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The Curiosity Department

Design Better co-hosts Eli Woolery and Aarron Walter explore the intersection of design, technology, and the creative process through conversations with guests across many creative fields, helping you hone your craft, unlock your creativity, and learn the art of collaboration.
Whether you’re design curious or a design pro, Design Better is guaranteed to inspire and inform. Vanity Fair calls Design Better, “sharp, to the point, and full of incredibly valuable information for anyone looking to better understand how to build a more innovative world.”

Design Better

We’ve worked alongside people for years, only to realize that we know nothing about their personal life. And it probably affected our working relationship. Knowing your colleagues as humans reframes inevitable challenges at work. Had we known our colleagues better, would we have worked through disagreements better or found new ways to collaborate? Yeah, we sure would have.

Alison Rand, who helped establish the discipline of design operations through roles at Hot Studio, Frog, Automattic, and SAP, explores building relationships at work in her new book Sentido—a term that encompasses both making sense of things and feeling them deeply.

In our conversation, Alison challenges the Silicon Valley orthodoxy of radical candor with her concept of radical humanity. She also explains why designops is fundamentally heart-driven work, and draws unexpected parallels between organizational dynamics and the regenerative systems of Puerto Rico’s El Yunque rainforest.

Bio

Alison Rand brings a unique perspective forged in the crucible of real experience. A native NewYorker who lost her mother at sixteen, she learned early that life rarely follows neat narratives. Her career trajectory—from navigating the male-dominated agency world to building design operations practices at scale—taught her that the skills needed to thrive professionally often mirror those learned navigating the New York subway in the 1980s. After being laid off the same week MIT Press accepted her book proposal, she retreated to the woods to write what became part memoir, part radical reimagining of design leadership.

She makes the case that organic intelligence matters as much as academic credentials, and that the future of design leadership lies not in prescriptive frameworks but in building cultures of genuine mutualism.

Whether you’re wrestling with organizational transformation or questioning the artificial boundaries between personal and professional identity, Alison offers hard-won wisdom about leading with both courage and compassion in spaces that often reward neither.

***

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Alison Rand: Leading with radical humanity instead of radical candor

In this issue of The Brief, we’re reflecting on what we learned about the past and future of design from our conversation with Paola Antonelli (The Museum of Modern Art), Mark Wilson (Fast Company), Kate Aronowitz (GV), Mike Davidson (Microsoft), and Meaghan Choi (Anthropic).

Looking back at 30 years of design

by Eli Woolery

Roughly thirty years ago, I was an undergrad, sitting in our dorm’s computer cluster —this was before the days when most students had laptops. I ran into something I hadn’t seen before. It was called Netscape Navigator, and it was one of the first commercial internet browsers (which our very first guest on Design Better, Irene Au, helped design).

I clicked on one of the buttons (probably, “What’s Cool”), and along with a nifty loading animation, the browser took me down some early internet rabbit hole.

I don’t remember where exactly I ended up, but I do remember being blown away by the experience. As a computer nerd kid in the 80’s, I had spent plenty of time with bulletin board systems (BBS’s) and things like America Online, which we could access through a dial-up modem from home.

But this was very different. It was fast—compared to what I was used to—and it felt like I could almost instantaneously access content from all around the world (even though the content online at the time was a miniscule fraction of what it is today).

I had entered school to study product design, but this was for products in the physical world…digital product design didn’t exist as we know it today. The first use of the phrase “User Experience” in a job title was Don Norman’s role a a User Experience Architect at Apple in the mid-90s.

Browsers like Netscape Navigator, and then the introduction of the iPhone in 2007, opened up a new world of opportunities and challenges for the field of design. In our conversation with Paola and Mark, we talked about four: the democratization paradox, design’s loss of innocence, the fragmentation of the design profession, and the shift from tangible to intangible design.

The Democratization Paradox

“We democratized all the tools and we democratized none of the platforms. And that gap is just in a nutshell, kind of what’s broken about the individual’s ability to communicate.”—Mark Wilson, Fast Company

While design tools and capabilities have been democratized (everyone can now access design software, create content, etc.), the platforms and systems remain highly centralized within a few large companies—Meta, Google, TikTok, etc.

The early, messy days of the internet (Geocities, MySpace) have been largely tamed, which can make for better user experiences, but we also miss the wild creativity that came from having an infinite number of ways to express yourself online. Back then, your personal web page could be a nightmare of animated GIFs, visitor counts, and autoplay music—terrible for usability, but at least it was yours.

Today, we’re all posting in the same formats, and are subjected to the same algorithmic rules for engagement. The tools to create have never been more powerful or accessible, yet we’re increasingly creating within narrower and narrower boundaries defined by a handful of tech giants.

