because I wasn’t like any of those defined as such.

I’d say it changed for me when I was admitted into a magnet high school (or the nerd school as we called it). I’d never seen so many Asians in my life. But now, instead of being compared to people of different races, I was ranked within my own, and it still didn’t feel great. I ended up deciding that my brain was prettier than my body. And eventually, I was okay and proud of that.

As women, inevitably, we’re always compared to other women’s physical appearances. To me, “pretty” always refers to an outward and shallow/surface-view of someone, so I prefer the term beautiful. Mainly because it describes a variety of things outside of physical appearance. A work of art can be beautiful, a novel, a story, the ocean, etc. But someone’s thinking can also be beautiful, or their soul beautiful. There’s more tenderness in this word. 

Where do you find strength?

Most often, when I’m at my wits’ end. It sounds dire because it is. There’s always a moment of quiet after you’ve broken down. You’ve been crying your eyes out, your head hurts, your brain refuses to function because it’s spent from letting out all your bottled emotions, and so it’s quiet. At that moment, you can do one of two things. You can quit (and most likely, no one will care). Or you can push past it. In the moments when I push past it, I discover a new skill, a new perspective, a new creative vision. I find strength in hardship.

What inspires you?

The most unexpected moments in life. It can be the sound as you pour your morning coffee or a bird that lands on a branch outside your window. It could be the moment you’re about to fall asleep in bed, or in the middle of watching a film. Inspiration is found in the unexpected!

What’s your favorite way to connect with your clients/partners/customers?

This is an interesting question. The business side of me says it’s to be on the same page. Have similar creative visions for the project, or are drawn to the same visual styles. But the personal side of me says that there’s no easy way to connect with them (introvert talking again). Sometimes it comes naturally because you may be similar to who you’re working with/for (personality-wise). Still, more often than not, I find I don’t have much in common with them at all. We’re incredibly different, and at the end of the day, it’s a business transaction. It’s okay not to connect with everyone. Just do good work.

Can you offer some advice to other women who are looking to start their own business and/or make a career switch?

There’s no perfect time to start a business or make a career switch, so just do it. Yes, the first few months will likely be tough emotionally, and it may be a complete schedule overhaul. But, ultimately, if it’s what you want to do, it won’t feel cumbersome. It’ll feel fun, exciting, rewarding, with the occasional daunting and confusing, but those will pass. A more concrete tip is don’t be afraid to reach out and ask questions. If you know someone who’s gone down a similar road or you look up to and aspire to be like them, just reach out (email, text, suggest a coffee run). I promise you, 9 out 10, they’ll be happy to answer any question and help get you on your way. Then when you’re in the boss position, pay-it-forward and help another poor soul who’s lost!

For more from the Pretty When We Win series, visit the Entrepreneurship section of The Mocha Minimalist.