The writer Annie Dillard is often attributed with the quote: “How we spend our days is, of course, how we spend our lives.” For Dillard, the beauty is in the details, and so is the learning. Social media and algorithms have led to the curation and proliferation of our best and most optimized moments, a form of personal propaganda that says, “We spend our days well, we spend our lives well, do you have FOMO yet?” The impulse to document the meaningful moments of our lives is an important one, and yet, it is often lacking transparency, omitting the critical (and more meaning-rich) moments of growth, struggle, learning, work; in short, our process.
Evidence builds trust. Trust enables agency. And agency leads to true learning.
We believe that in this new age, it’s important to document these authentic moments, not just for yourself, but for those you wish to communicate with, collaborate with, demonstrate capabilities to, and for those we wish to inspire. In an age where it’s increasingly difficult to discern what’s real and what’s faked or enhanced, authentic evidence of “the how” is critical. Evidence builds trust. Trust enables agency. And agency leads to true learning.
The Beginnings of Portable Documentation
Record keeping has been around for millennia. From early technologies like papyrus to stone tablets coated with wax, human civilizations have tried to keep a lasting record of our broader societies and cultures. The problem with many of these early technologies is that they were easy to adjust and doctor, wiping clean the slate in order to draft a new history. Although paper was invented by China well before it made its way to the West, Italy’s paper dominance began in 1264 and promptly found its way into a new package… the notebook. This innovation spurred an economic revolution on the backs of savvy merchants. Once written on paper, the accounting record couldn’t be changed, finally resulting in a lossless, portable technology. With this, for better or for worse, we were able to build rampant economies of scale and trade.
The notebook was also the origin story of a more humble use case, the sketchbook. Before the sketchbook, artists were beholden to sticking with their first draft and wasting professional-level resources on trial and error. This is incredibly apparent in the quality of their art. Once the sketchbook was adopted by artists, Venetian artists were able to run circles around the Byzantine masters. The reason for this is simple: a sketchbook enables the capturing of process, iteration, and growth. By capturing process, over time, artists were able to see where they went wrong, where they went right, and where they went… different. With continued reflection and pursuit of a more accurate picture, the fidelity of visual art made a massive leap in only a matter of years due to the ability to get closer to the source (sketching in nature near the source material, adjusting your position based on light, rapid trial and error) and with the enhancement of higher definition (the addition of shadows, three-dimensional space, etc.).
The sketchbook and its record-keeping counterparts are examples of documentation – an iterative record of learning, progress, and growth. As is the case with the advent of the notebook, the history of documentation has been accelerated and dramatically altered by technology, and there’s a new, game-changing one in town. In the same way that a painting improved based on repeated visual inputs and iterations, so too will new language models and AI agents—only, in this instance, we, not the paintings, are what’s being perceived. Authentic, quality and regular documentation just got a whole lot more important.
What is Documentation?
All learners, meaning all people, deserve to have a clear and well-articulated picture of who they are and what they know how to do. They also deserve for that picture to be seen clearly by their community and the outside world. High-fidelity documentation of learning journeys serves as a signal of competency and is critical for creating this clear image. It captures small moments and big journeys. Documentation created by and curated by the learner creates authentic evidence of what skills they gained and how they think about themselves and the wider world. To do this effectively, students must be proficient in the skills of telling their story. This goes beyond being digitally literate in the tools that many young people are already fluent in (social media, photo, video), but also developing the pathos, the purpose and the perspective to pivot based on audience and intentions.
One of the foremost thinkers in this work is Daemen University professor and documentation guiding light, Angela Stockman. In a field guide on documentation and reflection, Angela goes on to highlight three distinct phases:
- Document to Remember
- Document to Reflect
- Document to Act
Document to Remember
Angela taps into the power of in-the-moment documentation that acts as a future memory recall of what was created, experienced, or felt. This data is incredibly valuable for future reflection and for other stakeholders in your learning. Angela writes:
“When we gather evidence of learning as it unfolds, and reflect on it in ways that help us learn or teach better, we are documenting our learning. We often do this by snapping photographs or snagging a quick audio or video recording of something someone said or did or created. We can document things about the learning environment we’re in, too.”
