Writers of Silicon Valley

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Dave Connis is back on Writers of Silicon Valley after a very different eighteen months.
Since his last appearance, Dave has been laid off, thrown himself into experimenting with AI, built new product workflows, and started creating System Design Lab: an education platform focused on systems thinking for product and content designers.
In this episode, we talk about the emotional fallout of layoffs, the strange new roles appearing in content design, what AI actually looks like when you use it every day, and how to actually prove you're a systems thinker - both in an interview, and on the job. 
What we talked about:
✅ What getting laid off did to Dave's confidence, identity, and relationship with work
✅ Why trying to constantly "prove your value" can lead straight to burnout
✅ The new roles emerging around AI, including design technologists, system architects, and content architects
✅ Why today's job descriptions increasingly seem to be looking for impossible "unicorn" candidates
✅ What Dave learned from months of actually building with Claude, Figma MCP, and other AI tools
✅ Why AI workflows are much harder to make reliable than LinkedIn posts would have you believe
✅ How systems thinking helps designers define concepts, objects, attributes, and relationships before AI starts building
✅ How to demonstrate systems thinking in an interview
✅ Why Dave is building System Design Lab 
Where to find Dave:
System Design Lab
LinkedIn
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IT'S A "BEST OF" SERIES!
We're digging back into the archives and resurfacing some of the best episodes of the Writers of Silicon Valley podcast i the conversations that have held up, and in some cases gotten more relevant since they first aired.
This one's with Chelsea Larsson. She currently leads content design at Anthropic, but when this conversation happened she was at Expedia.
We got into the future of content design, UX writing, how AI is reshaping the work, and why content designers shouldn't cling to old definitions. And maybe…why content designers should learn Python?
Worth a second listen if you caught it the first time, and a good place to start if you didn't.
Things we discuss during this episode:
Generative artificial intelligence
Information Architecture for the Web
Open AI, ChatGPT, Gemini
Python
Chelsea and her stuff:
Chelsea on LinkedIn
Smallish Book (newsletter)

🎧 Start listening on Apple Podcasts, Spotify, subscribe on YouTube, or wherever you get your podcasts.
Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product. 
Oleksii Tkachenko has worked across software engineering, UX, and content design, which makes him unusually well-positioned to talk about what's happening in content design right now.
In this episode, we talk about the growing identity crisis inside content design: the pressure to become more technical, the race to automate workflows, and the uncomfortable question sitting underneath all of it...what parts of the craft are actually worth keeping?
We explore why so much AI discourse online feels detached from reality, why many companies still don't know what they want from content designers, and why the profession risks redefining itself around tools instead of outcomes.
Enjoy!
What we talked about:
✅ Why LinkedIn creates a distorted picture of AI adoption ✅ The three different types of companies hiring content designers right now ✅ Why "AI curiosity" means different things at different organizations ✅ The danger of optimizing for output instead of product quality ✅ The tension between craft, speed, and automation ✅ Why content designers are becoming the "context bearers" for AI systems ✅ The risk of redefining content design around tools instead of outcomes ✅ Why some people are quietly mourning the old version of the profession ✅ The similarities between today's AI shift and the rise of UX writing years ago
Where to find Adedayo:
Website
LinkedIn
Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

🎧 Start listening on Apple Podcasts, Spotify, subscribe on YouTube, or wherever you get your podcasts.
Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product. 
Adedayo Agarau is a poet, a Stanford Wallace Stegner Fellow, and a content designer who has worked on AI search at Google and on Grok at XAI. He came to content design through web writing, a Nigerian fintech startup, a browser company, and an MFA at Iowa - not the path anyone would have predicted, and exactly the kind of path that produces someone worth listening to.
We talk about what it actually means to design for a large language model: how personality gets built, why guide rails are a writing problem, why the distinction between an ideal response and just a response is what separates well-designed AI from the rest...and why content designers are the best ones to do this type of work.
What we talked about:
✅ How Adedayo discovered poetry through a Nigerian social app 
✅ What it was like contributing to AI-powered Google Search 
✅ Designing voice, tone, and personality for Grok 
✅ Why the X algorithm amplifies shock value and what that does to content designers 
✅ Why AI hype creates both overclaiming and unhealthy skepticism 
✅ What engineers actually want from content designers when building AI systems
✅ The case for treating data as content, not just content as data
✅ Why designing an AI agent is fundamentally the same as writing a character
Where to find Adedayo:
Website
LinkedIn
Github
Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

Want to learn how to use AI to build with other content designers? Join the Content Design AI Accelerator. Applications open until January 30.
Why wearable tech will change content design
Smart glasses and wearable devices have been "just around the corner" for years. But quietly, that's starting to change.
In this episode, I speak with Carly Gray, a content designer who's spent years working on AR and wearable products, including smart glasses at North and Meta. While much of the industry debates AI and screens, Carly has been designing content for products where there's little or no screen at all.
We talk about what changes when content moves off phones and into the physical world, why wearables raise entirely new design and ethical challenges, and what content designers need to start learning now if they want to stay relevant as new platforms emerge.
What we talked about:
✅ How Carly moved from technical writing into content design for AR and smart glasses ✅ Why smart glasses are different from VR, and why wearability matters more than novelty ✅ Designing content with extreme space constraints (or no screen at all) ✅ Using sound, voice, and companion apps to communicate when text isn't an option ✅ Why "designing for the bystander" is as important as designing for the user ✅ What wearable tech reveals about the future skill set of content designers ✅ Why conversation design and systems thinking matter more in emerging platforms
Where to find Carly:
Website: carlygray.ca LinkedIn: Carly Gray Twitter: @carlygray