Over my career, I’ve often left meetings flummoxed as to why my help wasn’t landing. “I can help the client optimize their funnel. Why aren’t they listening?” “I told this report exactly what they needed to do to solve their problem, but why did they seem annoyed?” I’ve now come to realize there are [different ways to advise people](https://www.statetransition.co/p/consulting-models-and-failure-modesat), and it’s crucial to know which skill to apply when.

There are four kinds of work you can do in an advisory role: coaching, consulting, mentoring, and managing. These terms seem interchangeable, but they’re not. They’re distinct skillsets that serve different purposes. Apply the wrong skill to the wrong problem, and you could get disastrous results.

The 4 types of advisory work

Coaching

Coaching is people-oriented. The primary goal of coaching is to help people grow and achieve their goals. To coach effectively, you need to listen actively and ask good questions. A good coach will get you to give an answer to a question that surprises even yourself.

Consulting

Consulting is solutions-oriented. The goal is to deliver information, expertise, and strategy. When consulting, you need to identify root causes and be able to give advice in a way people will hear. After a good consultation, you’ll feel you have a strategy and know exactly why you’re implementing it.

Managing

Managing is project-oriented. The goal is to close loops, move needles, and track performance. The most valuable management traits are the willingness to have uncomfortable conversations, make decisions, and take ownership. A good manager sets a high-quality bar, holds you to it, and brings out your best performance.

Mentoring

Mentoring is expertise-oriented. The goal is to share specific examples and lessons that help someone build knowledge and expertise. The most valuable mentoring skills are contextualizing expertise and showing, not telling. Your Miyagis, your Yodas, your Professors Xavier.

What happens when you apply the wrong skill

Know your role and shut your mouth

When I was a freelance web developer, I wanted to position myself as a ‘strategic partner’ for two reasons: the work was more interesting, and I could charge a higher hourly rate. I rubbed some clients the wrong way when I tried to contribute to the overall vision.

Once at a local bar, I ordered a whiskey bramble. “Are you sure?“ the server replied, “It’s a fruity and sugary drink.” I felt judged. I knew what I was doing; I was not looking for a more “masculine” order. If I want to put blackberry liqueur and lemon juice in my booze until it tastes like Dimetapp, that’s my business and mine alone. I understood how some of my clients must have felt.

You can’t coach those who don’t want to change, or consult those who don’t want advice. At best, you waste your time. At worst, you damage relationships. Unsolicited coaching or consulting is the professional equivalent of mansplaining.

When to help people, and when to let them struggle

When mentoring, your goal is to give answers. When coaching, your goal is to ask questions and help the coachee discover answers within themselves. The challenge is knowing when to help and when to step back and let people figure it out. It’s tempting to jump in and offer solutions when you see someone struggling. Growth requires discomfort; there is value in wrestling with a thorny challenge.

A heuristic: frustration is ok, confusion is not. People can grind on hard problems, but when they have zero idea what to try next, nudge them in the right direction.

Using the model

How would you rate yourself on each of these, on a scale of 1 to 10? If you broke your week down into a pie chart of the four types, what would it look like? When you think through the four models, you can pinpoint where to focus when skilling up.

“Are they asking for expertise, or do they just want a pair of hands?” “Does this person need help, or do I need to set expectations and hold them to it?” The four models help you pick the right tool for the job. This is why I think it’s important to draw these distinctions. If you can recognize when to apply each skill, you can be a more effective leader.

Previous posts:

In the past few weeks, agentic assistants have gone from helping people schedule meetings to [kickstarting a “religion” on Clanker Reddit](https://molt.church/). I’ve worked through multiple iterations of engineering management tooling and realized three things:

1. There is a certain skill to building these kinds of systems.

2. It requires a mental shift in how you work to use them effectively.

3. If you aren’t careful, you can get lost in the sauce and spend too much time working on your ‘systems’ instead of being productive.

1 - The art of agentic agent design

Context is everything

Context is the information you give the LLM to work with. The value you can get out of AI is directly proportional to how much of your work you can put in plain text.

When starting, build a capture spot: a place to easily capture data throughout your day. It could be a folder, an Obsidian vault, anything. It’s a reversible decision, don’t overthink it. You don’t want to think about where you put stuff.

Then, document processes. Start noticing repetitive tasks, and how you might automate them, in all or in part. The more structured and repeatable the process, the more effective the tool will be. Remember the rule: if you do the same thing three times, write it down.

