A Humbling Experience, Lessons Learned, and Adventures in Self-Hosting

Overview
This Substack post recounts a recent humbling experience that exposed a critical gap in the author's workflow. It explains why the author decided to adopt self-hosting for core services and outlines the steps taken to transition from third-party solutions to self-managed infrastructure.

Key Takeaways

• Recognize and own gaps in your tooling before they become blockers.
• Self-hosting can provide greater control, security, and cost predictability.
• Incremental migration reduces risk compared to a big-bang switch.
• Documentation and automation are essential for sustainable self-hosted operations.
• Leadership must balance short-term productivity with long-term strategic benefits.

Who Would Benefit

• Engineering managers looking to improve team autonomy.
• Technical leaders evaluating the trade-offs of self-hosting vs SaaS.
• DevOps practitioners interested in migration strategies.
• Software developers aiming to understand the operational impact of tooling choices.

Frameworks and Methodologies

• Incremental rollout (Canary releases)
• Infrastructure as Code (IaC)
• Continuous Delivery/Deployment (CD)
• Post-mortem analysis