Dealing with Regret in Software Design

Name: Dealing with Regret in Software Design
Start: 2025-10-28T09:00:00+02:00
End: 2025-10-29T17:00:00+02:00
Location: Kronwell Hotel

Schedule

Tue, 28 Oct, 2025 at 09:00 am to Wed, 29 Oct, 2025 at 05:00 pm

UTC+02:00

Location

Kronwell Hotel | Brasov, BV

Designing software is difficult, unpredictable, and emotionally charged. Even seasoned developers face uncertainty, pressure, and the ever-present risk of looking back at a codebase and thinking, “I wish we had done this differently.” Most of us aren’t taught what to do with that regret—so we ignore it, rationalize it, or let it quietly accumulate.
This Masterclass takes a different approach. Instead of trying to eliminate regret, we’ll learn how to work with it. We explore software design regret as a natural consequence of learning in complex environments—and help participants develop strategies to respond constructively, confidently, and collaboratively. The focus isn’t on getting things right the first time, but on becoming more aware of our blind spots, building systems that are resilient to change, and sharpening the judgment needed to improve designs under real-world conditions.
Through hands-on coding exercises, personal reflection, and structured group discussions, participants will practise concrete techniques for managing the costs of design mistakes and recovering from them. We’ll work with a curated, intentionally flawed codebase that’s complex enough to challenge, but small enough not to intimidate—along with optional space to apply techniques to your own codebase.
This Masterclass is also grounded in practical realism. We understand that participants will return to environments with inertia, time pressure, and varying levels of team support. Rather than promise transformation through idealized practices, we focus on skills and strategies that work within your constraints—helping individuals and teams pursue meaningful progress without disillusionment or burnout.
Throughout, participants are invited to engage with skepticism and even cynicism—not as obstacles, but as honest signals of past frustration. This is a psychologically safe environment where people can discuss failure, frustration, or fear of judgment without being told to “just do it better.” Whether you’re burned out from past efforts to improve things, or you simply want to make thoughtful design improvements with less risk and conflict, this workshop is designed to meet you where you are.
Course contents
Understanding Regret in Software Design
Why we feel regret in our work—and why we rarely talk about it
Design decisions under pressure: tradeoffs, uncertainty, and irreversibility
How design regret affects individuals, teams, and systems

The Various Costs of “Not Knowing Yet”
Understanding the U-curve of effort: design up-front vs. design later
The hidden toll of overconfidence, underplanning, and learned helplessness
Design uncertainty as a source of both cost and opportunity

Practising Where It’s Just Difficult Enough
Hands-on exercises with a curated, imperfect codebase
Exploring design flaws with just enough mess to be instructive
Option to bring your own codebase or use freely available open-source examples

Making Changes Safely Uses Techniques That Go Beyond Writing Unit Tests First
Balancing test-first and test-after workflows
Understanding how safety arises from habits, constraints, and skill—not just discipline
Common traps when trying to “test your way to safety”

Refactoring for Discovery and Direction
Purposeful refactoring: heading toward a known, intentional structure
Speculative refactoring: uncovering improvements without a fixed goal
When and how to stop refactoring

Practising Foundational Design Moves
Revealing intention: naming and organizing to expose design clarity
Isolating calculation from action: making logic reusable and testable
Removing duplication to discover missing abstractions and relationships

Collaborating Through Design Tension
Navigating disagreements about “what good design looks like”
Differentiating between design risks and personal preferences
Reducing unproductive conflict by surfacing assumptions

Building Design Confidence and Communicating Clearly
Turning hindsight into insight without spiraling into blame
Strategies for tracking and reflecting on design changes
Communicating regret constructively with peers and decision-makers
Planning future discussions and code work that apply these techniques at your job

Participants will leave with:
Specific techniques for making safer changes in unfamiliar code,
Insight into personal and team-level sources of design risk,
A plan to continue improving their refactoring and testing fluency, and
Strategies for aligning design work with team culture and organizational limits.

You’ll also receive curated post-class resources, including book recommendations, technique references, and ideas for follow-up experiments and conversations you can bring to your team. Facilitation support is available on request for teams who wish to continue this work with additional guidance.
Target audience and prerequisites
This Masterclass is for anyone who writes code and has ever felt regret about a software design decision—whether because of a missed opportunity, a rushed compromise, or something that just didn’t turn out the way they hoped. Participants will benefit if they want:
More clarity and confidence in navigating complex or ambiguous design choices,
Time and space to practise safe design improvement techniques, and
Guidance in translating those strategies to their everyday work.

All levels of experience are welcome. It will help if you already feel comfortable using at least one unit testing library and adding it to an existing project. If you don’t currently write code as a significant part of your job, you are still welcome to join—during hands-on segments, you’ll have the opportunity to engage in reflection, planning, or guided observation instead.
This Masterclass is designed to support a variety of technical contexts—including remote/distributed work, regulated environments, and legacy-heavy systems. While we won’t endorse any particular methodology or process framework (e.g., Scrum, Agile, DevOps), we’ll explore how to adapt core design practices within the organizational and technical constraints you already face.
https://codecamp.ro/masterclasses/dealing-with-regret-in-software-design-brasov-2025/