Nobody wakes up wanting to be a modernization director. In this deeply personal episode, I share my journey from writing simple code at NASA JPL to leading complex system transformations at a fintech startup—and the expensive failures that taught me everything about modernization leadership.
You'll hear the story of two catastrophic failures: turning atmospheric science research code into a production web portal, and failures with month end reporting systems as a junior developer. They taught me lessons that no certification or consultant ever could.
If you've ever had a "works on my machine" moment turn into a deployment disaster, this episode is for you.
Key Topics Covered
Key Takeaways
Lesson 1: Always Think About the Future State
Before writing a single line of code, ask: Where will this actually run? Who will maintain it? What happens when things fail? The gap between "works in dev" and "works in production" gets baked in at the architecture stage, not discovered at deployment.
Lesson 2: You Can't Deploy Something Impossibly Hard to Maintain
Elegant architecture means nothing if the team who has to run it can't understand, debug, or update it. Build for the maintainers, not for the architects. Meeting requirements includes sustainability.
Lesson 3: Empower Developers to Test and Embrace Failure
The best modernization teams fail early, fail small, fail visibly, and learn fast. Create realistic test environments. Give permission to break things. Make failure a learning opportunity, not a career-limiting move.
Lesson 4: Know When You're Going Down the Wrong Path—and Admit It
The worst thing in modernization is forcing a bad approach because you're too proud to pivot. Recognize the signs: projects that keep slipping, workarounds that multiply, excuses about the environment. Have the courage to stop, reassess, and choose a different path.
Sometimes the right answer is the simpler tool that works everywhere, not the sophisticated tool that requires expertise to deploy.