Ryan Stephen - Creativity, Storytelling, and Prototyping Playful Ideas

Summary

Dive Club 🤿 – Episode Summary

Episode Overview

Title: Ryan Stephen - Creativity, Storytelling, and Prototyping Playful Ideas
Host: Rid
Guest: Ryan Stephen (Designer, Microsoft; Twitter design experimenter)
Date: February 12, 2026

This episode dives deep into the creative and prototyping process of Ryan Stephen, whose playful, high-fidelity design experiments have captivated designers across the web. He and Rid discuss the intersection of creativity, spatial computing, rapid prototyping, storytelling, and the evolving toolkit of modern designers. The conversation traverses Ryan’s personal workflows, tools of choice, philosophies for ideation, and the growing value of visibility and sharing as a designer.

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Key Discussion Points & Insights

1. Making Ideas Feel Real

• [00:00] Ryan emphasizes the thrill and importance of designers’ ability to "make our ideas feel real," blending current tech with imagination for what's next.
  • Quote: “We have this opportunity to make our ideas feel real. And some of that is with the technology that's around us today, and some of that is looking off into the distance and imagining what is coming next.” (Ryan Stephen, 00:00)
• Importance of both practical and speculative design to stay adaptable as technology shifts.

2. Prototyping Playful Spatial Concepts

• [00:56–07:21] Ryan shares several experiments:
  • Compass in AR: Overlaying a compass in real-world video using After Effects and rotoscoping.
    Goal: Create a moment where viewers ask, "Wait, is this real?"
  • Spatial Desktop: “What if folders were physical objects you could fling around?” Built in Blender and Vision Pro’s screen share; playful, exaggerated 3D UX metaphors.
  • Hand Map Shader: A spatial map projected on the back of one’s hand—leveraging a shader and Vision Pro screen recording for playful, conceptual impact.
    • Quote: “Nothing about this is legible or anything, but it’s a really playful idea, and a shader was the best way.” (Ryan Stephen, 05:57)
• The tool informs the idea as much as the idea dictates the tool; quick, minimal learning to achieve convincing results.
  • Quote: “The tool is informing the ideas as much as my idea is informing what tool I use. It's like a two way street.” (Ryan Stephen, 03:05)
• Debunking the myth that spatial design requires heavy tools—sometimes just drawing over a phone video is enough.

3. From Notes to Prototypes: The Workflow

• [08:14–14:35]
  • Capture Everything: Ryan keeps a rolling phone note with thousands of playful, often absurd, raw ideas (“What if your mail app was a hot air balloon?”).
  • Low-fi Sketching: Initial explorations happen in Figma using mood board pieces, rough images, or random sketches; not all assets survive into the final product.
  • Form Study: He explores exaggeration vs. practicality—some ideas are near-satirical, others could become actual products.
  • Prototyping Blend: Builds custom tools (e.g., using Xcode + Blender for a “music player crank” prototype), focusing on what’s fastest to achieve the “suspension of disbelief.”
    • Quote: “What matters is the idea, really.” (Ryan Stephen, 15:47)
• Continual cross-pollination of video production, code, and physical device metaphors.

4. Collaboration and “Super Random” Projects

• [16:07–17:55]
  • Discusses "Then Gen," an interactive project with Chandler Simon (their duo "Super Random") that lets users blend image prompts using a Venn diagram interface.
    • Quote: “People could actually step into this idea in a different way than a video on Twitter.” (Ryan Stephen, 17:15)
  • This illustrates the spectrum from pure concept demos to “real” interactive tools.

5. The Impact of Sharing & Visibility

• [18:09–22:47]
  • Sharing ideas on Twitter has built Ryan’s network, gave him friends/mentors, directly impacted his career, and enhanced his creative practice.
    • Quote: “Professionally, prototyping is such an awesome way to test ideas or convince leadership...” (Ryan Stephen, 19:37)
  • Modern portfolios: playful, experimental side projects are now a major “green flag” for hiring.
  • Sharing is “all upside, with almost no downside” ([32:56]): the worst that happens is nothing, and you always learn for next time.

6. Ideation Techniques and Creative Process

• [22:47–27:45]
  • Capture Outlandishly: Notes are intentionally playful and not tied to current tools or feasibility: “I’ll work backwards later.”
  • Crazy Eight Sketching: Repurposes the “Crazy 8s” exercise for imagination, not problem-solving. Keeps all sketches for future reference rather than discarding.
    • Quote: “I use Sharpie because I don’t want the details to be too specific.” (Ryan Stephen, 25:17)
  • Time-boxing: Limits ideas to a day or two of work to keep momentum, avoid burnout, and focus fidelity on what matters most.
  • Pushing the Envelope: Avoids repeating idea forms, blending new metaphors, gestures, or mediums with each project.

7. Motivation & Energy

• [27:45–29:22]
  • Internal energy in the process itself—rush of learning, not the outcome.
  • Finds additional inspiration from collaboration; creating “fake studio” projects with friends helps bring in fresh perspectives and skills.

