The Documentation Time Paradox

I bet you've said (or at least thought) this phrase before: "I don't have time to document this right now."

I know I have. Probably thousands of times.

But here's the thing – we say this so often that we rarely stop to examine why documentation feels so time-consuming in the first place. Let's dig deeper into this paradox, because I think there's something fascinating happening beneath the surface. 🤔

The Great Documentation Illusion

There's a weird mental model most of us have about documentation. We picture it as this polished, perfect artifact – a carefully crafted document that distills all our wisdom into clear, organized paragraphs with just the right level of detail.

No wonder it feels like a chore... 💀 We're setting the bar impossibly high.

Think about your actual work process. Your thoughts aren't organized into neat sections with perfect headings. You try things that don't work. You make discoveries by accident. You follow hunches that sometimes lead nowhere.

But when it comes to documentation, we feel like we need to filter through all our messy design decisions and mental journeys to extract only what's "important enough" to record.

That's a massive, unecessary extra cognitive load we're taking on.

We're essentially asking ourselves to:

1. Do the work
2. Remember everything we did
3. Analyze what parts matter
4. Restructure it all into a coherent narrative
5. Format it properly

No wonder we push it off. It's exhausting just thinking about it.🥲

The Timing Problem

Here's another critical insight: most valuable context happens during the work, not after.

I'm sure you've had this experience – you're in the middle of solving a problem, and you have this perfect understanding of how all the pieces fit together. Your mental model is crystal clear.

Fast forward a few hours (or even just after lunch) and that clarity has begun to fade. The connections aren't as obvious. The reasoning behind certain decisions gets fuzzy.

By the time we finally sit down to "document properly," we've already lost significant portions of our thought process. The deep context that made our solutions make sense has evaporated.

This is why those hastily scribbled notes in a physical notebook or quick comments in code can be so valuable – they capture thinking in the moment. But they're also typically incomplete, personal, and often incomprehensible to others (or even to our future selves a few weeks later).

The "Where Does This Go?" Problem

Ever had a brilliant insight while working on something completely unrelated? Maybe you notice a pattern in some data that could help with another project. Or you discover a clever workaround that might be useful in the future.

What do you do with that information?

This is where many of us get stuck in documentation paralysis. The mental overhead of figuring out where to put this new information often exceeds the effort of actually writing it down.

• Should this go in the project wiki?
• Does it belong in Slack?
• Should I create a new Google Doc?
• Will I remember to tell the team about this?

By the time we've figured out the appropriate place for this insight, we've often lost the thought entirely or gotten distracted by more urgent matters.

I've personally lost countless valuable thoughts while searching for the right place to document them. Once I even had a brilliant idea vanish while I was in the middle of typing a completely different sentence. 😅 The thought appeared, I told myself "let me just finish this paragraph first," and poof – gone forever.

The Retrieval Problem

Even when we manage to document things, finding that information later is its own special nightmare.

"I know I wrote this down somewhere…" is the battle cry of knowledge workers everywhere.

Documenting something isn't helpful if you can't retrieve it when needed. And the more places documentation lives (personal notes, Slack, email, Google Docs, Confluence, JIRA, etc.), the harder it becomes to find anything.

This creates a vicious cycle: if we don't trust that we'll be able to find our documentation later, we're less motivated to create it in the first place.

A Different Approach: Journaling vs Documenting

What if the problem isn't that we need to "document better" but that our entire approach to documentation is flawed?

What if instead of treating documentation as a separate, polished activity, we embraced the messy reality of how work actually happens?

This is where the concept of work journaling comes in – capturing thoughts, findings, dead ends, and discoveries as they happen, tied to specific questions or problems you're trying to solve.

The key differences:

• Low friction: Journaling should be as easy as jotting a quick note – no need to figure out where it belongs or how to structure it perfectly
• In the moment: Record thoughts while they're fresh, not hours or days later
• Connected to context: Notes are attached to specific problems or questions, not floating in isolation
• Retrieval-focused: The system should help surface relevant past notes when you need them, without you having to remember where you put them

Making It Work in Practice

For journaling to succeed where documentation often fails, it needs to solve these core friction points:

1. Speed: It must be faster to write something down than to keep it in your head
2. Convenience: The tool should be immediately available whenever insights strike
3. Flexibility: It should handle structured and unstructured thoughts equally well
4. Intelligent retrieval: Past insights should resurface automatically when relevant

This is exactly what we're building at reconfigured – a journaling system that makes it ridiculously easy to capture thoughts in the moment and retrieve them when needed.

Instead of expecting you to create perfect documentation, we help you build a connected web of thoughts and findings that grows more valuable over time. And with AI assistance, you don't need to organize everything perfectly – the system helps surface relevant past notes and can even summarize your thinking.

The Bigger Picture

At a deeper level, I think our struggle with documentation reflects a fundamental mismatch between how knowledge work actually happens (messy, nonlinear, contextual) and how our tools expect us to work (structured, organized, compartmentalized).

The most valuable insights often come from unexpected connections, random discoveries, and iterative experiments. Yet our documentation tools ask us to flatten all that rich context into linear documents and rigid structures.

By shifting from "documentation as a product" to "journaling as a practice," we can capture more of our valuable thinking with less effort, while also making it easier to find and use that knowledge later.

So next time you feel that familiar "I don't have time to document this" sensation, ask yourself: what if the problem isn't you, but the approach to documentation itself?

Try journaling instead – quick, messy, in-the-moment notes about what you're learning and thinking. You might be surprised how much more knowledge you capture, and how much more useful it becomes.

Have you found better ways to document your work? Do you struggle with the same documentation challenges? I'd love to hear from you.

Chat me up on LinkedIn, either via DMs, or directly on the feed 🫶