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I’m building a design prototyping environment for my team right now. Using Claude Code, I’m pulling select primitives from our production system, standing up a space where designers can work in real code without touching the production pipeline.

The key decision isn’t what to include. It’s what to deliberately leave out.

Prototype code and production code serve fundamentally different purposes. That’s not a new idea. But vibe coding tools are making it dangerously easy to forget, tricking people into thinking they should generate code and ship it in one motion. That sounds like efficiency, but it often means skipping a crucial step that developers have understood for decades.

Prototype code explores. Production code endures.

Prototype code is exploratory. Its job is to make an idea tangible enough to react to, share, and refine. There’s often no backend, just static mock data standing in for the real thing. You’re not thinking about scale or security. You’re hacking, in the best sense of the word: making the thing exist so you can start to test it.

Kent Beck captured the right sequence in the context of test-driven development: make it work, make it right, make it fast. Prototype code lives in that first phase. The current vibe coding conversation tends to start and end with “make it work” and while that might hold up in small personal projects, large-scale production software requires more rigor.

Crafting production code for major applications is a different beast. You’re building for systems that other systems depend on. That means thinking carefully about scale, performance, security, edge cases, and the engineering constraints of whatever framework you’re operating inside. It’s not just having higher standards for the same code; it’s often a genuinely different kind of code.

The stakes clarify the separation

I’ve spent the last nine years designing cybersecurity software, where the distinction between prototype and production carries real weight.

In my current role at Sublime, our platform sits in the line of email processing for the companies we serve. If we miss something important, we don’t just cause a problem for ourselves; we affect our customers’ business operations. Pushing bad code doesn’t just take down our service, it potentially costs our customers thousands or even millions of dollars.

Production-grade engineering in this environment requires genuine thoroughness. Anything entering the codebase needs to be well vetted and understood by people with the context to evaluate it. That’s not unnecessary bureaucracy, it’s the appropriate level of diligence for what’s at risk.

However, operating purely within that production mindset means you don’t give yourself much freedom to experiment. You can’t explore as widely or move as fast as prototype work demands when every change carries that kind of consequence. A space for prototyping needs its own protection: not from thoughtfulness, but from production constraints it’s not meant to satisfy.

The goal should be two protected spaces with a deliberate pathway between them. The exploratory, expressive work stays in the prototype environment, doing its job by being unconstrained. And core elements from that workflow transfer over to the production environment to jumpstart the rigorous engineering process.

This pattern is older than vibe coding

My first job in tech was as a front-end developer embedded on a product design team at American Express. We built a standalone prototyping environment using Jekyll, with styles and scripts synced to and from production.

We built freely outside the Microsoft ASP.NET production pipeline AmEx ran on, avoiding technical constraints that were irrelevant to the design process. When prototypes were ready, we handed them off to the engineering org. They took the core pieces straight up and chopped up everything else to fit into their framework.

The separation was intentional, and it worked. The problem was that it required a team of five design engineers to make it happen. You needed dedicated specialists to write that prototype code. Most companies couldn’t staff for that, so despite its benefits, most design organizations didn’t follow this process.

The specialist requirement has changed. The distinction didn’t.

The distinction between prototype code and production code is as true as it’s ever been. What’s changed is how you can act on it.

If your team couldn’t afford to prototype in code before, that constraint just disappeared thanks to tools like Claude Code. I’ve been thinking about rebuilding something like that AmEx environment for years. But only now in the last few months, has it become feasible for me to do it.

My advice for teams right now? Invest in building this type of prototyping environment. Give your team a space to explore freely in code with AI assistance and stop worrying about whether that code is production-ready. It was never supposed to be. Then strategically sync relevant assets to safely jump-start production engineering.

Until next time,
Patrick

🎯 Try this

Audit your prototype-production boundary

Map your workflow from first idea to final handoff. Find the blur between exploration and production. Then decide what should cross the boundary between them and what shouldn’t.

1. Map and label your workflow stages as exploration or production.

2. Find the blur where you’re applying the wrong mindset to the wrong phase.

3. Draw the line. Which assets should sync across environments? Which ones should stay separate? Define boundaries that make each side stronger.

📚 Go deeper

• “Sneak Peek: Intercom’s AI Prototyping Workflow” — Jayneil Dalal

  • A behind-the-scenes look at how the design team at Intercom is actively building and using this kind of prototype-first workflow in practice. A useful proof point that this approach is already working at scale.

• “Prototypes and Production” — Jeremy Keith

  • Keith nails the mindset distinction at the heart of this essay. His test for whether you’re in the wrong mode is simple and useful: if you’re building a prototype and catch yourself thinking about the right class name for a component, you’ve drifted into production thinking.

• “Make It Work, Make It Right, Make It Fast” — C2 Wiki

  • The canonical discussion of the sequence referenced in today’s essay. Attributed to Kent Beck, with roots in Unix philosophy going back to the early 1980s. A quick read that unpacks what each phase actually means in practice.

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Ray Kroc’s genius wasn’t the hamburger.

When he built McDonald’s into a global franchise in the 1950s and 60s, his real innovation was the system. He created a strict operations manual and a training program so thorough that just about anyone could open a location and deliver a consistent experience. No extensive culinary training required. No institutional knowledge passed down by word of mouth. The business lived in the documentation. Anyone who could read it could run it.

That insight became one of the foundational ideas of modern business. The system is the product. If you want to scale, stop doing the work yourself and start designing the machine that does the work. As Michael Gerber summed it up in his classic book The E-Myth Revisited: “Work on your business, not in it”.

But Kroc’s model had a hard constraint baked in. Someone still had to pick up that manual and execute it. The ops manual was the asset, but it needed humans to run.

AI removes that constraint.

The plain-English instructions you write today don’t just inform people. They’re machine executable. A well-written prompt reads like a plain English operations manual but executes like code. Your documented thinking runs at machine scale, automatically.

I’m living this in two places right now. At my day job, I’m building a code prototype environment that Claude Code orchestrates while I give direction. To make that work, I’ve had to distill my intentions into markdown documents that live directly in the codebase. A Claude.md file captures some core preferences. Linked supporting docs specify more detailed instruction like library choices and project structure. All the knowledge that used to live only in my head now sits in a format Claude can reference and act on. My writing workflow works the same way. I’ve spent months refining the instructions I give Claude in my writing project: my expertise, my style preferences, my audience, how I want it to push back on my drafts. Everything I’d tell a human editor on day one. Neither of those is a clever prompt. They’re operations manuals I’ve distilled over time. And they now run every time I sit down to work.

This is the through-line of everything this series has been building toward in the last few weeks. Getting your thinking into text. Using voice to capture it faster. Curating it into sharp, reusable context. None of that was just about being organized. You were building an operations manual. One that your AI can now run directly.

Kroc needed a franchisee to pick up his manual and follow it. You don’t. Your instructions go straight from your head to execution, with AI as the engine in between.

Document your thinking like Kroc documented his system and you’ll tap into leverage he could only dream of. Then put it to work.

Until next time,
Patrick

🎯 Try this

Write your first executable operations manual

Pick one task you repeat often. Something you already do well and do consistently.

Now write it down as if you were onboarding someone who has never worked with you.

1. Name the task and its goal. As simply as possible: what is this, and what does a good result look like?

2. List the inputs. What does the AI need to have in order to start? Examples, context, reference material, a specific document?

3. Write the process. Step by step, in plain language. Nothing clever. Just: here’s what I do, here’s how I think about it, here’s what I’m looking for.

4. Add your taste. What makes a good version good? What would obviously miss the mark? Write those down too.

5. Save it as a Markdown file. Name it clearly. This is now a reusable asset.

Next time you sit down to do that task with your AI, give it this document. Watch what happens when you give it an operations manual instead of a generic prompt.

📚 Go deeper

• “The E-Myth Revisited” — Michael Gerber

  • The book behind the Ray Kroc example in today’s essay. Gerber’s core argument is that most small businesses fail because their owners never make the shift to architecting their business in a way that can operate without them.

• “Using CLAUDE.md Files” — Anthropic

  • The official guide to writing AI-readable instruction files that make your operations manual executable. Covers what to include, how to structure it across projects, and how to maintain it as your work evolves.

• “Introducing Agent Skills” — Anthropic

  • The next level of this idea. Skills let you package your instructions into reusable, portable capabilities that guide Claude’s work. Think of them as micro operations manuals that can run automatically when relevant.

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Your AI is only as good as the context you give it.

Too little context and it guesses wildly. Too much and it drowns in noise. But get it just right and suddenly the work hits the mark.

This is exactly the problem I’ve faced for years when working with new design clients. If all they tell me is “we need a new website,” I can make some baseline assumptions, but the odds of delivering what they actually want and need are low. I need more context.

But if they give me a massive data dump of everything about their company, their competitors, their quarterly reports—now I’m swimming in potentially irrelevant information. What do I pay attention to? What do I ignore?

The same dynamic plays out with AI. That curation skill—knowing what context matters and what’s just noise—is also essential for getting usable outputs from AI.

Over the last two weeks, I’ve written about getting your thinking into text and using voice to make that capture effortless. Now comes the next step: learning to curate that material so it actually works for you, not against you.

The digital hoarding trap

Creative professionals have always curated inspiration. Marketers keep swipe files of ads that work. Designers build mood boards before starting projects.

Digital tools made collecting all of this frictionless. Unlimited bookmarks. Endless screenshot folders. Voice memos that pile up. There’s no limit to what you can save so you just keep gathering.

But there’s a difference between collecting and curating.

With collecting, building the collection itself is often the end goal. Not so with curating. Curation brings intention to what’s being collected and points it towards a purpose. Collection gathers raw material. Curation creates the signal from it.

What’s changed with AI is that your collections can now function as machine-readable context and instruction. Your swipe file, your documented processes, your captured thoughts—none of this is just for your own reference anymore. It can inform an AI agent working alongside you. If you’ve curated this material wisely, your AI becomes a well-informed collaborator. If you haven’t, your information dump just pollutes the context window and you get results no better than if you’d provided nothing at all.

Curating the right signal

Language models have finite attention. Good context engineering means finding the smallest possible set of high-signal tokens that maximize the likelihood of your desired outcome.

You don’t give your agent all your context all the time. You build a library of potential context, then strategically select what matters for the work at hand.

The curation happens in two places.

First, what you choose to keep. You need to be active in maintaining this resource. Add things, remove things, update things. ‘More’ is not better in this environment. Do what you can to tend to the signal in the noise. This is the work that turns collecting into curating.

