Frustration and Failure as a Writer, and How I Finally Found the Right Teacher

When the student is ready the teacher appears, or so the expression goes.

I’ve been writing for over forty years, now. I quit no less than three times, declaring to myself and anyone who asked that, “I no longer write.”

But I came back each time. Despite my lack of success, I wanted to figure out creative writing.

Along with quitting, I pivoted half a dozen times, from short stories to screenplays, then to novels, then to producing short films, then to TV pilots, then back to screenplays, and, finally, back to novels. To pivot is a nice way of saying that you’ve quit one project in favor of another.

Some would say that writing makes you a writer, but I didn’t feel like I was tapping into my own creativity. All those years, it was more like I was doing what I saw others do. I wasn’t telling my stories; I was telling versions of stories I’d heard from someone else.

What kept me coming back was that desire to tell my stories.

While trying to get better at creative writing, I pursued improv, stand-up, humor, cartooning, music and dance. All of which is to say that I went in search of my source of creativity in order to harness it and channel it at some project or another. (I also wondered if maybe this other art form might be where I find success; alas, no. None of those other forms caught fire.)

This look inward was guided by a study of what is known about our creative intelligence. But without the right teacher, I’m not sure I would have figured out how to tell my stories.

In 2010, more than 20 years into my pursuit of creative writing, my brother-in-law died of cancer. Along with the grief of his death came the realization that my days were numbered. The stories I wanted to tell could easily fall silent. The tragedy of his death aside, it reminds me of a joke:

A guy goes into a bar, and the bartender says, “Hey buddy, you look terrible. What’s the problem?”

“Well,” the guy replies, “I just found out my brother-in-law only has a couple of days to live.”

“That’s too bad. You’re really upset?”

“I’ll say. He has tickets to the hockey game next week and I’m not sure where he keeps them.”

In my case, the death made me realize that after 27 years of writing, I hadn’t figured out much more than how to craft a decent story. Nothing I wrote was compelling enough to propel it towards the success I craved.

I needed help.

Worried that I might die before having success as a writer, I signed up for coaching from a “million-dollar” screenwriter who promised to teach his students his technique for success in Hollywood. He did exactly that, but it didn’t work any magic for me. What I learned is that he caught a break while in film school, sold a script, and was able to book some writing gigs. Years later, he launched this training program.

He had created a teachable system for writing a script, but it didn’t help me understand my creativity or how to harness it. We thrashed back and forth on story ideas, created a few revisions, and eventually I gave up. That is, I stopped paying for his coaching.

I craved success all the more because another year had gone by without any ability to share the stories I wanted to tell.

I found another teacher who focused on teaching techniques for the writer to tap into their creativity and harness it. Rather than teaching us directly how to tell a particular story, he coached us on how to shape a story by integrating our subconscious creativity with our conscious habits.

He emphasized the need for a growth mindset, connecting our values to a commercial story concept, journaling to explore and strengthen creativity, and various writing practices to advance projects.

The lessons took quite a while for me to learn, however. Having written for over two decades at this point, and having read dozens of books on writing and storytelling, I thought I knew plenty, and only needed to find the right idea and figure out how to write it.

What I lacked was humility and the ability to process feedback on my work. I couldn’t understand why my scenes were misunderstood. I had trouble effectively applying notes to my projects.

Still clinging to naïve hopes that success might come suddenly, I was frustrated until the very end of my lessons. On my last workshop discussion, I saw how the teacher worked through the story problem I presented.

His suggestions resonated. With a glimmer of hope, I took all the lessons to heart.

The lessons on storytelling delivered by this better teacher often included asides about caring for ourselves so that the creativity in our subconscious could emerge and work with our conscious self to create story.

Asides? What sort of asides?

The asides were about meditation, rest, and our values. Basically, the self-care necessary to enable our creativity. We might need to exercise to sharpen our thinking, sleep better to clear our mind, and practice yoga to learn how to calm our spirits. We also need to be clear about what it is we value so that, when we create, we are not betraying those values.

Over a period of a couple of years, I incorporated all these lessons into my life—the exercise, rest, meditation and values—and began to see improvements. I had renewed hope in my writing.

One of the core lessons was that a story can’t be rushed. You have to give your mind time to work it out, especially for longer works like novels and screenplays. Slowly, the stories I was attempting to write took shape.

Over the past eight years, my focus in writing is more about nurturing my creative spirit than the actual writing. I pursued the other arts I mentioned earlier (improv, standup, cartooning, music and dance). I practice yoga. I track my sleep.

I continue to read books and take classes on storytelling to strengthen my conscious knowledge of creative writing, just as I journal and use other practices to strengthen the connection with my subconscious creativity.

I know some writers don’t need as much work at the infrastructure of writing as I do. This used to bother me but there’s nothing I can do about that. I can only work at improving myself.

Every path to success is unique, and every artist is unique.

In fact, it’s something of a gift I’ve been given. Forced to figure out the hard way what it is to be a creative writer, I’m painfully aware of the steps I took to get there, allowing me to explain the process.

That’s what I’ll share in the Renewable Creativity newsletter.

I'm pulling together everything I've learned about creativity and storytelling to give it all back to the community.

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