Document to Reflect
Observing, synthesizing, and reflecting upon what was documented helps to reveal and understand patterns and growth. Angela writes:
As we hone these skills, we evolve. We become not just watchers, but witnesses. We’re the ones who get up close and personal with the raw, messy reality of learning as it unfolds. And here’s the kicker: we don’t just observe and record. We take what we’ve unearthed and spin it into theories— stories that ripple out, nourishing and enriching our communities. This isn’t about dry data or sterile observations. It’s about diving deep into our learning and emerging with insights that matter. It’s about transformation—of ourselves, our practice, and the communities we serve.
Document to Act
Documentation shifts learning from passive to active, imbuing it with agency and making it something that is truly regenerative rather than extractive. Documenting experiences of learning and growth creates a self-knowledge base of your experiences, accomplishments, failures, and moments of metacognition. Angela writes:
Documentation isn’t just a practice; it’s a challenge. It dares us to peel back the layers of learning, to tune our ears and sharpen our gaze. We’re called to be more than passive observers— we’re collectors of moments, gatherers of evidence. Our tools? Scribbled notes, found objects, snapshots frozen in time, voices captured in audio, and scenes immortalized on video.
While documenting for oneself is a valuable practice and process, documentation is often in service of a broader audience (resumes, transcripts, Instagram feeds), and these are just some of the many reasons to document. In these moments, we:
- Document to Demonstrate
- Document to Articulate/Communicate
Document to Demonstrate
Documentation has the potential to radically reshape assessment. Through documentation, learners are empowered to demonstrate what they are capable of in ways that make sense to them, enabling more powerful demonstrations of learning and competency. Angela writes,
“When learners use photos, audio, sketches, notes, and video, they paint vivid self-portraits that captivate and reveal far more than the sterile assessments adults often impose on them.”
When given the ability to use modalities that feel more authentic, a learner who may have struggled to unearth and communicate their gifts and skills now has a medium in which they feel more comfortable. Documentation can shine a light on worlds within a learner that previously were unseen.
Document to Articulate/Communicate
Knowing how to use a tool and how to curate/document experiences to affect different audiences are two different things. At its best, documentation and subsequent reflection are forms of communication, and what a learner chooses to document and curate will vary widely depending on who is in the audience (empathy matters).
These five drivers of documentation and reflection are foundational skills for learners in a post-AI landscape, and more importantly, for healthy human beings. They allow a learner to capture not just the products of their learning but their process as well. Through portfolios, multi-media artifacts and more, there are countless ways to tell our stories.
How We Use Our Tools Matters
This work is more important than ever in a post-AI landscape. Sci-fi author Ted Chiang asserts that the first draft is the most important part to do yourself, and while writing the stories of ourselves, this holds true. We are at risk of cognitively offloading some of the key parts of metacognition, including portfolio and experience curation, while repeating the same cycles of being told what was learned, rather than doing the important work of realizing what was learned. This is not a commentary on the tools themselves; rather, it is a commentary on the immense value of doing the reflective work for yourself.
A recent report from Microsoft shares some of the following on reducing cognitive effort:
- The goal of many AI tools is to increase productivity through offloading tasks, which reduces cognitive effort. Learning, however, generally requires a certain level of cognitive effort. More effective learning techniques are often more effortful than less effective ones.
- New approaches are needed to design AI tools in a way that can both support productivity and maintain or even improve human learning, understanding, and ultimately skills. For example, the newest AI tutors are finding success in guiding and challenging students more than simply providing answers.
In the same way that a painting improved based on repeated visual inputs and iterations, so too will new language models and AI agents—only, in this instance, we, not the paintings, are what’s being perceived. Authentic, quality and regular documentation just got a whole lot more important.
How we use our tools matters. We need to design tools that encourage and capture the most powerful parts of learning experiences. Tools that allow us to grow our human skills faster, not outsource them.
