In my 25 years of developing, designing, and maintaining websites both on a technical and content level for a wide range of organisations, I've used an even wider range of tools. And to this day, I use a good dozen different systems besides Plone. Some of these make me very happy, some drive me crazy. All of them have lessons to be learned. Especially when you don't just deliver websites, but also maintain them for a couple of years. An opinionated view on where we can learn, what we should stop doing, and how choices play out. Including but not limited to: • why WYSIWYG editing might have to go, in favor of simpler formats combined with integration, • simplicity and beauty deliver real value, in terms of training and maintenance costs, • "mobile first" has consequences. We should embrace it fully, • our core market is longer-term, higher volume content. Make that easier to maintain, find, present, repurpose, • smart integration beats own innovation, • oh heck, forms. We need to do better.