School curricula worldwide is becoming more about learning lifelong skills every year. It makes sense: knowing what to do with knowledge is as important as the knowledge itself. Furthermore, lifelong skills also include citizenship, and key tools to be happy like empathy and social skills. Schools are expected to teach a wide range of skills as well as the traditional content. And that is a good thing. I have seen skill teaching work and I have seen it improve. I believe it will get even better, with schools becoming places where human growth is as central as academics, reengaging many disillusioned learners. But we are not there yet. Skills continue to be mostly secondary to content in classroom delivery. It is like there are obstacles on the road ahead. How can we measure skill development? How do we map the process of someone getting better at research or communication? I have seen attempts like spreadsheets with tickboxes and skill based rubrics. These work for a small subset of skills, leaving a large amount of more qualitative ones out. To make matters worse, students seem to only be aware of a subset of that subset that is actually measured. Thus a big chunk of critical lifelong skills remain unmonitored, and quantifiable measurable goals (grades) take the focus of most teacher and students efforts worldwide. Skills that can be quantified fail to attract equal enthusiasm from stakeholders, since the quantification often oversimplifies a complex human process. Other solutions, like getting students to write long reflections, may deliver a bit more at the expense of long hours of work. But there is hope. Skill based teaching has improved: Skill articulation is more precise, digitalisation provides bigger data sets, and stakeholders value skills more every day. Can we overcome the obstacles on the road?