8. Growth as a Storyteller

• [35:39–39:21]
  • Tailoring Story to Audience: Different levels of storytelling for team feedback vs. leadership buy-in.
  • Quick, high-fidelity prototypes shortcut context-setting: prototypes cut through “10 slides of explaining.”
  • Shift from “just keep fidelity low” to “effort fidelity”: make the right details feel real—gesture, IA, or language—depending on what will sell the idea.
    • Quote: “What aspect of the idea needs to feel real? ... Maybe the only thing that needs to be real is the language.” (Ryan Stephen, 38:42)

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Notable Quotes & Memorable Moments

On tool-driven creativity:

• “The tool is informing the ideas as much as my idea is informing what tool I use. It's like a two way street.”
  — Ryan Stephen, [03:05]

On prototyping to drive belief:

• “The point is that end expression that makes you go, wait, is this real? And then respond to it in a really genuine way.”
  — Ryan Stephen, [01:43]

On playful experimentation:

• "I don't know any other way of working, but I think if you're zigzagging between solving really hard problems and just being almost unrelentlessly creative, it creates the best work in both of those worlds.”
  — Ryan Stephen, [12:38]

On sharing and visibility:

• “Visibility is a pretty important currency that people don't think about too much... That's way more powerful than a portfolio website because instead of the work statically being somewhere that you actively have to reach for, it's just presented to you.”
  — Ryan Stephen, [31:43]

On the safety and value of posting:

• “The worst case scenario is nothing happens. Actually, it’s better than nothing happens. You still learned something... and it gives you a starting place.”
  — Ryan Stephen, [33:27]

On tailored storytelling:

• “How you tell a story when you’re wanting feedback from a design team is super different from the type of story you would tell to a leader...”
  — Ryan Stephen, [35:59]

On fidelity in prototyping:

• “What I like to think about is effort fidelity more than visual fidelity. So if I can make something in a day...that fidelity is what matters, not necessarily how awesome the rectangles move around the screen.”
  — Ryan Stephen, [38:01]

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Important Segments & Timestamps

| Segment | Topic | Timestamps | |---------|-------|------------| | Opening Theme | What excites Ryan about design | [00:00–00:22] | | Spatial Design Explorations | AR compass, spatial desktop, hand map | [00:56–07:21] | | Tools & Process | Minimum learning for prototyping, blending filmmaking/code | [03:05–04:36], [13:34–14:35] | | Ideation Workflow | Idea capture, playful notes, Crazy 8s | [08:14–10:02], [23:10–25:17] | | Stake of Sharing | Public posting, career impact, “all upside” | [18:09–22:47], [31:43–34:38], [32:56–33:27] | | Collaboration & Super Random | Co-creation with Chandler Simon | [16:07–17:55], [28:04–29:22] | | Storytelling & Fidelity | Adapting narrative for audience, “effort fidelity” | [35:39–39:04] | | Motivation & Energy | Why keep prototyping playful ideas | [27:45–29:22] |

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Tone & Takeaways

• Vibe: Energetic, approachable, relentlessly playful yet deeply practical.
• For Designers: Permission to be weird, playful, and bold; share your work even if it’s unfinished or silly. Daring experiments are now a portfolio superpower, and social visibility is an underrated career accelerant.
• For Teams: Encourage high-frequency, low-stakes prototyping and storytelling internally—the line between design and code, play and product, is rapidly fading.

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TL;DR

Ryan Stephen’s creative practice is a blend of impulsive ideation, low-friction prototyping across many tools, and bold, public storytelling. It’s clear that in today’s design landscape, playful experimentation, visible sharing, and the ability to “make ideas feel real” are currency for both personal growth and professional opportunity. Whether for Twitter or within your team, bring your experiments to life, and don’t let the fear of crickets hold you back—the upside has never been greater.

Transcript

[Ryan Stephen]

I think part of what is really exciting about being a designer always for me, is that we have this opportunity to make our ideas feel real. And some of that is with the technology that's around us today, and some of that is looking off into the distance and imagining what is coming next.

[Rid]

Welcome to Dive Club. My name is Rid and this is where designers never stop learning. Today's episode is with Ryan Stephen, who's a designer at Microsoft. But the reason that I wanted to talk to him is he has some of the most impressive design experiments on all of Twitter. So he's going to give us a behind the scenes into his ideation process, all of the different tools that he uses and how he thinks about effective storytelling as a designer. There are some seriously impressive concepts in this demo. So let's dive right into some of his spatial experiments.

