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Challenge 7: Wear Makeup


Through and through, I am a creature of habit. My planner is the most important purchase of the year and I thrive off my Sunday night organization session where I outline my upcoming week in multi-colored pens. I have certain habits for grocery shopping and laundry and when I like to study foreign languages.

These routines, much like running and writing, keep me grounded and focused. But at some point, routines can become too much. It isn’t until you’ve stepped outside of yourself for a day or a week that you notice how much you’ve missed. You know that feeling of taking a long weekend trip? Suddenly, Saturday seems to last forever as you forget about buying bananas and bread and focus on enjoying wherever you are.

All this is to say that while I appreciate some of the structures I’ve given my life, I can’t help but wonder what’s just outside the box. The new idea for Sunday blog posts is to write about one experience I had in the previous week that was out of routine, that wasn’t predictable, that made me think a little differently about myself and the world I live in.

Challenge 7: Wear Makeup

I never got into makeup. Much to the dismay of a mother who had raised two boys before I came along, makeup just didn’t suit me. I was busy climbing trees and making obstacle courses for my dog in the backyard with picnic tables and camping chairs.

I dabbled with it in middle school and maybe occasionally in high school – trying to make likely expired eyeshadow appear put together instead of like a black eye. Eventually, I gave up and became used to my natural face.

In college, I got a pair of thick black glasses that covered a lot of my face. Since I wasn’t wearing my contacts as frequently, I accepted this new look. It wasn’t as obvious that I didn’t wear makeup anymore because I had giant glasses covering my eyes anyway.

Eventually, my glasses got a little beat up. Because I was wearing them constantly (including every marathon training run) they got a little scratched, a little dirty, and a lot yellow. I didn’t realize how bad they were until I went to the eye doctor last month. He thought that I certainly had tinted glasses or at the very least transition lens. I told him they were just very uncleanable.

He fitted me for a new pair to test my prescription and suddenly everything was clear again – like the first time I put on glasses as an elementary school child. It was beautiful. I had the same reaction when I was fitted for appropriate contacts. He looked at my childlike innocence of sight and I told him I really was turning over a new leaf with my eye health in 2018.

I left the appointment vowing to wear my contacts more. I wore them the next day, remembering for the first time in a long time how nice it was to run without glasses, amazed at how much better I could see with the contacts.

All of this leads me back to my original point: makeup. Last month, my roommate asked me to model for her. This involved her spending what felt like a century dolling my face to the desired look. That night as I took the makeup off and returned to my normal facade, I thought about something my mother had said about how “just a little eyeliner can go a long way.” It seemed like a last try bargaining effort.

I decided that I was going to wear eyeliner every day – just a little. I would learn how to put it on and that would be my one small victory over the world of cosmetics. And I did. I added “contacts” to my morning routine and even went to Duane Reade to buy eyeliner. (That in and of itself was an adventure. There are so many options! So many varieties! Infinite colors)!

I thought this would be a bigger challenge, but I quickly adjusted to the easy task. I got used to taking the eyeliner off at night and I finally felt like I had conquered “wearing makeup.” I think one of my fears with makeup is that I would become almost dependent on it. I was afraid I would wear it too frequently or in too high quantities that I would begin to loathe my natural face. I didn’t want to hide behind it.

Then I took my yellowed glasses off and realized I had been hiding behind my vision impairment for years. I was talking to a friend once about my glasses when I told them that I hide behind them. I told them that my face looked weird without glasses. I didn’t like it. They responded with some good friend response and the world spun on.

I’ve been thinking about that lately, as I’ve now gotten used to seeing myself without glasses. Wearing contacts has forced me to embrace a genuine natural look – for real this time. Sometimes I wear glasses. Sometimes I wear eyeliner. Both of those are perfectly okay.

Then a couple nights ago, I received a ball cap. I had already removed my eyeliner as I put the hat on to send a picture to my friend. It wasn’t until I looked at the picture later that I really saw my face. A quick picture of a hat. Contacts. No makeup. In this challenge of adjusting myself to wearing a little bit of makeup, the opposite of what I had feared had happened.

I saw my face, not hidden behind glasses or anything else and I didn’t think it looked “weird without glasses” or “weird without makeup” or anything else. This was just what I looked like – in the most authentic sense.

Reading a challenge that consisted of a two minute “put on eye liner routine” doesn’t seem like much, but this was a weirdly big hurdle for me to jump – and yes, I know I’m a little late to the game.

Point in case: do whatever you want. I promise your face doesn’t look as weird as you fear it might.

Love always,


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