Second, what you choose to share with the AI agent for a given task. You don’t have to (or want to) attach your entire library to every conversation. You pull the specific examples, processes, or thoughts that are actually relevant to the work at hand. Give the agent just what it needs to understand what you’re trying to achieve. Guide its attention purposefully and the results will show it.

This process is similar to how a seasoned creative director operates. You have years of references stored away, but you only pull what’s relevant for the specific brief at hand. You intuitively know what signal matters for a given project and what would just be distraction. This is the information you use to guide a team from creating anything to creating the specific thing a project demands.

Strategic context compounds

The difference between working with an agent that mostly guesses and gets a lot wrong versus one that mostly understands and gets a lot right comes down to this: whether you’ve done the work of curating its context.

Each piece you curate becomes reusable creative capital. A well crafted artifact doesn’t just help with one project, it provides a foundational reference for many. It helps the agent work from your perspective, getting better results, faster, more often.

That’s a whole lot of new value from adding just a bit more intentionality to the context you save and share.

Until next time,
Patrick

🎯 Try this

Add curation to what you’ve already captured

If you’ve been following along the last two weeks, you’ve been getting your thinking into text and using voice to capture it. Now it’s time to curate some of that material.

The goal: Transform raw captures into curated context you can strategically deploy. You’re not just collecting anymore, you’re building a library you can actually use.

Pick 2-3 notes you’ve created recently and add curation:

1. Open a note from the last two weeks
   Decide whether to keep it, kill it, or archive it

2. Add the “why”
   Add 2-3 sentences explaining:

   • What makes this valuable

   • What it relates to

   • When you might reference it again

3. Tag it for retrieval
   Make it easy to find when you need it (a clear filename, a tag, a folder—whatever works in your system)

4. Test strategic deployment
   Next time you work with AI on a relevant task, explicitly reference one of these curated notes in your prompt

📚 Go deeper

• “Effective Context Engineering for AI Agents” — Anthropic
  The technical foundation for understanding how context actually works in LLM systems and why “smallest possible set of high-signal tokens” matters.

• “The Collector’s Fallacy” — Zettelkasten
  Why saving without processing creates the illusion of knowledge. The same trap exists with AI context.

• “What Is A Swipe File? (+ How To Create One)” — Corey Haines / SwipeFiles
  How a marketing professional systematically curates examples for strategic reference.

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Last week, I wrote about why text matters for your AI workflow: it’s the format where human thinking and AI capability naturally meet.

But then comes the obvious question: “How do I actually get all my thinking into text?”

The answer: speak more.

I grew up watching my dad dictate medical reports into a tape recorder. He’s a doctor who came of age before personal computers, when typing was a burden rather than a baseline skill. Like many physicians of his generation, he relied on dictation to move quickly through patient analysis. He’d flip through hundreds of pages of medical records, speaking his findings into little tape cassettes, then hand them off to a secretary who’d transcribe everything.

I saw dictation work and knew it was valuable. But I never did it myself because the tools weren’t accessible, and I didn’t really need them. I could type well enough to get by.

That’s changed now. Not because typing got harder, but because the barrier to dictation has disappeared entirely.

Text is still the goal, voice is just the faster path

The chain from last week hasn’t changed: human thinking becomes text becomes AI context. Text remains the format that AI models read, reason over, and transform. This week’s addition is how we get there.

Voice is the natural bridge between thinking and text. When you speak your ideas, you explain things the way you would to a friend: messy, detailed, with all the context still fresh. You tap into your innate improvisation. Then AI transcription handles the mechanical work of turning that speech into reusable text.

This solves three problems at once.

First, it removes the blank page problem. Starting to write often feels heavy, like you need the idea fully formed before you can begin. Speaking sidesteps that. You just start explaining what’s in your head.

Second, it captures richer context. When you try to type a quick note, you often write something cryptic that doesn’t make much sense later. Speech lets you capture the detail quickly without the friction.

Third, it matches how thinking actually works. Ideas come in bursts, half-formed, connected to other thoughts. Speech preserves that natural flow in a way that typing rarely does.

You’re not trying to create perfect text through speech. You’re capturing the raw material that becomes valuable because it lives in text afterward.

The old voice memo problem is solved

In the past, voice memos were useful but had a fundamental limitation: they stayed as audio. If you recorded a two-minute idea, you had to spend two minutes listening to it again later. Audio files are hard to search, hard to build on over time, hard to share with AI.

Tools like Wispr Flow, Superwhisper, and Monologue change this. You speak naturally, and the output is text, immediately available in whatever application you happen to be using.

Even ChatGPT has dictation built in. You can speak entire conversations, then ask ChatGPT to export the output as markdown. The transcription quality is good enough that your rambling thoughts become readable text with minimal cleanup.

So rather than speaking your thoughts into a hard-to-use audio file, now you can speak them directly into text with AI handling the translation.

When to speak fast, when to speak slow

Voice works across different modes of creative work. You just need to modulate how you use it.

When you’re in ideation mode, speak freely. Let the thoughts flow, interrupt yourself, circle back. The messiness is actually useful because it gives AI rich context to work with. Your job is just to get ideas out before they disappear.

When you’re documenting what you know (what your work process looks like, what you like about an example, etc.), speaking also works beautifully. Just explain it out loud like you’re teaching someone. You’ll capture detail you’d never think to write down otherwise.

When you’re moving into execution (writing final drafts, building specific features, etc.), you need to slow down a bit. Not necessarily switch to typing, but modulate your speech. Speak more deliberately. Choose words more carefully. Pause between your thoughts. Take a moment to edit the text after you capture it.

I dictate most of my direction to AI now, even when I’m doing something technical like designing software. But I’ve learned to speak slowly and precisely when giving technical instructions. The medium is still voice, but I’m using it with the intentionality I used to reserve for writing.

This is a learnable skill. The free-flowing, improvisational voice tends to come more naturally. The precise, intentional voice takes practice. But developing both means you can stay in flow across all phases of work.

Start awkward, get fluent

If you’ve never dictated your thinking before, it will feel strange at first. That’s normal.

You’re learning to externalize your thought process in real-time. To speak ideas that aren’t fully formed yet. To trust that the words will come as you talk, rather than planning them all in advance.

But here’s what I’ve learned: speaking your thoughts is already something you do constantly—it’s a foundation of daily life. You’re just redirecting that capability to take full advantage of the powerful tech now at your disposal.

The tools are finally good enough and accessible enough to make this skill worth investing in. What was once a specialized ability requiring a human transcriptionist is now open to anyone with a phone or laptop.

If AI runs on text, and voice is how you naturally create it, then learning to dictate fluently is one of the highest-leverage skills you can develop right now.

The quiet advantage goes beyond having your thinking in text. It’s being able to put it there as fast as you can think.

Until next time,
Patrick

🎯 Try this

Practice dictation for 5 minutes right now

The goal: start to feel how speaking “writes” faster than typing ever could.

What to talk about:

• A quick thought currently on your mind

• How you do something in your work

• An example of work you admire and why

Pick one of these two approaches:

Option 1: Direct dictation (Wispr Flow)

1. Start a free trial of Wispr Flow

2. Open your notes app (Obsidian, Apple Notes, etc.)

3. Hit the Wispr hotkey and start speaking

4. Your words appear as text directly in your note

Best for: Quick capture into your existing system. What you speak is what you get.

Option 2: Conversational dictation (ChatGPT)

1. Open ChatGPT and click the dictation button

2. Speak your thoughts for 2-3 minutes on any topic

3. Ask: “Format these thoughts as a markdown note”

4. Copy the output to your notes system

Best for: Getting AI to synthesize your rambling into something more structured. You get your thoughts plus a layer of synthesis.

📚 Go deeper

• “10x Your Whole Workflow With One AI Tool” —

  • A 10-minute video demo-ing WisprFlow and comparing it with Apple Dictation.

• “Thinking Out Loud: How to Use Your Voice in Knowledge Work” — / Ness Labs

  • Explores the cognitive science behind verbal thinking—why speaking activates working memory and the self-explanation effect differently than writing.

• “Vibe Code With Your Voice in Google AI Studio” — Google for Developers

  • A one-minute demo of using voice dictation for vibe coding. While I don’t use Google AI Studio, this short video shows the basic workflow that applies to dictation across any AI tool

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If you’ve followed the AI discourse so far this year, you’ve probably noticed Claude Code becoming a focal point. Not because it’s flashier than other solutions, but because it’s starting to connect dots in the AI workflow that allow for doing real work over time.

For the first time, more people are seeing AI systems work directly with their existing files on their computer. The AI reads, writes, and modifies the same files you’ve been managing for years. So it’s not just that the model is smarter. It’s that it’s becoming fluent in the ways we’re accustomed to working.

And that fluency is most evident in one obvious form: text.

Text is where human and AI capabilities meet

AI runs on text. Code is text. Data is text. Notes, documentation, ideas—all text. This is the material AI models excel at reading, reasoning over, and transforming.

Since ChatGPT launched, we’ve gotten used to chatting with AI. But there’s a difference between having a fleeting conversation and collaborating on an asset you both work on. When your thinking lives in plain text—especially Markdown—it becomes legible not just to you, but to an AI that can read across hundreds of files, notice patterns, and act at scale.

Personal knowledge management is far from a new concept. Honestly, it’s a topic I started to ignore because too many people were trying to sell me on yet another “life changing” system. Even when I tried to jump through the hoops, it was all just too much for me for too little return. But now that’s changed. With AI, the value is much greater and the barrier to entry much lower. I don’t need an elaborate system. I just need to get my thinking in text so I can share it with my AI.

What thinking in text actually looks like

I beg you to not overthink this.

But at the foundation layer, I suggest:

• Quick thoughts

• Documentation of your personal processes

• Collections of examples that inform your taste

The exact format doesn’t matter as much as having it accessible, in text, on your computer. A folder of Markdown files. A notes app that exports to text. Even a simple directory structure with .txt files (though I have to admit that feels a little masochistic).

What matters is that the ideas are there, externalized, in a form both you and AI can read and work with.

The leverage point

When your thinking lives in text, things that used to feel like a big lift now become almost trivial thanks to AI leverage. AI can:

• Synthesize patterns across years of notes and find connections you didn’t see

• Reorganize and restructure in seconds

• Draft new work based on your documented taste and processes

The goal here isn’t to replace your own thinking. It’s to better understand it and put it into action.

It’s to take all that knowledge floating around in your brain and allow it to live in a format where it becomes a real asset you can iterate on and use over time.

