We have all dealt with Technical Debt in one way or another throughout our careers. We’ve tried to prevent it, manage it, or mitigate its impact—and if we’re honest, we’ve probably introduced some ourselves. But is technical debt always something to be avoided at all costs? Let’s use Martin Fowler’s Technical Debt Quadrant to explore the ideas of Reckless and Prudent Debt, while distinguishing between deliberate and inadvertent cases. Drawing on real-world examples from various web application projects that migrated to React and TypeScript, we’ll break down these types of debt and uncover four key lessons and strategies for effectively managing technical debt in a sustainable and practical way. References and sources: Martin Fowler - Technical Debt Quadrant: https://martinfowler.com/bliki/TechnicalDebtQuadrant.html Martin Fowler - Design Stamina Hypothesis: https://martinfowler.com/bliki/DesignStaminaHypothesis.html Dr. Rebecca Parsons - Building Evolutionary Architectures: https://www.slideshare.net/ThoughtWorks/building-evolutionary-architectures-rebecca-parsons#12 Mark Richards, Neal Ford - Fundamentals of Software Architecture: https://www.oreilly.com/library/view/fundamentals-of-software/9781492043447/ Economics Explained - The Anatomy of a Failed Economy: https://www.youtube.com/watch?v=1EkIpMkCVwk