Visit our Substack to read the whole article: ⁠https://designbetterpodcast.com/p/the-brief-how-our-recent-past-should⁠

The Brief: How our recent past should prepare us for the age of AI

This is a preview of a premium Design Better episode. Visit our Substack to hear the whole interview, for bonus content, and more: ⁠https://designbetterpodcast.com/p/fitz-and-the-tantrums

With the 150th official episode of Design Better, we’ve got something special for you.

For many of us, if we haven’t had creative success by our 40’s, we feel like we may have missed the boat. But Michael “Fitz” Fitzpatrick of Fitz and the Tantrums didn’t achieve pop star status until he was well into his 40’s, and now that he’s in his 50’s he feels like he’s just getting started.

Haven’t heard of Fitz and the Tantrums? Yes you have...their hit single "HandClap" has rocked stadiums at sporting events around the world.

In our conversation, Fitz reveals how the band prototypes their live performances and why constraint has been essential to their creative evolution. He talks to us about the parallels of songwriting and product design, the importance of reading the room—whether it’s 50 or 50,000 people—and why the best performances, like the best designs, create space for the audience to become co-creators.

Fitz also opens up about how even after achieving his creative dreams, there was an emptiness that he struggled with, and where he found true happiness.

Bio

Michael “Fitz” Fitzpatrick (born Michael Sean Fitzpatrick on July 21, 1970) is a French-American musician, singer, and songwriter best known as the frontman and creative force behind the indie pop and neo-soul band Fitz and the Tantrums. Born in Montluçon, France and raised in Los Angeles, Fitzpatrick studied vocal music in high school and later attended the California Institute of the Arts, where he explored experimental film. Before forming his own band, he worked behind the scenes as a sound engineer, collaborating with producer Mickey Petralia.

In 2008, Fitzpatrick bought a used church organ for fifty dollars and wrote “Breakin’ the Chains of Love” that same night — the song that would inspire the creation of Fitz and the Tantrums. As lead vocalist and keyboardist, he helped the group rise quickly with their debut album Pickin’ Up the Pieces (2010), which drew praise for its blend of Motown soul, indie pop, and modern energy. Subsequent albums such as More Than Just a Dream and their self-titled 2016 release, featuring the breakout hit “HandClap,” cemented the band’s place in the modern pop landscape.

Fitz and the Tantrums: Finding your creative voice in your 40's and why success feels different than you think

Visit our Substack for bonus content and more:https://designbetterpodcast.com/p/bonus-episode-30-years-of-design

Today we celebrate 30 years of Wert&Co.—the quiet champions of design who have shaped our field by placing the brightest designers in roles of influence at brands that impact culture, commerce, and community.

Design Better is brought to you by Wix Studio, the most powerful web design platform for entrepreneurs, agencies, and creative thinkers. Learn more →

To mark the occasion, Design Better is live in New York City with an inspiring panel. We’ll look back at how design has shaped the world over the past three decades and look ahead to the essential role design must play as technology reshapes the human experience.

Our conversation begins with Paola Antonelli, Senior Curator of Architecture and Design and Director of Research & Development at The Museum of Modern Art. Paola is one of the most influential voices in contemporary design, exploring how design shapes culture, technology, and society.

We’re also joined by Mark Wilson, Global Design Editor at Fast Company. Mark covers the intersection of design, technology, and culture, bringing a journalist’s rigor and a designer’s eye to stories that reach millions.

In the second half of our conversation, we shift our focus to the present and future of design—the teams, the individual contributors, and the leaders who are navigating this evolution in real time.

Kate Aronowitz, and Meaghan Choi, and Mike Davidson are three leaders who have different perspectives on where design is headed, and what it means to build meaningful careers in this rapidly changing landscape.

Kate Aronowitz is a Design Partner at GV, where she helps companies of all sizes build design-driven cultures.

Meaghan Choi is a Product Designer at Anthropic, focused on developer experiences for emerging technologies like AI and cloud computing, including her work on Claude Code.

Mike Davidson is VP of Design and User Research at Microsoft AI, with more than two decades leading design at companies including Twitter, Disney, and ESPN.

Bonus Episode: 30 years of design with Wert&Co, live in NYC featuring Paola Antonelli, Mark Wilson,Kate Aronowitz, Mike Davidson, and Meaghan Choi

Visit our Substack for bonus content and more: https://designbetterpodcast.com/p/rewind-paola-antonelli

Design Better has been on the road recently, recording a live episode in Manhattan for design search firm Wert & Co’s 30th anniversary. Guests for the episode included Paola Antonelli (senior curator in the Department of Architecture and Design at MoMA) Mike Davidson (VP of Design and User Research at Microsoft AI), Kate Aronowitz (Design Partner at Google Ventures), Meaghan Choi (Product Designer at Anthropic), & Mark Wilson (Global Design Editor at Fast Company).