The quiet advantage

Savvy creative people have always collected inspiration. Good businesses have always documented their processes. What’s changed is that this material can now be shaped, reorganized, and activated by AI... so long as you curate it in the right format.

Plain text isn’t glamorous. But it’s the meeting place where human thinking and machine intelligence overlap. And increasingly, it’s where the real leverage lives for getting ahead in the AI economy.

If AI runs on text, the quiet advantage is having your thinking already there.

Until next time,

🎯 Try this

It’s time to start taking notes with newfound intention:

Create three new Markdown notes with different roles

1. One instruction note
   Write down a process you already use. How you prepare for a meeting. How you evaluate an idea. Etc. Plain language is enough.

2. One inspiration note
   Related to your instruction, capture an example that inspires you. Something that represents what “good” looks like in your eyes. Add one sentence explaining what you like about it and why it matters.

3. One quick thought note
   Just capture whatever’s on your mind. Raw thinking still matters.

Name these however you like. Don’t overthink it. Just start curating inspiration and instructions in a format that’s legible for you and your AI. Structure can emerge later.

This is how your private thinking becomes shared context.

📚 Go deeper

• Steph Ango — “File over app”
  A clear articulation of why centering your work on files, not platforms, preserves ownership, portability, and long-term leverage.

• Bret Victor — “Up and Down the Ladder of Abstraction”
  An essay on how tools should help us move fluidly between concrete artifacts and abstract thinking. A lens that maps cleanly onto AI-assisted work.

• Andy Matuschak — “Evergreen Notes”
  A practical philosophy for treating notes as living, reusable units of thought rather than static documents, which pairs naturally with agent-readable text.

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Hello friends,

Another year closes, and I find myself in a familiar, yet unexpected, place.

I started 2025 with clear intentions. I’d focus on AI and keep building my momentum in that area. And for the first few months, I did. Then in March, I joined Sublime Security as its first IC product designer, and everything shifted.

Taking the job was the right decision but came with trade-offs. After my 18-month sabbatical, I was ready to get back in the trenches (and recoup the savings I’d spent on my time off). But I underestimated how long it would take me to find a new balance in my work life.

After fully controlling my own time, stepping back into a demanding role as an employee meant relearning how to fit everything together. Where do creative writing ideas go when your brain is already full from work? How do you sustain weekly publishing when you barely have mental bandwidth left by Friday? What gets priority when your evenings and weekends suddenly matter in a different way?

I tried different approaches. First, I wrote about whatever came up at work. That burned me out fast — it just felt like working overtime for free. Then I pivoted to broader creativity topics. But every time I sat down to write, I’d ask myself: “Why am I the one who should be writing this?” Usually, I had no good answer and I’d get stuck spinning my wheels.

So I fell well short of my writing goals this year.

I published 24 new pieces and 6 reprints — about half my goal. The newsletter grew from 6,300 to 7,400 subscribers, but the engagement felt flat. Open rates slid from the mid-40s to 37%.

And here’s the thing that stung the most: when I was job hunting, literally no one cared that I’d written hundreds of essays and built an audience of thousands. The only things that mattered for landing product design jobs were my portfolio, prototypes, and connections. The thousands of hours I’d poured into writing, hoping they would make me more valuable as a designer, hadn’t moved the needle at all.

So I had to confront a harder question: What was I still writing for?

The real reckoning

This project feels different than it did when I started writing online 4 years ago.

It needs to continue to earn its place in my life alongside other things: time with friends and family, romantic relationships, making music and performing, fitness, and travel (to name a few). All pursuits that enrich my life.

That’s a high bar. But it’s the right bar.

No one is demanding I continue, but I feel compelled to.

Because the truth is, I still believe there’s something important here I haven’t fully realized yet.

So now I’m once again back to exploring how I can make my continuous effort worth it for myself and everyone reading around the world.

Finding what works

As I looked back at the year, here’s what became clear: the writing that energized me most — and that resonated most with readers — was about AI.

This isn’t a surprise revelation. It’s literally what I said I’d focus on this time last year. But apparently, I had to go through an extended readjustment period to find my way back to it.

AI is where my interests and skills actually converge with what’s relevant right now. The creative practice, the technical product experience, the education in philosophy, the cultural sense from my advertising days — there are very few people with this specific overlap. Working on AI workflows at Sublime now gives me another perspective on how this technology manifests in real business contexts.

AI is the rare topic that hits all the criteria for me to keep putting in the work:

• Interesting for me - I’m genuinely curious and want to learn this stuff

• Useful for you - Practical applications you can actually use

• Important for everyone - The philosophical and societal implications are massive

• Benefits from my experience - My unique blend of skills offers real differentiation

• Creates opportunities - It opens paths to other work and financial incentives

That last point matters. I don’t want to paywall my core newsletter — I want it free forever. But knowing I can offer paid workshops, skill sessions, and consulting for specific applications of AI gives me the incentive to put in the extra work this requires alongside a job that already demands a lot of my time but compensates me very well.

Moving forward

In 2026, expect:

• The return of weekly publishing

• Deep focus on AI - practical workflows and philosophical implications

• Paid offerings (workshops, skill sessions, consulting) in addition to the free newsletter

• Continued honesty about what I’m seeing and feeling while immersing myself in this space

This year taught me that finding your rhythm sometimes means losing it first. And that readjustment is part of the creative journey too.

Thank you for being here. For reading, for staying, for giving me the space to figure this out in public. If you have any specific questions or areas you’d like to see covered, please let me know.

Let’s see what 2026 brings.

Happy holidays,

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Author’s Note: Today, I’m resurfacing a piece I published over a year ago. It resonated then, and it still feels central to the questions we’ve been exploring lately. I’m also beginning to pull these themes together into an e-book, which I’m aiming to release in January.

Your perfectionism is holding you back more than you realize.

I know, because I've been there.

Time and again, I'd envision something brilliant—a creation I knew would resonate if I could just bring it to life. But as soon as I'd start, that initial surge of energy would slam into the brick wall of reality.

The sheer amount of work would overwhelm me. My skills weren't up to the task of executing my vision yet. And with each attempt falling short, my energy and hope would drain away. I'd stare at the seemingly impossible gap between my ideal and what I could produce, and I’d feel defeated.

The nagging voice in my head would whisper, "If you can't make it perfect, why even bother?" And just like that, I'd be stuck—my longing for perfection blocking me from creating anything at all.

Perfectionism isn't the virtue we've been led to believe.

We're bombarded daily with images of supposed perfection online:

• Instagram feeds curated to magazine standards

• LinkedIn profiles that read like flawless resumes

• YouTube videos polished to a cinema-level sheen

In this environment, it's no wonder we feel our work needs to be perfect just to have a chance. We start to believe that perfectionism isn't just helpful—it's essential.

But here's where we go wrong: we look at successful creatives and misattribute the source of their success. We see their attention to detail and strong work ethic, and we mistake these qualities for perfectionism.

This misconception can lead us to imposing paralyzing pressure on ourselves.

The truth is, perfectionism isn't the gift we thought it was. It's a curse in disguise, holding us back when we most need to move forward.

The costs of perfectionism are higher than you think

On the surface, the pursuit of perfection seems noble. But dig a little deeper, and you'll find the costs mount rapidly.

Perfectionism often sneaks in disguised as procrastination. You delay starting projects, fearing you can't produce work that's "good enough." Then, when you do begin, perfectionism morphs into an obsession with polishing what's already there.

Your completion rate and learning grind to a halt. You become so focused on refining one thing that you miss out on new experiences that lead to growth and skill development.

You become blind to a critical truth: In the realm of creativity, completion is currency.

If you want your work to get recognized, you need to finish first. You need to have work available for people to find.

As if these drawbacks weren’t enough to give you pause on their own, here's the real kicker...

Chasing perfectionism leads to imperfection.

The ultimate irony is this relentless pursuit of perfection often results in work that's far from perfect.

Your obsession with minute details obscures the big picture. The time you pour into endless tweaks and adjustments yields less and less improvement. And in your quest for flawlessness, you overwork your ideas until they lose their original spark.

This means perfectionism not only blocks you from achieving your dreams indirectly (by slowing you down), but it actively degrades the quality of your current work.

So, what's the solution?

How can you break free from this perfectionist paralysis?

Shift your goal from perfect to prolific

Instead of endlessly polishing one idea, complete it and move on to the next. It's through these repeated cycles of creation that you truly build skill.

If you're fearing the idea of “done”, reframe it as "done for now." Release your work into the world and give it some time and space. You can always revisit it later, particularly in digital mediums.

As someone who's worn many creative hats, I've experienced this shift across disciplines. By embracing it, I've developed skills, built creative confidence, grown more resilient, and learned to create my own momentum.

The results? My output skyrocketed. My skills grew exponentially. And you know what? The quality of my work improved dramatically.

It’s not easy, but this mindset shift from perfect to prolific is the key to unlocking your best work and making your biggest impact.

Final Thoughts

I get it. The desire to create something great burns within you.

That existential drive for excellence? I feel it every single day.

But over time I’ve calmed my perfectionist tendency. I’m not trying to force out a singular great work. I’m trying to create the conditions where greatness can emerge naturally.

I’m not chiseling away a sculpture set in stone. I’m tending to a garden: planting many seeds, nurturing them, and trusting the growth process.

So here's your new mantra:

Create abundantly. Judge less harshly. Share more bravely.

Be prolific.

And remember, quantity often paves the path to quality.

Until next time,

🎯 Try this

The 48-Hour Draft-and-Ship Challenge

Pick one idea you’ve been sitting on. Something you’ve delayed because it never feels “ready.” Then:

1. Give yourself 50 minutes to outline it. No editing.

2. Spend up to 2 hours creating a rough draft or prototype.

3. Walk away for a day.

4. Return with fresh eyes and give it one more pass (another 50mins or so).

5. Publish or ship it not as the final word, but as “Version 1.”

The goal is to teach your brain the feeling of finishing and build the muscle of momentum, not create a masterpiece.

📚 Go deeper

• “Mediocrity and Perfectionism” —

  A succinct Godin blog arguing that perfectionism and mediocrity are two sides of the same coin: ways we hide from shipping our best work.

• “Why Trying to Be Perfect Won’t Help You Achieve Your Goals (And What Will)” — James Clear

  An excerpt from Clear’s Atomic Habits showing how output volume steadily improves skill and work quality.

• “Quantity leads to quality (the origin of a parable)” —

  Kleon reflects on why making more (even imperfect) work tends to produce better eventual results.

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As a guy with many creative hobbies, Gear Acquisition Syndrome (GAS) hits me hard during the holiday shopping season.

