As much as I love writing, many of the people who inspire me most don’t spend most of their time penning essays. Instead, their preferred means of articulating a vision for technology is to build something and launch it into the world—creating products and prototypes that are just as opinionated as any text.
So that’s why I’m planning to spend more time on the Reboot Podcast™: a series of conversations with technologists about how they approach their craft and careers. My hopes are twofold: first, to expand folks’ imagination around what they can do with a tech career, and second, to dig into the strange sites where theory and practice collide.
Listen here on Substack (web or app), or subscribe on Apple Podcasts or Spotify. A transcript and takeaways will be published with each episode.
Building Software With a Soul
The first episode is today’s podcast with independent designer, artist, and programmer Kelin Carolyn Zhang.
I wanted to talk to her for two main reasons:
Kelin has had a broad and winding career path. She was the first design hire at design studio Ueno, worked on political campaign software, and was a staff designer on Twitter 1.0 and 2.0 under Elon. In 2022, she made the leap to independent work. Now, Kelin is a creative resident at IDEO CoLab, and the co-creator of Poetry Camera and TRASH BABY.
We've also had a lot of great conversations about AI and media. She approaches generative AI with an artist’s mind, and is thus one of the only people who can get me genuinely excited about its creative possibilities—not in spite of, but because of its hiccups and strangenesses.
I recommend plugging in your headphones and listening to our full conversation, but here’s a few tidbits that will stay with me (edited for length & clarity):
What did you learn from working at the design studio Ueno? (04:39)
If you were to ask me much earlier in my career, it would have been that I learned the craft of design. I learned how to execute really well.
Now looking back, what I've really learned was customer service and how to maintain a relationship, how to run a services-based business, and how to make sure that you're able to turn a successful relationship into good work. A good working relationship is the basis of good work, not the other way around.
One other really big thing: I saw Halli, the founder of Ueno, build a business on the back of posting on social media. He was coming into the industry as a total outsider. Other folks who have been in the industry for a long time have done the traditional advancement route. But he was able to shortcut all of that by just posting on Twitter. Being visible online can open up doors that you never knew existed.
What did you learn from working in political campaign tech? (06:12)
In political tech, the thing that was really valuable for me to learn is a lot of what I thought was important in the craft of design—the beauty and the pixels and the harmony—none of that matters.
I do really love making beautiful things, but when you're looking at it in the context of there's a national election happening and the stakes are really high, do these button radii really matter?
It was a really painful lesson to learn. I felt like I was making work that I would be ashamed of showing to other designers, but was really effective at achieving our goals, which is convert people to volunteer for campaigns with the very limited resources that we have.
What did you learn from working at Twitter? (07:19)
The main thing I learned from Twitter was just all the weirdness that happened around the acquisition. When you’re working at a company for someone else, as empowered as you might feel, ultimately some things are totally outside of your control. After that, I was really seeking control. That very directly led me to independent life.
How did you make the jump to independent work? How did you get over self-doubt? (08:17)
I had reached the point in my career where I want to do my own thing. I want to explore. I want to see what that looks like. I want to know if I really got it.
I told myself, I'm just going to take a year to explore after Twitter, whenever that would be. The acquisition really strengthened my resolve to not fall into another job. What I really wanted was to ask myself, what do I really want? Taking away all of what everyone else is asking of me, what is it that I really want to make, and how do I want to spend my limited time on this earth?
I tried taking on some client work because this is a very typical way of having an independent practice. I was making mock-ups in Figma, doing traditional product design. And I realized that this is not the way I want to work anymore.
At the same time, one of my projects, Poetry Camera, was taking off. The good thing about one of your projects getting recognition is that people finally understand what you're doing. In the past year of working on Poetry Camera, I was working really hard, but in a way that was still laying the foundation. Other people would look by and see an empty lot—there's no house there. Then, I finally built enough to have a little bit of a visible structure, and people will be like, look at that cute little shed, nice.
When you're working by yourself and for yourself, you have to constantly explain yourself to others. People can understand a job. They can understand starting a business. The stage before that is the hardest part.
What is it about working with generative AI that excites you? (14:58)
it. I see some of the image generators. I'm not viscerally interested in it. But when ChatGPT came out, I was like, holy crap. I just felt like a kid again. This technology upended all my ideas about how computers should work. A computer was talking back to me in a way that was extremely believable. I stayed up until 5am playing with it; I was having so much fun.
As a designer, ChatGPT was interesting because the material you're working with was previously very deterministic. I want this pixel here, or I want this word here. But this material—the LLM—has changed into something that is not fully predictable. That's what's really exciting. So many new interactions can come from that, so many new products can come from that. It’s going back to that initial feeling of play and joy. This is like a new little creature that I can play with now, and see what it grows up into.