[Ryan Stephen]

I think spatial ideas are really cool because they exist, exist in the world. And a lot of the technology really hasn't caught up quite yet. Like, we've all seen the bulky headsets, we've seen some experiments with glasses, but it's really fun to, as a designer, make ideas feel real and imagine what it likes once those constraints come in towards today. And so this is a really simple idea of like a compass laid out around with your friends. Basically what you're seeing on the right is some BTs of after effects where I was rotoscoping out. Basically this is footage that was shot on phone in a park somewhere. And then there's a simple pass of rotoscoping. It's a film technique, if you haven't heard of that before, for visual effects. And what that allows us to do is composite people on top of elements that we're placing in the scene. So, you know, that foot can actually go on top of that compass. Blurred view, really the point is the idea and the point is that end expression that makes you go, wait, is this real? And then respond to it in a really genuine way. So the next one I had was actually on the other end of that same gradient. This was called Spatial Desktop. The end video is on the left here. And basically the idea was, what if folders actually were physical in spatial world and you could fling them around. It's a very playful idea. It's super exaggerated. Like you can see them bouncing off the couch and different things like that. And what I wanted to show with this example was you can see on the right, I'm using blender to make this basic model. And then actually how this is working is this is just a screen Share on Vision Pro. So it's actually just taking the model and making a basic physics scene to be able to fling these 3D objects around across the scene.

[Rid]

Had you built anything in the Vision Pro world before? Like this is such a black box for me. Like I look at that and I'm like, I get you got the blender model, you're able to insert it. I've never even scratched the surface of this. I'm kind of just curious what goes into this.

[Ryan Stephen]

It's funny because it's kind of almost the same thing as like I don't know after effects rotoscoping to now I do. I just slowly, slowly started getting whatever I needed to make the minimum idea. I'm sure this actual example started off in my head as or on my sketchbook as more grandiose. I'm sure I had ideas of like windows coming in and everything. But it's kind of that thing where the tool is informing the ideas as much as I'm idea is informing what tool I use. It's like a two way street. And so once I got this and I started realizing I'm done, like that's the idea. They bounce around. Like that's it, it's over. So that happens more than you think with some of these things too because you can start really grand. But you know, if you're working with the tool and really letting it inform you, then you can, you can be done faster than you think.

[Rid]

I've even noticed that more as I'm doing more of my like design explorations in code where I get to focus more on interaction design earlier on and the tool is kind of informing where I end up because I might have like loose ideas of what I kind of want. But then I see something and I'm like, oh, that's so interesting. And even just this morning I made a thing where I was like, oh yeah, that's it. I'm not even going to do the thing that was originally in my head. That's just it. Like I like that more and I'm kind of just wrapped up and it took me somewhere I didn't quite expect. So I'm feeling that like almost loss of control. But you have more of these creative happy accidents and the finish lines are not quite where you would expect, but it all ends up good.

[Ryan Stephen]

I think that's the best case scenario for, you know, using mo tools but not getting overwhelmed by them. You know, like using them to drive your decision.

[Rid]

Real quick message and then we can jump back into it. Big News animations just launched in Maubin, so you can see how world class apps use motion to guide, delight and create seamless experiences. It's just another reason why Mabin is an absolute cheat code for your entire design team. We use it all the time and I can't wait to start sending animation ideas to the rest of the team. So head to Dive Club Slash Mobin to check it out today. That's M O B B I N. You probably already know about paper shaders. It feels like every time I open up Twitter, I see somebody creating some new beautiful halftone effect. But did you know paper uses real CSS as you design? That means your layouts are already code, so you can just one click, copy as, react and paste into your coding agent of choice. Paper is shipping more of their core editor every single week. And it's becoming so clear to me that this is what the future of design tools should look like. So if you haven't tried it yet, head to Dive Club Slash Paper Paper and start designing today. Okay, now on to the episode. Do you have more spatial explorations that you've been doing? This is pretty.

[Ryan Stephen]

I got one more I wanted to share. There's a whole bunch more, obviously that I've been working on. But if we're thinking about this gradient of like, filmmaking to code and like, all we want to do is make the idea feel real, sometimes there's a need to go on the top end of this. So this is actually using a shader. And so the idea here was really simple. It's. I know this place like the back of my hand. And so having the spatial map actually on the back of your hand, like that metafloor saying, that's sick. And so to make this feel real, I thought it would be really fun if the city, little landscape I had, obviously it's not functional, right? Like, nothing about this is legible or anything, but it's a really playful idea and a shader was the best way. Again, this one's screen recorded in Vision Pro. And to literally do this, all I'm doing is that same process. What's the bare minimum I need to learn to make this feel real.

[Rid]

The fact that all three of these examples have a different tool on the right side of the screen is so inspiring to me. I love it.

[Ryan Stephen]

It's the Wild West, I think spatial especially you can lean into doing whatever. Like sometimes I'll literally just film a video on my phone and I'm just drawing right on top of it. In Sigma or Illustrator or whatever. It doesn't even need to be one of these heavy tools necessarily. I think that's kind of a myth of some of these, like, spatial videos you might be seeing.

[Rid]

And you don't do anything related to spatial in your actual day job, right?

[Ryan Stephen]

No. I think part of what is really exciting about being a designer always for me is that we have this opportunity to make our ideas feel real. And some of that is with the technology that's around us today and. And some of that is looking off into the distance and imagining what is coming next. And I think there's a real practical part of that too, which is, of course, in five or 10 years, I want to be able to still express my ideas on what other medium we're all interacting with every day. Right. That's kind of the incentive is. Yes, I think this is a really fun emerging space to play in, but it's also just really empowering, I think, to be able to know how to shape these materials that are coming in, you know, several years maybe.

