Self-hosting started as a simple way for me to have more control over the software and data I use every day. But after running my own services for years, I realized that getting something running is often the easiest part. The real challenge is living with that setup over time. Some decisions that seemed perfectly reasonable at first ended up creating unnecessary work later. Others taught me things I wouldn’t have understood from simply reading a setup guide. Looking back, those experiences changed how I approach self-hosting today. These are the mistakes that shaped that change and the ones I would avoid if I were starting again.