About TechDebt.win
Built by developers, for developers - with 35 years of combined coding and leadership experience
RJ Lindelof
Creator & Technical Debt Survivor
I've been writing code professionally for over 34 years and leading engineering teams globally for 21 years. If there's one thing I've learned in that time, it's this: every team underestimates tech debt until it's too late.
I've seen tech debt kill products, burn out teams, and tank companies. I've also seen it conquered - not through heroic rewrites or infinite refactoring time, but through smart, incremental strategies that balance business needs with engineering reality.
TechDebt.win exists because I got tired of having the same conversations over and over:
- "How do I convince my manager we need to fix this?"
- "When is the right time to pay down tech debt?"
- "How do I measure if we're improving?"
- "Is a rewrite really the answer?" (Spoiler: usually not)
This site is the resource I wish existed 30 years ago - practical, no-BS guidance for developers and leaders dealing with the reality of technical debt.
Why Listen to Me?
34 Years in the Trenches
From C++ to Java, from monoliths to microservices, from Waterfall to DevOps. I've written (and refactored) millions of lines of code across dozens of languages and frameworks.
21 Years of Leadership
As a VP/Director of Engineering and CTO across many companies, I've managed teams from 5 to 150+ engineers. I've fought (and won) the battles for tech debt budgets.
Global Scale Operations
Built and managed Remote Teams distributed engineering teams across North America, Europe, and Asia. Tech debt problems are the same everywhere - just in different timezones.
Battle Scars & Victories
I've survived (and learned from) catastrophic tech debt failures, successful migrations, rewrites that worked, and rewrites that didn't. Every lesson on this site cost me sleep.
The Philosophy Behind TechDebt.win
1. Tech debt is inevitable. Perfect code doesn't exist. Every decision is a tradeoff. The goal isn't zero debt - it's managed, intentional debt.
2. Business value matters. Code quality isn't an end in itself. Clean code enables faster delivery, fewer bugs, and happier developers - THOSE are the goals.
3. Small wins compound. You don't need a 6-month refactoring project. The Boy Scout Rule - leaving code slightly better than you found it - is often more effective than big-bang rewrites.
4. Metrics beat feelings. "The code is bad" doesn't get budget. "Velocity dropped 50% and bugs cost us $40K/month" does. Measure everything.
5. Developers and managers need each other. Engineers can't fix tech debt without time and support. Managers can't ship products without engineering effectiveness. This is a partnership, not a war.
What Makes TechDebt.win Different
Dual Perspective
I've been both the developer begging for refactoring time AND the executive trying to justify tech investments to the board. I speak both languages fluently.
Practical, Not Theoretical
Every technique on this site has been used in real production environments. No ivory tower advice - just battle-tested strategies that actually work.
Developer-First
This site is made BY developers FOR developers. No corporate jargon, no vendor pitches, no $50K enterprise solutions. Just honest advice from someone who's been there.
Balanced Approach
I won't tell you to fight for 6 months of refactoring time (unrealistic) or to just "ship faster and ignore quality" (unsustainable). The answer is always somewhere in between.
Get In Touch
Questions? War stories to share? Just want to vent about legacy code?
Tech debt doesn't have to be a crisis. With the right strategies, it's just another engineering challenge - one we can solve together.
- RJ Lindelof