Technical debt is inevitable. I learned this the hard way. At one company, I joined to lead Engineering just as the team started building a new product for a new market. The team had worked for five years on a different product that they described as riddled with technical debt. It was a support nightmare. They were thrilled to start fresh. It was a chance to get it right! I shouldn’t have been surprised when we chose technologies and made architectural and implementation decisions that we later...