Drawing Letters: How AI Transformed This Designer into a Writer
Confessions of a reluctant writer who finally found his process
Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.
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For most of my life, I thought writing was for other people: the ones who read voraciously and who kept journals. After all, I spent much of my early career as a designer who thought in sketches and systems, not sentences. But leadership changed that. I struggled to translate my thinking into writing until AI gave me the bridge I didn't know I needed.
As an undergrad at the University of Georgia's Terry College of Business (Goooo Dawgs, sic 'em!), I never had to write long papers. Class was all about case studies, group projects, and presentations so I never built the habit of writing to wrestle with complex ideas.
Over time, I noticed that people who could write clearly were the ones who could think clearly. They could cut through noise, make sense of ambiguity, and bring others along with them. These days, writing is my intellectual home base. But it wasn't always that way.
From Sketches to Sentences
I've always been an intentional communicator but just not through writing.
As a UX designer, I relied on whiteboarding and sketching. Visual thinking let me rapidly iterate on concepts and spot relationships that would have been buried in paragraphs. These drawings evolved from personal thinking tools to powerful ways to collaborate and align teams.
Then leadership changed everything. In one meeting, I sketched out a product roadmap, only to hear: "Can you put that in writing for the executive team?" Suddenly, my go-to tools weren't enough and in some cases, they were frowned upon. Sketching was seen as micromanaging. Stay in your lane, Frank! I had to articulate ideas without leaning on visuals. And if I'm being honest, as someone who isn't an avid reader, I doubted my ability to be an effective writer.
But in a world that runs on documents, writing wasn't optional. What started as a necessary chore became something more: a way to sharpen my thinking, connect with others, and scale my impact. Writing cuts across disciplines and works for designers, product managers, engineers, and sales teams alike. At its best, its clarity is unmatched.
When Writing Forces Honesty
I'm a good bullshitter in meetings where charm and fast talking can gloss over contradictions. Oh, the charisma. But words on a page don't move; they just sit there staring back at you, exposing every logical gap.
If I can write something that feels both true to me and valuable to others, I know I'm onto something. Writing forces clarity in a way that speaking doesn't. The finite nature of putting something down on paper curbs the hand-wavy explanations you can get away with in conversation.
Now, as a product and leadership coach, writing has become one of the most effective ways to communicate what I offer: Here's what you'll get working with me. Just like writing for my team created a reusable artifact that scales beyond one conversation writing as a coach allows me to do the same for the broader industry. That's deeply rewarding.
And that's what led to Frank Takeaways — the newsletter you're reading now and my most sustained writing practice to date.
The Problem Wasn't Writing; It Was Bridging Design Thinking to Writing
For years, I thought my problem with writing was discipline. But then I realized: what if my brain just wasn't wired for traditional writing? What if I needed a different process?
AI completely changed how I understand my own writing process.
When AI writing tools emerged, I didn't think, Finally, I can become a better writer. I thought, Thank god — something to make this torturous process less painful. I approached AI like someone with a toothache approaches Novocaine: not to improve the visit, just to get through it.
What I discovered was surprising.
As a designer, I was used to rapid iteration of sketching, scrapping, and refining ideas visually until patterns emerged. Traditional writing forced me to commit too early in a linear format, interrupting the design thinking flow I relied on. What I needed wasn't better writing skills but a bridge between my visual, iterative thinking process and the written word.
AI didn't dilute my voice but amplified what was already there, making my writing more authentically mine. Before, I spent 70% of my energy on structure and basic phrasing, leaving little room for deeper insights. Now, I can focus almost entirely on the perspectives only I can provide like how design thinking applies to organizational change or the patterns I've noticed in successful (and failed) product launches.
AI applied design thinking principles to writing. The rapid prototyping, iteration, and feedback loops that defined my design process now shaped my writing process too.
How AI Became My Digital Whiteboard
A whiteboard lets me rearrange ideas before the marker dries. AI does the same for writing by keeping my words in pencil, not ink. Here's my actual workflow:
Organize, Scaffold & Scale Method: AI helps me transform raw thoughts into coherent frameworks. I can brain-dump observations and quickly identify underlying patterns for a newsletter or map connections across multiple newsletters.
Possibility Explorer: Stuck? I ask AI: "What if decision-making worked like cooking?" Boom. Mise en place as a leadership model.
Resistance Test: I'll write an initial draft, then ask the AI to challenge my assumptions and identify logical gaps. This process forces me to dig deeper in a judgment-free environment, often revealing insights I hadn't recognized in my own thinking.
The Paradox: More Human Than Human
AI doesn't generate my insights or experiences. It can't tell you about the product launch that failed because we optimized for the wrong metrics, or how I learned to balance confidence with curiosity as a leader. Those lessons come from my lived experience. What AI does is help me package those insights in a way that resonates.
For leaders, this shift is transformative. The math is simple: meetings scale linearly; writing scales exponentially. AI removes the friction that kept us trapped in the limited bandwidth of conversations.
Here's the paradox: AI makes writing more human, not less. It gives me the same fluidity I loved about whiteboarding, letting ideas flow without mechanical friction.
Many leaders remain trapped in the myth that writing isn't worth the effort. If that's you, you're missing your greatest leverage point. AI won't write for you but removes your last excuse not to.
So write. The excuses are gone. Ironically, AI didn't make my writing less human but more me.
As a fellow writer who took this same class, you summarized the takeaways nicely.