While Aarron and I are catching up from travel, and as a lead-in to the live episode airing next week, we’re rewinding to our interview with Paola Antonelli. We hope you enjoy the episode.

And if you haven’t checked it out yet, did you know you can save over $1600 on popular productivity tools and design and AI courses with the Design Better Toolkit? Just head over to dbtr.co/toolkit to learn more.

***

The Museum of Modern Art brings to mind images of Van Gough’s Starry Night, Salvador Dali’s Persistence of Memory, and Andy Warhol’s Campbell Soup Cans. But thanks to Paola Antonelli, senior curator in the Department of Architecture and Design, MoMA exhibitions also encompass the role design has played in shaping culture and the human experience.

We talk with Paola about how we can look at digital design through a historic lens, some of the most important design movements in the past 100 years, and how the creative process has evolved through these different movements.

We also talk about the history of the @ symbol, why craftsmanship is necessary to experimentation, and some of the current challenges in design education.

We hope you enjoy this episode which is a part of our series on design history, with upcoming episodes on typography with Jonathan Hoefler, and the history and philosophy of design with Professor Barry Katz.

Paola Antonelli joined The Museum of Modern Art in 1994 and is the Museum’s Senior Curator in the Department of Architecture and Design, as well as MoMA’s founding Director of Research and Development. Her work investigates design in all its forms, from architecture to video games, often expanding its reach to include overlooked objects and practices.

An architect trained at the Polytechnic of Milan and a pasionaria of design, Antonelli has been named one of the 25 most incisive design visionaries in the world by TIME magazine, has earned the Design Mind Smithsonian Institution’s National Design Award, has been inducted in the US Art Directors Club Hall of Fame, and has received the AIGA (American Institute of Graphic Artists,) the London Design Medal, and the German Design Award, among other accolades.

Rewind: Paola Antonelli: How design shapes culture

This is a preview of a premium episode on Design Better. To listen to the whole episode, head to our Substack: https://designbetterpodcast.com/p/keith-sawyer

The key to creativity isn’t about having brilliant ideas in isolation, but about cultivating our ability to observe the world around us, and make the intuitive leaps that connect disparate ideas. Keith Sawyer, a creativity researcher who spent over a decade interviewing hundreds of art and design professors and students to understand how creative professionals learn to see—and think—differently, writes about this in his new book, Learning to See.

Keith brings a unique perspective to creativity research. A jazz pianist turned MIT computer science graduate, he designed video games in the early 1980s before pivoting to study the science of creativity under the legendary Mihaly Csikszentmihalyi at the University of Chicago. His latest book challenges common myths about the creative process and reveals why the most successful artists and designers don’t start with a vision—they discover it through an iterative dialogue with their work.

In our conversation, Keith shares insights from his research on improvisational creativity, explains why ambiguity is essential to the creative process, and discusses how AI is reshaping—but not replacing—human creativity.

Bio

Dr. Keith Sawyer is the Morgan Distinguished Professor in Educational Innovations at the University of North Carolina at Chapel Hill. Dr. Sawyer is one of the world’s leading creativity researchers. He’s studied jazz ensembles, Chicago improv theater, children’s play, and creative classrooms. He’s published 20 books, including Group Genius: The Creative Power of Collaboration and Zig Zag: The Surprising Path to Greater Creativity.

Books & Links mentioned:

 
The Science of Creativity, Keith Sawyer’s podcast (and his Substack).

 
Flow and Creativity by Mihaly Csikszentmihalyi:

 
Creative Confidence by Tom Kelley and David Kelley

 
The Artist’s Way by Julia Cameron

The Creative Act by Rick Rubin

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Saily: Saily solves the hassle of staying connected while traveling by offering affordable, data-only eSIM plans that activate seamlessly when you arrive—no physical SIM swap needed. Plus, it layers in built-in security features like ad blocking, web protection, and virtual location for safer browsing on the go.

Keith Sawyer: Become more creative by learning to see

Visit our Substack for bonus content and more: https://designbetterpodcast.com/p/jae-park

As designers and creatives, many of us spent years of our career looking at blank canvases and attempting to find the best place to start solving the problems in front of us. Now that AI can churn out designs and imagery, not to mention writing, video, and even music in seconds, what are we losing from the friction that is being removed from the creative process?

