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 October 20th ↓
Poster for Exploring Stuckness on Tuesday, October 20, 2026 at 8:30am PDT / 5:30pm CEST. This month's stuckness vignette: Stuckness That Feels Like Motion. With Blake Lindsay, Arty Starr, Russ Miles.

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: Stuckness That Feels Like Motion

The Challenge: Moving Fast, But Losing Touch With Whether We're Moving Toward the Right Thing

Working with agents, it's easier than ever to get moving. We have a fuzzy idea of what we want to build, the agent proposes a direction, and it looks pretty good. Sure, let's go! Before long, we're producing enormous amounts of code, merging PRs, and building out new functionality. It feels like we're making tremendous progress. But the ease of moving means we may not really be understanding the problem, questioning our assumptions, or discovering whether what we are building is the right thing. The frictions that would ordinarily cause us to pause, talk, reconsider, and learn are replaced by ready-made answers that look plausible enough, and we are moving fast! There's so much activity, so much code, but underneath it all, a growing unease and wondering whether we’re moving in the right direction at all. Are we really making progress toward what matters, or have we just gotten fast at moving?

Community Member Experiencing the Stuck Blake Lindsay
Your Co-Hosts Arty Starr, Russ Miles
Date & Time Tuesday, October 20, 2026 8:30am - 10am PDT / 5:30pm CEST
Registration opens soon

Who you'll be exploring with

The people bringing 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.

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.

Tuesday, October 20, 2026 · 8:30am PDT / 5:30pm 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.

Registration opens soon
Kent Beck Thinkies were created by Kent Beck. Learn more →

"Stuckness Vignettes" are inspired by an academic paper by N. Anderson et al., "ChatGPT: Friend or Foe When Comprehending and Changing Unfamiliar Code" (2026). Read the paper on arXiv →