Think in building blocks

In building blocks of agentic agents, I inventoried the individual units of a system. A skill, a standard operating procedure, a file, a folder—these can all be blocks. In software development, blocks are "modules" or "units of code." When working with these systems, it helps to think in building blocks.

There are three software development heuristics I’ve found useful with modules and building blocks alike:

1. The Single Responsibility Principle - A block should only have one job or responsibility.

2. Loose coupling - A block should depend on other blocks as little as possible.

3. High cohesion - The elements of a block should belong together.

You shouldn't try to build one skill that does everything. Even a single process could have several sub-processes. Let's say you want to build your system to help you better handle meetings. That may include:

1. A skill that reviews your notes and helps you prep for meetings

2. A skill that integrates with your calendar to schedule meetings

3. A 3rd-party tool that transcribes meetings and adds them to your capture spot

4. A skill that processes meeting transcriptions and pulls out relevant information

hink about building each part of the system individually. You don’t have to solve everything. Solving one piece can be a win.

It requires practice to figure out the right level of abstraction for ‘block.’ From above, I could in theory have a different skill for each type of meeting. It may be valuable, it may be overkill. How similar are the meetings? That’s where cohesion comes into play.

If you can’t describe what a block does without using the word “and” twice, it should be split up.

When you want to modify or swap out a block, you want to do so with as little friction and side effects as possible. Building self-contained single purpose tooling speeds up iteration.

Check out Anthropic’s collection of official plugins. Imagine if you had to install all of them just to use one feature. Instead, they split their tooling into a few dozen different blocks, so you can pick and choose what to bring into your system.

Single responsibility applies to chats as well. LLMs get dumber the longer they run. They keep every message in context. The further you are from your initial instructions, the more likely they are to drift. Mistakes and misunderstandings accumulate1. Better to clear out the chat and start a new one every time you switch tasks. Even if you are doing the same kind of task many times over, it can be useful to start fresh regularly.

Define your primitives

When starting, think about the primitives of your work and how to model them in plain text. A primitive is any core object you want in your system. Here are some examples from mine:

• projects

• tasks

• people

• teams

• meetings

What's fun is coming up with features that map to your idiosyncrasies, that you don't find in many other projects. I added the monkey primitive, inspired by the HBR piece "Management Time: Who's got the Monkey?" I can track when I'm waiting on a response or feedback from someone (monkey on their back) or someone is waiting on something from me (monkey on my back).

Iteration is (also) everything

Fighter pilot John Boyd gave us the OODA loop: observe, orient, decide, act. Read the situation, pick your move, execute, repeat. You don’t have time to strategize in the middle of a dogfight. You have to act fast and stay in the flow.

In a tactical sense, these multi-dimensional interactions suggest a spontaneous, synthetic/creative, and flowing action/counteraction, rather than a step-by-step, analytical/logical, and discrete move/countermove game. — John Boyd, Patterns of Conflict, p.177

AI enables OODA looping at a quicker tempo. You can build, test, and iterate faster than ever before. Experimentation is fast and cheap. Don’t be afraid to try something, and throw it away if it doesn’t work. There will be throwaway work. This isn’t waste; this is part of the process. In creative work there is a cycle of expansion and compression.

That’s why you want well-designed modules. Faster to iterate on small, well-contained subsystems than a sprawling mess.

The difference between a good product and a great one is the number of iteration loops. Quality in creative work comes from labor, not genius. Author John McPhee wrote the book “Draft No. 4.” You don’t have to read it—the title alone can make you a better author if you’ve never considered starting a draft over for the fourth time.

Don’t try to get things perfect on the first shot. Make something, examine what went wrong, adjust your system, and try again.

Use LLMs for design & ideation

Whenever I start a non-trivial piece of work, I go through this "spec-driven development" process:

1. Sketch out a plan of what you want to achieve. Provide as much context as you can. Let’s call this doc spec.md

2. Here’s the important step many skip: Go to Claude with this prompt: study spec.md. interview me and ask me questions so you can improve the spec and then write an implementation plan.

3. After you answer the questions, ask it to write an implementation plan.

4. Start a new chat and ask it to start on the next phase of the implementation plan. (Planning and building are two different tasks, so we clear the memory.)