People really get on these LLMs’ case for hallucinations. I'm not trying to use it for anything that requires accuracy. If anything, I think it's a really cool property of this material. We should lean into that. It can make stuff up. How weird can it get? I'm much more interested in the creative use case.
I used to be so sad that I would be making apps that would be redesigned in a year or two, and that the feature I'd worked so hard on would go away. But the beauty of software is that it's dynamic, and that it changes. What can you do that is unique to the property of this material? Now, the generative model material on top of that—not only is it malleable, but it can respond to you in a new and unpredictable way. I'm very open and embracing of the fact that this new material has different properties. If you’re an artist, your selection of materials has an implication on what you're trying to communicate with the art.
Now show me Poetry Camera! (24:12)
Poetry Camera is a camera that writes poems of what it sees. It is a collaboration with my friend, Ryan Mather. Ryan has done the industrial design, the extra 3D modeling, and the 3D printing. I do the software, the hardware prototyping.
Basically, it's two prompts in a trench coat. But my focus is with this project is how can we break the ice at a party? How can we bring people together, have them react to the machine collectively, and start a conversation? Then we can stop the focus being on the machine, and just bring people together. Once you have a camera and a receipt printer, what creative things can you do with it?
Live demo (watch the video, it’s worth it):
Wow, it’s really good! (25:45)
One thing that you'll notice is that I was reading the poem out loud to you. There are so many ways we could have executed on the idea of a picture turns into a poem. But it was really important to me that the photographer is gifting a poem to the subject. It's not just about, Let’s look at the machine that gave me a poem, then moving on with your day. There is this moment of connection between two people.
Another thing that's really important in a poetry camera poem is that it does feel accurate, that it does mention details of what is in the scene. If I, as a poet, were here to write about this scene right now, I would probably write something very different. We're not trying to churn out the most human-like AI prose. It's more about subverting your expectations around photography and capturing this memory in a slightly different way.
All of those things are so important and so helpful in achieving this overall experience. As a designer, as a creative, the overall goal is always to have fun together, enabled by this new technology.
How are you thinking about your artistic versus commercial goals? Is there tension between them? (30:00)
When we built this polished enclosure, everyone started asking, Oh my gosh, are you going to sell it? Can I buy one? And for a couple months, I was just like, no, you can't buy one. You can make your own. Here are the instructions.
I initially wanted to leave money out of it because I was afraid of corrupting the intentions around the project. I mentioned the social goals before, and what I had known of making products was just, Let's try to get money from the consumer. I didn't want to do it that way, so there was only this one unit we made.
What changed my mind was the fact that people were continuing to ask. The first hundred times people asked, we said no. And then the hundred and first time, we thought, Maybe there's something there. Maybe people really, really want it. Could we make this more available to them in a way that still feels true to our values?
I talked to other friends who are creative and they said, It's not a bad thing to have commercial success. It doesn't muddy up the values of the project. After all, Poetry Camera is currently not a scalable experience. I can't physically go around to every single gathering of people in the world and give them the experience. We think we can figure out a way to make it more available to people but still live by our values.
But we’re adamant that Poetry Camera is not going to become a VC-funded startup. It shouldn't turn into some sort of obligation that we've tied ourselves to because this becomes our main moneymaker. Commercializing is a means to the end of having more people experience this project.
A friend also reminded me, Hey, you want to make other creative projects as well. A lot of people are interested in buying this as a product. If you end up making money from this, you can use that to fund future creative projects. That's what helped me become more comfortable. I just didn't want to become someone doing a cash grab at the expense of the creative work that I really wanted to do.
What makes a fruitful creative collaboration? (37:54)
As I was entering this independent phase of my career, at first I was really enjoying the freedom. Like, I don't have to answer to anyone! Then I recognized that it's hard to do everything on my own. Also, I missed having a team to bounce ideas around.
All the significant projects that I've worked on as an independent creative—Poetry Camera, and an app called TRASH BABY—I worked on with other people. I was able to learn from them and have some emotional support. If it's just you, then you're left with the ups and downs of your own mind. If I'm not feeling good today, then nothing happens. It's so much easier and more sustainable knowing that at least one other person is there. That's one of the keys for me in continuing independent work: I want to be working with friends.
Another great thing that I've learned from Ryan is from very early on, when we were bouncing ideas around. I was probably shooting down some ideas, and Ryan said something to me that has stuck with me since, which is: I learned from a screenwriting class that the energy in the room is often more important than the quality of the ideas. That’s so important whenever you're trying to create something that's not just a business for these users or a client. Psychological safety is key, and from there, the right ideas will be able to emerge. It's a more proactive sort of expression and creation.
