This either evokes a gasp or rolling of the eyes. I’m on both sides of that fence. After the Doctor ordered no makeup for at least one week I immediately blocked off seven days to stay inside my home and I pushed all my meetings out. Seriously. I’m in hiding. And I was okay with that but over the past two days I’m suddenly feeling rebellious and tantalized by the potential of BEING someone else. Could I possibly BE one of those women that can live comfortably in her own skin?

One thing I love about my life is that I have all different kinds of friends. I have friends that never wear makeup and I have friends that won’t leave their house without it. When my au natural friends actually touch up their lashes and dab some lip gloss on for a big event I immediately gush. Then I have this nasty little rant in my head for praising their beauty simply because they are wearing a bit of makeup. That is so not feminist of me. So shallow. I admire my non makeup wearing friends. Secretly I have calculated the minutes they have saved and I’ve converted them into the number of free days they’ve gained in their lifetime by not wearing makeup. I want to be like them. Kind of.

I’ve been a makeup wearer my whole life so I have a deep love for my makeup wearing friends too. They nod their head in understanding when I admit that I have to make room in my carry on for my makeup bag when flying. Oh God what if my luggage is lost? They share their tips for pool parties and water proof products. I’ve had countless conversations with these friends about which three items are the ‘must haves’ before leaving the house. For me it has always been mascara, eye brows and lipstick. But while I’m at it a little bit of eyeliner is usually applied. And most days include blush, eye shadow and bronzer.

Two years ago my husband and I decided to make our health a top priority and we joined the nearby gym and hired personal trainers. Prior to that I had never left the house without at least a tiny bit of makeup so before going to the gym I applied the basic eye wear. After three sessions it became clear that there is no room for makeup at the gym. At all. I was wiping the dripping sweat off my face with a towel and my mascara was at my chin.

This was quite a shift in my life. For the past two years I have successfully turned into that workout chic that can go to the gym without makeup as long as my ponytail is high and my workout outfit is cute enough. I have learned to go to the store without makeup too…but again, I have to throw workout clothes on before I go, even if there are no plans of working out. This creates the affect that I’m either coming from or on my way to the gym if, god forbid, I’m seen without makeup. It gives me a free pass.

Oh my god. Free pass for what? I seriously listen to myself and taste a tiny bit of vomit in my mouth. Shallow. Vain. High maintenance. Who do I think really cares what I look like? My beauty is inside of me and I certainly don’t need makeup to light up the world with my sparkle. I try saying that out loud and wish I could believe it but the reality is that I’m not there. Yet.

I grew up hearing, ‘pretty but dumb’ and associated any worth that I possibly had to how pretty I was. I am a product of the horrible middle and high school years of fitting in, being pretty and popular and getting what I wanted based on my looks. I saw how the world around me worked and I quickly figured out how to make it work for me. I was born with bright blue eyes. I didn’t have to work for them. I didn’t have to study a lot or even know the right people to capitalize on them. I could get strangers to stare a bit too long and compliment the color of my eyes by strategically standing in the light and wearing the right shade of liner.

It became a power trip. I tasted the power I got from my eyes, using my looks and simply being a woman. And when used well I was winning.

Take the combination of experiencing the “pretty power” at such a young age with the books from my women studies classes in college and I became one conflicted mujer. So I shoved the contradiction down to a quiet place and wore enough makeup to feel pretty but not so much that I would feel like a fake. I fit in with both sides…the au natural and the well plastered look. It created a nice balanced look on the outside with conflicting discontent on the inside (isn’t that the story of my life?).

“Pretty” annoys me. It worries me and it upsets me. I see the angst of my friends raising their daughters and I think critically about how I’m raising my two sons. Yet “pretty” is what I know. It is what has worked.

“Pretty” annoys me and confidence lights me up. I know what confidence does and I want every woman to feel it like I’ve felt it. Walking into a room when my hair is fabulous, my clothes fit comfortably, the look is finished with the perfect shoes and my lipstick is fresh. I feel like a million dollars. I feel strong, bold and prepared to handle any situation with grace and confidence.

That feeling comes with makeup. I don’t know that feeling without makeup. Just sayin’. Maybe someday I will but I have never experienced it.

Last night I asked my friend if she and her family wanted to meet us out for dinner. She confirmed via text and I added that I wouldn’t be wearing makeup. I felt like I needed to warn her. I don’t know why. Maybe I thought she would see me and think something was terribly wrong. Again, vain, and self-centered are the words that come to mind here. She replied with two words: For Freedom.

For Freedom.

It never occurred to me that I was being held captive by my makeup wearing practice. Being without makeup didn’t make me feel free but I wanted it to so badly. Being without makeup makes me feel bare naked and ugly. I feel vulnerable and nervous to be out in the world without the comfort of extended lashes and brighter lips.

I have two more days of being makeup free according to the Doctor. Yet I’m tempted to move beyond the safety of my friends and beyond masking the bare face with a cute yoga outfit and colorful running shoes. What if I schedule a work meeting and I don’t wear makeup?

Perhaps I’ll grow up and into a new kind of a woman. Or maybe not. Maybe I’ll just tuck the confliction away again and pretend that this makeup free week never happened.

PS and what I really don’t want you to know about me is that the Doctor’s orders are a result of an eye operation to correct my old lady droopy left eyelid. Snap! That’s right…not covered by insurance.