[Rid]

How quickly are you acting on an idea? Like, do you have a notepad of all of the ideas? And you're like, I want to build something today and pick one, or is it like, I have an idea and I just got to take the first few steps as quickly as possible? Where do you fit on that spectrum?

[Ryan Stephen]

I think both happen. I keep a rolling note on my phone that is literally just a text note that's got thousands of little things. A certain idea might not be fitting into the current project that I'm working on at work or something like that. And there's always this desire, I think, to scope down and find the MVP for whatever it is you're working on. And I think that's valid. Like, every idea should not be shipped. But I think there's also this other part of it where I'm wanting to be able to express the ideas I have. And I'm not always necessarily inspired the same way ebbs and flows. So it's awesome to be able to have a long scrolling note on my phone that I can come back to and pick up on a Saturday or, you know, after work or something like that. So that's kind of a little bit about the, like, idea process. A lot of the times they are just little text ideas that are as silly as what if your mail app was a hot air balloon? Or what if your notifications were laid across your desk like little speech bubble? You know, they can be really playful and out there. What I've had on my note app Forever is being able to drift around your feed so you can actually like make turns and stuff. What that looks like, I have no idea. But usually what the next step is for an idea. So the one you're looking at right now is a music app. As a crank, I remember seeing this on Twitter.

[Rid]

It's cool to see all the different sketches behind the scenes.

[Ryan Stephen]

Yeah. So kind of the chronological top left to bottom right is like the flow that I did real. And I started with just crank. That was the idea. It was just, I want to make a crank and that's it. And I. I think that, you know, when you're expressing these, like, playful ideas, it can be as simple as that. And I kind of worked backwards. You can see me kind of iterating into, oh, what if there was a music player? Oh, it makes sense to actually maybe adjust the speed or volume or something like that. And so this all just happens in Figma usually. And I'm using image generation tools. I'm bringing in sketches that I have. It's extremely low fi because usually I'm moving to either filmmaking or code to make the actual end product. So these are almost like just lightweight sketches to be able to kind of like finish my ideas.

[Rid]

I guess for something like the crank, I mean, you have a few different variations of it. Is that something you're generating? Are you creating that? Is that just an image that you grabbed on Google Images and you're using it like as a placeholder right now?

[Ryan Stephen]

Yeah. A lot of these, like those waveforms in the bottom or different things like that, Those might be from arena or somewhere online or some mood board, and they'll never ever make it into the final idea, but they're just a way to feel out the form. And I think a part of doing this too, is exploring how exaggerated I want to be in that particular idea. Like, I think there's some that are maybe on the teetering almost I could use this, maybe I could see how this would be really delightful. And some that are much more almost like satire, where they're exaggerating some idea that people have been sharing or, you know, something that's of the moment. So that's another part I'm kind of working through as I'm doing, like these form explorations.

[Rid]

Yeah, that spectrum is so fascinating to me because I think the things that I find most interesting are slightly more towards the exaggerated end because that's where it's like, really creative. You know, I don't know so much of design, at least my practice of design is derived from honestly solving problems. Right. Like improving flows and like all of it's very valid and real and necessary. And yet it's that kind of satirical and that is so out of the box, so deeply creative and frankly is just not somewhere where I play. So I love watching people play. Like yourself. Like, your feed is so fun for me to scroll through for that reason.

[Ryan Stephen]

I don't know any other way of working, but I think if you're zigzagging between solving really hard problems and just being almost unrelentlessly creative, it creates the best work in both of those worlds.

[Rid]

Yeah. I'd imagine this feeds back into your work at Microsoft, even though it has very, very little overlap.

[Ryan Stephen]

Yeah, you'd be surprised. So I wanted to show the rest of this crank idea while we're talking through it. So, you know, just to feed it through the thread. Maybe this started as a note. Maybe we're sketching forms in here, but what something I found myself doing more and more and happened with the crank is making bespoke little vibe coded tools that help me tune and actually find the right final thing. That feels awesome. So what you're looking at here is the final video on the left, and then this is Xcode on the right.

[Rid]

Tool number four. Yeah, I'm counting.

[Ryan Stephen]

And really there was probably a bunch of ways I could have made the crank, and there's probably more correct ways I could have made the crank. But the easiest way I could make it, or the fastest was actually just rendering the crank in blender. And so what you're looking at is each crank frame is playing flame by frame, powered by a swift prototype, basically.

[Rid]

Oh, interesting.

[Ryan Stephen]

That lets you blend tools. And then what you're noticing, what the actual tool is doing on the right is I made a simple little tool that can speed up or speed down how fast those flames playback. So it lets me fake having an ease curve at the beginning. So it up speeds, speeds up, and then it slows down and it's actually just playing the flames faster or slower, which is pretty fun.

[Rid]

Oh, now I get it. Yeah, I wasn't sure what that number was up top now, but these, you literally have 250 little frames.

[Ryan Stephen]

Yeah.

[Rid]

That you're just moving in between. Wow, that's fascinating. And it feels so fluid too. On the left.

