Of the many axioms in the world of software, few rise to the occasion of Thou Shall Not Rewrite Your Application. Spolsky called it the “single worst strategic mistake that any software company can make” in his seminal 2000 essay Things You Should Never Do.

The Big Rewrite has been likened to all sorts of terrible things, but perhaps the most damning is its association with declaring technical bankruptcy. Basically, the only time it’s reasonable to embark on the terribleness of the rewrite, is when you’ve been profligate cowboy coder. When your mountain of technical debt is crashing down upon you.

So it’s the white flag, then. It’s giving up. Capitulation! The error of your inadequacy has finally caught up and will be taking you to the cleaners. Who the hell wants to be that sorry sob of a programmer!?

No wonder programmers are loathe to question the wisdom of NEVER REWRITE. Either they’ll reveal their own morally deficient ways, or they’ll be seen as apologists for others traveling that deviant path.

Now, axioms develop for a reason. Many a rewrite has been started and gone astray for all the wrong reasons. Either it truly was a result of technical bankruptcy, or, perhaps even worse, it was a result of perceived technical bankruptcy by a new team uninterested in learning why things became the way they are. As Spolsky quips, such a rewrite is basically the same software with more and different bugs!

But there are other types of rewrites. The one most dear to me is the “Don’t Try To Turn A Chair Into A Table” rewrite. It’s the one we committed when we launched the new version of Basecamp a couple of years ago. A full, start-over, everything-is-reimplemented rewrite of Basecamp because we wanted it to do different things.

Yes, Basecamp Classic and the new Basecamp both juggle many of the same ingredients of project management and collaboration, but they’re mixed together in very different curations. So while we could have gotten from A to B one carefully tested refactoring and commit at the time, it would have been a fool’s errand.

Starting over allowed us to question the fundamentals of how the application worked and how it was implemented. We were able to make leaps, not just skips.

A chair can indeed be turned into a table with enough effort. Both have four legs, and all you need to do is chop off the back of the chair, and somehow refasten it to the base to extend the surface. Oh, and maybe some new wood to raise the legs up higher. It can be done, but why on earth would you?

So we decided to leave the chair alone. People were using the chair, and still are – years after the new table premiered! And we got to build a beautiful new table that’s been serving us so very well for the last couple of years.

That’s really the bottom line here: We rewrote Basecamp from scratch and it turned out great! Better than great, actually. We got to leave well enough alone for people who had adopted and grown accustomed to Basecamp Classic, we got to offer a brand-new product to new customers that was the very best we knew how to make, and we got a greenfield codebase to enjoy as well. Plus-plus, would do again!

So what am I saying here? Rewrite willy nilly whenever you get blue over seeing a few modes of progress made cumbersome because of poor past decisions? Of course not. Embarking on The Big Rewrite is not a choice to be made lightly, but a choice it remains. It should be one of the options on the table.

If you’ve accumulated enough fresh ideas about how your application can be radically different and better, The Big Rewrite may very well be just what the carpenter ordered.