The Prescribed Sabbatical That Wasn't

There's an old saying: How do you eat an elephant? One bite at a time.

At Semicon West, an Nvidia engineer updated it: "You don't have to do it in one bite, but you do need to eat quickly."

That was my 4-month transition. Elephant-sized chaos. Had to move fast. But couldn't take one calm, measured bite at a time.

Initially, I tried to reframe it as a prescribed sabbatical.

I had one overdue from Intel—20 years without a real break. When it cashed out as part of my severance, I decided: treat August and September that way.

I scheduled trips. Seattle (Go Mariners!). San Diego twice. Dove deeply into Agentic AI. Got consumed by MindStudio's 30-Day Bootcamp—which became hundreds of hours.

This was imbalanced by design.

I'd fill in with career transition meetings, networking, rebuilding my LinkedIn from scratch. But I wanted to find a rhythm I could sustain. An energy that built positively. Giving back where I could. Learning and building publicly. Talking about frustrations and revelations.

Soaking up the outside world as I took my Intel blinders off.

This may not work for everyone. There's always a tendency to judge yourself in hindsight. But I tried to focus on the horizon—even when the waves were choppy and it seemed summer and 100+ degree temperatures would never end.

Then reality hit.

The chaos wasn't going away. The job search stretched. The learning accelerated. The newsletter ideas multiplied. Family still needed me present.

The elephant wasn't getting smaller. And I couldn't just take calm, measured bites.

So I did something counterintuitive: I built structure in the middle of the chaos.

The elephant in the room: How do you navigate chaos when you can't take calm, measured bites?

When the Waves Became a Loop

At first, I was aware of the situation and leaned into it.

My tendency to let creative exercises take over—AI agents, newsletter drafts, engagement with voices that excited me. Going with the waves. Not fighting them. Not forcing a specific path. Letting motion and signals converge over time.

No pressure to regiment my workflows. Just flow.

This lasted 6-8 weeks.

Then I started to realize: this could become an endless infinite loop.

There was never enough time to learn everything. Tools and voices in tech—or adjacent fields—were emerging faster than I could keep up with.

Even the creative process became a struggle. Endless editorial loops.

I built an editor agent to ensure my voice and narrative arc stayed consistent. Then spent hours iterating and testing it—forgetting my newsletter cadence in the process.

I didn't want to stop writing or become robotic. But I needed to embrace the same principles and frameworks I was writing about.

The 68-95-99.7 Rule applied to my life.

Where was 68% good enough—just making progress?

Where was I chasing 99.7% and hitting diminishing returns when I was already at 95%?

Would two more rounds of editing really improve what I was writing? Or would I just lose my voice, chase a new tangent, and burn a bunch of Claude tokens along the way?

I'd spent nearly my entire career in program and product management roles.

I knew how to build structure. How to establish guardrails, scaffolding, support systems that amplified effort and gave purposeful engagement.

But I was letting the chaos overwhelm me.

I needed to pause and establish process.

The first step: learning how Notion could be applied.

It was a fascinating tool—used throughout the MindStudio Bootcamp curriculum. But not something I'd used at Intel.

I had to fight ShinyStack Syndrome. Not just add one more login to my tech bookmark list.

But Notion proved different.

Carefully and purposefully documenting my actions. Linking items together. Tying threads to what mattered.

Not trying to keep everything managed through a dozen separate LLM chat windows.

Structure started to emerge from the chaos.

The System Emerges—And the Maximization Trap

I did what any AI-fluent person would do: I asked the AI.

Leaned into Gemini and Claude. Is Notion actually the right tool for this? How would the workflow look? What types of items benefit? What's the balance between recreating my entire history versus focusing on future efforts?

Small and large observations started to emerge.

It was the right tool. A powerful tool. Something I could make work for my needs without adding another paid subscription.

The first win came from simply working through my newsletter archive.

It helped me realize I'd lost count—overlooked one edition in my process. Forgotten the PDF archival step.

Small miss. But the kind that compounds into confusion later.

Then the bigger patterns emerged.

A way to connect discussion topics. Establish a digital mood board. See how key papers and pieces of inspiration circled back.

Items I wanted to address had a timeline and connection to the future.

It wasn't simply "out of sight, out of mind" anymore. It became written down. Captured and managed.

So I could free up energy for new items—without worry about what was already closed.

But here's what mattered most:

I realized I'd been trapped in a false choice.

Chasing perfection (endless editorial loops, building the perfect agent, 99.7% polished)

versus

Leaving everything uncharted (treating every newsletter as a one-off, no system, pure creative chaos)

Both sides of the same maximization trap.

All or nothing. Perfect control or complete flow. System everything or system nothing.

The real question wasn't "should I have structure?"

It was: What's good enough? What can I do without impacting my flow?

What might a colleague—or my future self—appreciate most?