[Ryan Stephen]

If you look at it really hard, you can tell it's dropping flames as it leeches the end. But it, you're, you know, it suspends disbelief just the same. So it works great.

[Rid]

Yeah. It comes back to that phrase Again, suspends disbelief. I get it now.

[Ryan Stephen]

Yeah, yeah, yeah.

[Rid]

How much of a coding background do you have? Like, are you handwriting any of this? Is this all just with Claude? Talk to me a little about that part.

[Ryan Stephen]

I'm using Claude Code, GitHub, Copilot, switching between all of them usually. I actually found design through making apps back in, like 2014 or so. And again, it was just a way to express ideas. Like, I could make something and you could hold it. And that kind of spirit has stuck with me even if I've learned, like, the professional craft of design. And so, yeah, I still blend those worlds. I don't know any other way to do it.

[Rid]

It's a fun reflection of, I think, in many ways where the world is headed or just have less clear lines between the two. And, like, you probably don't even really assign too much value in having one of those titles, you know, it's like, well, I just. I just make things and sometimes it's code and sometimes it's video and, you know, just a creative builder. That's a phrase I've been using more recently. And you definitely fall into that category, which is a high compliment.

[Ryan Stephen]

Appreciate it. Yeah, I think Designer, prototyp, maker. We're still finding the right words, I think. And it all comes back to the same thing of I can play two different videos and there can be completely different tools, but what matters is the idea, really. The other example that I wanted to.

[Rid]

Share, I love this one.

[Ryan Stephen]

You might have seen this. Yeah. So this is called Then Gen. And before I get into the idea, what Then Gen is, is it's a collaboration with a very talented designer and maker, Chandler Simon. And together we have this duo called Super Random. And we had this really idea in a day of what if then diagrams were a way to make images and so you could scroll these things on the left and right. And then you get this blended image that's a blend of your prompt and these different modifiers in the middle.

[Rid]

I remember when you published this and I just sat there and just played with it for like 15 minutes. Like, it's really. It's fun and it's an idea where, I don't know, it's like pretty different than some of the other things that you showed where there's like, there's technical hurdles that you kind of have to overcome or learning new tools that you have to overcome. Whereas with an effective plan mode and an ability to articulate what I actually want, I could almost one shot this thing. Yeah, that's not the hard Part for this concept, it's just a really clever idea, and the concept itself is kind of where the magic happens.

[Ryan Stephen]

Part of what was exciting about this one too, is that people could actually step into this idea in a different way than a video on Twitter, and they could actually experiment with it as a tool. And so I think that's something that's really exciting, is always thinking about, like, how real do I want to make this idea feel? And sometimes if you push those upper limits, it can be actually something that people can hold and interact with themselves or make images.

[Rid]

That's one of my favorite parts about Twitter right now, is you'll get, like, a concept that's very cool, and then it'll just be like a random Vercel link underneath. Yes. Like, this is. This is a fun era to be on the Internet, building and sharing things.

[Ryan Stephen]

And then sometimes I'll make things, and it's actually not worth it to make it all the way real. And then I revert back to a filmmaking tool or something like that. So, yeah, it's all over the place in between. But this was a really fun one to work on.

[Rid]

I've been designing products every day for the last 15 years, but in the last six months, everything has changed. With AI in the mix, I'm cranking out ideas faster than ever. But none of that matters if I can't get the feedback that I need to get the team aligned. And right now, getting async feedback still kind of sucks. So I'm building the product I've always wanted, and it's called Inflight. I use it every day to share ideas and get feedback from the team, and it's totally changing the way that I work. So I'm excited to show you. Right now I'm only giving access to Dive Club listeners, so head to to Dive Club Inflight to claim your spot. I shared a little bit about my coding workflow with Conductor last week and had, like, three comments with very specific pieces of feedback where they're like, hey, if you did this, it would help you do X, Y, Z. And I'm like, oh, wow. I didn't. I didn't even realize that. And now it's changed how I approach the entire practice, and that keeps happening. Like, I'm able to look back so clearly over the last five years of honestly just hitting send on tweet and you just learn a little thing or you're introduced to a slightly different concept. I'm curious how much that resonates for your own journey. As somebody who I Don't know how long you've been putting things out there, maybe like a couple years or something like that. But are you able to look back and see the impact that sharing online has had on career, but even more broadly, you know, just life as a creative.

[Ryan Stephen]

Yeah, 100% first. And maybe most important is I've made so many amazing friends and mentors from that broader community. I think that can't be understated. And it's also just so much more fun to do it that way. But definitely, I mean, professionally, prototyping is such an awesome way to test ideas or convince leadership or run a research study. And I think you're starting to see more of that across the industry. I'm really excited to see how these tools keep shaping that. So that's maybe one of the most obvious translations of like playful ideas into like real impactful, you know, career outcome. But I think there's less obvious ones where really just the practice of day in, day out zigzagging between playful ideas and like really practical functional product making, it creates so many like network effect connects between different ideas, whether it's a certain animation playing a certain way, maybe it's something as high level as like a certain concept, like, hey, this idea, the Venn diagram, maybe that makes me think about image generation differently. And maybe I start to really question some of the core fundamental ideas I was having when I put my serious hat on, which was important. So I think that's really been another key area. It's just, it's allowed me to question maybe decisions that I wouldn't have otherwise because I took the constraints off for a second, which is pretty powerful.

