Personal Knowledge Management saved my career

Issue 254: Knowledge management that accommodates your needs

Personal Knowledge Management (PKM) is the practice of capturing, organizing, and refining your thoughts, insights, and information over time to make better decisions and communicate more clearly. It turns fleeting ideas into durable, reusable knowledge you can draw from in your work and leadership.

Though I am a huge proponent of PKM, I am the first to tell you you tread dangerous territory of over-indexing on the knowledge management vs. the work itself. There are people who've made careers and professions updating Notion, Jira, or any tool where it becomes talking about the work vs. doing the work. On the flip side, PKM is a methodology that saved my career.

The chaos before PKM

The Second Brain is a system for Personal Knowledge Management that helps you capture, organize, and retrieve ideas, notes, and insights outside your head. It enables creative thinking and long-term learning by turning scattered information into a trusted, accessible digital archive. My perspective is not to build a Second Brain, but augment the First Brain; mine.

Challenge: Retaining information

One of the most underrated skills for any manager is the ability to retain the context of others. You’re expected to remember what matters to your team, your peers, your leadership, and your customers—often across dozens of conversations a week. I’ve always struggled with this. While I’ve never been diagnosed with ADHD, I’ve found myself constantly forgetting key details that seem like they should stick. It’s a strange paradox: I can still name the 1995 Dallas Cowboys offensive line by heart—Mark Tuinei, Nate Newton, Ray Donaldson, Larry Allen, and Erik Williams (with Darryl “Moose” Johnston leading the charge)—but I’ll forget an acronym from a meeting earlier that day. When you’re running a department, remembering your own priorities isn’t enough; you need to hold the collective memory for everyone you lead.

Remedy: Backlinks and flashcards.

Rather than rely on long-form notes, I build networks of connected concepts. By linking notes together—say, a person’s name to their project, or a goal to a metric—I recreate the context web that makes retention easier. I’ve also started creating flashcards for critical concepts: company OKRs, key decisions, or even high-stakes vocabulary. It’s like training memory with intentional reps instead of just hoping something sticks.

Challenge: Consistent writing and messaging

At One Medical, our CEO, Amir, often repeated the words Perform, Innovate, Grow. Yes, he laughed about the unfortunate acronym—PIG—but no one ever forgot it. The clarity and consistency of that message stuck with me. Early in my leadership journey, I struggled to repeat myself in a good way. I’d slightly reword the same idea in different settings—thinking I was being thoughtful—but instead, I was creating confusion. Slight deviations add up over time, and before you know it, your team is pulling in different directions.

Remedy: Personal frameworks and principles.

I began writing things down—not just what I said, but how I said it. Over time, I built my internal library of repeatable language. Now, when I talk about our AI team, I always reference the same three pillars: Product, Platform, and Practice. It’s a framework that’s memorable, but more importantly, it’s consistent. I don’t just write these things for my team—I write them so I don’t forget them.

Challenge: Transcription

I’ve tried every AI notetaker under the sun. While they do a decent job at capturing what was said, they rarely help me remember what mattered. The nuance, the intent, the implications for my work—it all gets flattened. At worst, I start deferring too much to the transcript instead of forming my understanding. For me, transcription is too passive. It’s like watching someone else live your meeting for you.

Remedy: Sketch notes and handwriting.

Instead of trying to multitask, I lean into focused attention. I take brief, bullet-style notes by hand, often with little relational diagrams—what this connects to, who needs to follow up, why it matters. The goal isn’t to capture everything, but to crystallize what I need to act on. It’s the difference between recording a lecture and learning something from it.

Challenge: Keeping context

Capturing information is one thing. Maintaining context is another. As a leader, you’re expected to track not just the “what” of work, but the “why,” “who,” and “how it landed.” That means holding multiple perspectives on the same event—team wins, 1:1 dynamics, stakeholder expectations, and even misalignments. Without structure, these moments blend into noise.