You can even take it a step before that, and ask the LLM to figure out how you could use the LLM. A tweet from my former coworker Kris Puckett:

Based on what I shared, ask me 5-7 questions to understand my workflow better. Then suggest 3 things I could build, ranked by impact vs complexity.

Work in these kinds of loops. Get comfortable with them. I can’t emphasize this enough. More iterations get you to where you want to be faster.

2 - A mental shift in how you work

Try working chat-first

The best way to figure out what LLMs can do is to start working chat-first. Whatever you want to do, start with a prompt. If you are already comfortable working in text, this shouldn’t be a large shift for you.

The Dual Loop Framework

When I’m cooking, I have two Claude terminals open in parallel. I call these, borrowing terminology from The E-Myth Revisited: the “working on the business” loop and the “working in the business” loop. The “on the business” loop is the system working on itself. I notice a problem, and I deal with it there. The “in the business” loop is getting the work done. These are separate enough that they can work together without running into one another.

That’s why you want well-designed modules. Easier to parallelize work with small, well-contained subsystems than with a sprawling mess.

The out-to-lunch task

Occasionally, there will be tasks that take a while for the LLM to complete. Something that has helped me: kick these off when you leave at the end of the day, or go to lunch. The agent can chug away while you’re away, and you can review the output when you return.

3 - Avoid getting lost in the sauce

Years ago, I spent too much time playing the game Cookie Clicker2. This is an idle game where you click a cookie. It taught us all that number-go-up is fun in and of itself—you don’t need the game itself to be fun. There was something hypnotic about building up the cookie clicker system and letting it farm points in the background.

If you’ve been sniped by similar dopamine-hijacking games, watch yourself when working with an LLM. They are a Skinner box, a slot machine where the jackpot is that it does your job for you. They can be hypnotic, even addictive.

There may come a time when you’ve heard of vibe coding, you are tired of typing in a chat box, and so you decide to build a piece of software to support your system. That’s awesome, and you can make a powerful tool. Just maintain focus, and don’t get too distracted building the system instead of building with the system.

I justify this meta-work to myself because I see the value as two-fold: It’s not just a productivity system, it’s a skunkworks project to test new LLM-powered coding techniques. Still, there are diminishing returns on that as well.

If you go down this route, a few words of caution:

Think hard about the architecture, languages, and data storage tools you use to build your system. These will be the hardest to reverse. If you have no idea, I recommend building it as a web app you run locally, with NextJS, TypeScript, SQLite, and a UI framework of your choosing.

Make sure your system has back pressure. Add testing and typechecking early and keep them up to date.

4 - Where do we go from here?

It’s nice to have a system that can automate some tasks for me, and take random unstructured data and help keep it organized. A big part of management is making sure everyone has the information they need, knows who to ask, and is empowered to make decisions.

A question I’ve asked myself during my recent career transition: Which job is more AI-proof, an engineering manager or an engineer? After using LLMs for both, I feel confident that both are safe. LLMs cannot replace the systems design skills needed to engineer software that scales and has a long lifespan. LLMs cannot provide the human connection, empathy, and support that a good manager, mentor, or coach can.

Read part 1 here:

A bin of building blocks

When I was a kid, I loved Lego. What kid didn't? Most of the time, I had a bin, a menagerie of simple colors and cubic pieces. Christmas was the only time I got a set, with themed pieces and instructions. A medieval castle is a medieval castle set, but a bin? It can be anything! It could even be a castle!

The joy of personalized software is that it can be anything, built by you, for you. Instead of giving you instrcutions, I’m giving you a bin. You can study the list, and think about how you can connect these together to build not just any system, but your system.

An example

I have projects and tasks stored in Obsidian files. Then I added a prioritizer agent with a rubric for prioritizing tasks, and a /plan-day command that fetches my agenda from Google Calendar via the gog skill and uses that to rough out a plan for the day. Then it creates a daily journal note for me, with the agenda at the top.

Each bolded word is one Lego in the system. Now to break down what each Lego looks like and how they fit together.

1 - Basic Tools

Claude

Claude, built by Anthropic, is the tool I’m most bullish on. I have a theory that the first follower into a market ends up winning. The Sega Saturn crashed, the Sony Playstation thrived. N*Sync had bigger hits than the Backstreet Boys. ChatGPT is the default, but I find Anthropic’s tooling more useful, so I’ll focus on it.

