Design Matters with Debbie Millman – 20th Anniversary Celebration

Guests: Bill Moggridge, Jason Kottke, Anil Dash, Kevin Kelly

Date: December 1, 2025

Overview

In this special 20th-anniversary episode of Design Matters, Debbie Millman reflects on two decades of exploring creativity, design, technology, and culture. She presents a curated time-capsule of conversations with some of technology’s most influential thinkers: Bill Moggridge (IDEO co-founder and laptop pioneer), Jason Kottke (blogging trailblazer), Anil Dash (software engineer and tech ethicist), and Kevin Kelly (co-founder of Wired, prolific technology writer).
The episode focuses on the evolution of human-centered design, the nature of the internet and technology, ethical responsibility in tech, and the inevitabilities – as well as the choices – within technological progress.

Key Discussion Points & Insights

1. Human-Centered Design & the Birth of the Laptop

Guest: Bill Moggridge
Timestamp: [04:14]–[11:39]

• The Principle of Starting with People:
  Moggridge, reflecting on decades of design, emphasizes that design begins and ends with people:

  "If there’s a simple, easy principle that binds everything together, it’s probably about starting with the people. And so the relationship people have to whatever you’re designing is the most important factor." – Bill Moggridge [04:14]

• Laptop Design Philosophy and Longevity:
  Even as tablets and e-readers emerged, Moggridge predicted the laptop’s endurance:

  "All the laptop is is an input and output structure. ... Until we find something a lot better than the mouse, the mouse still remains pretty good." – Bill Moggridge [05:32]

• Designing for Usability:
  Practical examples, like testing the weight people could comfortably carry, demonstrated user-focused design:

  "[We] gave them one pound weights and said, carry as many of these ... as you can ... and then tell me when it gets unbearable. ... We tried to design the thing to weigh eight pounds." – Bill Moggridge [10:49]

• Legacy and Impact:
  Moggridge viewed his work as precedent-setting but couldn’t have predicted its cultural spread:

  "You don’t predict it’s going to spread in the way it spread. You just have no idea about that." – Bill Moggridge [09:46]

2. The Culture and Creation of Blogging

Guest: Jason Kottke
Timestamp: [12:28]–[20:58]

• Early Blogging:
  Kottke started blogging before the word existed, seeing it as an extension of episodic creative work.

  "I decided that I wanted to try my hand at it and sort of produced what became kottke.org as an episode of Oscillate." – Jason Kottke [12:28]

• Embracing the Blogger Identity:
  Kottke prefers "blogger" over "curator," embracing its humble connotation:

  "Curating strikes me as a term that’s a little bit highfalutin… What I do is not highfalutin at all." – Jason Kottke [13:28]
  “Yeah, I'm a blogger. This is my blog and this is what I do. Even though it's a horrible, ugly sort of word…” – Jason Kottke [14:03]

• Evolution of Voice and Responsibility:
  After significant events like Hurricane Sandy and the Connecticut shootings, Kottke grappled with how – or whether – to use his platform for advocacy.

  "Maybe I should be telling them to do something or maybe I should be encouraging them to think about these more weighty issues..." – Jason Kottke [15:53]

  He also describes the personal, almost reflexive nature of blogging after years of practice:

  “I've got the [Malcolm Gladwell] 10,000 hours of deliberate practice… it's like a second nature sort of thing to me.” [15:04]

• Deciding What’s ‘Kottke-worthy’:
  Kottke aims for timelessness in content selection:

  “Maybe one thing I try to focus on a lot is picking stuff that’s gonna be more or less timeless rather than, here’s what’s going on right now in the news.” – Jason Kottke [19:59]

3. Tech’s Human Impact & the Ethics of Social Networks

Guest: Anil Dash
Timestamp: [23:16]–[34:13]

• Tech as Continuously Redefined:
  Dash frames technology as whatever is invented after you’re born and observes generational shifts in what is considered "tech":

  "There was a time when the technology industry was the wheel… the first people to do agriculture were the technologists of their time." – paraphrased by Debbie Millman from Dash [23:16]

• Meaning Comes from Connection:
  On our relationship to devices:

  "As humans we feel that connection is meaning. ... We anthropomorphize all the devices and the objects that we use, [and] try to project upon them that connection is meaning for them too." – Anil Dash [24:20]
  "The real world is full of strangers. This phone is full of people I love." – Anil Dash [26:08]

• Accountability and Mistakes in Social Media Design:
  Dash reflects on being at the heart of the social media boom, aware the original architects made lasting, sometimes harmful decisions:

  "Every single one of those [problems] is traceable to design decisions in the creation of social media and social networking tools. ... They would never have been prevented, but they could have been greatly diminished or not been so empowered had we made different choices." – Anil Dash [27:33]

• Ethics in Tech:
  Dash is critical of the lack of ethics training and awareness about technology’s societal impact:

  "Our computer science programs seldom contain ethics curriculum. ... So you just aren’t taught how to think about the social impacts of what you do." – Anil Dash [30:18]