How might someone approach finding creative collaborators? (41:26)
It might help to start making things on your own. Alone, you don't have as much time or expertise or resources, but you can start making things that reflect your own perspective as a creative. It can be super lightweight. It could be a video of a prototype that you post on social media.
The key is to be visible, express that you're interested in making things, show that you are able to make some little thing at least, and start attracting the type of creative energy that you want to put out into the world. Once you start sharing and attracting folks who you vibe with, then it becomes so much easier. Just make friends.
That’s the reason I make anything at the end of the day—it's to help other people understand what I'm about and to try to bring the right people into my life. Before I started my own projects, I felt so lonely, because I felt like the only way to fully let other people see me was through my work. But I was surrounded by people who didn't get that, and I was putting all my energy towards things that didn't reflect who I am. So this goes back to “software with a soul”: I wanted to put my soul in the work so that people could see me for who I really am.
How do you relate these days to “being online”? (44:39)
I use a flip phone for a month every year. I started doing that while I was working at Twitter. I was just like, I am too online. It was also the middle of the pandemic, so it was screens everywhere. There’s so much noise. And it's all fake! At Twitter, it felt we had established a fake status system that was all meaningless, where I could type the right words in a Twitter bio and that affects how people see me. I was inside the machine, yet trying so hard to make sure that I still had my own agency outside of the machine.
I've done the flip phone experiment for three years now. The first time, it was so hard, but honestly, so charming. I tried all of these workarounds to using a smartphone. I'm going to get a digital camera. I'm going to read on my Kindle. I also got off social media.
So much of my brain is filled with these digital inputs that I'm not inviting into my life. It's just like, oh, notification, notification, Twitter feed. Once I erase them from my mind, my mind is actually looking for stimulation. It starts to go a little haywire, and it starts having interesting creative ideas.
The flip phone is not sustainable because modern life is entirely structured around the smartphone. But anything we can do to remember what life was like without it is very valuable.
How do you relate to social media nowadays? (48:15)
I try to not put much stock into what's going on on Twitter anymore. Fortunately or unfortunately, though, I do recognize that it is so important to be telling your own story, especially when you're working for yourself. If you're not out there explaining what you're doing and why, then other people are going to write that story for you, and that can demoralize you.
Social media helps me share what I'm doing, and it helps bring collaborators and opportunities into my life. But I don't attach my personal value to it. It's a tool like anything else. And I treat it like work. I see my work as 50 percent making things, and 50 percent sharing things.
Lightning round! What’s a website, app, or product you’ve been loving lately? (50:16)
My friend Nolen made a website called One Million Checkboxes. It's a page with a million checkboxes. If you check the checkbox or uncheck the checkbox, it unchecks it for everyone. So it's just this global multiplayer page of checkboxes.
His website instantly went viral. People have been doing the most creative things, like scripting and checking all these interesting patterns in it. The best and most fun things are just that simple sometimes.
Recommend me something totally unrelated to tech. (51:14)
I got really into press-on nails this year. I have had issues with picking my nails for my entire life. This year, I was working on Poetry Camera, and I was always ashamed of how my hands looked in photos. Then I was in Target, and I saw a stand with them. I put them on and immediately was like, wow, my hands look great. I'm not picking my nails anymore. They look good in photos, and I feel so polished every time I look at my hands.
I think press-ons are the biggest lifestyle improvement I've made this year. To have made a conscious change that has completely changed my own attitude towards my hands… For me, it's a reminder of my own ability to change my life. But I don't think the average person looking at their press-ons is going to have that reaction.
I like the brand Glamnetic. Olive and June is also very solid. I also started looking into all the handmade press-ons that are available on Etsy and Instagram.
What’s the best way for people to keep up with you? (53:04)
The best place is probably Twitter, unfortunately. Aside from that, my own website, kelin.online, and I'm trying to post more on TikTok at @kelin.online.
Reboot publishes essays on tech, humanity, and power every week. If you want to keep up with the community, subscribe below ⚡️
closing note
You’ll notice some first-time podcast production funkiness—I didn’t realize the SD card maxed out at 1 hour so some of the footage is audio-only, I was a bit over-aggressive with editing out filler words in Descript, the watermarks are misaligned… But I hope this didn’t take away from how fun and valuable the conversation with Kelin was.
I’m definitely looking for more guest or topic recommendations, especially for folks in the Bay Area (in-person is so much more fun!), so feel free to leave a reply or a comment with suggestions.
Thanks for listening,
—Jasmine & Reboot team
Building Software With a Soul