Remedy: Just enough CRM.

I’ve built a lightweight system that mirrors a CRM, but for people and relationships instead of customers. It includes short notes from 1:1s, snapshots of team wins, and even rough SBI (Situation-Behavior-Impact) sketches. It’s not overly complex—it just gives me a structured, revisitable way to retain human context without pretending I can memorize everything. It helps me be more present because I don’t have to rely on my brain alone to carry the narrative.

Beware of dogma

The biggest trap in any productivity system is mistaking the system for the work. You’ve probably seen the memes—someone with a $5,000 rig and a wall of monitors… just to update their Notion dashboard. When the tools become the main event, you’ve lost the plot.

I’m not here to preach Zettelkasten, the Cornell Note-Taking System, or any capital-F Framework. I don’t follow any of them religiously. Like Bruce Lee’s philosophy in Jeet Kune Do, my approach to PKM is grounded in adaptability: absorb what is useful, discard what is not, and add what is uniquely your own.

Your goal isn’t to obey the system. It’s to build intuition. Use the methods, yes—but only in service of clarity, creativity, and doing the real work.

My PKM system

The system

Here’s what I use—and more importantly, how I use it.

Pen and paper
Ironically, for someone working deeply in AI, my process starts with no AI at all. I rely on pen and paper—specifically my trusted LEUCHTTURM1917 notebook—as the primary space to think, sketch, and observe. Writing and drawing are how I process ideas. Capturing notes by hand frees me from the pressure of deciding what’s worth remembering in the moment.

Once a notebook is full, I scan it, bundle the pages into a PDF, and archive them in a folder. I’ve gone so deep on this that I bought a dedicated book scanner. Occasionally, I’ll run OCR with a language model to extract digital text, but that’s optional—not essential.

Obsidian
I’m a huge fan of Obsidian, not because it’s powerful (though it is), but because it scales with your needs. It can be as minimal or modular as you want. When people ask me how to get started, my advice is simple: just start writing. Most people overthink it—installing plugins before they’ve even taken a single note. Tools should support thinking, not distract from it.

Best practices

Decouple the knowledge from the publishing system
I never write directly in Google Docs, Confluence, WordPress, or Substack. My raw markdown notes are my knowledge base—everything else is a layer on top. By separating thinking from shipping, I keep my ideas portable and reusable.

Study your notes
Two things will level up your writing: First, read what you wrote as if you were your audience. Second, make sure your notes still make sense days or weeks later. If future-you can’t understand them, they’re not useful. Nick Milo says note-making over note-taking, and I’ve fully embraced that mindset. Your notes aren’t just records—they’re raw material for insight.

Impact of PKM

Without exaggeration, building a personal knowledge system saved my career. It gave structure to the chaos. I’m more consistent, more present, and less reliant on memory alone. I still don’t need to write down the 1995 Dallas Cowboys offensive line—but I’ve built a system to remember what matters now: what I said in that meeting, what we decided, what I promised, and what comes next.

Since embracing PKM, I’ve seen real improvements in:

• Sharper decision-making

• Clearer communication and messaging

• Stronger recall of context across meetings

• Lower stress and higher presence in leadership moments

Recap

• Everyone's brain is wired differently. Find a system that works for you, not against you.

• Leverage systems and methods to develop your intuition and style.

• Note-making over note taking; capture what is worth remembering

• Digitize what's worth remembering

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Hyperlinks + notes

A collection of references for this post, updates, and weekly reads.

• The Power of Role Models by

  Sofia Qin

• MCP for Designers: A Short Explainer Video on Model Context Protocol

• Replit Collaborates with Microsoft to bring Vibe Coding to Enterprise Customers

• Design Leadership in the Age of AI: Seize the Narrative Before It’s Too Late by Andy Budd

• Learning as Growth: Seeing, Thinking, and Feeling in Design, Tech, and Business by John Maeda