Complex vs Complicated Software Projects

Trivial projects are easy to build and you know what you're building. These make perfect freelancing projects. Think brochure website for a restaurant, a self contained data visualization widget. Any tightly scoped project with a clear beginning and end, and no unknowns.

Challenging projects are easy to build, but you don't know what the end result looks like. These projects work best with an internal team. Growth engineering is a good example – you're driving an OKR (conversions, retention) and trying different things to optimize. Each individual feature is easy to build, but you can't know in advance what's gonna work.

Complicated projects are hard to build, but you know what the end result looks like. These are good agency or internal crack team of experts projects. By default they fall on a platform team of some sort. Think refactoring a creaky codebase to modern standards, upgrading an ancient framework to a new version, or building a tightly scoped feature in an area with no unknowns.

Complex projects are hard to build and you don't know what the end result looks like. These require an internal team with skin in the game. This, in my opinion, is the good stuff. Think whole SaaS products, new features in an environment with unknowns, adapting old code to new requirements, … You need iterative development and a way to measure progress. Everything about these projects is hard.