Over the years, I’ve gone through GAS cycles in nearly every area of my creative life.

When I was making music, I built and rebuilt my home studio more times than I can count, each rebuild convincing me I was just one purchase away from a great song. When I got into photography, I convinced myself I needed a better camera to get better results. And as a remote tech worker, I’ve felt the same pull toward things like new monitors, microphones, and keyboards for my home office.

These days, I’ve learned to temper my instinct to buy new gear. I’ve accepted a simpler setup — the result of gradually realizing the truth that I do my best work when I give myself fewer choices, not more.

Procrastination disguised as preparation

GAS is tough to fight because it feels like progress, but it’s really procrastination wearing productivity’s clothes.

Buying new gear gives you a simple checklist: research, compare, purchase. There’s a clear beginning, middle, and end.

Creating, on the other hand, provides none of that certainty. It’s messy. It’s trial and error. It’s staring at your work wondering why it’s not connecting yet. It’s banging your head on the desk until a good idea falls out. Shopping for gear becomes a way to avoid that discomfort while still convincing yourself you’re making progress.

The digital media distortion field

The modern media ecosystem amplifies this urge. Every day I’m flooded with content from creators pitching me new gear whose livelihoods depend on selling novelty. While I enjoy my fair share of YouTube product reviews, when we start taking too many cues from them, we inherit a distorted idea of what we actually need to create. We start to attribute creative breakthroughs to new gear instead of the uphill battle of personal growth.

Great art rarely came from optimal conditions. Bon Iver recorded his breakout album For Emma, Forever Ago alone in a Wisconsin cabin with a laptop, an old guitar, and a single mic. Casey Neistat built a global creative identity shooting daily vlogs on any camera he had available. Eric Barone designed Stardew Valley entirely on his own using simple pixel-art tools. The common thread behind these three isn’t great equipment; it’s fluency in their craft and the intention to create regardless of the gear at hand. The tools were basic, but the focus was absolute.

Constraints build fluency

There’s another reason to keep your kit small: fluency.

Each creative tool has its own language. You can stay fluent in a handful of tools but not an endless collection. It’s like speaking multiple languages: it’s possible to be fluent in several, but only if you’re using them routinely.

The more tools you juggle, the harder it becomes to master any of them. The goal isn’t to own every instrument but rather to use a few so fluently that they disappear into muscle memory.

A tight, familiar setup keeps your creative brain focused on the idea, not the interface.

The paradox of abundance

More gear often means more friction. Ten music plug-ins become ten micro-decisions to make on top of capturing the essence of a song. Three cameras mean three ways to doubt yourself before snapping the photo. What feels like freedom quickly turns into paralysis.

Constraints, on the other hand, sharpen instincts. Limiting your tools forces invention. You find new angles, textures, and tricks because you have to. The fewer variables you manage, the more attention you have for the work itself.

So before buying anything new this holiday season, pause. Ask whether you’re solving a real limitation or simply delaying the next hard moment in your creative process. If you’re anything like me, most of the time, the problem isn’t your gear — it’s your tolerance for the inevitable creative discomfort.

And that’s the one upgrade you can’t order online.

Until next time,

🎯 Try this

Before making any purchases this month, finish one creative project using only your current setup. No upgrades, no replacements.

Invest in building fluency: learn your tools until they disappear.

If you find a true limitation, upgrade with intention.

📚 Go deeper

• “Gear Acquisition Syndrome” - Isaac Elliot

  A good blog post on the topic from a fellow creative technology person who’s all too familiar with the feeling.

• “When the Cymbals Come In” –

  A nice metaphor/heuristic for considering whether a new piece of gear will really make a difference for your creation.

• “How the Internet Ruined Hobbies” -

  Tangential to GAS, but an interesting exploration of how consuming content about hobbies has started to replace the actual act of doing a hobby for many people in the modern world.

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Most people assume that if you want to get better at something — faster, stronger, more skilled — you should just go harder more often and you’ll get results.

“You get out what you put in”… that’s how progress works, right?

Not quite. It’s not that simple.

I’ve been re-learning this lesson lately through running. After taking time off to recover from Achilles tendinitis last year, I’ve been getting back into it and joining some run clubs here in LA in the process. In my conversations with people who are newer to running, I’ve noticed a familiar pattern.

They’re excited to improve. They want to run faster, farther, more consistently. But they don’t yet understand the structure behind how improvement actually works.

Most default to some version of:

1. Just run more — run the same distance and pace more days.

2. Just go harder — run the same amount but keep ratcheting up the intensity.

Both sound logical, but they’re not how endurance is built.

What actually works is a training plan with variety built in — varying distance and intensity in a potent combination of growth stimulus and recovery. You do mostly easy runs mixed with a small but meaningful injection of challenging days. You build a weekly cadence around distinct goals: a long run to build endurance, a speed workout to improve leg turnover, and recovery runs to help your body absorb the effort. Then you layer on a seasonal cadence building up to a temporary window of peak performance.

It’s not about pushing constantly. It’s about knowing when to push and when to back off. It’s about setting yourself up to perform at your best when the moment calls for it. By definition, most days will be average (or worse). It’s the commitment to showing up day after day mixed with listening to your internal compass for kind of stimulus you need that compounds into achieving new heights.

I’ve found this same principle applies to every creative skill I’ve ever developed.

Whether it’s writing, music, acting, design, or programming, the biggest leaps haven’t come from Internet Hustle Culture’s favorite suggestion to “grind harder”. They’ve come from layering the foundation of my steady daily effort with well-timed bursts of intensity — a project that pushes my limits, a deadline that forces focus, a constraint that spurs a novel insight. But those bursts only work if they’re followed by something softer: a return to baseline, a moment of reflection, a lower-stakes rhythm where skills settle and deepen.

As a runner, if you train hard all the time, you get injured.

As a creative, if you grind the same way every day, you burn out.

But if you work with rhythm — building foundation, pushing, recovering, repeating — you improve, slowly but surely.

So if you’re feeling stuck in your creative practice or frustrated that your hard work isn’t leading to visible improvement it’s probably not time to do more of the same. It’s probably time to switch phase.

• If you’re struggling to get moving, you might need to shrink the scope of your efforts to start building some momentum.

• If you have a foundational practice but aren’t making much progress, you might need a clear, time-limited challenge to spark growth.

• If you’ve been pushing hard but are seeing diminishing returns, you might need an intentional recovery to come back stronger.

In any case, adhering blindly to doing more of the same probably isn’t the answer.

Instead, embrace the cyclical rhythm of creative progress and don’t be afraid to switch phase. That humble understanding will carry you further than any amount of force.

Until next time,

🎯 Try this

Pick one area of your life where you’ve been grinding without much visible progress.

• Step 1: Name the “training phase” you’ve been in — what’s your current intensity and frequency?

• Step 2: Identify which phase you’ve been neglecting: foundation, push, or recover & reflect.

• Step 3: Design a simple 4-week cycle that includes all three. For example: two weeks of consistent foundation, one week of higher intensity, and one week of intentional recovery. At the end of the month, reflect on how your energy and output have changed.

📚 Go deeper

• The Art Assignment – Sarah Urist Green

  • A series from John & Hank Green’s company Complexly that turns creative growth into practice: part routine, part challenge, part reflection.

• Infrastructures for Inspiration: The Routine Construction of Creative Identity and Inspiration – Ellen Simpson & Bryan Semaan

  • A 2025 academic study showing how creative identity emerges through structured variation.

• Your Elusive Creative Genius – Elizabeth Gilbert

  • A TED talk from the writer of Eat, Pray, Love about reframing creativity as a rhythm of partnership and persistence, not constant pressure.

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I’ve worked remotely for years now, and in many ways, it suits me. I can design my days, live where I want, travel when I need to, avoid LA traffic… All great things.

But over time, I’ve realized what disappeared when work stopped being a place. The real loss isn’t offices or productivity. It’s community, apprenticeship, and the quiet ways people used to learn from and rely on each other.

Learning by immersion

When I started my career in 2012 I had no idea what I was doing. I had talent and some basic skills but no experience to guide me. I learned by working alongside senior professionals.

I watched how they approached their work and how they made decisions. Most of that learning happened by osmosis, absorbing lessons naturally through immersion like a student of a foreign language. Other lessons arrived in the informal moments between work: a quick hallway conversation, a walk around the block to get some fresh air, a coffee chat where I could ask a dumb question without scheduling a call. Everything was a learning moment.

Slowly but surely, that was how I became fluent in my profession. It didn’t come from a structured educational program, and it didn’t come from winging it on my own. It came from immersion: the everyday rhythm of being in the presence of people worth learning from.

Why remote work works for me now

Now, 13 years into my career, I’m fluent enough to work alone. I know how to navigate the ambiguity and lead projects. I don’t need constant guidance or feedback. And in that sense, remote work works well for me.

For a lot of people at my life stage balancing work and family responsibility, remote work is a gift. It allows more flexibility, fewer interruptions, and deeper focus. It’s rational to want that.

But that same structure that works so well for the experienced leaves fewer ways for others to get that experience in the first place. As a junior teammate, you can’t feel a leader read the room and make a tough call on Slack. You can’t absorb their intuition from a calendar invite. You just can’t develop judgment in a vacuum.

The invisible scaffolding we dismantled

When work was a place, it wasn’t just where people did the work—it was where they learned to do the work. The office was never really an efficiency machine; it was an ecosystem for knowledge sharing and apprenticeship.

Where I live in the United States, work also became the main way for adults to find community (for better or worse). It’s where people made friends, got invited to things, maybe even met their spouse. Companies organized happy hours, recreational sports leagues, charity drives and volunteer days. That stuff may have felt like fluff, but it also served an important role: it was civic glue.

Now, that layer is gone for many people. It’s easy to recommend that someone “join a club” or “find a place to volunteer”, but the truth is most people don’t. It requires too much activation energy to gather and so many people just stop gathering. And over time, participation quietly declines and the bonds of the community dissolve.

What gets lost

Remote work allows more personal freedom, but it also makes personal connection harder to come by. There’s still no substitute for simply being in someone’s physical presence. Without that connection, it’s easy for relationships to feel purely transactional. People become nodes in a system instead of members of a community.

When everyone optimizes rationally for autonomy, the collective fabric thins. We lose the informal support networks that build future experts, and we lose one of the main social structures that kept us connected.

A million rational choices—to save time, to stay flexible, to work where we feel most focused—add up to something irrational in aggregate: a society that allows itself to weaken and leaves its next generation to fend for itself.

