I Asked AI How My Writing Has Evolved Since 2009. Here's What It Found.

The famous cellist Pablo Casals continued his intense practicing well into his eighties and nineties. When asked why he still did it, he responded, "I think I’m making progress. I think I see some improvement."¹

The timeless quote manifests his humility, but also something profound: the desire of many creators to hone their skills. The musicians, actors, and comedians I most admire refuse to be complacent; they need to keep raising the bar. (As an aside, if you fail to up your game after a prolonged period of time, it may be time to consider changing vocations. If not, then your profession will probably make that decision for you.)

In this vein, I was curious about how my writing has evolved since I started blogging in 2009. I asked AI to evaluate my words—and, by extension, me.

Background and Motivation

Before moving this website from WordPress to Ghost, I did my homework. Others had documented their journeys. A one-day project this was not. Yeah, AI could help. If I wanted my site to look good out of the gate, though, I would still have to:

• Recreate all of my site's pages.
• Revisit my earliest posts.
• Fix plenty of broken images and links that had accumulated since I started blogging.
• Identify and remove all theme-specific shortcodes.
• Work with my developer to write new formatting and redirect rules.

I'll spare you the rest of the deets.

Even before I began the process, I knew that my writing had changed from 2009 in at least two ways: content and tone. With all of the blog posts, white papers, and books I've written and ghostwritten, I would have been surprised if my prose had remained constant over that period of time. Plus, I'm inherently curious—sometimes to my own detriment.

Specific questions included:

• How has my writing changed?
• What were the shifts, and when did they occur?
• Would AI hallucinate, get it partially right, or stick the landing?
• Ultimately, is my writing somehow better or worse now?

Let's see what it had to say.

Enter Claude

Here's my prompt: