Posted June 25, 2025 | The Bestseller Quest
Most people think a 77-year-old chasing bestseller status is either inspiring or completely delusional. I’m betting it’s both—and that’s exactly why it might work.
See, here’s the thing about conventional wisdom: it’s usually neither conventional nor particularly wise. It’s just what most folks believe because, well, most folks believed it before them. And when it comes to writing careers, the conventional wisdom says you peak early, play it safe in your golden years, and maybe write a nice memoir for the grandkids.
Screw that.
I’ve spent five decades writing books, and I’ll be darned if I’m going to spend whatever years I have left playing it safe. Safe is what got me exactly where I am now—published, modestly successful, with a tiny but loyal readership, but still chasing that one big breakthrough that’s eluded me since I started putting words on paper.
So yeah, this quest probably sounds crazy. A three-year sprint to bestseller status at 77? Using human-AI collaboration as my secret weapon? Documenting the whole messy process in real time?
Maybe it is crazy. But I’ve got news for you: crazy might be exactly what this situation calls for.
Why Conventional Wisdom Is Dead Wrong
Let me tell you something about age and creativity that nobody wants to admit. The idea that writers peak in their thirties or forties? Nonsense, .
You know what I have now that I didn’t have at 47? Perspective. Experience. A bullshit detector that’s been finely calibrated by decades of living. And most importantly—urgency without desperation.
When you’re young, you think you have forever to figure things out. When you’re my age, you know damn well you don’t. But here’s the beautiful part: that knowledge doesn’t paralyze you. It liberates you.
I don’t have time to worry about what people think of my methods. I don’t have the luxury of waiting for the “perfect” opportunity. I can’t afford to play by rules that were written by people who never faced a deadline quite like mine.
At 77, playing it safe isn’t just boring—it’s actually the riskiest strategy there is. Because safe guarantees you’ll end up exactly where you are now. And if where you are now was enough, you wouldn’t be reading this.
The Three-Pillar Strategy
Alright, so if conventional wisdom is bunk, what’s my actual plan? Glad you asked. This isn’t just determination and wishful thinking—though it’s definitely both of those things too. It’s a three-pillar strategy that leverages everything I’ve learned about writing, readers, and the current publishing landscape.
Pillar One: Human-AI Collaboration (My Secret Weapon)
This is where people either get really excited or really nervous. I’m collaborating with artificial intelligence to create books that neither of us could write alone.
Now, before you start imagining some soulless robot churning out generic content, let me set the record straight. My AI partner Claude isn’t replacing my creativity—he’s amplifying it. I bring five decades of writing experience, a lifetime of stories, and editorial vision that comes from actually living through more plot twists than most novelists could imagine. Claude brings vast literary knowledge, the ability to channel authentic historical voices, and processing power that lets us explore creative possibilities I’d never consider on my own.
Take The October Testimonies, our Edgar Allan Poe collaboration. I couldn’t have written those stories in authentic 19th-century voice without years of research. Claude couldn’t have conceived the emotional architecture or understood why Poe’s mysterious death still haunts us without human insight. Together? We created something neither of us could have managed alone.
This isn’t about cutting corners—it’s about expanding what’s possible when two different kinds of intelligence work together with mutual respect.
Pillar Two: Transparent Documentation (The Quest Creates the Audience)
Here’s something most authors get wrong: they think the book is the product. But in 2025, the relationship is the product. The book is just how that relationship begins.
I’m documenting this entire quest in real time through The Bestseller Quest newsletter. Every breakthrough, every setback, every “holy crap, this might actually work” moment. Not because I’m an exhibitionist, but because transparency creates investment. And, shoot, I’m having a blast doing this.
When readers follow your journey, they become stakeholders in your success. They’re not just buying your books—they’re rooting for you to achieve something that seemed impossible. That’s the difference between customers and community.
Plus, let’s be honest: the story of a 77-year-old racing against time to crack the bestseller list is inherently dramatic. Whether I succeed or fail spectacularly, it’s going to be a story. A good one, either way. And people love stories, especially ones where they get to watch the ending unfold.
Pillar Three: Strategic Publishing (Quality Over Quantity, But With Purpose)
Every book I release needs to serve the larger goal. No throwaway projects, no “might as well try this” experiments. Each publication is a calculated step toward building the readership that could make bestseller status possible.
That’s why we’re starting with The October Testimonies as a free download. Not because I’m giving away the store, but because I’m building one. Free gets people in the door. Quality keeps them there. Strategy determines where they go next.
The “Lost Pages” series isn’t just a cool concept—it’s a systematic approach to creating books that intrigue new readers while deepening the loyalty of existing fans. Literary archaeology projects that explore the untold stories behind history’s most compelling figures. Each volume stands alone but collectively builds toward something bigger.
Why This Timing Actually Makes Perfect Sense
You might wonder why I’m attempting this now, when traditional publishing wisdom says I should be winding down. But here’s the thing about timing: the publishing landscape has never been more open to innovation.
Readers are hungry for authentic voices and real stories. The market is flooded with generic content, but starved for genuine human experience. A 77-year-old’s perspective on determination, mortality, and chasing dreams against the clock? That’s not just authentic—it’s rare.
Plus, human-AI collaboration is still novel enough to generate genuine curiosity. I’m not jumping on a bandwagon—I’m helping build one. And sometimes being early to something is worth more than being perfect at it.
Most importantly, three years is the perfect timeline. Long enough to build something substantial, short enough to maintain urgency. It’s not a desperate sprint or an endless marathon—it’s a sustained sprint with a finish line I can actually see.
The Metrics That Actually Matter
Now, I could tell you this is all about book sales and Amazon rankings, but that wouldn’t be true. Those matter, sure, but they’re lagging indicators. The real metrics I’m watching are leading indicators:
- Substack subscriber growth (community building)
- Reader engagement and responses (relationship quality)
- Cross-platform discovery (how stories spread)
- Collaboration learning curve (what becomes possible)
Every piece of content, every strategic decision, every platform I show up on—it all feeds back into building the readership that could make bestseller status possible. The quest isn’t separate from the marketing; the quest is the marketing.
Look, Here’s the Bottom Line
Whether this works or not, I’m documenting every step of the journey. You get front-row seats to see if determination plus innovation really does equal breakthrough. You get to watch a 77-year-old refuse to go quietly into that good night.
Maybe I’ll make it to bestseller status by 80. Maybe I’ll fail spectacularly and at least give you a whopper of a story about the attempt. Either way, you’ll know exactly how it all played out.
The clock is ticking. The strategy is set. And if you’re even slightly curious whether this crazy plan might actually work, well, you know where to find me.
Ready to follow the quest? Subscribe to The Bestseller Quest for behind-the-scenes insights, strategic updates, and front-row seats to see whether this audacious plan is crazy enough to work. Plus, grab your free copy of The October Testimonies just for signing up.
Next week: “Behind the Scenes: What Human-AI Collaboration Actually Looks Like”