The question that remains

To be clear, I’m not arguing for the end of remote work (I benefit from it!). But I do think it’s time we discuss more openly the macro level costs and how we might reduce them.

The question isn’t whether we should work remotely. Many inevitably will. It’s how we rebuild community and support structures for the next generation when work no longer provides them.

Until next time,

🎯 Try this

Think back to your early jobs. Who did you learn from simply by being near them?

Now ask: who’s learning from you today?

Pick one small way to recreate proximity: invite a junior colleague to shadow a meeting, start a recurring “open studio” hour where people can drop in, write an article or record a video to share your thinking or process with the world.

📚 Go deeper

• On Work by — A thoughtful collection of essays exploring how the meaning of work has shifted in the modern era.

• Social Connection and Worker Well-Being — A CDC report exploring how social networks, belonging, and informal workplace relationships shape worker health and productivity.

• Working from home Is here to stay, but how does it affect workplace learning? — A 2024 study examining how remote and hybrid environments reduce opportunities for practical knowledge transfer and mentorship, especially for early-career employees.

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The room is quiet, but my mind isn’t.

I spend most of my days alone — working, thinking, creating — yet I rarely feel the calm and clarity that solitude is supposed to bring. The silence of modern life hums with hidden noise: notifications, messages, other people’s thoughts bleeding through the glass of every screen.

Solitude used to mean physical space. The poet’s cabin, the monk’s quarters, the artist’s retreat — all places where you could get a bit of distance from society. You stepped away from the world so your inner voice could grow louder.

But today, even though we’re alone more than ever, the world follows us home. I’m surrounded all the time, not by physical noise, but by digital noise. Emails, messages, and algorithmic feeds give me hundreds of daily invitations to react. Every time I pick up my phone or open a browser tab, someone is pitching me something: an idea, a belief, a product, a way I should be. My mind is rarely empty enough for my own thoughts to find their way to the surface.

I’ve come to realize that modern solitude has inverted: being alone no longer guarantees being with yourself.

The illusion of digital solitude

Remote work and social media have merged our public and private selves into a single, continuous feed. We are technically alone but ambiently social, perpetually connected to a world that craves our attention. And that ambient sociality eats away at the kind of stillness creative work requires.

What older generations of artists had, even amid their struggles, was psychic space. When they closed the door, the world stayed outside. Today, the world slips in through the cracks of every device we own.

Solitude used to describe a physical environment. Now it describes a mental discipline.

It’s the deliberate act of choosing not to fill every quiet moment with someone else’s noise.

Our limited mental bandwidth

Our brains aren’t built to absorb the thoughts of thousands of strangers per day.

Human beings evolved to handle roughly the social bandwidth of a small tribe, maybe a few dozen or hundred people whose names and faces we could remember. Online, that number stretches to infinity. The result isn’t just more connection; it’s less bandwidth for our own thoughts and the world we’re present in.

We become mentally crowded even when we’re physically alone.

And when the bandwidth of your attention is saturated, creativity has nowhere to surface. You can’t incubate ideas, you can’t connect the dots on a novel insight, you can’t listen inwardly long enough for the signal to emerge from the noise.

When solitude returns

Ironically, the times I’ve felt the most solitude this year were when I was surrounded by people in real life. Dinner with friends. A walk with my girlfriend. A weekend with family.

Those moments feel quiet in a way my “alone” time often doesn’t. The difference isn’t the number of people around me; it’s the number of subjects pulling on my focus. A few embodied humans are far less taxing on my attention than a thousand disembodied voices on a screen.

When I’m truly present with others, the digital world disappears, and my headspace opens back up. The noise floor drops, the signal returns, and I can hear myself think again.

Redefining good solitude

Good solitude today isn’t about isolation, but rather presence.

It’s the state where your mental bandwidth is your own — not rented out to feeds, alerts, or the constant chatter of the online crowd.

And for modern creators, reclaiming that solitude may be the most urgent creative act of all. Because without space to be, there will be no space to make.

Until next time,

🎯 Try this

Spend one day this week in intentional solitude, but do it around others.

The goal isn’t to be alone. It’s to create mental spaciousness.

Turn off your devices. Stay fully present with whoever you’re with — talking, walking, eating, or simply sitting together. Ignore everything outside your immediate surroundings.

Notice how your thoughts feel. They might be calmer, less reactive, more your own. That’s the signal you’re trying to preserve.

📚 Go deeper

1. The Art of Stillness by Pico Iyer (TED Talk) — A meditation on slowing down and finding inner quiet in a restless world.

2. The Lost Art of Solitude by Leo Babauta (Zen Habits) — A reflection on how quiet time alone can help us reconnect with ourselves, cultivate mindfulness, and rediscover clarity amid digital distraction.

3. Digital Minimalism by Cal Newport — A guide to reclaiming focus and intentionality in a hyperconnected world, arguing that true creativity and contentment require periods of deliberate disconnection.

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You don’t need to fear rejection. You need to become fluent in it.

I’m 35, and I’m only now getting good at handling rejection. Not just hearing “no”, but saying it. Letting people down clearly and compassionately. Choosing what’s right for me, even when it disappoints someone else.

It’s rarely taught as a skill. But it’s one you have to learn if you’re trying to forge your own path.

For a long time, I avoided both sides. I held back from asking for things I wanted because I feared the potential rejection. And I dodged decisions, delaying hard conversations because I didn’t want to be the one doing the rejecting. I convinced myself I was sparing someone pain. But really, I was just avoiding my own discomfort.

Rejection is a skill

Here’s what I’ve learned: rejection isn’t failure or conflict. It’s just an inevitable function of trying to move forward honestly.

More importantly, it’s a skill. One that can be developed through practice.

There are two sides to rejection and you can train both:

1. Taking a “no” without falling apart

2. Delivering a “no” without disappearing

Think of rejection as a compass with two axes: how you take it (resilient vs. fragile) and how you give it (clear vs. avoidant).

You want to live in the resilient + clear quadrant. At least, I do.

Some professions force you to master one side:

Taking rejection becomes second nature when your goals are clearly on the other side of mountains of “no”:

• Founders pitching to find early customers

• Actors auditioning hundreds of times to get cast

• Comics testing material that might bomb

They hear “no” constantly and learn to move through it, building resilience by necessity.

Giving rejection becomes a core skill when protecting what matters requires clear boundaries:

• Investors rejecting pitches with clarity

• Directors casting with honesty

• Creative leads protecting the work by saying “not yet”

When done right, rejection is an act of respect. It’s not personal, it sets a clear, present boundary. And that clear guidance, while tough to accept with grace, is often exactly what the moment calls for. It’s a form of leadership that invites people to redirect their energy rather than waste it.

Building fluency

Being graceful and clear in your handling of rejection is easier to say than do. It never gets easy. The discomfort doesn’t vanish, but your capacity to move through it develops.

Each time you practice, you build evidence for yourself. You ask for something and hear “no” and realize you’re still standing. You deliver a clear “no” and see that honesty doesn’t destroy relationships—often it strengthens them. That evidence compounds. It doesn’t eliminate the discomfort, but it makes you more willing to move through it next time.

Chris Dixon wrote that “if you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough.” Daily is a bit strong for my taste, but the principle is sound: if you’re never facing rejection, you’re probably not pushing hard enough on either side.

The compounding effect

Here’s what surprises me about developing this skill: it doesn’t just make rejection easier. It increases your agency.

When you can take rejection well, you ask for more. You pursue opportunities you would have talked yourself out of. When you can give rejection clearly, you protect your time and energy for what matters most. You help others redirect faster rather than leaving them in limbo.

Both sides work together. And the better you get at navigating rejection, the more ambitious you can be about building the life and work you actually want.

Until next time,

🎯 Try this

Pick one practice from each axis:

• On taking rejection: Where have you been holding back out of fear of hearing “no”? Ask anyway. Take a big swing.

• On giving rejection: Where have you been softening a “no” that needs to be said? Rip the band-aid off and say it clearly.

There’s valuable guidance waiting in both.

📚 Go deeper

• What I Learned From 100 Days of Rejection – Jia Jiang – How an entrepreneur conquered his fear of rejection by intentionally seeking it out every day, turning “no” into opportunities for growth.

• Seth Godin on Overcoming Rejection – Tim Ferriss Show – A conversation about choosing your attitude, dealing with fear of failure, and pursuing meaning over comfort.

• From Rejection to Resilience – Sources of Insight – Five inspiring stories of how rejection became the catalyst for extraordinary success, from Rocky to Harry Potter.

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A decade ago, I chose tech over the arts. Not because I was more talented at code than performing, but because I watched my creative friends struggle: actors waiting tables, musicians scrounging for gigs, writers churning out words for pennies. I wanted interesting, creative work without the feast-or-famine anxiety.

Tech promised that trade and for years, it delivered. But now those days are ending.

Today’s tech job market feels like it’s drying up: more layoffs, fewer roles, harder to get your foot in the door even with years of experience. Yet compensation for a small elite is exploding—like the $250M+ pay packages for top AI researchers at Meta. Unfortunately, this isn’t a temporary dip. It’s a structural shift in how value gets distributed.

Most people still imagine careers as a bell curve: a few underperform, most cluster in the middle, a handful rise to the top. That model doesn’t reflect reality. Digital economies have replaced it with something more extreme: the power law.

In power law markets, a tiny fraction of top performers takes home a massive share of the rewards, followed by a long tail competing for what’s left. The best don’t earn twice as much as average—they earn 10x, 100x, even 1,000x more. Not because they work harder or are 1000x more skilled, but because they operate with vastly more leverage.

We’ve seen this before in music, sports, and film. The superstars—Taylor Swift, LeBron, Steven Spielberg—capture enormous value from the market while everyone else competes for small returns on the hopes of one day hitting it big. I thought I’d escaped that world by choosing tech. Turns out I just delayed the inevitable.

This reallocation of resources to top performers is already happening in tech. Picture a hiring manager with a $1M budget. Ten years ago, they might hire ten capable engineers at $100K each. Today, that same budget is more likely to go to four senior engineers at $250K or two at $500K.

Why? When your work scales massively, one talented person can outperform a team while also introducing less overhead and complexity for the business. A single engineer who builds the right feature or invents the right model can generate millions in value. It’s economically rational to pay that person accordingly (aka “a lot”). But this results in a predictable outcome: the middle class of tech jobs gets hollowed out.

Power law careers don’t reward steady progression or tenure (typical ways for an average tech worker to prove their value). They reward irreplaceable leverage.

Here’s what that means for anyone trying to build a career right now: being average isn’t enough. Being great isn’t enough. You need to offer something a company can’t find elsewhere. You need to be the person whose unique knowledge, perspective, or capability generates enough leverage that paying you becomes more efficient than distributing the work. In other words, you need to be irreplaceable. If you achieve that leverage, you’ll be paid handsomely. But if not, you’ll be duking it out with the many other undifferentiated candidates for an ever-smaller portion of the pie.

So where does this leave me?

The stability I thought I’d found a decade ago is evaporating, and I’m making peace with it. Not because I like it, but because I see it clearly now. I’d rather navigate this shift with my eyes open than pretend it isn’t happening and I hope you feel the same. The sooner you understand the new shape of the landscape, the better you can position yourself within it. And that’s the most important move any of us can make right now.

Until next time,

📚 Go Deeper

• Doug Shapiro: Power Laws in Culture

  A crisp explainer on how power laws show up across culture, entertainment, and media and what that means for careers in creative industries.

• Andrew Chen: Creator Economy 2.0

  Why success in the creator world is now governed by power laws and how scale, platforms, and audience dynamics are reshaping who gets paid.

• Why Google quietly uses the power-law rule to pay its superstar employees ‘unfairly’

  An overview of how even companies known for standardization like Google make exceptions for top performers because the math demands it.

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Even Picasso couldn't skip the humble beginnings of creative work.

Between 1945 and 1946, he created eleven drawings of a bull, starting with a detailed, realistic sketch and ending with just a few flowing lines. What most people miss is that despite his mastery he couldn't have started with those elegant final strokes. He had to earn his way to simplicity through every iteration in between.

Picasso's bull sequence is a masterclass in purposeful reduction. The first drawing leans into concrete, anatomical detail—a realistic representation. Through the iterations, he first adds complexity, then systematically strips it away while preserving what's essential. The bull becomes more geometric and distilled but still recognizable.

By the final drawing, the entire animal exists in just a few confident lines.

Here's the crucial insight: each drawing in the sequence is valuable and necessary.

The detailed first bull isn't a "rough draft" to be discarded, it's the foundation that makes the final abstraction possible and meaningful. That starting material informed every choice as Picasso worked toward those elegant final lines.

This pattern shows up everywhere in creative work. Want a succinct essay? Write one that rambles but gets the point across, then edit. Want an efficient computer program? Write one that works but isn't optimized, then refactor. The first step to elegant solutions is surfacing raw material you can shape.

I learned this the hard way. Over the years, many ideas have burned bright in my head, clear and elegant. But when I started creating, what emerged felt so raw compared to my vision that it was easy to feel defeated—like I was moving further away from the goal rather than toward it. It was tempting to abandon the work entirely or get lost in rabbit holes that felt productive but weren't actually supporting the essence of what I was trying to create. Gradually, I learned to fight these instincts because I knew if I gave in, the idea would die in the space between vision and execution.

Modern AI tools are disrupting this creative process in contradictory ways. On one hand, they make it seem like you can skip the raw stage entirely. When you can prompt for polished output instantly, your own messy first attempts feel inadequate or inefficient by comparison. On the other hand, AI can also flood you with so much raw material that you get lost in generation, never making the shift to focus on the critical work of thoughtful reduction. Either way, you end up disconnected from the iterative process that's essential for sticking the landing with creative execution.

The path to meaningful simplicity requires methodical progression. Start with the fullness of your idea—the whole "bull." Get something tangible down, even if it's not the final form. Then systematically refine and distill toward the purest essence.

This process gives your final abstraction real weight. Every element that remains earned its place through conscious editing, and the result resonates because it emerged from understanding the full complexity, not from avoiding it.

The art isn't just in making something simple.

The art is in earning it through intentional reduction.

Until next time,

🎯 Try this

Pick one project you’ve been overthinking and commit to putting the raw version down this week. The refinement can only happen after you have something to refine.

📚 Go deeper

• Picasso’s Drawings of Bulls Inspired Apple’s Famously Simple Designs - Abigail Cain

  • How tech companies study artistic masters to achieve their own version of elegant simplicity.

• Imitate. We are imperfect mirrors. - Derek Sivers

  • One of the best ways to get started making raw material is to imitate. This is a great piece from Derek on the topic.

• Shitty First Drafts - Anne Lamott

  • An excerpt from Lamott’s Bird by Bird, arguing for letting go and writing the “shitty first drafts” that lead to clarity and sometimes brilliance in later iterations.

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A “dream job” is meaningless if you feel like a ghost inside it.

In 2021, I knew this, but didn’t know how to say it.

I had all the trappings of modern success: a high-paying tech job, remote work freedom, and a luxury apartment in LA. But none of it felt meaningful.

My days blurred. Comfortable, but numb.

One day, while getting high to take the edge off a lonely stretch of pandemic isolation, a lyric from Mac Miller’s song Small Worlds stopped me cold:

You never told me being rich was so lonely
Nobody know me, oh well
Hard to complain from this five-star hotel

Those lines named the feeling I was numbing and led me through Mac’s tragic story, my own confusing circumstance, and a question more of us in my generation are starting to face:

What do we do when the life we worked for leaves us feeling hollow?

Mac’s story

On September 7, 2018, Mac Miller was found dead in his home in the Los Angeles hills. He was 26 years old.

A gifted musician. Beloved by fans. Acclaimed by critics. By all external measures, Mac had “made it”. Rich enough to live in near-total comfort. Famous enough to be adored anywhere he went.

And yet, he seemed profoundly sad and alone.

In the years leading up to his death, Mac’s music shifted. The bravado and youthful exuberance of early hits like The Spins gave way to something more introspective. His later work sounded like someone searching for peace in the quiet aftermath of success. Still young, still brilliant, but humbled by the weight of it. Living in a dream realized, yet still looking for the meaning that never materialized.

From the outside, it’s easy to dismiss: what’s there to complain about when you’ve won the game? But that’s exactly what makes it so isolating. When the conditions of your life look perfect on paper, it becomes harder to admit that something essential is missing.

I’d heard Small Worlds many times before, but at the height of the pandemic, with my own life hollowed out in a similar way, the dissonance finally landed.

My connection to the feeling

I woke up one morning and realized I was living in a comfortable but sterile loop.

Wake up, make coffee, sit at desk, open laptop, and wonder—what’s the point of all this?

The startup I worked for had been acquired, and I landed in the kind of position I used to dream about. Cash in the bank. Steady paycheck. Light workload. Fully remote. I was earning more than ever, but nothing I spent money on seemed to matter. Each purchase brought only marginal improvement to an already comfortable life.

Meanwhile, the community I had built in LA quietly dissolved under pandemic restrictions. Social clubs went dormant. Friends moved away. Dating reduced to an awkward string of video calls and outdoor meetups.

After a decade of building a career to support a good life, was this really it?

A Groundhog Day of semi-luxury alone?

Another of Mac’s lyrics lingered in my head: “Do you want it all if it’s all mediocre?”

My work began to feel like a simulation—just a game to pass the time, nothing really meaningful. I started to wonder why I kept showing up at all and where the meaning I’d expected to find in this achievement had gone.

Because my life looked great on paper, I told myself I had no right to complain. My loneliness and crisis of meaning felt like a small price to pay compared to what so many others were facing. But that’s the trap: when your suffering feels illegitimate, you keep quiet. And that silence only deepens the pain.

My life had become remote in every sense of the word. I was an avatar on Slack. A square on a Zoom call. A mechanical turk with a W-2.

I wasn’t living—just clicking my way forward, one day at a time.

But gradually, I realized it wasn’t just me. Friends and coworkers described the same flatness. Lives that looked enviable on paper but felt strangely hollow.

The bigger picture

In my conversations, the same pattern kept surfacing: lives rich in comfort yet thin in meaning. We had sought-after jobs, flexible schedules, and comfortable homes, yet still felt ourselves quietly unraveling.

It wasn’t burnout in the traditional sense. More like an ambient numbness. A low-grade hum of disconnection that never quite resolved.

Tech jobs gave us disposable income and remote work gave us freedom, but they also stripped away the small touchstones that gave shape to our days. We lost the healthy friction that provides traction on the road to a meaningful life: shared meals, chance encounters, the rhythm of little in-person rituals. Without it, life became flatter. More efficient, sure, but also more abstract.

The digital tools that made this possible blurred the boundary between work and self. We became profiles instead of people, async components plugging in and out of a perpetual motion machine. Every message another task on a todo list. Every interaction a transaction.

If we weren’t careful, the very conditions we once aspired to turned out to erode the elements of daily life that made it rewarding.

Ways forward

There isn’t a single fix for this erosion of meaning.

It’s not a problem you can optimize away.

What I’ve been learning instead is that meaning comes from presence. From contact. From commitments that don’t scale.

The old definition of success I carried was all about independence: make enough money, own your time, escape the need for others. But after achieving that version of success, I’ve found the story is empty if you’re the only one in it.

Now I’m more interested in interdependence—community, family, the kind of bonds you can’t outsource or automate.

The shift shows up in small ways: saying yes to things that feel “inefficient,” like crossing town just to see a friend; or showing up at a local event, not because it’s the best option, but because it’s part of the fabric of your community. None of it is glamorous or optimal. But it’s real. And real is what I was missing.

Mac hints at a similar prescription later in Small Worlds:

I'm always in a rush
I've been thinking too much
Keep it on the hush, no one need to know, just us
That's really all it takes
We don't need nothing but today

Maybe that Zen disguised as hip-hop is the closest thing to a cure—slowing down, not overthinking, and sharing the time right in front of us.

It’s not a sure thing, but it’s something. A way to let the friction of real life give you some traction again. A reminder to shrink your digital sprawl back into small worlds worth living in.

Until next time,

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Last weekend, I was sitting in my hotel room on a rainy day in Portland, putting some words down for the weekly newsletter, when I had a sudden realization: I didn't feel connected to what I was saying. So I closed my laptop and decided to take a pause.

Since 2022, I've sent 182 newsletters — more than one per week. I've tried different styles, lengths, and formats and built this email list to 7,400+ subscribers, but I still haven't found anything that really clicked. To use a baseball analogy, I've hit a lot of singles and a few doubles, but definitely no home runs. And so now, three years later, I find myself in creative limbo.

The problem became clear when I started my new job at Sublime. Short on time, I figured I could shift my focus to writing about whatever was on my mind at work that week. But that quickly wore me down. Forcing my writing to become an extension of my day job made me feel like I was working overtime for no reward. Even if the insights were useful to people, there was no joy for me in the writing — and joy is essential for the sustainability of any creative act.

I want to still be doing this a decade from now and the only way to ensure I achieve that is to use my writing as a vehicle for my genuine curiosity.

Remembering the guiding story

Et ignotas animum dimittit in artes. (And he sets his mind to unknown arts)
Ovid, Metamorphoses, VIII, 18

The name Unknown Arts comes from the story of Daedalus in Ovid's Metamorphoses, later echoed in James Joyce's novel "A Portrait of the Artist as a Young Man." It signifies turning toward unfamiliar creative endeavors, building a fulfilling creative life marked by continuous evolution and the exploration required to chart new paths.

That's what this newsletter is really about: creative flourishing and creative leverage. Building a satisfying and meaningful creative life for yourself, and using systems and technology to support you on that journey.

A reality check on who I serve

I need to be clear about who I want to serve. If you're looking for something just to help you succeed in the tech industry, I'm not your guide. I'm more interested in what I'd call the "post-tech professional" — people who aren't focused on climbing tech career ladders but rather in finding success on their own terms, using technology.

I know many creative people who have had successful tech careers and the reality is that they're often left wondering how to thrive despite their professional and financial success. They feel more lost than ever when they consider stepping away because there's no benchmark for what success looks like. They know on some level that their fulfillment lies in uncharted territory, but have a hard time pursuing new paths that feel more aligned.

That's the space I want to explore.

Four changes to align this project to its purpose

For this project to be sustainable long-term, I need to optimize for what energizes me. Here's what I'm adjusting:

• I'm expanding what I write about. I care about many topics more than I care about the tech industry: the arts, community, style, travel, philosophy, AI applications and implications, and more. Product design is my day job, but it's not my passion. And honestly, a lot of what sets me apart as a product designer is the breadth of my studies outside of tech. As a foundational rule, I don't want my writing to be tangential to the things I care about — I want it to be the channel through which I share those things.

• I'm changing my publish day to Monday morning (pacific time). Working full-time means I often don't have dedicated writing time until the weekend. I need the full weekend to make sure I can do the work without feeling too crunched.

• I'm not going to force publish to hit a certain cadence. I aim to publish as often as possible to exercise the muscle, but I'm not going to force an idea out just to hit the weekly mark. At this point, I've done lots of quantity. It's time for more quality.

• I'm going to start making video content. In a world where text is increasingly filtered through AI, there's something about speaking my words that feels increasingly important. If nothing else, it enables a kind of authenticity that's different and complementary to what I can share through words alone.

Moving forward

This isn't a hard pivot, but rather an attempt to focus and reengergize. As someone with broad interests and skills, I'm always tempted to try to be all things to all people, but I'm trying to accept that I can't be. Expanding what I write about might seem like going broader, but it's actually going deeper — focusing on who I'm serving rather than what subjects I'm covering. I'm excited about what becomes possible if I allow myself to follow this thread.

Unknown Arts is about evolving in service of authenticity and creative flourishing. I want to model what that looks like for the community: the honesty about what isn't working, the courage to step away from performance in favor of alignment, and the willingness to follow genuine energy even when it's less predictable than safer directions.

Thank you for being part of this journey. I'm excited about where we're headed, even as we discover what that looks like together.

Until next time,

Patrick

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Creative career paths aren’t linear.

Forget your 5 or 10-year plan.

Follow your curiosity and ride the wave.

Become a “Skill Surfer” and watch your natural momentum carry you to a career you didn’t even know was possible.

What’s a “Skill Surfer”?

A Skill Surfer navigates their career by mastering skills that follow their curiosity.

They don't follow a predetermined path. Rather they embrace change and seek new learning opportunities. They adapt to the evolving demands of the job market much like a surfer adapts to the changing waves of the ocean.

This approach focuses on continuous growth, flexibility, and the pursuit of curiosity. It might be unconventional, but great rewards await those who ride the waves.

My journey as a Skill Surfer

Over the last 12 years, I pursued a wide range of interests leading me to four distinct careers. First, I became an advertising strategist. Then a software engineer. Then a product designer. And now, a writer. I couldn’t have planned it, even if I tried.

I was always curious about new creative skills but more school wasn't for me. I chose to follow my curiosity and build my way forward. This allowed me to try out new roles without feeling over-committed due to a costly degree. When the swell of the curiosity wave would surface I’d hop aboard, follow its momentum, and eventually end up on a new shore.

I got into advertising because I was curious about how psychology affected business.

I got into software development because I was curious about how to build my ideas.

I got into design because I was curious about how to improve the software I was building.

Most recently, I got into writing because I was curious about how to help others by sharing what I'd learned.

In each case, I began pursuing the new skills well in advance of when I started to believe they’d be central to my career. I just thought they were cool and would be useful in my quest to live a rich creative life.

I didn't have a master plan or a guide for how to hop from one wave to the next. But I kept sitting in the ocean staying mindful of new swells coming to the surface. I didn’t ride every wave, but I’m proud to say that when the big ones arose I was brave enough to go with the flow.

How to Become a Skill Surfer

Test the waters first

Before you can ride a wave you have to go sit in the ocean. If you’re curious about what it’s like to do a new kind of work, the only way to assess it is to do it.

It's tempting to pursue more book learning as a way to test the waters. But that’s not how creative skill development works. The first step is to get in the water and start paddling: do the activity.

These days, it’s easy to find ways to test the waters for cheap on the internet. Just get started. Once you do, you’ll begin to notice areas where you want to improve.

That’s when seeking out the guidance of teachers becomes valuable. They can remove your blockers and speed up the progress you’re already making.

Ride one wave at a time

Every discipline has interesting and useful techniques to teach you.

It’s tempting to try to pursue them all at once. Don’t.

It will spread you too thin, put you out of balance, and knock you off your wave.

Ride the one wave that you feel has the most momentum for you right now.

Trust that this wave will one day subside and a new one will follow.

Exercise your patience

Mastering a skill takes longer than productivity gurus want you to believe.

You might be riding one wave or waiting on another for years at a time. That’s okay. This is natural and shouldn’t dishearten you.

Instead, focus on the present by expanding the perspective of your timeline. Considering the decades of your working life, it seems reasonable to spend years on a topic. As a Skill Surfer, you can go deep for much longer than you expect and not get stuck.

Some waves are long. Others are short.

Your job is to go along for the ride as long as it will carry you.

Final thoughts

Skill Surfing is more than a way to find a new job. It's about loving what you learn and always being ready to embrace what comes next.

Use your curiosity as a guide.

I bet the waves that surface and where you end up will delight you.

Until next time,

Patrick

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A design portfolio is like a first date.

You can have the looks, but you won't know if there's chemistry until you talk — which is why I went video-first when I started applying to jobs again earlier this year.

Most teams don't just want to see your work. They want to know what it feels like to work with you. Video makes that visible, fast. When someone lands on my portfolio, they can immediately hear how I talk through problems, see how I communicate design intent, and get a feel for how I show up to work without having to book time with me.

In a world of remote work, async collaboration, and overloaded calendars, that just feels like the honest move for me and for anyone evaluating me.

But I didn't just drop a video on my homepage and call it a day. I rethought how I created the content of my portfolio website starting with the presentations I'm expected to give — then built everything else around that.

I’m not the only one thinking about the potential impact of video portfolios. Designer and Inflight founder, Michael Riddering, shared his thoughts on my approach in a recent edition of his show ‘Dive Club’ on Youtube. We’re in the early days, but it definitely feels like this format is on the rise.

Here’s how I approached it, step-by-step — and the results.

1. View the site → www.patrickmorgan.org

2. View the slide deck → Figma Slides Portfolio 2025

3. View a sample project → Making a Complex Query Language Approachable

Working within my existing visual system

Before diving into the specifics, I want to call out that this wasn't a full brand or website redesign. I'd already designed and shipped an earlier version of my portfolio with Framer last year, and I'd spent time refining a personal visual language through my work on Unknown Arts — establishing type, color, and other styles that I liked.

That meant I could focus this effort on upgrading the content of my core projects and communication strategy.

This separation helped me focus and freed up a lot of headspace. I wasn't getting distracted by visual or UI design rabbit holes. I was focused on the clarity of the storytelling.

Starting with the presentation

Instead of jumping straight into updating my website, I began with the portfolio presentation I knew I'd have to give in interviews. I wanted to create a clear, compelling narrative for a few representative projects — each chosen to highlight different facets of my design skillset.

I used Figma Slides to build the presentation, keeping the process lean and in the same environment where all my assets already lived.

I also created a dedicated Figma file to support this process — a central place to gather existing work samples and create new visuals specifically for storytelling. This became my portfolio asset library that I could pull from as I shaped each presentation.

Refining the story by speaking it out loud

As I practiced the presentations, I found myself naturally iterating. I'd hear when the story didn't land or when I was rambling. And I’d feel when my points lacked visual support.

This speaking-first approach solved a problem I'd struggled with before when creating case studies directly as web pages: I never felt like I could strike the right balance of detail, visual aids, and storytelling. But when I had to speak my story out loud, I naturally found the right level of detail and pacing. The constraint forced clarity.

It kicked off an iterative loop:

• I'd speak the story out loud

• Identify gaps in the visuals or narrative

• Jump into my Figma asset file to either pull an existing image or build something new

• Update the story and repeat

Sometimes I needed to swap a quick screenshot. Other times I needed to design new graphics or build small prototypes. The storytelling shaped the visuals, and the visuals sharpened the story.

Each project went through this process. Over time, I compiled a master slide deck with all my material — 87 slides across four projects, a career overview, and my work on Unknown Arts. I didn’t intend to present it all at once, but it gave me a central library I could draw from depending on the audience.

Recording with purpose

Once the presentations were tight, I recorded myself delivering each one using Screen Studio. This tool let me pan and zoom on the fly, directing the viewer's attention almost like giving a live talk.

I did multiple takes for each video — not because I wanted perfection, but because those reps helped me dial in the rhythm and clarity. The result was a set of videos that felt polished but natural, and true to how I work.

I uploaded the recordings to YouTube as unlisted videos so they'd be easy to embed in Framer but not publicly searchable. These became the centerpiece of each project page.

Retrofitting content into the site

Because I'd already shaped the story and built the assets, updating the site itself was straightforward.

This is one of those classic web design lessons: knowing what the content is makes designing the UI a lot more approachable. I wasn't guessing what to say or filling placeholders; I had the structure, narrative, and visuals dialed in. Updating the site became a matter of slotting a few new pieces into place.

For each project page, I created a consistent structure with three ways to engage:

1. The video — front and center for a complete walkthrough

2. A short text summary — highlighting core points from the presentation

3. The slide deck — embedded from Figma for quick visual reference

The goal was simple: progressive disclosure with a lightweight touch. Just enough structure for people to engage on their terms.

Adding interactive cues

To hint at video presence on the landing page without a major overhaul, I updated my project overview component to reveal short video snippets on hover.

For each project, I exported a few-second, muted, square video clip from the presentation and used it to replace the static project feature image on hover.

This small interaction helped signal there was more available than the typical portfolio site.

Why video makes sense now

Three forces converged to make this approach possible and, in my opinion, necessary:

1. The tools have made it feasible — Recording with Screen Studio, hosting on YouTube, and embedding in Framer turned what used to be a laborious video production project into an afternoon's work.

2. Design work demands it — Modern software design isn’t static. Interaction, flow, and animation are central to what we do and static images struggle to tell the full story.

3. Remote work makes it inevitable — Most of my day-to-day collaboration already happens via async content. I'm constantly sharing Slack posts with design assets, writing Notion docs, and using Loom videos to explain thinking. These videos just reflect how I communicate professionally with a bit more polish.

The early advantage

We're still early in this trend. I'm not even sure it's a first-mover advantage yet… we might just be ahead of the curve.

But I feel confident about this video-first approach because it benefits both job applicants and hiring teams. Why jump through hoops scheduling multiple calls to gather information that can be provided upfront?

As these tools become familiar and expectations shift, I believe video-first portfolios will become standard. But for now, most people still think in terms of traditional resumes, static case studies, and live presentations. There's room to stand out by being more upfront, comprehensive, and authentic than anyone expects.

Final thoughts

This whole approach is about making the first impression more real, more human, and more useful for both sides.

Video doesn't replace real conversations, but it does make them more productive. Instead of starting from zero, we begin with shared context. Instead of spending early calls figuring out basic compatibility, we can dive deeper, faster.

Top-notch execution is the baseline in today's job market. What sets you apart is how you communicate, how you collaborate, and how you show up with a team.

The setup is simple. The payoff is real.

If you can record a Loom, you can make a video-first portfolio.

And whether it leads to a job or not, the more you practice telling your story, the better it gets.

Until next time,

Patrick

PS. Yes, I wrote 1,500 words to tell you to use video. The irony’s not lost on me. Let’s just pretend I narrated it for today. 😇

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Nobody wants to hear this, but creating and landing a new design system in existing software is an 18-month project. At best.

Most teams don't make it that far.

I know because I've been the designer on three of these projects, working on complex enterprise apps in cybersecurity and dev tools. Each attempt taught me something new, gradually learning why rollout strategy matters more than immediate aesthetic design choices. What started as hard-won lessons became a framework I now use to guide these decisions.

The products looked different, the teams varied, but the pattern was consistent: great designs failed when implementation was an afterthought, while strategic rollouts succeeded regardless of aesthetic ambition.

Here's what those three attempts taught me.

The "blow it up" strategy (and why it crushed us)

At Tenable, we went big with a clean-slate redesign of the entire security platform. New visual system, modern components, the works. We spent months crafting something that looked incredible in our design files—the kind of work that gets featured on Dribbble and design twitter.

But once we tried to land it in the actual product, the complexity crushed us. We weren't just updating a visual theme; we were rewiring years of logic and layout. Dependencies stacked up like dominoes. Every component touched three others. Every page required six teams to coordinate.

A year later, the project was dead and the product was worse off than when we started. The head of product design was removed. The CPO followed soon after. We'd burned through enormous resources chasing a vision that couldn't survive contact with reality.

The "blow it up" approach feels creatively satisfying in the moment because it gives you a blank canvas. But software isn't built for wholesale change. It's built for iteration. Fighting that fundamental truth is a losing battle.

The "Ship of Theseus" strategy (and why it stalled)

At Signal Sciences (now a part of Fastly), we tried the opposite approach. Instead of redesigning everything at once, we'd replace components gradually—like the ancient thought experiment where Theseus replaces every plank of his ship over time.

This felt smarter. More aligned with how software actually works. We'd swap out discrete elements over time: style tokens first, then form elements, then navigation patterns, etc. Piece by piece, we’d build our way into a completely new system.

It was working... until it wasn't. Progress was slow and it was hard for the team to maintain momentum. We lacked a sense of urgency and slowly came to a standstill. The company got acquired, and the project froze, half-done.

We ended up with the same old ship, just with 50% new parts. Not worse than before, but not the transformation we'd promised either.

The "land and expand" strategy (and why it worked)

At JupiterOne, I tried a different approach. Instead of redesigning everything or replacing pieces one by one, we picked one major feature as our pilot project.

This gave us a contained space to design holistically while limiting scope and risk. We built our component library (we called it "Juno") alongside the feature refresh. The real-world context informed the design of the components; the design of the components shaped the real-world feature we shipped.

Once we had the core of a working system and a showcase of what it could do, expanding to other parts of the platform became easier. Other teams could see the value, they had concrete examples to work with, and the organizational support built naturally.

Eighteen months later, the system was live across the platform. Not because we forced it everywhere at once, but because we gave it room to prove itself first and then gradually expand to fit the needs of every product surface.

Why implementation strategy beats aesthetics

Here's the uncomfortable truth: your beautiful design mockups don't matter if you can't land them in the product.

I've seen teams spend months perfecting component libraries that never get implemented. I've watched gorgeous redesigns die in development hell. I've been part of projects where the design quality was exceptional but the rollout strategy was nonexistent.

The difference in a successful project isn't just having better designers or more skilled developers (although that helps, of course). It's about understanding that replacing a system isn't a visual exercise—it's an architectural one. In most cases, you're not just changing how things look; you're changing how they're built, maintained, and evolved.

That's why implementation strategy is just as crucial as design quality - you need both to succeed. An aesthetically bland system that actually ships beats a perfect system that never sees production. Even if it doesn’t satisfy your immediate urge for novelty, that well-architected UI system will give you the runway to dial in the visual aesthetics over time to the level of fidelity you’re seeking.

What this means for your next system

If you're starting a design system overhaul, resist the urge to redesign everything.

Instead:

• Pick your landing zone carefully. Choose a feature that's important but not mission-critical. Complex enough to test your system and visible enough to build support, but contained enough to manage risk.

• Design in context, not isolation. Build your components alongside real feature work. Let the constraints of actual implementation inform your decisions.

• Plan for expansion from day one. Your pilot isn't just a proof of concept, it's the foundation everything else will build on. Make sure what you’re building can support that weight.

• Measure adoption, not perfection. Success isn't having the most beautiful component library. It's having a system that teams actually use to ship better products faster.

Nobody wants to hear that their beautiful designs might fail because of boring implementation decisions.

But in my experience, that's exactly what happens.

The sooner you accept that reality and plan accordingly, the sooner you can ship systems that make the impact you’re hoping for.

Until next time,

Patrick

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I wasted too much time early in my design career sweating the wrong details. Now I ask one question before every UI decision:

"Default it, or design it?"

This simple heuristic has saved me countless hours and arguments, especially in startup environments where resources are limited and speed matters.

Every design project requires you to make hundreds of decisions. Some are big like the overall layout. Others are small like the hover state of a button. Facing too many choices can lead to analysis paralysis, making it hard to move forward.

Why this matters

Problems arise when designers spend too much time on lower-value minutia at the expense of big, strategic decisions: projects stall, deadlines slip, and teams get frustrated.

I've been guilty of this more times than I'd like to admit.

Looking back, I used to get lost trying to solve details that weren't immediately relevant. Like, I'd polish edge cases before the core flow was even solid. I thought I was being thorough but really, I was just misallocating energy.

Now I try to spot where the real leverage is. Not every moment in the product deserves the same attention. Some things just need to work. Others need to shine.

The two paths

When you default it, you're leaning on existing solutions: design systems, platform conventions, or vendor tools. You're not ignoring the problem, you're delegating the decision to something (or someone) that's already solved it well enough.

When you design it, you're choosing to spend the time because you believe that decision has the potential to differentiate. You're investing creative energy where it can make a meaningful impact.

Both paths are valid. The power comes from choosing intentionally.

The "Default It" approach

The "Default It" approach is most valuable when you’re getting hung up on a micro-level detail while working on a macro-level project.

It's not that the detail is unimportant, but it's not the intent of that work. By defaulting micro-level decisions to existing resources, you can expedite macro-level projects.

In my experience, many product managers lean toward this approach. "Defaulting it" helps move projects along faster by reducing scope. But if we default every decision, we're likely to miss opportunities to innovate.

The "Design It" approach

The "Design It" approach is most valuable when you need headspace to work in-depth on critical choices that shape outcomes in significant ways.

You can make time to "design it" with micro or macro-level work, but each requires your full attention. It can be difficult to toggle between these different points of view, so I find it helpful to scope projects intentionally to focus on one at a time.

Designers naturally gravitate toward this approach. It's where creativity and innovation shine. However, trying to design every small detail can slow projects to a crawl and lead to blown budgets.

Finding the right balance

Finding the right balance means negotiating which decisions to default and which to design so your team can focus attention in the right places at the right times.

Product managers might push for "defaulting it" to save time and stay on schedule, while designers might advocate for "designing it" to explore creative solutions. This healthy tension can lead to finding the sweet spot for product development.

For example, on one product I worked on, we needed to visualize large graph databases. Building a vector-based visualization library from scratch would have given us flexibility, but it wasn't going to move the needle for our customer experience. We decided to “default” that data viz solution to a third-party vendor whose entire focus was on building that technology. This freed our team to focus on applying those tools to solve our customers' problems more quickly and effectively.

How design systems fit In

As projects grow, certain decisions come up repeatedly. This is where design systems become valuable.

A design system is essentially your collection of team approved defaults.

While in the early days of a product you might default mostly to external industry standards, over time you'll encapsulate more of your own decision-making into custom defaults specific to your service.

By storing your "defaulted" decisions in a central repository, you reduce the overhead for making solid baseline design choices. This list evolves to reflect updated defaults as new projects demand new solutions, freeing up time to focus on unique challenges.

Final thoughts

"Default it or design it" helps me triage.

It helps my team align.

And it helps us ship.

By intentionally choosing when to default and when to design, I save time, focus on what's critical, and direct my creative energy to the most pressing problems.

Some moments in a product just need to work. Others need to shine.

“Default it or design it” helps me know the difference.

Until next time,

Patrick

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