[Rid]

I love the idea of taking the constraints off. And it even ties back to something that I've kind of been noticing as a trend in these conversations where design leaders, when they're trying to figure out, you know, what talent do we want to bring into this company? Who do I want to surround myself with? They're placing a lot more weight on these experiments. And if you have a little playground of experiments on like your portfolio or your website, it's a pretty big deal, like a way bigger deal than it has been in the past because we have a different set of constraints with these new tools and people don't even really understand like, where are the lines? What, what is possible? What can we do? And so I'm looking at this project right here. Yeah, it doesn't have business impact or stakeholder management attached to a portfolio piece, but it's pretty compelling. As somebody who looks at a lot of portfolios. This would be a giant green flag. And it was something that you did in a day. But it has real impact, especially in today's market too.

[Ryan Stephen]

It's like you're doing five awesome things at once, right? You're learning new skills and those can be hard skills, those can be more collaborative skills. You're jamming with a friend, which is awesome. Maybe you watched a new YouTube tutorial to put part of your idea together. And then the other skills are like, if you're willing to take the courageous risk to be able to put those ideas out there, like, gosh, you put your idea in front of so many more people. And I think if you're doing all of that, like, what an exciting way to go about making and a design career for sure.

[Rid]

Let's go all the way back to the beginning here, because we've used the word idea like 50 times in this conversation and there's some really good ones in this presentation. Talk to me a little bit more about your ideation process. Like, are you doing anything intentionally to cultivate these ideas or spark this level of creativity?

[Ryan Stephen]

I think the two biggest, like, tactical processes that I'm using to come up with ideas, and this is just for me, Like, I'm sure everyone has different ways of going about it, but for me, I really love a capturing ideas in a note as I'm going through my day and really trying to make them as outlandish as I possibly can and is not tied to the tools as I can. I'll work backwards later on that. And then I really like sketching as a way to express and ideate on ideas. So I'm a big fan of the Crazy 8 method, but I use it like backwards, if you haven't heard of it. Basically the Crazy eight method is you said an eight minute timer and you have to sketch eight different ideas in eight minutes. And if you haven't done it before, it flies by, it's the fastest eight minutes you'll ever experience.

[Rid]

Yeah, sometimes I get stressed by like minute six or I'm like, oh my God, do I really have three more in me?

[Ryan Stephen]

And usually if you know, you're in design school or out there in the field, how they use Crazy Eights is we've done all this generative research, we've identified a problem, and, you know, we want to ideate basically and open the diamond. But the problem with the Crazy Eights is that you delete almost all the ideas once it's done. And so how I use the Crazy eights for my personal practice is I'm actually just sketching on the prompt usually of like what metaphors or interactions or things that I see that day that are really funny or really exaggerated or something like that. So I might have seen something at the gas station before and I'm adding that in my eight minutes. And that like time pressure too allows you to really just pull things for me from everyday life that I can go blow up. And maybe it's something from Twitter online too that I'm seeing, but that's been like a really fun way to push the ideas much farther.

[Rid]

This is like in an actual notebook, like you. Pen and paper type sketching, huh?

[Ryan Stephen]

Yeah, yeah. I only use Sharpie because I don't want the details to be too specific. And so it's just.

[Rid]

Is that from. Is that from Basecamp? Shape up by chance, have you ever heard of like fat marker sketches from. I think it's part of Shape Up.

[Ryan Stephen]

No.

[Rid]

Which is like Basecamp. That's their entire premise, is that you can only do sketching with fat marker because it forces you to stay to that level of fidelity.

[Ryan Stephen]

Yeah. And you can't erase it like it's in the notebook.

[Rid]

At what point do you then start thinking about tools and the exact shape that you want to take? Because from what I'm looking at, I mean it feels like you don't wait to start until you have something figured out. You know, I can tell you kind of just start and get momentum. And at some point you probably have to take a tool which like you were talking about earlier, earlier shapes, the output, there's that two way street. So when do you make that decision?

[Ryan Stephen]

I think the best way to do it is for me just time boxing to a day or two and it lets me just remove that pressure of, gosh, I'm going to go work on this for a month or something like that. Other ones had side projects, right. That go on too long and you never finish it. But I think that's part of it. And I think the other part is right in here. When I'm using Figma and I'm doing this form sketching explorations. Part of the process, I think part of that too is thinking through like it. Well, first off, what kind of platform or thing do I want this idea to exist on? And then I'm also thinking like, how real do I want it to be? Like for the Venn Diagram website, I want it to be realer maybe because I want people to be able to experience it. And I think I know enough to be able to do that. So it's kind of this happy medium of, like, meeting me, like, where am I at? Like, I don't want to be dishonest with myself and, like, think I'm going to learn unity in an afternoon. And it makes them awesome, you know, 3D game. But taking what I know so far and how can I push that 5% farther for what I'm doing next? And then for me, I'm really. I don't like doing an idea the same twice. So if you scroll through my Twitter feed, you won't find two that are even, like, remotely similar with gestures or devices or whatever. That's part of the excitement for me. And so that comes in here too, as part of the filtering process of, like, I'm genuinely doing something new that feels like it pushes the envelope. Besides just being a playful idea, eventually.