• Amplification and Distortion in Tech & Media:
  Comparing journalism and technology, Dash notes both set "the boundaries of acceptable conversation" and can distort reality through what they amplify:

  "...falsehoods, sure, there are lies through emphasis. And this is a thing that journalism and tech are probably equally guilty of..." – Anil Dash [32:09]

4. Technological Inevitability and the “Technium”

Guest: Kevin Kelly
Timestamp: [34:13]–[48:11]

• Inevitable Progress, Unique Outcomes:
  Kelly argues some technologies (e.g., the internet, AI) are inevitable given certain foundations—but the particulars are not:

  "The Internet was inevitable, but the character of the Internet was not inevitable." – Kevin Kelly [35:39]
  "...Once you invent electricity and copper wires and switches, you’re going to invent the telephone. And once you have the telephone, you’re going to invent the Internet." – paraphrased by Debbie Millman [34:13]

• Evolution’s Mirror in Technology:
  Kelly likens the development of technology to biological evolution—driven by tendencies toward complexity, specialization, and mutualism:

  "...the evolution of technology follows the same thing, the evolution of life. ... It’s evolution accelerated." – Kevin Kelly [37:11]
  "AI is coming. Making minds is something that evolution wanted to do many, many times. ... So minds and artificial minds are inevitable." [35:39]

• The "Technium": Technology as an Ecosystem:
  Kelly introduces the idea of the “technium”—an interconnected system of technologies with emergent properties:

  "We have really something that’s much more like a rainforest of different technologies that are interdependent, codependent on each other. ... All the technologies together make up this technium." – Kevin Kelly [40:20]

• Creativity as Elemental:
  The episode explores the universality of creativity:

  "One of the things AI has shown us is that creativity, rather than being a high order, rarefied quality, is actually very primitive. It’s so elemental that we can actually make machines do it." – Kevin Kelly [46:46]

• Systems & Evolution:
  Kelly relates the technium’s evolution to that of biological systems, noting technology rarely goes truly extinct:

  "The behavior of this as it progresses through time is very, very similar to biology. … Unlike biology, it is very, very, very rare for anything to go extinct in the technium." – Kevin Kelly [43:19]

Notable Quotes

• Bill Moggridge:

  "...the relationship people have to whatever you’re designing is the most important factor." [04:14]

• Jason Kottke:

  "Curating strikes me as a term that’s a little bit highfalutin… what I do is not highfalutin at all." [13:28]
  "I've got the [Malcolm Gladwell] 10,000 hours of deliberate practice. Like, I’ve got that in. And so I… can just do it. It's not something I have to think about doing." [15:04]

• Anil Dash:

  "Our computer science programs seldom contain ethics curriculum. And there are implications from that where you just aren’t taught how to think about the social impacts of what you do." [30:18]
  "The real world is full of strangers. This phone is full of people I love." [26:08]
  "Every single one of those is traceable to design decisions in the creation of social media and social networking tools." [27:33]

• Kevin Kelly:

  "The Internet was inevitable, but the character of the Internet was not inevitable." [35:39]
  "One of the things AI has shown us is that creativity, rather than being a high order, rarefied quality, is actually very primitive. It’s actually elemental." [46:46]
  "We have really something that’s much more like a rainforest of different technologies that are interdependent, codependent on each other. ... All the technologies together make up this technium." [40:20]

Timestamps for Important Segments

• [04:14] – Bill Moggridge on the core principle of “start with the people”
• [05:32] – Prediction about laptop longevity and importance of input devices
• [10:49] – User-focused design: testing laptop portability through real-life prototypes
• [12:28] – Jason Kottke on the beginnings of blogging
• [15:53] – The impact of world events on the purpose of blogging
• [23:16] – Anil Dash on technology’s shifting definitions and device connectivity
• [27:33] – Ethics and responsibility in early social media design
• [30:18] – The issue of ethics education in tech
• [32:09] – Tech and journalism as gatekeepers and amplifiers of culture
• [35:39] – Kevin Kelly on technological inevitability and societal choices
• [40:20] – Introducing the concept of the “technium”
• [46:46] – AI, creativity, and instinctive invention

Memorable Moments

• Bill Moggridge describing "walking around with briefcases full of weights" to settle on the right weight for the first laptop [10:49]
• Jason Kottke quipping about blogging: "Even though it's a horrible, ugly sort of word that doesn't roll off the tongue." [14:03]
• Anil Dash highlighting how design choices in social networking echo and amplify real-world inequalities [33:38]
• Kevin Kelly’s analogy of the technium to a rainforest and a beehive, underscoring the emergent and interdependent nature of technology systems [40:20, 43:08]

Conclusion

This anniversary episode of Design Matters serves as both a time capsule and a living dialogue about design, technology, and our collective future. It brings together foundational voices who’ve shaped how we think and feel about the intersection of people and technology, reminding us of our power—and our duty—to shape what comes next.