Four ways to interact with Claude:

1. Standard - I’m lumping the web browser and mobile apps together here. It’s fine if you just want to ask a question, but there is little room to systemize.

2. Installed app - the chat, but a little more featured. You can manage integrations and connect to your file system.

3. Cowork - a research preview behind the paywall, Claude Cowork is Anthropic’s response to latent demand for agentic personal assistants. I haven’t tried this one yet because my preferred method is...

4. Claude Code - a command-line tool that leverages Anthropic’s LLMs. My personal favorite. The command line is the most powerful way to use the computer and the one I’m most used to as a programmer. The terminal can be intimidating, but if you’re moving your work towards text files and automation, it’s a useful skill to have, and not as hard as it looks.

Think of the command line like cooking: it’s as complicated and skill-based as you want it to be. Some people are master chefs who know a litany of techniques. Some, like me, are more utilitarian. I can roast a vegetable, fry an egg, pop a tart. You don’t have to be an expert. A few skills go a long way.

A demo of cowork:

Obsidian

Obsidian is a note-taking tool. The perfect mix of simplicity, utility, and power. You write notes stored as plain-text files. You can link files with wikilinks like [[this]]. Thousands of plugins are available to extend functionality. You can add graphs (Excalidraw), queries (Dataview), or task management (Tasks). If you're interested in an Obsidian + Claude Code setup, there's a plugin that brings a terminal directly into your notes. Plain text is the easiest way to feed an LLM. It gives you permanent storage that is readable and writable by man and machine alike.

Optional: IDE (Cursor or VSCode)

If you’re getting into managing code as part of this exercise, you may want a tool for editing it. These super-powered text editors are called IDEs (Integrated Development Environments). The two best options: VSCode, Microsoft’s editor and the standard choice in the biz, and Cursor, an AI-powered fork. You can use AI via Cursor directly, but if you’re using Claude Code it may not be necessary1.

Extending Claude Code

Assume any LLM-based tool is 60% ready-to-go out of the box. You have to put in some effort to get it working how you want. It doesn’t know you, your goals, or your processes. The better you are at getting context out of your head and into Markdown files, the more effective you’ll be. Claude offers a variety of structures to customize and amplify its abilities:

Claude.md

If you’re getting started, put your rules and general logic into Claude.md. Think of this as an initial prompt Claude has at the start of every conversation. You can tell it how you want it to behave, your goals, boundaries, and constraints. Here’s an example (credit to Alex Hillman for this one) to set a communication style:

## Communication Style
- Never end sentences with ellipses (...) - it comes across as passive aggressive
- Ask questions one at a time
- Acknowledge requests neutrally without enthusiasm inflation
- Skip validation language ("great idea!", "perfect!", "excellent!", "amazing!", "kick ass!")
- Skip affirmations ("you're right!", "exactly!", "absolutely!")
- Use neutral confirmations: "Got it", "On it", "Understood", "Starting now"
- Focus on execution over commentary

💡 Pro-tip: Claude loves structured information. Headers and bulleted lists are easier for it to parse.

Slash commands

Slash commands are reusable commands you call while typing into the terminal. Claude has many built in by default, like /clear to empty its memory and /model to select the model. You can also write custom commands for repeatable processes.

If you aren’t sure how to write a slash command (and this will be a recurring theme), ask Claude to write one for you. LLMs are adept at writing text that LLMs can read. You can ask Claude to make modifications later, or go in and make more surgical edits yourself.

Example: have a /fetch-calendar command that gets your daily agenda, or a /line-edit command that does an editing pass on your article.

Agents

If you do this for a while, your Claude.md file will get large. You’ll realize a lot of the rules only matter in certain contexts. When that happens, break it down into agent files. Claude has a slash command, /agents, to help you write them.

Example: I have a frontend-engineer agent that knows how to write code according to my guidelines and style. I have an appointment-maker that knows my meeting preferences and how it integrates with Google Calendar (more on integrations in a bit).

MCPs

MCPs, short for Model Context Protocol, bridge Claude and third-party systems. Think: wrapper for an API. Claude has a list of common MCPs people integrate with.

Example: Two that I find useful, that you can install with a single command, are Notion and Playwright. If you use Notion for work, this gives your system an easy way to read and write files. Playwright, and this is a fun one, gives Claude the ability to open and use a web browser. You can add it with a single command:

claude mcp add playwright npx ‘@playwright/mcp@latest’

In theory, Playwright is the only MCP you need to integrate with every website on the planet. It’s slower and less reliable than direct integrations, though. If you’re worried about handling credentials, what I do is say: “If you run into a login or account verification page, show it to me and I’ll log in.” Then the system won’t have access to your credentials.

