Reflecting on the 200 series
Issue 300: A look back at the past 100 issues
Proof of Concept hit 300 issues; a milestone I never set out when starting in 2020. I started Proof of Concept as part of the On Deck Writing Fellowship in 2020. At that time, I was the flaky writer who said they wanted to publish more, and did about once a year. In one of the fireside chats I remember Polina Marinova saying a phrase I’ll never forget, “Consistency builds trust.”
I needed to build trust, not with an audience, but myself to write. Since the early days, I have not missed a Sunday morning to share my thoughts on software, creativity, entrepreneurship, and experimentation. Some weeks are better than others, but what’s important to me is showing up and being consistent.
The 200 Series spanned from September 7, 2024 to May 31, 2026. To say there was a big emphasis on AI in the latter parts is an underestimate. Though I try not to write only about AI, it’s a relevant topic for many. Let’s reflect on themes throughout the years and the top posts that resonated with people, which I opened up for free to read.
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Themes
The essentialism of craft in the AI era
I truly believe the craft layer is the most important factor that remains when AI becomes normalized and commoditized. Building the best AI product means building the best product, even if it didn’t have AI. In 2023, people were excited to make something end-to-end, regardless of quality. Then the creation became abundant, and AI slop was what you strived to avoid.
Related posts:
Software architecture and surfaces are changing
The way we are building software is changing. It’s both terrifying and exciting at the same time. People who never wrote a line of code are now shipping to the app store. Meanwhile, walled gardens and moats are coming down in favor of bridges and partnerships. As a Growth and Ecosystem designer throughout my career, this makes me very excited. It’s now a competitive disadvantaged to build in isolation. Apps and integrations need to go hand-in-hand.
Top posts:
Operating and leading
Operators and leaders haven’t been replaced yet. In fact, the ones who can adapt their way of working will compound everyone’s autonomy an agency. It’s a great era for the highly convicted, craft-oriented, and decisive.
Top posts:
Ship, don’t speculate
Herb Keller, CEO of Southwest Airlines once had a saying, “We have a strategy. It’s called doing things.” As strategy goes from thoughtful planning to retroactively pattern matching what’s working. The iteration cycle is nearly zero, so the way we work needs to drastically change.
Top posts
Career and people
Finally, there was a heavy theme on career and people. We are in the multi-modal and multi-generational era. I am towards the end of my career and seeing incredibly talented designers and founders rise up in the next generation. Despite the wonderful autonomy, many people want connection and guidance.
Top posts:
Top posts
The ten most popular issues from this series, made free.
Protect human and craft layer as we make sense of AI
Reflecting on the 200 Series, I realized how I am not an AI maximalist at all. I use it daily, work in the field of applied AI, but I’m a cautious optimist, which is what I think every Head of AI Design should be anyway. What’s important to me is to retain the craft and human layer of AI along the way; not because it’s holding on to an old way of working, but the skills of that area are more important than ever.
Whether you started reading from Issue 1 or 299, thank you for your readership; its what keeps me motivated to write the next 100.
Hyperlinks + notes
AI in Design Report 2026 → Such a well-crafted report by Designer Fund
Incredible few days at Hatch Leadership Ateliers. My recap
Charlie Sutton, Chief Design Officer at Atlassian is now on Substack
Regardless of what you think of the car, I love Cleo Abraham’s interview with Jony Ive and Flavio Manzoni on the new Ferrari
every book you read becomes a part of how you see by Sindhu Shivaprasad
What an amazing gift of a summary to all your current and future readers. If Substack has a pinned feature type thing, pin this one. Thank you! 🥰🙏
And yes consistency is the key to making progress on anything. 🙌
As someone who's had the opportunity to see your work up close at Atlassian, I'm extremely fortunate to have also read your polished takes on how product building changes (and remains the same) with improvements to AI through this Substack.
The big takeaway to "keep going" has been pretty inspiring for me as a budding builder/writer (which is honestly the hardest thing to do). Looking forward to the 300 series!