How I Learned To Love My (Digital) Self

I’ve told the simplified version of this story countless times. The “how I learned to love myself” story that everyone thinks has a finite finish line, and the moment you cross over the universe gives you $200 and a great ass. Reporters and moderators love to ask me about confidence like I’m somehow holding this magical confidence-bestowing gift card close and if you ask me the correct series of questions, I’ll share my gift with you, too.

The thing about confidence (in any area of life, not just as it relates to beauty or your body) is that it’s never the same moment to moment. In my experience, my confidence rises and falls with a series of variables that my brain is constantly calculating. Am I entering a familiar situation and know exactly what to expect, or is everything unfamiliar except [insert thing that makes me feel powerful/strong/beautiful/desirable/smart]? “Confidence” as it is presented to us in popular culture is rooted in how great we feel about our bodies, how educated we are, and how strong we can appear in the face of oppression. It is my experience, however, that true confidence comes from a steeled belief that you are capable of handling whatever unknown variable that you might encounter.

But here in this expansive digital ocean, we’re all jockeying for attention. Likes, comments, recognition, money, and fame are how we measure our “success”. Even more fleeting than confidence is this notion that the more of any of the above that we get, the more successful we are. We place our value directly into the fickle hands of others, close our eyes, and hope that they will be able to fully appreciate our body of work based on a two-dimensional representation of a static moment in time.

The story I mentioned at the top of this post is the story of how I began posting photos of myself online and where the confidence to put myself out there came from. Back in 2006 when I started my site, the internet was a very different place. I started my career working for a woman who sat front row at Oscar de la Renta as a digital pioneer. There was never a goal too lofty or an achievement too unattainable because I witnessed her work being seen as legitimate in the eyes of the industry.

Those of us who were lucky to launch in 2006 (or even earlier) knew that our professionalism, or the appearance thereof, made all the difference. We took our early cues from the magazines, using brand-provided product images (if we weren’t “stealing” them from their websites) and used the royal we to talk about ourselves. Unlike magazines in their big glass towers, we formed deep connections to our readers that allowed us to truly listen to their needs.

We listened, we adapted, and we opened up. We pulled back the curtain and began to show ourselves. It wasn’t easy, even though we made it appear like it was because the internet has never been particularly kind to women. For those of us that were outside the Hollywood standard of beauty, we had a particularly high barrier to entry.

Style It Daily Booth To overcome my fears and the disparity between what I believed I looked like and the way I was represented in photos, I challenged myself. Using a site called DailyBooth (RIP), I challenged myself to upload a photo of myself every workday for 30 days. I had to upload the first photo I took, no takebacks, and be happy with the image that was presented. In today’s selfie-obsessed society, that doesn’t seem like a tall order, but in 2010 we hadn’t quite reached that tipping point.

I uploaded my 30 selfies and became comfortable with what I saw on the screen. The image I saw of myself in my mind and what was presented became to move closer together. Six years later, there are still days that I struggle with this disparity. The truth is, we can’t accept a 2D recreation of a single moment as a representation of the whole of who we are.

Sure, the photo at the top of this post (taken by the incredible Kristin Booker) is beautiful. But you can’t see the sweat on my forehead because I was stressed, or how much the energy from our creative exchange was fueling my spirit. You also can’t see the compliments I paid to strangers, the time I lost my patience or the work I’d done that morning. Perhaps the best photos are still worth 1,000 words, but these days it feels like we’d settle for 1,000 likes or 1,000 emojis.

My point is, nearly 800 words later, that it’s important to find strength and beauty within yourself, outside of and independent of any other measurement. Your Chanel bag doesn’t do you a bit of good at the oncologist and a leather dress won’t comfort you at the end of an emotionally taxing day. Hollow confidence is what comes attached to people, things, and interactions outside yourself, but finding a way to be there for yourself in the shadow times is the truest form of love there is.