[Rid]

The novelty starts to wear off a little bit. You've been doing this for two years.

[Ryan Stephen]

Yeah.

[Rid]

Can you talk to me a little bit about, like, what's the underlying motivation? You know, like, you're putting a lot of time and effort into this and there's not, like, this perfectly clear ROI at the end of the tunnel, you know? So is this something you plan to continue doing? Where does it come from?

[Ryan Stephen]

It gives me endless energy to actually do it, which sounds really counterintuitive, but I leave having made one of these things with more energy than I came into it. Not every single time, especially the ones that are frustrating or fizzle out or like. Like don't quite meet the bar. But I find so much energy in it. And then I think the other thing that's really inspiring, increasingly, is collaboration. And so working on something like, super random. This container studio that's fake, we don't have any clients, and it's just a collaboration with two of us. That is one way that I think I'm still mixing up the format and allowing me to bring in perspectives and skills that I don't have and making something brand new so I don't know. Both those parts of it, I think, keep me, like, really engaged with it. And I'm always trying to mix it up so there's more to share, I'm sure.

[Rid]

Yeah. I can tell just listening to you talk that you're not. It's not all about the output. Like, you are motivated in just learning and new things and trying new things and, you know, gathering new types of skills, which it's just so evident. Even in looking at this body of work, you can tell it's exciting for you. It's like almost like, conquer a new tool. Like, does that. Does it feel like that at all?

[Ryan Stephen]

I think it's conquering a new tool, but also, I never know how an idea is going to resonate until I post it, you know, and I've had ideas fizzle out, and I've had ones where it literally was a joke and I put it up and I got way more response or ideas back. And to me, that's really energizing is when people are so suspended by disbelief, they're not even holding the phone or device that has your prototype on it. They're watching a square rectangle that's jammed between, like, 40 other, you know, unrelated things, and they're stopping in their day and imagining what it would be like to live with that. That is so powerful. And why I spend so much time pushing the fidelity so far is so that you can step into the idea without even having to be there to hold it.

[Rid]

Do you already have the next idea in progress? What are you thinking about right now?

[Ryan Stephen]

I got some things in the works. I'm really excited about AI as material. I've done AI things in the past, and I think there's a big opportunity to keep pushing what the forms and general software architecture is for interacting with these things. And I think one way to go about that is to be really serious and have a structured process, and there's plenty of work happening on that end. But the other way is to zigzag and what's the most playful way to interact with AI? And so I'm really excited to keep pushing on those threads this year, too.

[Rid]

I want to ask one more question before I let you go, and it might feel slightly off topic, but I think a lot of people listening are in this place where there's a lot of career strategy top of mind right now with the tectonic plates of tech and design, everything's shifting and everything's up for grabs. And you obviously love design. I would imagine that you want to be able to continue to make money as a professional designer for years to come. Given that and where you're at, how do you think about what that future might look like for you or what you need to adapt to in order to get there, or where you need to invest? Like, when you just think about, like, how can I play out my career and keep making this happen? What comes to mind, I think a.

[Ryan Stephen]

Big one, is that visibility is a pretty important currency that people don't think about too much. And there's a couple examples I can give of that. One is the Twitter example, which is a little obvious, which is by sharing my work, I've been really fortunate that people are excited and they're really playful and they get a lot of energy. That's so, you know, thankful for that and energized by it. That's way more powerful than a portfolio website because instead of the work statically being somewhere that you actively have to reach for, it's just presented to you like whether you want it or not, you know, at 7:00am on a Tuesday, you're going to see a playful idea from me. And I think that's a really powerful mechanism that if I was, you know, another designer or something thinking about exploring, I wouldn't try it. I think the stakes are so low. Like if it doesn't work, then nothing happens. Especially if you can time box it in a really small way. Like just make something that's really exaggerated and playful in a day and you'll be really surprised where that can take you.

[Rid]

I want to underline something that you just said. I want to something that you just said because you said like, like the worst case scenario is nothing happens. And it's actually so important to recognize because I think we all feel this fear where it's like, if my work sucks, I'm going to be publicly shamed in front of everyone. It's like, no, that's not the floor. Actually, the floor is that it's just crickets and people don't really care. So you have almost uncapped upside with a pretty safe floor. Putting yourself out there is like the greatest investment that you can make because it's all upside down.

[Ryan Stephen]

I think it's actually better than nothing happens. You still learned something. You made exactly, really like bold and awesome and it gives you a starting place. You no longer have a blank page. You have a thing to compare to and then go make the next thing. But on the same note of like visibility as currency, I think that's true internally too. I view companies and studios and organizations and as social networks the same way that you think of traditional social networks. And so I can go viral internally too. I can go make and use the same skills, the hard skills and the filmmaking, all of that together to tell an awesome story internally. And it can be really short, it can be like a 22nd thing or it can be a whole long loom or screen recording, right? And that professionally I think is really, really impactful and can take you so many places is when you can just share ideas and see how far they can go when you make them feel real for other people.

