Here’s What Happened When I Made Myself “Look Pretty” for 30 Days

make up

I haven't done a 30-day challenge in a hot minute, (read the one from February here…)which is sad because I love them so much. As I've stated before, I think they're fun and a great way to really focus on learning something new or shaking up your routine. This time I tackled making myself look pretty, but it had some stiff competition.

So, I was trolling for new “30 day challenge” ideas and I had a few at the top of my mind:

  • I could give up drinking (eeee, unlikely)
  • Try working out every day for 30 days (even more unlikely)
  • Try meditating once a day for 30 days.

But when I pick a 30 day challenge, I'm looking for something that can have a BIG impact on my personal life, career, or financial routine…preferably all three! So, I instead turned to my outward appearance.

I was frustrated with how many people told me I looked “tired” when we met up because I wasn't wearing mascara, or a friend commenting “You're dressed up!” when I wore jeans instead of yoga pants.

I knew it was out of control. I just didn't want to admit it.

So instead of not drinking, working out, or meditating I decided to take on the task of actually making myself look good for the world for 30 days.

I'd been feeling like a horrible slob as of late and had a lot of negative feelings about my physical appearance.  I wondered what would happen if I committed to getting dressed and made up every day, regardless of where I was going or what I was doing. Here's how it went.

It Kinda Just…Happened

I must admit that, while amazing, working for yourself does come with a few downsides: I don't have to leave my apartment every day if I don't want to, and I don't have people I have to see every single day. Sometimes it's great – for example if it's rainy out and I want to stay and snuggle with my dog, Roo, in bed.

But some days it gets lonely. (I wrote about this challenge here. )

And since I started working for myself in April 2015, the amount of energy and effort I put into my appearance has gone from minimal to non-existent.

Unless I had a meeting or a lunch with a friend or client, I would roll out of bed from my “bedtime pajamas” into my yoga pants and tee…which, while comfy and amazing, are really just pajamas you can wear outside.

Hell, let's be real. There's been more thana handful of times where I wore yoga pants to my friend lunches and happy hours too. Eeps.

How I Made Myself Look Pretty by Coming Up with a New Routine

Sometimes (especially in the beginning when I first left my full time job), the yoga pants were a necessity. I'd put them on to actually go to a yoga class or workout and then just leave them on for the rest of the day.

They were comfy, and why bother if I wasn't going anywhere afterward?

But things were getting a little out of control when I saw my workout routine slack off, while my yoga-pant-habit ramped up.

At first, finding the right time to get ready for the day was a problem. One of the things I love about my job is that each day is different, but this makes it difficult to get into a tried and true routine.

So, to complete this challenge I started getting up earlier every morning. I'd do my “drink coffee and browse the internet” while I eat breakfast tradition. Then after that I get ready for the day.

An outfit, hair AND makeup. And some days I really didn't go anywhere.

At first it felt silly, being so made up just to wander around my own home.

I did miss my yoga pants…

…but after awhile I didn't. Here's what I learned.

Looking Good = Feeling Good

Not surprisingly, looking better did make me feel better about who I was and what I was able to accomplish. I felt more confident even on my conference calls.  I can't believe that I actually began to believe that clothes and personal appearance simply didn't matter just because I was working from home.

It matters less, sure, but it should never disappear entirely.

Looking Good = Greater Productivity and More Initiative

The ritual of getting ready each day made me more productive when I went out to face it. And the funny thing about getting ready with nowhere to go? You invent places to go and make those interactions happen, so instead of saying “Oh, I don't want to go out because then I have to get ready,” I'd think “I'm ready! Where are we going?”

It introduced a lot of fun into my life.

Anything Worth Doing…..

It's not enough to just not put on yoga pants. The entire thirty days I thought..”Well, if I'm going to make the effort to dress, I might as well complete the package.”

Which made me think about other areas of my life where I wasn't going the extra mile.

If anything, getting dressed every day teaches that if something is worth doing…it's worth doing well. 

Getting Ready Can Be Fun

I think when we “have” to do things like go to work, pick up groceries, look presentable – they inherently become a lot less fun. I think I shunned getting ready for each day (like I used to in my 9-5 gig) because it felt like part of the trappings of a life I knew I didn't want.

