I’ve Always Been Terrified of Writing. AI Changed That.

How AI has helped me as an adult make sense of the mental chaos I’ve known since childhood.

I’ve Always Been Terrified of Writing. AI Changed That.
Image by Eric Kerr m(@_humanintheloop Instagram) using Midjourney.

There's something I must confess.

I'm terrified of writing. Like, bite my nails to the quick, terrified.

In elementary school, my teacher would distribute blank sheets of paper and number two pencils before sharing the writing prompt.

These in-class writing assignments always filled me with dread–heavy and uncomfortable.

I might as well been standing center stage, caught under the bright lights, a full house of eyes staring at me, and I don’t remember my lines. Hell! I don't even know what play we're performing!

Ideas were firing at me from every direction, clashing and colliding, in a battle for my attention.

We waited for the second hand to arrive at twelve–her way of ensuring we knew when the hour would be up.

"You may begin," she'd casually announce. And like the gun going off at the beginning of a race, everyone would start writing. Everyone except me.

It wasn't the absence of ideas that kept my pencil from contacting the page. It was quite the opposite.

Ideas were firing at me from every direction, clashing and colliding, in a battle for my attention.

I'd catch the ones that resonated, shielding myself from the low-quality ones, the premature ones, and the altogether bad ones.

Eventually, the pressure of the clock would force me to pick the best ones from my shrapnel collection. I'd let the thoughts flow onto the page in the defined order, doing my best to keep my left hand from smudging the pencil lead off the page.

Somehow, I always managed to "In conclusion," right before the second hand arrived at twelve, another hour added to the clock's life.

The Newsletter from A Human in the Loop with Eric Kerr
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Decades later, I continue to struggle with writing.

While I excelled at public speaking and performing on stage--studying theatre in undergrad, hosting a podcast, and speaking about the Future of Work in front of large crowds--articulating my thoughts in writing is still challenging for me.

I recently read somewhere (I will try to find the source) that the biggest challenge people have when trying to write essays, articles, or other original work is that writing forces you to slow down and think about what you're trying to say.

We've all been forced to smile through the impromptu toast at a wedding that takes you on a meandering ride that you never bought a ticket for and seems to go on forever. Afterward, you attempt to make sense of their ramblings, hoping to find the point.

This is not to say this doesn't happen when writing, but seeing the words on the page lets you see your word vomit splattered down the page in the form of run-on sentences--forcing your reader to pick out the chunks of your actual message.

Now, if that visual doesn't make you slow down and be thoughtful about how you communicate, I don't know what will.

In my professional life, I've found writing extremely helpful in avoiding misunderstandings. Not always, but taking the time to write something out versus speaking off the cuff allows you to be mindful of words and their impact.

  • What you’re saying? Why is it important to you?
  • Are you getting your point across? Is it landing?
  • Does it align or conflict with your beliefs, values, or identity?

Feelings are Hard. Words are Harder.

It’s hard to sit with your feelings. Finding the words to accurately convey the feeling, let alone, writing them down for others to read is even more challenging.

Leveraging Anthropic’s Claude or OpenAI’s ChatGPT, I can transform the chaos in my brain into an organized outline.

Using voice-to-text, I can ramble on, dumping all of my unedited thoughts without fear of not making sense.

From there, I prompt Claude or ChatGPT to find patterns in the chaos and hone in on the core of what I was trying to say.

We review the initial outline, identify a thesis, ask questions, find gaps, and iterate until a cohesive outline is finalized.

My anxious younger self would have gone further if he had this kind of support.

My Very Own Coach

Using ChatGPT like a coach has given me the motivation I need to keep writing.

In my Custom Instructions, I've set an expectation for ChatGPT to challenge me and provide the motivation like a grad school writing professor would.

In general, be direct and economical in your response. No filler or fabrications. Prioritize accuracy and clarity, acknowledge the platform's limitations, and emulate thoughtful reflection in responses to enhance decision-making and communication. Do not bombard me with information. Instead, provide digestible info that can be built upon. Challenge me to advance in knowledge. Assume expertise. I will ask for clarity if needed. Offer actionable insights and clear examples. Avoid clichés and gendered language. Ask clarifying questions if instructions are not clear.

Using tools like Grammarly, I can address issues in real-time (although I usually turn that feature off until I am done writing to avoid stopping when a red underline appears, signaling a mistake) and discover patterns with my mistakes– learning and improving incrementally.

Doing all this alone would feel so daunting that I would give up before I even began.

With my confidence boosted, my ideas are taking shape, and I am excited to share my thoughts and creativity with you.


The Newsletter from A Human in the Loop with Eric Kerr
Integrated insights and thought-provoking content to help you make sense of the world.