Quality Documentation Means Quality Evidence
Everyone has had the experience of asking a young person “what did you learn today?” or “how was your day?” at the dinner table, only to *crickets* or the ever enlightening “fine” — what would it take to turn these responses into a data rich recap of growth and learning? Part of it is collecting artifacts that turn these stump speeches into a charted TED Talk of discovery, supported by rich multimedia evidence of impact, relationship and exploration.
To document well, students need to learn how to prompt themselves all along the learning journey, reflecting over and over again upon growth, what they care about, where they’ve failed, and what they’re good at. Similarly, educators and all school staff members (families too) need to become facilitators of story, key places of reprieve along each individual learning journey for reflection and digging deeper. We all need to become journalists, unpeeling the onion of learning one layer at a time.
Once again, this is so critical because new technologies are forcing our hand. AI Skills extraction will be a part of our future. These tools are optimized to scan resumes, project descriptions, uploaded portfolios, etc. and output a set of skills as a result of it—insert the 4Cs, durable skills, transferable skills here—but without good evidence as an input, the chatbot can only know so much and assess with so much confidence. SchoolJoy, SkillsAware, Skills Validation Network, Ropes, and others are leading the charge in this space. In this race to feed the AI tools, AI is going to feast, rewarding whoever has the richest data.
Think of it this way, Student A mows a few lawns a week (this was Mason). He uploads photo evidence, multiple thoughtful reflections about how it is building his determination and grit and multiple “client” testimonials into his LER, LMS, learner wallet, etc.
Meanwhile, Student B develops an organization that provides temporary shelter for temporarily unhoused folks using the spare bedrooms of his friends and family. This student simply submits the sentence “I made an organization that helps unhoused people. It was hard but felt good.”
Despite the complexity difference between these two tasks, Student A’s ability to provide context and evidence will be rewarded, and there will be a much higher confidence level associated with those disaggregated skills. This evaluation of experience quality and context is a critical part of effectively communicating competencies.
What Does This Mean For Educators and Schools?
The long story short is that students need to graduate from high school as confident and dynamic storytellers, authentically and effectively showcasing how they spend their days and, thereby, their lives. We need students to embody what Angela Stockman defines as a “documentarian”,
“This work demands we pause, look closer. It’s about truly seeing, then sharing those revelations. We question more than we conclude, always striving to tell fuller, truer stories of learning – our own and others’. This is assessment and instruction in its purest form, with the power to revolutionize our purpose and passion.”
They will need to be comfortable being journalists, documentarians and storytellers of both their own learning and, critically, their classmates’ learning. Basically, they need to take (and use!) the equivalent of a sketchbook with them wherever they go, making iteration upon iteration of their own self-portrait to find clarity, purpose and articulation.
To do this requires a radical reframing of how learning happens, what outcomes are most important and how educators can be co-pilots on this journey. This new educator role is a co-author of the learner’s story, guiding them to learn skills of connection and curation in order to accurately convey their story to the outside world. This requires revisiting broader questions of “what is school for,” radical shifts in assessment, and new accountability systems that ensure that every learner lands on their feet. Some forward-thinking schools are already embracing this shift. A few examples are:
- Making Certifications Even Richer Cañon City High School requires students to complete industry certifications, earning over 600 per year. To augment these certifications, they have students document the process of these experiences and showcase that documentation during public exhibitions of learning.
- Capstone & Advisory Programs ensure students graduate with documented projects that reflect their skills, not just their test scores. Hillbrook School has their capstone students reflect on the evolution of their projects and display how they’ve grown and gained new skills as learners on a weekly basis. This allows students to have textured evidence of the products and process of their capstone.
- Internship & Mentorship Integration connects students with industry professionals, reinforcing learning through real-world application. Cary Academy has students documenting their internships (both the what and how) in a digital portfolio that is also communal. Students are documenting and sharing their reflections with each other, allowing the entire cohort of students to have access to each other’s experiences and learning. They’re creating an internship ecosystem.
- Learner-Led Portfolio Curation At JeffCo Open School, students create their own portfolio of learning instead of a transcript, frequently resulting in 50+ documents of their journey.
We will be publishing a series of posts digging deeper into the how and the why of many of these subjects. If you have examples of incredible schools doing this work, please send to: Mason@GettingSmart.com.
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