[mtzet]

Chesterton's Fence is a valid point, but I dislike how the article celebrates it. Doing the archeology required to figure out why things are the way they are is oftentimes much more expensive than building it was in the first place. This leads to terrible situations where it's cheaper to simply build an expressway over the fence rather than tear it down.

This is the stuff technical debt is made of.

Sometimes it's the right decision to risk second-order regressions in order to make forward progress. This of course depends on the circumstances and the costs of regressions.

[satyrnein]

This is the stuff technical debt is made of.

True, but also ignoring Chesterton's Fence is what catastrophic rewrites are made of.

If you know why the fence is there and have confidence the reasons no longer apply, you can be bold. If you're not sure because the archeology is expensive, you should take baby steps if possible. (Which I think you get at with the cost of regressions.)

For my team, that's often flipping a feature flag where we don't expect any difference, and watching the output for a while to verify. First sign of surprise, we can quickly flip back. We get surprised more than we would like.

[JamesSwift]

Its a process obviously. Sure it is painful to spelunk the first time. But it gets easier over time. And it definitely gets easier if you are able to remove things over time and eliminate all that unneeded code/architecture noise.

[robertlagrant]

With technical debt you know why something was done a certain way. It was a deliberate shortcut, done for a reason, to be fixed later (paying off the debt).