The problem with coupled CMS
Most organisations reach for a headless CMS after pain, not after planning. A replatform that's taken too long. A content team blocked by developers. A publisher trying to push content to three channels from one system that was only ever designed for one. The good news: the decision to go headless is usually the right one. The bad news: most teams underestimate what it takes to do it well.
Content modelling is the real work
The database migration, the new API layer, the frontend rebuild — those are well-understood engineering problems. The part that derails headless projects is content modelling: deciding what a 'page' actually is, which fields are required, how assets relate to entries, and what a content editor's workflow looks like. Get this wrong and you'll be restructuring your model six months in, which means migrating data you already migrated.
Structure your content for reuse, not for pages
The mental shift that separates successful headless implementations from failed ones: stop thinking about pages, start thinking about content components. A 'page' in a coupled CMS is a snapshot — it knows where it lives and what it looks like. A content entry in a headless CMS should know only what it *is* — not where it appears, what device will render it, or what language it's in. That's the consuming application's job.
Migration is a product, not a project
The teams that get migration right treat it as a product release, not a one-time project. That means: phased rollout, rollback capability, editorial team training before go-live (not after), and a clear definition of 'done' that includes the content team being fully self-sufficient. If your migration plan ends at 'all entries moved', it's not done.