Not a perfect archive. Not zero process.

But a PM flywheel in action: discipline and organization that became freeing and friction-reducing.

Not just one more checklist to stress over.

Structure freed creativity. Process enabled flow.

The system wasn't about control. It was about trust.

Trust that I'd captured it. Trust that I could find it later. Trust that the threads would connect when they needed to.

The counterintuitive move worked.

What This Actually Looks Like

Here's what the system became:

A Notion workspace with three core databases:

1. Newsletter Pipeline

  • Ideas captured from conversations, articles, AI experiments

  • Status tracking: Seed → Outline → Draft → Published

  • Links to source material, related topics, future connections

  • Archive with searchable tags (frameworks, tools, case studies)

2. Learning & Tools Tracker

  • MindStudio agents built (what worked, what didn't)

  • Articles and papers worth revisiting

  • Tools evaluated (what made the cut, what was ShinyStack)

  • Patterns emerging across domains

3. Job Search & Clarity Log

  • Applications (less than one per week, each a clarity exercise)

  • What I learned about each company, role, my own positioning

  • Patterns: Where does my breadth solve problems they can't solve otherwise?

  • Connections between seemingly different opportunities

The magic wasn't in the databases themselves.

It was in the connections between them.

Chaos → Structure → Clarity: How the system transformed scattered inputs into purposeful outputs

A newsletter idea would surface from a tool experiment. A job application would clarify a framework concept. A learning insight would become the next episode.

Example: The episode I almost lost

Working through my newsletter archive in Notion, I discovered I'd miscounted. An episode existed but wasn't properly archived. Without the system, it would have stayed lost—or created confusion later.

Small win. But the kind that builds trust in the process.

Another example: This very episode

Originally seeded weeks ago as "structure in chaos." Sat in the database. Connected to other ideas about systems, discipline, the 68-95-99.7 Rule.

When it was time to write? The outline practically wrote itself. The connections were already there.

And here's the honest part:

I lost track for a couple weeks with travel and other tasks.

But the foundation was still there.

Adding recent episodes? A few minutes of time. Threads aren't forgotten.

Dumping screenshots off my phone—key LinkedIn comments, posts, papers—saved and not lost to the depths of my camera roll.

This keeps me invigorated and excited for new items without losing myself.

The system doesn't demand perfection. It just needs to exist.

The system didn't add overhead. It removed friction.

Less "where did I put that?" More "oh right, it's connected to this other thing."

Less creative anxiety. More flow.

Even when I fall behind, I can catch up in minutes instead of hours.

What Actually Transfers

The system I built during those 4 months isn't just for job transitions—it's for any moment when growth feels like chaos.

But here's the critical test: A system that adds friction or delays progress will be abandoned.

Big companies struggle with this constantly. Extra layers insulating and preventing flow through decision-making. Scale-ups face the opposite challenge: treating every task as a one-off firefight. Neither is sustainable. You need a frictionless "glide path" from insight to action. When a system worsens outcomes, adds friction, or buries you under other tasks, it can do more harm than good—or devolve into performance theater, checking boxes to predetermined outcomes while losing clarity and agency.

The discipline isn't about the tool.

I've seen countless ways to capture information and drive progress. There are elements of art and science—finding flow, personal balance, something with longevity that can be adapted when necessary but applied consistently.

This is the marathon, not the sprint.

This isn't chasing an easy button or a magic pill. No genie to do the hard work. It's trusting that sustainable leads to thriving.

As I add a task or expand scope, have I grasped the implications?

Can it be scoped to what success looks like? Do I know what it means for me and the team—is it in harmony or conflict with other actions?

There's fluidity, like a dance or cadence. Not just a balloon squeeze of work where one team's problems get shifted to another without making the collective stronger.

This is the difference between maximization—pushing one dimension to extremes—and true optimization across multiple factors. Not one-size-fits-all, but balancing scalability with flexibility. Rigid enough to support the work, flexible enough to adapt to it.

The core principle: Capture without acting. Guardrails without prison. Momentum through process.

How do I intake and evaluate insights? Build threads, find partners to validate assumptions or impressions? What's real, what's false understanding? How do small and large tasks weave together?

Finding a way to tackle new priorities without falling into the trap of overcommitting or abandoning before completion—this helps me avoid ShinyStack Syndrome in my own projects too.

The PM flywheel still applies:

Document enough to remember. Connect enough to see patterns. Review enough to build trust.

The 68-95-99.7 Rule still applies: Where is "captured" good enough?

This is what I'm carrying forward:

Not the perfect system. Just the practice of building structure when chaos hits.

The discipline of choosing clarity over activity. The trust that I can navigate the next wave—whatever it is—because I've built the scaffolding.

Because there's always a next wave.

You don't have to eat the elephant in one bite.

But you do need to eat quickly.

Structure is how you do both.

—Joseph

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