Succeeding as a WordPress publisher entails many elements, including timely and engaging content, knowing your audience, outstanding SEO, listening to your users, amplifying your content, and others. And since we know that UX is of paramount importance for successful content strategies, and UX is directly related to the performance, you also need a consistently high-performant site. As if all that was little, you need to measure how your site is doing in the real world, what is working and what is not working on your content strategy, sustainably monetize your value offerings, and monitor and evaluate your performance over dynamic conditions. Succeeding on all these aspects consistently from the inception of our products and sites and as our sites evolve is not a trivial matter. In this talk we will analyze this probabilistic conundrum, and discuss the notion of Progressive WordPress, that is, modern web solutions, the WordPress Way.