Unlike agents and slash commands, I never write custom MCPs. Some are useful, but I find skills and scripted integrations more effective. Still, I can’t deny a one-line command for web access is powerful. If you want to dive deeper on why MCPs may not be the best choice, highly recommend: Your MCP doesn’t need 30 tools, it needs code.

Skills

Skills add extended capabilities to Claude’s toolkit. They contain three key parts: a SKILL.md file explaining what it is, what it does, and how; scripts, code the skill can execute; and examples, which the skill uses to inform its work. Skills can be used by you, or by an agent.

(As a rule, Claude loves patterns and examples. Show, don’t tell, if you want consistency).

When starting with skills, shop the shelf. Anthropic offers skills you can download: Anthropic skills library. A few that might interest you:

• skill-creator - always install this one. You’ll want it when you start creating custom skills.

• The ones that allow Claude to read and write other file types: pdf, pptx, docx, xlsx.

Another source worth checking: Clawdbot. Clawdbot is an open-source, out-of-the-box agent framework. You could start using it as a base, but be warned, it can get expensive. Anthropic has two billing models: Monthly (a set amount of usage each month) and API billing (charges per use). Clawdbot runs exclusively on API billing, which can get pricey. I have run up $25 bills in a couple hours of usage.

BUT, Clawdbot is open source, which means you can browse its internal skill library and copy some into your project. Here are a few I’ve been experimenting with:

• gog - integration with Google Drive and Google Calendar.

• obsidian - for creating Obsidian bases.

• things-mac - integrate with my personal todo list app.

• apple-reminders - programmatically set reminders for myself.

There are many ways to manage context in Claude Code. For a deeper dive, I recommend Understanding Skills, Agents, Subagents, and MCP in Claude Code: When to Use What

2 - Data structures

How will you store and manage the data you’re working with? As stated earlier, plain text is king. Plain text integrates with everything. Free forever. Lasts forever. Start with plain text files. Two syntaxes in particular:

Markdown

Markdown is the lingua franca of plain-text formatting. You can apply simple syntax: bolding, headers, links, lists. No, you cannot change the font or colors. Yes, this is a feature. Everything I write, I draft in Markdown first.

Example

# Markdown

This is a paragraph in markdown. Some text is *bold* and some is _italic_. You can have a

## Hierarchy

### Of Headings

#### To give your document structure

You can even
* make
* a
* list.

• Frontmatter - Frontmatter is a flavor of YAML (which stands for “YAML Ain’t a Markup Language”... yes, it’s a corny recursive acronym). All you need to know: it lets you add structured data to a Markdown file. In Obsidian, these are called “properties.”

Example:

---
title: Building blocks of agentic systems
publish_date: 2026-01-26
section: Root Nodes
blogchain: Prompt Protocols
---

JSON

The next step up: JSON files, which stands for “JavaScript Object Notation.” JSON is a file of nested structured objects. Common use case: config files. Once you start a Claude project, you’ll see ./claude/settings.json as an example.

{
  title: "Building blocks of agentic systems",
  publishDate: "2026-01-26",
  section: "Root Nodes",
  blogchain: "Prompt Protocols"
}

SQLite

SQLite is a dead simple database that lives in a single file. Useful when you have several types of data and want to map relationships between them. SQLite helps when you need to aggregate records or create relations between them. If you’re an accountant who’s put 600 transactions in Markdown files, it might be time to consider SQLite.

3 - Computing

LLMs are cool and advanced, but as we’ve seen with plain text, the most powerful tooling combines them with simple computing practices that have been around for decades.

You may have seen the GPT ‘gotcha’ where many LLMs could not correctly count the number of ‘R’s in the word ‘Strawberry’

A brief explanation of why this happens (hat tip to Zhu Liang):

LLMs break text into smaller chunks for processing through a process called tokenization. Then they catalog them with token IDs. When an LLM “sees” the word “strawberry,” what it gets is a series of token IDs {496, 675, 15717} that map to certain tokens {”str”,”aw”,”berry”}. It sees 2 tokens with an ‘R’, so it thinks there are two ‘R’s.

