One of the hardest won lessons of my career is the power of incrementalism. I am, at my core, an idealist. When i look at a product or code base i tend to see the ways it deviates from my ideals, rather than the ways it is useful or does match my ideals. That is a nice way of saying i tend come off negative and cynical when discussing… well, almost anything.
This idealism is a powerful motivator to produce elegant code and good products. I suspect it is one of the reasons i have become a good software developer. It does have its dark side though. Overcoming some of the weaknesses of my idealism is an ongoing theme in my life. Most importantly idealism makes developing a sense of “good enough” very difficult. Paying attention to good enough is one of the most important skills any engineer can develop because otherwise you constantly produce solutions in search of a problem. An almost sure sign of an underdeveloped sense of good enough is the big rewrite. Early in my career i was involved in a couple of big rewrites. Both were successful from a technical perspective but both were a complete failure from a business perspective. They took too long and did not provide any immediate benefits to the customer.
In both cases i was crucial in convincing the business to do the big rewrite.
In the intervening years i have come to realize that, to use a football analogy, real progress is made 4 yards and a cloud of dust at a time. If you want a successful product, or a nice code base you will get it one small improvement at a time. The bigger the change you are contemplating the more uncomfortable you should be. If it is going to take more than a few man weeks of effort there is almost certainly a better, more incremental, way to achieve the goal.
I am not saying you should not rewrite the products you work on. Quite the contrary actually. If you are not in the middle of completely rewriting your code base you are Doing It Wrong. But that rewrite should be broken into many small improvements and it should never end. Those improvements will, over time, constitute a complete rewrite in practical terms. However, the business and customers will continue to get value out of the improvements as they are made, rather than having to wait many months. The developers benefit too, because the changes get released and battle tested in smaller, easier to debug pieces.
While i think all projects should be engaged in the continuous incremental rewrite, every rewrite needs to have a strategic vision. You need to know where you want to be in 1-3 years. Without such a vision you won’t know which incremental improvements to make. Once your team has a shared vision for where the product is headed you can make surprisingly rapid progress toward those goals without disrupting the day to day business. Be prepared for this strategic vision to change over time. As you gain more information about the domain and customers it is inevitable that your thinking will evolve. This is a key benefit of this model. You are continually able to make course corrections because you are always getting new information by putting the improvements in front of customers and getting feed back with very little delay.