Discover how one founder is adapting traditional writing practices with AI tools while maintaining authentic voice and encouraging interactions.

It's quite surprising, but I haven't composed a single newsletter post from scratch this year. Not one. While I've published numerous pieces, they did not originate from my own two hands typing at a keyboard, a method I proudly relied on for the first twenty-one years of my publication. Nowadays, starting with a blank screen feels a bit antiquated, akin to using a fountain pen in elementary school.

This shift brings to mind my friend Amanda McGrory, a seven-time Paralympic medalist who uses a wheelchair. She often invites folks to “walk over there,” and though she uses an aide to move, I walk alongside her, understanding the essence of her words. Reality or representation, it’s the outcome that matters. In a similar vein, while my preferred method of writing has evolved and may seem influenced by tools like AI, the authentic voice remains intact.
The crux of my current challenge lies in a time crunch for writing. I aspire to produce more content while ensuring it reflects my true self. Since launching my newsletter in 2004, it's purely been about Charlie—my thoughts, my style—free from any corporate branding or outside influences. Maintaining this authenticity while harnessing the benefits of AI requires a structured process I want to share.
Understanding Writing as a Multi-Faceted Skill
Writing isn't monolithic; it's a layered process. First, you select a topic, then clarify your perspective, and subsequently organize those thoughts before translating them into well-formed sentences. Lastly, editing ensures that what you've produced is coherent and effectively communicates your message. Each component requires distinct skills, and I don’t excel at every aspect.
For instance, merely transcribing thoughts into sentences feels like a commoditized task—something that AI tools can do just as well as I can. The common pitfall arises when people rely solely on AI to transcribe ideas without investing in the thought process. The ideal approach is to articulate your thoughts on a subject and then enlist AI assistance to refine and structure those ideas into a draft.
Leveraging Voice Conversations
Interestingly, rather than merely transcribing while seated, I've turned to conducting voice conversations, or what I call “Claude interviews,” during my daily activities like exercising or making lunch for my daughter. Here, AI's role isn't about composing or providing insights; it primarily facilitates when I can articulate my thoughts. By outlining my ideas beforehand, I can prompt AI to draft these thoughts while ensuring it preserves my unique vocabulary and tone.
This strategy capitalizes on my tendency to think in spoken words. With extensive experience in panels and podcasts, it makes sense that my voice flourishes in conversation. Essentially, typing was merely a transcription step that has taken a backseat to a more dynamic interplay of speech and technology.
Integrating Writing with Business Needs
An additional benefit of voice conversations is their transactional nature. Recently, for example, I needed to inform my audience about an upcoming comedy event. Tying this communication back to my business goals—like announcing new cohorts—helps me generate effective marketing leads. This level of integration isn’t something I proficiently managed in the past, but it proves remarkably productive when executed thoughtfully.
Professional writing not only should captivate and inform but also convert. Great writing can lead to coaching opportunities, teaching engagements, and even funding chances. Viewing oneself as a business entity can reshape how we perceive our writing; it brings an essential focus on 'ideal customer profiles' and what truly interests an audience.
Ensuring Authenticity and Voice
Despite my successful integration of AI, it hasn’t been flawless. A concept from a friend pointed out that a post lacked my authentic voice, mainly because the language didn’t resonate with me. It was an important reminder of the nuances of voice. I realized the insight being shared wasn’t initially mine, which hindered me from taking ownership of the language. Essentially, I found myself playing the role of a muse rather than the author.
Typically, I start drafts with interviews, ensuring that my raw material is always grounded in my authentic perspective. A recent topic on pitching illustrated the editing process; while the initial draft was competent, it missed my unique voice. The AI had inserted a self-deprecating remark about being a “coward,” a portrayal that couldn’t be further from my own self-image. I swiftly corrected this misconception and reshaped it into a stronger narrative—one more aligned with my truth.
The Art of Editing and Revising
The secret to effective editing lies in engaging with the draft actively. Rather than solely polishing lines, it’s about examining specific claims made by AI. A vague draft won’t incite a compelling argument or reflection. However, a specific, erroneous draft invites immediate engagement. For instance, realizing that any concept perceived as challenging typically falls off my radar for viable business opportunities sparked valuable dialogue and insight.
This aspect of interaction is why the mistake of skipping an editing pass caught up with me; failing to examine the language resulted in less authentic output. Yet, artfully refining these drafts transforms them into something distinctly mine. The engagement I have with the draft shapes my output in highly fulfilling ways, emphasizing the importance of fighting for clarity rather than settling for adequacy.
Lessons Learned and Looking Forward
As I continue to navigate the intersection of traditional writing, voice, and AI, an essential lesson emerges: writing isn’t about mere transcription; it's an argument in progress. The engagement with the text brings forth individual voices and opinions, enabling deeper conversations. Though the tools have transformed the medium, the end product still resonates with my personal essence, making the outcomes meaningful.
For now, I’ll keep referring to this process as “writing” because the time spent parallels my earlier experiences. While the environments and methods may have evolved, my dedication to authentic communication has remained constant.
P.S. If you're interested in enhancing your thought leadership, consider joining my upcoming cohort at Visible Work. I hope you found value in this exploration of writing and AI.