This editorial was originally published on February 28, 2019. It is being re-run as Steve is on sabbatical.
I've worked on some large scale software projects. For the purposes of this discussion, I'll define a large scale project as one that takes more than a two man-years to develop. I've never spent two years on a project, but I certainly have been involved with some that took more than two people, all more than a year to complete to some level. Even while working in a DevOps style environment where we released software every week, I would count a project that followed this process across a year for multiple developers as a large scale project.
When working on a large project, it's hard to sometimes keep perspective on whether to keep going or stop and change directions. We often try to continue to improve and fix a project, even when it is not going well. There's a term for this: Concorde fallacy. I've seen this similar situation occur pre-Concorde in other industries, who often have made an investment and continue to do so because of the weight of that previous investment on them. If I've spent $20 or $20mm on a project and I am evaluating whether to spent an equivalent amount moving forward, I can't continue to worry about the money I've already spent.
That money is gone whether I stop now or continue on. What I ought to do is look forward and decide if future spending is worth the investment. Certainly my reputation, and often some pain for switching or decommissioning existing work is to be considered, but that's part of the value and too often we become afraid of abandoning something we ought to get rid of for a newer, better something else.
This is discussed a little in the case of legacy technology in this piece about pulling the plug. If you start to avoid maintenance, especially in this day and age of additional regulation, you need to upgrade. If your staff or users are starting to pick other software because you can't maintain your application, you ought to abandon it and move on. Does some application take too many resources to keep going? Look for something else. In fact, some portion of your staff ought to be making evaluations on alternatives. Not as a full time job, but with some framework to help them perform a cost benefit analysis.
This doesn't mean pick the shiny new thing or move to the cloud or make everything self-service, but it should be an evaluation of how well you can get software to your users. One of the best lessons of The Phoenix Project, to me, is that continuing to bet on a bad software project isn't as good as building a plan to get replace it with something better, often something that is built with a more agile, DevOps process. This may not be the cheapest or quickest way to move, but if can often be the best way to change.