Chapter 1: My Love-Hate Relationship with Writing

Writing has always been a complex mix of passion and frustration for me. I relish the process of immersing myself in a subject, distilling it into coherent logic and relatable terms. My enthusiasm for sharing knowledge has defined my career as a tech advocate. However, I also grapple with the challenges of writing. As a big-picture thinker, I often find myself bogged down by minutiae. Spending an hour refining a single paragraph feels restrictive, as I have an inherent urge to keep moving forward and to maintain freshness in my work.

This characteristic has been evident since my school days. My high school teacher doubted my potential in AP English, predicting I wouldn't excel because of my reluctance to invest time in detailed writing. His predictions didn’t deter me, and I enrolled anyway. He was right about one thing: writing can be tough. It demands time and patience, both of which I find challenging.

Yet, I possess a unique ability to translate complex jargon into relatable language, often bringing humor into the mix. To write effectively and efficiently, I've learned that I require assistance.

I previously depended on structured processes and a team to enhance my productivity. A decade ago, I led the blogging efforts for VMware's app stack, vFabric, and later for Pivotal, producing over 250 detailed technical articles annually. Each piece underwent my careful scrutiny and edits, but to prevent my shortcomings from derailing the process, I relied heavily on collaboration.

Drafts originated from others—either subject matter experts or staff writers. This approach significantly sped up the process, as responding to an existing draft was far quicker than starting from scratch. Data collection was also a team effort; I initiated it, but another teammate ensured accuracy and completeness.

We utilized Google Docs for all our work, benefiting from its collaborative features and real-time updates. I insisted on this format, converting any submitted drafts into Google Docs immediately. My initial feedback typically came in the form of comments, where I would guide staff writers by suggesting revisions and sharing my thought process to foster their growth.

We standardized our visuals by working with a graphic designer I’ve collaborated with for nearly two decades. To streamline costs and expedite publication, we developed user-friendly design templates in Photoshop, enabling writers to update images with ease. Custom design work was reserved for larger projects.

Before publishing, we meticulously planned our promotional content, drafting social media posts and metadata while the story was fresh in our minds. Typically, we created a library of ten promotional posts to maximize exposure after publication.

In terms of editing, I always ensured a fresh pair of eyes reviewed the content. Whether waiting a day or bringing in a colleague, this small separation made a significant difference in catching overlooked details.

The final post staging was usually handled by someone else, allowing me to review it one last time before publication. We published and promoted articles simultaneously, using scheduling tools to spread ten social media posts over three months. This systematic approach meant that the entire process of creating an article typically spanned 5–8 hours, with my input accounting for only 1–3 of those hours, usually spread over several days.

While this method proved effective, it required meticulous orchestration and a dedicated team of professionals.

Chapter 2: The Impact of AI on My Writing Experience

Today, AI has taken the place of my former team, revolutionizing my writing experience for the better.

Fast forward a few years; I've shifted away from client work. I haven't taken on new clients in nearly four years, and while I still collaborate with my designer, I’ve largely dissolved my team. Most of my existing projects have naturally concluded, allowing me to pivot towards writing on my own terms. My physical well-being demands a break from prolonged computer use, so choosing my deadlines and establishing a sustainable work pace is crucial.

Part of my new direction involves exploring real estate, which naturally keeps me away from screens. Additionally, I've returned to writing on Medium, where I've felt a renewed urge to express myself, initially focusing on the Enneagram.

The Enneagram's Relevance in Business

Understanding the Enneagram has deepened my empathy for myself and my colleagues. As a type 7—The Enthusiast Adventurer—I’m passionate about discussing it, which is essential for my role as an advocate.

My initial posts took over a week to draft, and writing solo felt tedious. I realized this wouldn’t be sustainable, and I found myself disheartened. Meanwhile, AI technology began to gain traction. In the past year, I'd experimented with basic writing tools but found them underwhelming, dubbing them "dumb writers" due to their gimmicky nature.

However, with my 25 years in emerging tech, I recognized that the next few years would be transformative, especially as Web 3—the next evolution of the internet—gained momentum.

Realizing I could dive into AI while being on the forefront of a significant trend, I was pleasantly surprised to discover how much more enjoyable writing could become. Researching became more efficient with AI-enhanced search capabilities. Google’s Bard proved effective for starting searches, while Microsoft Bing’s chatbot, with its Insights tab, allowed me to skim through articles with ease.

AI now generates my first drafts, albeit they often require substantial revision. These initial drafts can be lacking—too brief, uninspiring, or riddled with inaccuracies. However, they help me bypass the daunting blank page and enable productive writing in mere moments, allowing me to refine and expand upon my ideas independently.

I've transitioned to writing drafts directly in Medium, which is more convenient since I'm no longer collaborating with others. AI tools now assist me in data scraping, from Bard to Browse AI, streamlining the process of creating charts and visual data representations.

For visuals, Canva and Midjourney have become invaluable. They allow me to produce high-quality images quickly and add an element of excitement to my creative process. Each time I generate an image, it feels like a thrilling gamble, and I eagerly await the results.

AI also aids in suggesting social media posts. At present, I typically create only one or two promotional posts, but as my writing gains traction, I anticipate expanding this. AI can even generate a comprehensive list of social media posts, providing a wealth of options in one go.

Additionally, I utilize AI for copy editing by requesting suggestions in bullet points. This means I no longer have to wait for external feedback, as my AI assistants offer insights on my writing. While I often reject tone changes, they help me catch those pesky grammatical errors that I might overlook due to being too close to the content.

The writing process has vastly improved for me. Partnering with an always-available digital assistant means I no longer rely on others, yet I still receive the support I need—all for under $50 a month. Ironically, this subscription cost is comparable to what I used to pay hourly for team members.

AI alleviates many of the tedious tasks that previously slowed me down, allowing me to focus on the creative aspects of writing. This shift has rekindled my passion for writing, making it more enjoyable and encouraging me to return consistently.

Moreover, every AI tool brings its own creative flair to the writing process, adding to the excitement. The thrill of waiting to see what AI generates next fuels my enthusiasm for writing and exploration.

Ultimately, while I won't allow AI to take complete control of my writing, I genuinely appreciate how it has elevated my experience.

That's all for now—thank you for reading!