[Rid]

I love that. It reminds me of something that my friend Gabe Valdivia said probably a long time ago at this point on the show where you talked about how the best designers are almost content creators within their org and everything you're saying, I'm just like nodding around. Yep, that makes sense. Like you are asking for people's attention. It's not a given that you're going to get it. You have to do something that is compelling and interesting or makes people stop and be like, huh, didn't think about that.

[Ryan Stephen]

Yeah. I think also too, we work increasingly on global experiences and collaborations. Right. So if I can send you Async video that tells a story and uses a lot of these same techniques that we looked at today, like what an impactful career thing to not need a synchronous 30 minute meeting to maybe walk through part of your thing. For me, it's like, how do we tell an idea without getting lost in the tool shed? You know, there's more tools today than ever before. So, you know, how do we tell a story and go from there?

[Rid]

As somebody who's been kind of putting the reps in on storytelling, potentially even internally and externally, are you able to look back on your last few years and see clear areas where you've grown as a storyteller or potentially lessons that you've learned or techniques that you've adopted over time?

[Ryan Stephen]

I think the biggest one has been being able to tailor the story to who I'm talking to as the audience. So obviously we've talked a lot today about very iteratively getting better at telling these bite sized stories online. But internally too, I think how you tell a story when you're wanting feedback from a design team is super different from the type of story you would tell to a leader that may not be in the weeds as much. I think prototypes are an awesome way to kind of move out of all the context setting sometimes and move out of 10 slides of explaining, you know, what the perfect thing is and really letting someone just evaluate the thing, which is, you know, what matters at the end of the day.

[Rid]

Yeah. Something I think a lot about is how, I don't know, for years I had this idea presented to me from so many different designers, which is like, you have to reduce the fidelity as long as possible so you can make sure that you're aligned before getting lost in the details. And like, there's this fear that if I show too much detail, I'll get bad feedback. And I have had that happen before for sure. I've lost control because people are, you know, obsessing a little UI piece, and that's not the reason that we're here. That being said, the flip side, I almost never hear people talk about, which is if you keep the fidelity low, people can kind of just nod along in agreement because they totally agree with all of the high level stuff. And then you get to the point where you're like, okay, here it is. And then they look at it and it's like, oh, that wasn't what I had in my head at all. And you almost assume that, well, the details will get fleshed out when we increase the fidelity, but it's like, yeah, but there's still a pretty large execution gap there. And the longer that we push that off, I don't know, I've. I've run into that issue many times where I feel like I've felt the pain of keeping the fidelity low. Whereas, like, if you show somebody a really slick prototype right out of the gate, they're going to know if they like it or not. You know, they're going to be able to point to it very specifically and say, like, I don't like this part or. Yeah, that makes sense.

[Ryan Stephen]

Yeah. What I like to think about is effort fidelity more than visual fidelity. So if I can make something in a day or, or a weekend or a week, internally or externally, that fidelity is what matters. Not necessarily how awesome the rectangles move around the screen.

[Rid]

And that's so important too, with the tools, because it used to be a lot more clear in terms of the correlation between fidelity and time. It's like, yeah, of course it's gonna take you more time to make the high fidelity thing. But now it's like, actually nobody knows anymore. You know, like, you can make something incredibly high fidelity in one good prompt. And that kind of changes the equation a little bit.

[Ryan Stephen]

And I think also as designers, we have a role of, if we're making ideas feel real, what aspect of the idea needs to feel real? Do the visuals need to feel real? Does this gesture need to feel really real? Does this information architecture need to feel real? Maybe the actual only thing that needs to be real is the language you're using on the screen.

[Rid]

Okay, yeah, it might just be like a data thing.

[Ryan Stephen]

Yeah, yeah, yeah, exactly. So I think that's also something to think critically on and something I'm challenging myself every day of. I'll make something and kind of ahead, play an own feedback loop of hey, was this real in the right way?

[Rid]

Well, Ryan, I appreciate you coming on and giving us a little tour of your work and helping us get inside of your brain and just how you ideate and your process for creativity, everything in that bucket has been really just fascinating. And you have one of the more interesting bodies of work of any designer that I've met, and I appreciate you for it. So thanks for coming on today and sharing it with us.

[Ryan Stephen]

Thank you. Pleasure chatting.

[Rid]

Before I let you go, I want to take just one minute to run you through my favorite products because I'm constantly asked what's in my stack. Framer is how I build websites. Genway is how I do research. Granite Granola is how I take notes during crit. Jitter is how I animate my designs. Lovable is how I build my ideas in code. Mobin is how I find design inspiration. Paper is how I design like a creative. And Raycast is my shortcut every step of the way. Now, I've hand selected these companies so that I can do these episodes full time. So by far the number one way to support the show is to check them out. You can find the full list at Dive Club Partners.