Readiness Is More Than a Checklist

At ISTE 2026, I sat down with Jacob Pulma, an assistant principal for Monroe County School District, to talk about career and technical education, artificial intelligence, student readiness, and the growing need to rethink what success looks like in schools. The conversation began with a simple but important idea. Readiness cannot be reduced to a test score, a grade, or a list of completed requirements. Real readiness is about opening doors.

For Jacob, one of the greatest responsibilities schools carry is recognizing that success will not look the same for every student. Some students will enter the marine industry. Others will pursue welding, construction, computer science, military service, technical education, university, or the workforce. Each of those paths can represent a meaningful and successful future, but only if students are given the opportunity to discover them.

That is where career and technical education becomes especially powerful. CTE can expose students to industries, skills, and professions they may never encounter in a traditional classroom. It can help learners connect what they are studying to real possibilities beyond graduation. More importantly, it can help schools stop treating every student as though they are moving toward the same destination.

The challenge is that schools often face practical limits. A student may want to explore a particular career field, but the district may not have enough interested students to justify a full course. There may not be an available teacher, classroom, schedule, or local program. Geography and funding can determine which opportunities students receive, even when their curiosity points them in another direction.

Jacob sees technology and strategic partnerships as ways to expand access. When used thoughtfully, digital learning can help schools meet student interests that would otherwise go unsupported. It can allow a learner in a smaller or more isolated community to explore a pathway that may not be available locally. In that sense, technology is not simply a convenience. It can become a tool for educational equity.

Read about Bailey’s journey to taking the subject of AI head on here:

The goal is not to push every student toward the same career. The goal is to inspire as many students as possible across as many pathways as possible. That requires schools to think beyond the traditional idea that readiness means passing a collection of courses and assessments.

Much of the current education system still relies heavily on memorization and repetition. Students are often asked to retain information long enough to reproduce it on a test, even though the world outside of school rarely rewards that skill in isolation. Jacob reflected on his own experience and noted that he has never been asked in a professional setting to recite information from a civics course. What has mattered is the ability to use that knowledge to think critically about the world.

That distinction is central to the future of learning. Knowledge still matters, but its value comes from what students can do with it. Can they analyze information? Can they connect ideas? Can they solve problems? Can they communicate their thinking and adapt when circumstances change?

This is also where artificial intelligence enters the conversation. Although the interview initially focused on CTE, AI quickly became impossible to avoid because it is already influencing nearly every part of education. Jacob described technology not as the goal, but as an accelerator. It can help students move further and faster, but only when it is used to support thinking rather than replace it.

One phrase he heard during the conference captured that idea clearly. Instead of thinking about AI as artificial intelligence, educators might consider it additional intelligence. That framing shifts the conversation away from fear and toward purpose. It asks how technology can augment human ability, expand access to knowledge, and create space for deeper learning.

The difference between productive and unproductive use often comes down to the task itself. When students are given assignments based entirely on recall, AI can easily produce the answers. A worksheet filled with simple questions can be photographed, uploaded, and completed in seconds. That does not necessarily reveal a failure in the student. It may reveal that the assignment no longer measures the kind of thinking schools actually value.

This reality will require educators to rethink classroom design. Learning will need to become more inquiry based, more project based, and more centered on authentic problem solving. Students should be placed in situations where technology can support their work but cannot complete the thinking for them.

Learn more about Thinkering partner, Jarred Gellar on his journey from Musk’s Space X Lab School to his own AI tool endeavour here:

Jacob emphasized that this shift must begin with teachers. Schools cannot expect educators to guide students through a rapidly changing technological environment without giving those educators the time, training, and support to understand it themselves. A single assembly, presentation, or professional development session will not be enough. AI is not a separate topic that can be addressed once and then set aside. It is becoming part of the environment in which teaching and learning occur.

That means districts must first help teachers feel prepared. Educators need opportunities to explore how AI works, where it can be useful, where it creates risks, and how it may change lesson design. Only then can schools build clear and honest expectations for students.

Transparency will also matter. Schools need to understand how educators are using AI and how students are using it. Without that conversation, assumptions quickly fill the gaps. Adults may believe students are using AI to avoid all effort, while students may feel that schools are ignoring tools that already shape the world outside the classroom. Honest dialogue can help communities move beyond suspicion and toward shared responsibility.

The future report card may also need to change. Traditional grades communicate how a student performed in subjects such as geometry or world history, but they often reveal very little about the learner’s ability to collaborate, adapt, create, solve problems, or navigate unfamiliar situations. These are the skills that employers and communities increasingly value, yet schools still struggle to represent them clearly.

Jacob acknowledged that education systems are trying to determine what a broader model of readiness could look like. The difficulty is that technology moves far more quickly than curriculum, legislation, and district planning. Schools are constantly attempting to catch up with tools and workplace changes that evolve faster than formal systems can respond.

That gap creates uncertainty, but it also creates an opportunity. Schools may not be able to predict every career students will enter, but they can identify the qualities students will need. Career titles will change. Technologies will change. Entire industries may appear that do not exist today.

A generation ago, few people imagined that social media influencer or professional video game streamer would become viable careers. Today, students can earn scholarships and sponsorships because of skills that were once dismissed as hobbies. Schools cannot predict what comes next, but they can prepare students to approach the unknown with confidence.

That preparation begins with curiosity. A curious student knows how to ask questions, pursue knowledge, and continue learning when the answer is not immediately available. Curiosity allows learners to adapt when tools, expectations, and opportunities change. It is one of the few skills that remains valuable across every pathway.

This idea closely reflects our belief at Thinkering Collective that curiosity propels change. Students do not need schools to predict their entire futures. They need schools to preserve their desire to explore, give them access to meaningful experiences, and help them develop the skills to navigate whatever comes next.

The future of education will not be defined by how many facts students can repeat. It will be defined by how well they can think, adapt, create, and act on what they know. Readiness is not a box to be checked. It is the ability to recognize an open door and have the confidence to walk through it.