Letters

Letters

Personal meditations from experienced mentors

Inspired by Seneca's Letters to Lucilius, these letters take the form of personal communications from experienced mentors to those earlier in their journey. Each letter is a meditation on topics like leadership, code quality, technical debt, scaling teams, delegation, or failure, written in the first person, as though a wise voice is writing to someone they care about.

On Technical Debt and Moral Courage

A letter from a CTO to a mid-level developer about the ethical dimensions of maintaining code quality amid pressure to deliver features quickly.

On Building Teams That Thrive

A letter from an Engineering Director to a new Tech Lead about creating high-performing engineering teams built on trust, psychological safety, and clear direction.

On Reclaiming the Joy in Coding

A letter from a Recovering Burnout to a disillusioned developer about finding your way back to meaningful work and sustainable passion.

On Navigating Technology Trends

A letter from a Seasoned CTO to an ambitious architect about evaluating new technologies through the lens of business value, organizational readiness, and sustainability.

On Becoming an Engineer

A letter from a Seasoned Architect to a promising junior developer about the path of growth and the essence of engineering excellence.

On Architectural Thinking

A letter from a Technical Architect to a mid-level developer about developing a systems thinking mindset and balancing technical elegance with practical constraints.

On Strategic Technology

A letter from a CTO to a newly appointed Technical Director about aligning technology decisions with business strategy and long-term organizational goals.

On Leadership Evolution

A letter from an Engineering Director to a new Engineering Manager about the transition from technical contributor to leader, and the necessary evolution of mindset and skills.

On Sustainable Practice

A letter from a Recovering Burnout to a hard-driving developer about building a fulfilling career that can be maintained for decades, not just years.

On Team Dynamics

A letter from an Engineering Manager to a first-time Tech Lead about understanding, navigating, and shaping the complex interpersonal dynamics of engineering teams.

On Pragmatic Craftsmanship

A letter from a Technical Architect to a promising mid-level developer about finding fulfillment through delivery-focused engineering and balancing idealism with pragmatism.

On Code Quality and Velocity

A letter from a Seasoned CTO to a team lead about balancing high technical standards with consistent delivery, and fostering a team culture that values both craftsmanship and results.

On Cultivating a Continuous Delivery Mindset

A letter from an Engineering Manager to a senior engineer transitioning to DevOps about embracing the philosophy of continuous delivery and connecting technical practices to human impact.

On Cross-Functional Harmony

A letter from an Engineering Director to a Technical Leader about balancing the needs of different teams within a SaaS organization to create sustainable growth and value.

On Decisive Commitment

A letter from an Engineering Manager to a Rising Team Lead about moving beyond vague attempts to clear, decisive commitment and active problem-solving in software teams.

On Meaningful Indentation

A letter from The Technical Architect to a team lead amidst a formatting debate about how the tabs versus spaces decision reveals deeper principles of accessibility, semantics, and engineering values.

On Understanding Technical Debt Quadrants

A letter from an Engineering Director to a Team Lead about recognizing different types of technical debt and developing strategies for managing each effectively.

Last updated: Sat Aug 16, 2025, 16:19:43