Dana Gioia on Writing
March 3, 2025 • #This is a phenomenal extended (3 hour!) interview with Dana Gioia on his background, poetry, his writing process, and the habits he’s curated that make him into a prolific and interesting writer.
Good stuff here on building with Cursor. Some takeaways:
I’ve had much better results getting in the weeds with PRDs well before having agents go off and build. And you can have multiple AIs work on and refine your documents, too.
Some technologies are unpredicted, but evolve. Others are predicted don’t seem to materialize (or not yet). Then there are those that are expected AND appear. The unexpected tend to be the most disruptive — no one’s had the chance to prepare.
But the expected, if they do finally arrive, have been ruminated on for a long time. When we eventually realize the expected, we’re more prepared socially for their impacts. Though often we’re wrong about their societal impacts until they show up.
Kevin Kelly writes about this in the context of AI, a technology long-predicted, but always with a bent toward the negative. Toward the destructive social consequences of creating artificial beings.
Artificial beings – robots, AI – are in the Expected category. They have been so long anticipated that there has been no other technology or invention as widely or thoroughly anticipated before it arrived as AI. What invention might even be second to AI in terms of anticipation? Flying machines may have been longer desired, but there was relatively little thought put into imagining what their consequences might be. Whereas from the start of the machine age, humans have not only expected intelligent machines, but have expected significant social ramifications from them as well. We’ve spent a full century contemplating what robots and AI would do when it arrived. And, sorry to say, most of our predictions are worrisome.
Here’s the example list from Arthur C. Clarke’s 1963 book, Profiles of the Future:
This is a phenomenal extended (3 hour!) interview with Dana Gioia on his background, poetry, his writing process, and the habits he’s curated that make him into a prolific and interesting writer.
When capturing hundreds of problems during product discovery, we generate at least as many potential solutions. We can’t build everything at once, so how do we decide what to tackle first? Ryan Singer has a suggestion:
The counterintuitive thing is, we often feel like our task is to get to a “yes.” But what we actually need is a way to say “no.” It’s the ability to eliminate many, many things that aligns us on the one thing. It’s the “no, no, no, … YES!” that gives us the power to move forward and to stick with a project.
Finding the “reasons to build” for any given solution is easy — every idea is “good” on some continuum. When faced with a hundred ideas, each with compelling reasons to build it, we’re left with the fuzzy question of “how good?”
Ryan’s suggestion inverts the question: look for the reasons to not build it. Is there a workaround? Is it merely annoying but not a dealbreaker? What are users doing today instead? What are the real consequences of the status quo?
This inversion approach is more likely to highlight the acute pains — the missing solutions causing real negative consequences, the ones with no good alternatives or workarounds.
The first key to prioritizing is to triage the obvious “not now”s first. If we can cut our list down significantly, we can focus attention on where we’ll make the biggest impact.
In this AI era, I’ve been thinking a lot about what it means for humans in the loop of formerly human tasks. When AI is inserted in all layers of the stack, what’s left for us?
Sari Azout hits on something I agree with: that the intangibles are (at least for now) resistant to AI. And these areas tend to be where we humans find joy in creativity in the first place. Taste, building context, intersecting divergent ideas, a respect for the tactile, the ephemeral, the unpredictable.
First, you need to cultivate a deeper relationship with your gut. The more our world becomes measurable and quantifiable, the more we need spaces that preserve what can’t be measured—the hunches we can’t explain, the patterns we feel but can’t prove. A jazz musician knows when to break rules in ways no theory explains. A good copywriter can feel what words will land without having a single data point to prove it. Taste isn’t some mysterious gift bestowed at birth—it’s simply what happens when you pay close attention to what moves you.
Our minds are good at finding patterns in the unquantifiable.
As I watch my kids learn, it sits with me how much we learn by copying. Imitation isn’t the enemy of originality — it’s the foundation of it. We learn by copying, refine through practice, and ultimately create something uniquely ours. My latest post on Res Extensa:
In our rush to be original, we often dismiss copying as somehow lesser than “true” learning. But mimicry isn’t just a shortcut — it’s fundamental to how we master skills. We see it in my daughter’s creative reproductions, in my son’s workbench discoveries, and in every artist who’s traced the footsteps of masters before them.
The path to originality paradoxically begins with imitation. First, we copy to build competence. Then we understand. Finally, we create.
Charles Mann on the unseen, unappreciated wonders of modern infrastructure:
The great European cathedrals were built over generations by thousands of people and sustained entire communities. Similarly, the electric grid, the public-water supply, the food-distribution network, and the public-health system took the collective labor of thousands of people over many decades. They are the cathedrals of our secular era. They are high among the great accomplishments of our civilization. But they don’t inspire bestselling novels or blockbuster films. No poets celebrate the sewage treatment plants that prevent them from dying of dysentery. Like almost everyone else, they rarely note the existence of the systems around them, let alone understand how they work.
The invisible, yet essential, layer of infrastructure he’s describing becomes extremely visible during something like an extended power outage during a hurricane. Even with our communications still up, generators in our yards, and food in our refrigerators, even a few days without power are like an eternity.
Jason Carman’s S3 project has been relaunched (no pun intended) as The Story Company, continuing his incredible work on documenting the hard tech scene.
At the start of the year they published their first feature documentary, New Space. A story about the current state of the space industry, and what’s different this time in the marriage between government-backed and private spaceflight.
A great little paean to curiosity from Henrik Karlsson:
There is something frustratingly Tao about curiosity. (1) It is by following your curiosity that you can bring something new and beautiful into the world as a gift to others. But (2) to go there you have to do things that you fear others will think are stupid or embarrassing. That is, you can only find the Tao by not looking for the Tao. By losing yourself in your line.
In the latest Res Extensa, I explored how craftsmen build expertise through deep understanding of their medium. It starts with the nature and properties of their raw materials, then moves to the individual parts, assemblies of parts, and their relationships to one another.
All sorts of woodworking, done well, benefit from skillful selection of material. The furniture builder making an arch at the top of a dresser will help themselves if they find a board with grain that flows in the direction that agrees with their design. You want your material to move with you, not fight against you.
This process perfectly illustrates a fundamental truth: mastery requires rich understanding of your craft’s raw materials. The path to expertise runs through the mastery of your medium.
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