Even when I worked 9-5 and needed to look presentable, there were some mornings where I didn't want to get dressed or overslept and didn't have the time.

If there's a silver lining to my time as a yoga pant couch worm it's this: when I went back to my closet, getting dressed became fun again.

A lot of the impetus for this challenge was my decision to dye my hair full on blonde back in July.

Everything in my closet looks different now that my hair color is different, which made it more fun to play with my wardrobe. My skin tone also looks a lot more washed out with the blonde hair, so I can't quite get away with the makeup free look like I used to, unless the look I'm going for is pasty, white ghost.

I'm now experimenting with makeup more than I used to as well.

Looking Good = Greater Emphasis on Self Care

It is one of life's greatest ironies (at least to me) that the minute I became the master of my own schedule and started working less hours, the less time I felt I had to take care of myself.

Sure, my forty hours aren't spent in an office – but there's still work: writing, meetings, phone calls, networking events. Before the challenge, there were days that I didn't get “dress” because I didn't have time but admittedly, those days are few and far between.

And really, not getting ready because I thought I “didn't” have time fed into the fallacy that I didn't have time to take care of myself. Because that's what I was saying isn't it?

The One Big Takeaway from This Simple 30 Day Challenge

I think the biggest thing I learned during this latest 30 day challenge is that….there's always a minute to take care of ourselves. There's a minute to do your makeup, there's an extra five minutes to do the hair or face mask, there's a minute to match jewelry to your outfit.

Just remember that everything (even yoga pant entrepreneurship) is best in moderation. As an added bonus, the days I do leave on the yoga pants now feel incredibly decadent and splurge-worthy, just like they used to on weekends when I worked 9-5.

At the end of the day, you don't look good for others – you do it to put your own best foot forward.

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I haven't done a 30-day challenge in a hot minute...but this time I tackled making myself look pretty every day. Ditching the yoga pants was tough!


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  • Erica
    October 26, 2016 at 5:30 pm

    Loved this post! I certainly know I am more productive when I feel good about the way I look and get ready for the day in an intentional way. While I work in an office environment, I can appreciate the temptation to stay in sweats if you work from home. All the more reason to make an extra effort to prepare yourself for the day!

    Thanks again for this post!

  • Laura Leiva
    October 21, 2016 at 1:44 pm

    LOVE THIS SO MUCH. You basically described me, as a freelance writer working from my apartment home office. I will be doing this challenge and know that it will be beneficial for me. Thank you so much for sharing!

  • Melinda
    October 19, 2016 at 5:01 pm

    I am also guilty of the yoga pants and tee shirt crime…also seldom do makeup….I knew I was in trouble when I went to my volunteer gig in makeup with hair done, contacts, dress, and “real” shoes and nobody recognized me–seriously…Yikes, think I need to up my game:-) lol

  • Giulia Lombardo
    October 18, 2016 at 4:46 am

    Interesting experiment,.. I’ ve done several declutter into my closet keeping only items that can mix together creating combo from casual to elegant, but yes I’m pretty sure that be dressed every day also if you stay at home had good effect on your mind, a minute or two for ourself is absolutely necessary!!!

  • LaTisha Styles
    October 17, 2016 at 4:12 pm

    I really like this idea. I dressed up full hair and makeup the first few days of a recent trip so I could get photos. And it really does make a difference in how you feel!

    • Lauren Bowling
      October 18, 2016 at 8:33 am

      I couldn’t believe how much more I got done. Like, literally mind blown. Loved your new pics by the way!

  • Stefanie OConnell
    October 17, 2016 at 2:11 pm

    Sitting here reading along in my yoga pants at 2pm 🙂 I definitely get excited when I have a reason to dress up. I need to institute the practice more often!

    • Lauren Bowling
      October 18, 2016 at 8:34 am

      Girl, you always look cute.

  • Amanda @ centsiblyrich
    October 17, 2016 at 11:53 am

    Honestly, I need to give this a go. I can totally relate. I’ve felt like I can’t answer the door because I was still in my yoga pants with no makeup on. Thanks for sharing your experience! I’m definitely going to try this out!

    • Lauren Bowling
      October 17, 2016 at 1:50 pm

      Let me know how it goes!!