DigitalOcean falling down

I was on the founding team that made digitalocean a thing. It died a lot in the early days, here are the most important tech things I learned from that time:

  • Minimize external dependencies, especially for critical functionality. Each third-party service or library you integrate adds a small but compounding risk of outages or unexpected behavior. Carefully evaluate whether the benefits outweigh the potential downsides before adding new dependencies. When possible, host critical dependencies yourself and pin them to specific versions rather than using "live" dependencies that can change without your control.
  • Implement robust error handling and fallbacks. Design your system so that failures in non-critical components (like analytics or monitoring tools) don't take down core functionality. Use techniques like circuit breakers, timeouts, and graceful degradation to isolate issues. Have a "safe mode" that disables optional features if needed.
  • Maintain comprehensive logging and monitoring. Implement detailed logging throughout your system, not just for errors but also for important events and state changes. Set up monitoring and alerting to quickly detect and respond to issues. A service dependency graph can be extremely valuable for troubleshooting complex problems.
  • Practice systematic debugging. When faced with an urgent issue, resist the urge to make random changes in panic. Instead, take a deep breath and approach the problem methodically. Start by clearly defining the symptoms and scope of the issue. Then systematically test hypotheses, ruling things out one by one. Work from the user-facing problem back through the system, checking each component along the way.
  • Keep development and production environments as similar as possible. While some differences are inevitable, strive to minimize them. Use configuration management and infrastructure-as-code practices to ensure consistency. Thoroughly test in a pre-production environment that closely mirrors production before deploying changes.
  • Have a clear incident response plan. Define roles, communication channels, and escalation procedures in advance. Practice handling incidents so the team is prepared when real issues arise. After each incident, conduct a blameless post-mortem to identify root causes and areas for improvement.
  • Build resilience into your infrastructure and processes. Implement redundancy, automatic failover, and self-healing mechanisms where possible. Have clear procedures for rolling back changes if issues are detected. Regularly test disaster recovery plans. Consider chaos engineering practices to proactively identify weaknesses.
  • Avoid making critical decisions or changes when sleep-deprived or overly stressed. Have an on-call rotation so no one person is always responsible for middle-of-the-night issues.
  • Foster a blameless culture focused on learning. When issues occur, focus on understanding root causes and improving systems rather than finding someone to blame. Encourage open communication about mistakes and near-misses. Recognize that complex systems will always have some level of failure, and the goal is to learn and improve continuously.
  • Maintain perspective on the true impact of technical issues. While reliability is important, most outages are not life-threatening emergencies. Avoid letting the stress of the moment cloud your judgment or lead to hasty decisions that could make things worse. Step back and assess the actual business impact to prioritize your response appropriately.