When developing systems which push the frontiers of their own foundational theory, Insight through making suggests that you’ll need to make simultaneous progress in theory-space and system-space to spot the new implications in their conjoined space. Effective system design requires insights drawn from serious contexts of use: you must constantly instantiate new theoretical ideas in new systems, then observe their impact in some serious context of use.
These small feedback loops are better suited to bricolage than to big design up front. Critically, though, you must try to make the bricolage accrete: the temptation is often to move in more of a drunkard’s walk.
I suspect that this is part of why Ted Nelson’s systems weren’t as successful as they could have been: he and his colleagues engaged in endless up-front design without seriously using any of their ideas to author text or do their work.