Why I’m Writing 100 Words Every Day for 100 Days

#1/100

Kayden Hines
100 Naked Words
4 min readApr 12, 2017

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This is my first “100 Naked Words” post, where I’ll be writing (at least) 100 words a day for 100 days.

Why am I doing this?

It took me three months to write my first post on Medium. THREE MONTHS to write a post that takes six minutes to read. It was a painful process and I hated every minute of it.

I wrote about how I took a conventional path to success and lost parts of myself along the way. My hypothesis (my hope, really) is that re-awakening my creativity will help me rediscover myself and figure out what I’m supposed to do.

Because this topic is very real and meaningful to me, and because I’ve done a ton of research on creativity, I had so much to say. I wanted my post to convey everything — all the nuances of my thoughts and feelings — in a coherent and cohesive way, while also maintaining my authentic voice.

Easier said than done.

I struggled — a lot. I’d write the same sentence ten different ways, and agonize over choosing the “best” one. I over-explained. I under-explained. I cut out entire sections, then added them back.

I felt frustrated that the topic in my head — my voice — didn’t translate into words in the way I wanted. After years of essay writing (and business writing), I was desperately out of touch with my natural, conversational tone.

The more I wrote, the more I learned about how I was feeling. Sometimes, I’d read a Medium post, or listen to a podcast — and something would click. “Ah that’s really what I should write about!” A pathway in my brain would open, illuminating a set of new possibilities, directions, and destinations to take my writing.

Trying to fit my messy inner thoughts into well-structured and readable sentences was suddenly the hardest thing I’ve ever done. I no longer knew what my thesis was. It got to the point where I stopped knowing if I was making any sense at all.

As my draft ballooned into 20 pages of convoluted, repetitive words and thoughts, my frustration and self-doubt grew too.

I should just give up.

Clearly, I’m not meant to write if I hate writing so much.

I’m better at speaking than I am at writing, more of my personality shows through.

But I didn’t give up. I was so sick of reading and rewriting my drafts — so sick of myself — that I wanted to put myself out of my misery and finish even more than I wanted to quit.

After giving myself a few days to regroup, I started reading my drafts out loud, trying to capture my speaking voice. I made my husband to listen to my spoken drafts — aka, the worst audiobook ever — and tell me where I was trying too hard (the irony of “trying to appear like I wasn’t trying hard” wasn’t lost on me). I sent a draft to my friends before I felt ready, and braced myself for feedback. When they told me that my writing made sense — that they understood me — I almost cried. Having this outside perspective helped so much, and gave me the confidence I needed to finish writing.

And then I posted. At first, I felt relief. And a strong desire to drink wine.

But when no one had read my post days later, I started questioning why I put myself through this painful process. Why had I pushed myself to produce and share something so personal — if no one was going to read it?

And then, one person commented. “This really resonates with me.” Then another. “I feel the exact same way.” That dialogue was enough to reinvigorate me. I remembered why I wanted to do this. Out of thin air, my thoughts turned to words, which then turned into connections. I had created a community — however small — of people who feel connected to the words I wrote.

The experience of writing my first post taught me a lot about myself. I knew I was a perfectionist — but I didn’t realize how detrimental this quality was to my creativity. I need to get over my perfectionism, otherwise, I will remain stuck. And I don’t want to stay stuck. I am so ready to break away from all the constraints I’ve put on myself and tap into my full potential.

That’s why I am joining 100 Naked Words. I want to push myself to create and share something every single day — even though this means my work won’t be perfect. Especially because my work won’t be perfect. I also know that being held accountable to a community will make me more successful at breaking through my inner resistance.

Maybe I’m not meant to be a writer. And I’m fine with that. But I’m not going to let myself come to that conclusion before I even get started.

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Kayden Hines
100 Naked Words

Chief Executive Overanalyzer ~ Silicon Valley ~ Tech / Media ~ Humor Enthusiast ~ Stanford GSB Grad