Every morning I put on makeup, and I’m not talking about a smear of BB cream and a swipe of mascara. I’m talking about a face so beat RuPaul would be proud.

I want to tell you why this routine—no, this ritual—is important to me as a woman and an entrepreneur:

Since my first tube of frosty lipgloss, I understood that makeup was about trying hard without looking like you’re trying at all. If I wore too little, I wasn’t taking care of myself. If I wore too much, I was insecure (and as a business woman, irresponsible with my time). I let these silent rules—upheld by generations of Southern women—govern my hair, too. Curly hair wasn’t professional, so I fired up the straightening iron before every interview, coffee date, and client meeting.


In the corporate world, those beliefs served me well. But I can’t continue to believe those things, and be a boss woman and business owner.

Being boss is about going to battle every day for the life you really want. Lipstick is my war paint.

Defining my new life as a boss began with putting on the makeup I wanted to wear to work. Agency and expression apart from the status quo is why I became an entrepreneur.

As my own boss, I say curly hair is professional. Purple lips are professional. Winged eyeliner and unabated enthusiasm is always, always professional. My makeup routine is a place to declare my own rules.

My makeup routine is a place to declare my own rules. Click To Tweet

It’s also a creative outlet. Makeup allows me to communicate my individuality without commitment or consequence. It’s just fun, and expressing myself just for fun is refreshing in an industry so saturated with seriousness and a serious lack of self-care.

My makeup is, more than anything, an act of self-care.

See, self-care does not come in order of correctness. My morning ritual doesn’t have to involve green juice or meditation. Makeup is my meditation. And it can be yours, too.

Makeup is my meditation. And it can be yours, too. Click To Tweet

The bossiest thing I ever heard was Kathleen’s belief in “the blend.” And in makeup, blending well is the most important and professional technique there is. Blending your curiosities, acts of self-care, and career together doesn’t make you silly. It makes you truly boss.

If you want to learn more about makeup techniques, here are a few of my favorite artists. Watching their online businesses taught me more than just how to apply a false lash. They taught me about the power of the creator/audience relationship, funding new ventures, how to say ‘no’ to projects, and how to fail publicly but with grace. So putting on my makeup isn’t just about the products. I’m also putting on the personas of boss babes (and dudes) I admire so much. Makeup helps you fake it until you make it. On days I feel fraudy, I put on my lipstick and hustle.

On days I feel fraudy, I put on my lipstick and hustle. Click To Tweet

In the words of RuPaul, “We were born naked and all the rest is drag.” My business thrives in part because of my natural abilities, but also thanks to all the things I decided to pick up, put on, and own fully. My contour included.


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Jessica Willingham writes creative copy to help business owners share who they are, what they do, and why it matters, so they can grow their dreams and catch the clients they love. She co-owns Rarest Fortune, a branding studio for born creatives. Find her online at JessicaWillingham.com.