Our guest today, Jae Park, VP of Digital Product Design at Ford's Electric Vehicle Digital Design division, posed this question to us. Jae previously led design teams at Microsoft, Amazon, and Google—companies that epitomize the "move fast and break things" mentality of Silicon Valley. But he questions whether our obsession with speed is actually how we want to live.

We talk with Jae about the "valley" between disruptions, why Ford's pivot to affordable EVs matters for American manufacturing, how Gen Alpha will reshape our expectations of vehicles, and why the Socratic method might be more important than any design tool in the age of AI.

Jae also discusses what might be his most complex challenge yet: helping a 120-year-old automotive icon compete in an era where, as he puts it, "the phone and the car are becoming the same thing"—at least in rapidly evolving markets like China.

Bio

Jae Park is a design leader with a track record of building teams and driving innovation at the intersection of business, technology, and human needs. At Ford’s EVDD group, he leads cross-functional designers shaping the company’s digital product strategy to make mobility a fundamental right while advancing sustainability. His career includes inspiring new ways of working at Google, creating the award-winning Metro design system at Microsoft, and leading the invention of Amazon’s Echo Show, which defined a new multimodal product category.

Guided by a belief that innovation begins with people, Jae’s leadership style emphasizes curiosity, collaboration, and empowerment. He nurtures diverse teams of designers and technologists, ensuring they have the perspective and support to create products that serve humanity and improve the world at scale.

***

Visiting the links below is one of the best ways to support our show:

Saily: Saily solves the hassle of staying connected while traveling by offering affordable, data-only eSIM plans that activate seamlessly when you arrive—no physical SIM swap needed. Plus, it layers in built-in security features like ad blocking, web protection, and virtual location for safer browsing on the go.

Download their app on your phone and you can buy an eSIM before you fly so you’re connected the minute you land. And if you’re traveling between countries, you only need one eSIM. You can get a global or a regional plan and travel with the same eSIM plan.

Get an exclusive 15% discount on your first Saily data plans! Use code DESIGNBETTER at checkout. Download Saily app or go to ⁠https://saily.com/designbetter⁠

Jae Park: Designing a new generation of vehicles at Ford, and why friction matters in the creative process

This is a preview of a premium episode. To hear the full episode, head to our Substack: ⁠https://designbetterpodcast.com/p/astro-teller-and-ivo-stivoric-why⁠

When a company talks about taking a “moonshot,” it often ends up being something trivial: a new emoji keyboard, or delivering a pizza in less than 30 minutes.

But at X, the Moonshot Factory, which is part of Google, they’re tackling some of the world’s thorniest problems: sustainably feeding the world’s population, climate change, education, and much more.

Today we’re speaking with Astro Teller, Captain of Moonshots, and Ivo Stivoric, Vice President at X. Astro has a PhD in artificial intelligence from Carnegie Mellon and wrote a prophetic 1997 novel about AI called Exegesis. He's the grandson of Edward Teller of Manhattan Project fame, but his own legacy is built on creating protected spaces where multidisciplinary teams can tackle humanity's biggest challenges—from self-driving cars to internet access delivered by balloons.

Ivo leads a portfolio focused on climate, sustainability, and social justice. A designer by training who cut his teeth in the early days of wearable computing at Carnegie Mellon's Engineering Design Research Center, Ivo brings a unique perspective on bridging human needs with breakthrough technology. Together with Astro, he co-founded BodyMedia, one of the pioneering companies in wearable health monitors, which was later acquired by Jawbone.

We chat with Astro and Ivo about how they've maintained one of tech's longest creative partnerships, why moonshots require unlearning everything you know about building products, and how they're using their "moonshot factory" push the boundaries of what's possible when you combine emerging technology with empathy for human needs.

Links

https://x.company/projects/tidal/

https://x.company/moonshotpodcast/

***

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

***

Visiting the links below is one of the best ways to support our show:

Saily: Saily solves the hassle of staying connected while traveling by offering affordable, data-only eSIM plans that activate seamlessly when you arrive—no physical SIM swap needed. Plus, it layers in built-in security features like ad blocking, web protection, and virtual location for safer browsing on the go.

Download their app on your phone and you can buy an eSIM before you fly so you’re connected the minute you land. And if you’re traveling between countries, you only need one eSIM. You can get a global or a regional plan and travel with the same eSIM plan.

Get an exclusive 15% discount on your first Saily data plans! Use code DESIGNBETTER at checkout. Download Saily app or go to ⁠https://saily.com/designbetter⁠

Astro Teller & Ivo Stivoric: Why moonshots require unlearning everything you know

Find bonus content and more on our Substack: https://designbetterpodcast.com/p/henry-modisett

AI isn’t just another layer in our digital toolkit—it’s reshaping the tools themselves, and in the process, transforming how we work, think, and solve problems.

