The Infinite Jeff on the Shelf with Illusions

Creativeness, Insecurity, and Permission to Fail

Will Holcomb
The Startup
Published in
5 min readMar 27, 2020

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My story of becoming a writer starts with, “I never planned on being a writer, it just happened …” That journey is fraught with insecurity because there are so many people whose life long dreams are to become writers and they worked hard to hone their craft. I had story ideas and thought about writing them at different points in my life, but it was never a goal in life, only passing thoughts. I’d imagine it’s common for people to toy with story ideas.

But, when it happened, it happened. I had an hour and forty-five-minute commute one-way and was going through public-domain audio at an impressive rate. One of them sparked a story idea and I called my sister who is a writer, always dreamed of being a writer, and worked hard to hone her craft. She liked the story idea, said she couldn’t write it, but if I gave her an outline, she could write it from that.

An outline? Even in college, I wrote my outlines after I wrote my papers. I had ideas for the story, concepts I wanted in the story, but I didn’t know the story, so how could I write an outline? I handled it just like my college days, I wrote and wrote. After about six months of late nights, I gave my sister a poorly written rough draft. At that point, she did something amazing, she ignored all the bad grammar, all the typos, all the plot holes, everything else that was wrong and focused on what was right. She saw a great story. She saw an important story. Over the next year(s), she gently guided me through the process of turning my rough draft into a story that has made a difference in the lives of many.

The title of this article is about insecurity and permission. I’m still working on those, but I’ve made a lot of progress. My book was out in the wild and getting 5-star reviews from people all over the world. It was being compared to books that changed my life and changed the lives of many others. It was sitting on a bookshelf in a bookstore right next to the book that actually did put my life on a different path. I can’t even begin to explain how surreal it was looking at my book next to such an amazing book. I’m a guy with a regular job who goes home to his family after work. We watch too much TV, struggle with homework, pay bills, and don’t go camping anywhere near enough. I was getting plenty of kudos and praise, but I wasn’t a writer. I was just this guy who, with much help from my sister, happened to string a lot of words together that meant something to people.

But there was something I continued to do. I continued to write and I continued to write with less and less guidance from my mentor. As I commuted, another story came to my mind. I’ve been involved in community theatre for a long time and I decided to write the story as a play. I gave the rough draft to the owner/director of the local theatre and he said, “Let’s do it!”

We rehearsed and I rewrote. Dress rehearsal night, I watched the longest, most boring production I think I’ve ever seen. All I could think about was all the people from my town, people I knew, were going to watch this show and it was going to be embarrassing. I texted a friend of mine to go get a drink. He couldn’t make it but asked what was up. I explained how bad it was going to be and he sent one of the most important texts of my life. “I’ll be there tomorrow. If it sucks, I’ll wait until everyone leaves and tell you how bad it was, then walk away jealous because I’ll never do anything like it.”

That statement was like a lightning bolt throughout my body. I was putting on a play. How cool was that? How many people have the opportunity and the drive to do what I was doing? Even if the play was a flop, I was doing something special that very few get the opportunity to do. His text freed me, gave me permission to fail.

Opening night, to a full house, my amazing cast pulled it together. The show flowed, the actors were in their zone and the audience gave them a standing ovation. The show sold out every other showing, was brought back to the playhouse for a second run the next season, and then became the highest-grossing show at a bigger theater in the next town over. Without the permission to fail, I would have never taken the risk and would have never had the success.

But I still didn’t think of myself as a writer. I was still a guy with a job, pretending to be a writer. One night, while pretending to be a writer, I was editing one of my stories and an idea popped in my head for a poem. I pulled up another window, wrote what was in my head, decided I’d finish it in the morning, and went back to the dreadful task of editing. When I looked at the poem in the morning, I was shocked. It was the only time I’ve ever looked at what I wrote and couldn’t deny it was amazing. I didn’t even care if others liked it. I thought it was amazing. That morning, I became a writer. That morning, I gave myself permission to call myself a writer. I still don’t make much money writing, I still have a day job, I still struggle to pay the bills, but I am a writer because I gave myself permission to be a writer. I like what I write. It’s still important others see value in what I write but I’ve given myself permission to fail in that aspect also. If my only goal is getting validation from others, who am I writing for? I have to be my main audience. I have to write to please me first then risk putting my work in front of others. Others may fail to see the value, maybe I’d listen to them or maybe I won’t. If what they suggest makes me like my writing more, I am making the changes. If they tell me I need to change it because “that is the way it should be done”, and I don’t like it, I stick with what I like.

I’m still growing and learning as a writer. I entered a short story in a contest and got it ripped apart. My ego took a hit and it took a while to recover, but it showed me I have more to learn as a writer. I didn’t start off with the goal of being a writer. I need to listen to feedback and grow. My main audience may be myself, but the feedback from others is important because good writing doesn’t happen in a vacuum. I am a writer but I am a growing writer.

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Will Holcomb
The Startup

Will Holcomb, author of the bestselling series “The Infinite Jeff” and a playwright. He’s on Amazon https://amzn.to/2VdgaaP and Goodreads http://bit.ly/2H6ZHAt