While I don’t agree with everything in this article — many people rely too heavily on metrics rather than their own intuition — I particularly like the section which describes how a website can become totaled.
While there are many ways to tackle tech and UX debt on an incremental level, there comes a point when the website, in essence, becomes “totalled.” Like a car that has sustained damage greater in cost than its value, your website gets to the point where starting over would be cheaper than fixing all of the items on your debt list.
This reminds me of a quote I learned in college which goes, “Build one to throw away because you will anyway.” The key phrase being “you will anyway”. Of course, nowadays we put this under the umbrella of “iterative development”. Not all iterations are the equal in size though. Sometimes you need to take a step back and embark on a larger iteration which involves rethinking the entire structure of your site. If you don’t chances are good your site will slowly become irrelevant. Or worse, never become relevant in the first place.
Look at the amazing transformation Path made when they redesigned their product not long ago. One rule I would add is this. If after 12 months you haven’t gained significant traction in your market you seriously need to rethink your product.
