Monthly · Community · Workshop

Exploring Stuckness

A monthly community gathering for exploring our
real experiences of stuckness in software development

Every month, someone brings a real stuckness they're currently facing in software development, distilled into a "stuckness vignette." We spend some time understanding the situation, asking questions, and exploring it together. Then we use Thinkies to discover new ways of looking at the challenge to see if we can get ourselves unstuck.

Join the conversation on August 12th ↓

Engage in a hands-on community workshop

No lectures. This isn't a conference talk. Just a small circle of practitioners thinking together and getting practice with Thinkies in a real-world context.

Step 01 Understand the Stuck

Understand the Stuck

Our Community Member Experiencing the Stuck shares more about their situation and answers questions from the group. Together, we build a shared understanding of the challenge.

Step 02 Explore with Thinkies

Explore with Thinkies

We practice with Thinkies to find new ways of looking at the challenge, expand the space of options, and spark new ideas. And you're always welcome to invent your own Thinkie in the moment. The ones we have are a starting point, not the only way to get unstuck.

Step 03 Reflect & Take Away

Reflect & Take Away

Finally, we reflect on what resonated, what patterns we see, and any potential strategies for getting unstuck. Everyone leaves with new perspectives, some fresh ideas, and a bit more practice with applying Thinkies.

A map of Thinkies to think with

Each Thinkie is a small, reusable move for shifting how you see a stuck situation. Tap any card to read Kent Beck's write-up on his newsletter.

ObviouslyEasy BitFun BitDirect FeedbackEnd to EndPut Skin in the GameForce DecisionMore General SolutionHard ProblemParallel DecisionAbundanceHalf and Half

Each month, one real Stuckness

Meet the challenge we'll explore together, and let's see if we can get ourselves unstuck.

Our Next Event

Stuckness Vignette: The Shallow Mental Model

The Challenge: Acting Without Understanding

Development used to involve gradually building a detailed mental model of the system. Working with AI now often means operating from a much shallower understanding. Developers can still make progress, but they experience themselves as not really understanding what is happening or why particular changes are being suggested, and missing an intuition about what to do.

Community Member Experiencing the Stuck Blake Lindsay
Special Guest Norman Anderson author of the "Stuckness Vignettes" paper
Your Co-Hosts Arty Starr, Russ Miles
Date & Time Wednesday, August 12, 2026 9am - 10:30am PST / 6pm CEST
Save your spot on Eventbrite

Who you'll be exploring with

The people bringing, framing, and hosting this month's stuckness.

Blake Lindsay

Blake Lindsay

Community Member Experiencing the Stuck

Blake Lindsay

Software engineer at RentSpree with 20+ years of experience in industry, and co-organizer for Thinkies World Congress. Arty and Blake had a chat about Blake's first-hand experiences with the shifts happening with this new agentic coding world, and how it feels different from our “coding-by-hand” world in the before times. We talked about the new stucknesses, what is shifting in the cognitive experience, and took lots of notes about the different patterns. From this, we distilled 8 stuckness vignettes. Now that we have Thinkies as a cognitive tool that we can apply when we're stuck, this seemed like a great opportunity to practice Thinkies in a real world context. Blake will be sharing about the situations where he's experiencing the stuck, and as a community, we'll try to get a better understanding of the challenge.

Norman Anderson

Norman Anderson

Special Guest · Author of the "Stuckness Vignettes" paper

Norman Anderson

Author of the “Stuckness Vignettes” paper, a masters student at University of Victoria, that did a deep qualitative lab study of developer experiences with-and-without AI-assisted software development, then distilled the different patterns of stuck into stuckness vignettes. These little vignette stories help us characterize the situation when we’re feeling a bit stuck, then give the pattern a name, so we can have a conversation about it. We want to thank Norman for the ideas and contributions and helping inspire the theme of our community events!

Arty Starr

Arty Starr

Co-Host

Arty Starr

Artist, researcher, PhD student at University of Victoria, and software engineer with 20+ years of experience, constructing a theory of the developer’s cognitive experience as two interwoven processes of momentum and troubleshooting. Originator of troubleshooting theory, giving developers words to explain the loss of understanding, loss of intuitive hunches, and loss of control in software systems (cognitive debt phenomena). Also a co-organizer for Thinkies World Congress.

Russ Miles

Russ Miles

Co-Host

Russ Miles

Author of “The Sovereign Engineer: AI Literacy for Software Professionals” and pioneer of Habitat Thinking, Habitat Theory and Habitat Engineering. Expert in Platform, Agentic, Chaos & Resilience, and Software Engineering, and on a mission as an author, listener, speaker and developer to help people thrive in one of the harshest and potentially impactful working environments: software system engineering with AI.

Wednesday, August 12, 2026 · 9am - 10:30am PST / 6pm CEST

Come explore the stuckness with us

Pull up a chair, bring your curiosity, and let's see if we can break the stuck together.

Save your spot on Eventbrite