Henry Modisett, VP of Design at Perplexity, is in a unique position to challenge many of the norms that have shaped tech for some time now. Perplexity just released a beautiful new browser called Comet that puts AI at the heart of the user experience. We have been thoroughly impressed with it all ready.

As a designer with a computer science background, Henry takes a unique approach to his work. Rather than designing in Figma like most of us mortals, he and his team design in React, building working versions of interfaces so they can use it while they shape it.

Henry shares how his team approaches the design of AI-native products, and why traditional UX patterns often fall short in this new landscape. We explore the role of curiosity in AI interaction, how transparency and trust are earned (not assumed), and why embracing ambiguity might just be the most human-centered design move of all.

By the way, you may have heard that we just launched the Design Better Toolkit, a collection of resources we love and use regularly. The Toolkit gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Perplexity just happens to be a part of this bundle. You’ll get 6 months free of Perplexity Pro (an $180 value), as well as credits and discounts on tools like Airtable, Read AI, and other tools, and courses like Prototyping with Cursor and more. To get access you’ll need to be a Design Better Premium member at the annual subscription level. Visit dbtr.co/toolkit to learn more.

Get an exclusive 15% discount on your first Saily data plans! Use code DESIGNBETTER at checkout. Download Saily app or go to https://saily.com/designbetter

Henry Modisett: Perplexity’s VP of Design on embracing ambiguity and leading with curiosity

This is a preview of a premium episode on Design Better. Head to our Substack to get access to the full episode: https://designbetterpodcast.com/p/elizabeth-lin

Have you played around with Cursor? If not, it’s time. Designers with no coding skills are passing Cursor Figma files and getting working apps out the other side. And if you have no design, you can just prompt this AI powered development environment to get a solid prototype of your idea.

Elizabeth Lin, founder of Design is a Party, recognizes that Cursor is going to expand the capabilities of designers. She’s built a course that introduces designers to Cursor and challenges you to build while you design.

We talk with Elizabeth about how she's using AI tools like Cursor to help designers prototype faster than ever before, why she thinks now might be the perfect time to try something new in your career, and what's missing from traditional design education. Elizabeth also shares what she's learned about "vibe coding," why debugging is the hardest skill for new students to master, and how she's building a business around the idea that learning should feel more like a party than work.

By the way, you may have heard that we just launched the Design Better Toolkit, a collection of resources we love and use regularly. The Toolkit gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

One of Elizabeth’s courses, Prototyping with Cursor, just happens to be a part of this bundle. You’ll get $100 off her course, as well as a $500 credit towards Airtable, discounts on Read.ai, Perplexity, Miro, and other tools, and discounts on other courses from platforms like ShiftNudge. To get access you’ll need to be a Design Better Premium member at the annual subscription level. Visit dbtr.co/toolkit to learn more.

Bio

Elizabeth is a design educator with 10 years of experience whose love for design began in the early internet days of Neopets, creating playful graphics and websites with tools like MS Paint. She went on to study computer science at UC Berkeley, where she discovered a community of design enthusiasts and began teaching her first course on Illustrator and Photoshop as a sophomore. That experience sparked a lasting passion for teaching, which she continued to pursue through workshops and courses during her time at Berkeley.

After graduating, Elizabeth worked as a product designer at education-focused companies like Khan Academy and Primer, designing tools for teachers and students while expanding her perspective on learning. In 2023, she founded Design is a Party, an alternative design school that reflects her playful yet rigorous approach to teaching. Since then, she has launched a two-course series on visual design, developed portfolio-building resources, and led workshops to help the next generation of designers grow their craft.

Elizabeth Lin: Rethinking design education in the age of AI

Show notes: https://designbetterpodcast.com/p/detria-williamson
In an interview with the Wall Street Journal last year, Detria Williamson, former Chief Marketing Officer of IDEO, said that “diversity can be engineered and inclusion cannot.”
In this episode, we dive deeper into that statement, and also ask Detria what roadblocks she encountered over the course of her career—from working as a head of marketing in Dubai, to her most recent role at IDEO. We also ask her about what it means when design becomes commoditized, and how remote and hybrid work impact inclusivity.
Bio
Detria Williamson is an internationally recognized digital marketer, who for over 20 years has helped category-leading companies become experience-led and content-driven. Informed by her experiences living and working from the U.S., London, Singapore, and the Middle East, she created the ICX (inclusive customer experience) approach, enabling visionary leaders to embrace inclusivity as an end-to-end element of their business ecosystem.

Detria Williamson: IDEO CMO on making collaboration more inclusive

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