Now, let’s compare that to Python code that does the same thing.

word = "Strawberry"
word.count('r')

None of that tokenizing and indexing. Your computer doesn’t have to send a prompt to a model in a data center and wait for a response. It just. Counts. the. letters.

What I’m saying: there’s a lot of work that doesn’t require intelligence. If a process is repeatable and doesn’t require judgment or abstract reasoning, you’re better off having code do the job than an LLM.

Scripts

But hasn’t this always been possible? Code to automate tasks is nothing new. What’s new is how easy it is to have an LLM write simple scripts for you and run them. This is what made the command line interface such a powerful pattern: LLMs run on text. Command lines are built on a philosophy of text in, text out. Combine them and you can build powerful systems.

A script is a single-file, single-purpose computer program. Typically written in Bash, Python, or JavaScript. Sometimes the model writes, executes, and deletes a script behind the scenes.

Web based UIs

Some tasks are arduous to work in via text. Maybe you want to add some pizazz to your work. One option: ask Claude to build a small web page or app that runs on your local computer.

It will not get it right the first time. There will be bugs. You’ll need to iterate.

Be wary: this is an easy rabbit hole. If you aren’t careful, iterating and maintaining your UI system becomes a job of its own and a distraction from your original goals.

I prefer Next.js for these. You also don’t need great design skills: several free off-the-shelf design systems exist. Here’s a list. Pick one that matches your vibe:

• Retro UI

• AI SDK Agents

• Cult UI

• Tailark

• Kokonut UI

• Magic UI

• Eldora UI

• Aceternity UI

• shadcn/ui

• Kibo UI

• Mantine

• Naive UI

• Ionic Framework

• Shoelace

• daisyUI

• Paper CSS

Cron

Cron jobs let you run scripts or commands at regular intervals. Maybe you wrote a “check-inbox” command that you run manually to sync with your inbox. With a cron, you could have it run every hour. Crons let you trigger scripts at different parts of the day.

Version control (Git)

I don’t know how other document-based knowledge workers survive without a version control system like Git. Git lets you keep a changelog of all committed changesets to your pile of files. Typically it’s used for code, but nothing stops you from using it for Markdown files. You can also create branches, like a temporary copy, and try something. If it works, you merge changes into your main copy. If it doesn’t, throw the branch away, no harm done, no permanent changes made.

Version control lets you iterate fearlessly. You can also use tools like GitHub to back up your work online, and even share it publicly.

A good rule of thumb: add a directive to your Claude.md to make a git commit when it finishes a unit of work.

4 - Integrations

Lastly, think about what tools you use in your day-to-day work. Apps your job provides, or tools you use personally to be more productive. Common culprits: Email, Google Drive, Notion, Slack, task trackers, and calendar apps.

Can you think of ways you might want your system to interact with them? To fetch data, write to them, or take actions? See if they have a publicly available MCP or API. Maybe you can find a Claude Code skill on GitHub or another marketplace. Between all of this, there are ways to create new slash commands, skills, or documents that help you do your job more effectively.

What comes next

Building these systems takes time and several rounds of iteration. In the next and final part, I’ll go through my notes and process for building my agentic assistant over the past few weeks.

Update: Part 3 is live:

My feeds have been overrun with take after take after take after take after take about how "Claude Code isn't just for code anymore." Everyone seems to be supercharging their "second brains" and building "LifeOSes" and "Agentic Assistants." So, of course I had to try it. And I was surprised how quickly I was willing to let it run a small part of my life.

Opus 4.5 was a step-level change. Anthropic's model hit a point where it's smart, fast, and reliable enough that people, myself included, can hand off tasks to it with a good amount of confidence. Then Clawdbot got people's heads turning. The "Claude Code for everyone" era begins. I am become Linguini, Opus, my rat.

I was already keeping an engineering manager notebook, inspired by the CTO's hidden notebook. I've long believed in the file over app philosophy. I was already using Claude Code for note cleanup and line editing. Then, my step-level change came when I watched Alex Hillman's video demonstrating his "JFDI system":

After watching, I started building new tooling around my day-to-day work. I went from manually tracking meetings in Obsidian to having an agent fetch my calendar, book my meetings, and pull in AI transcriptions and synthesizing them into status updates and task lists.

A different kind of unicorn…

Alex hit on something in his video: no project management system or CRM ever fits quite right. Work is idiosyncratic. Everyone has unique contexts, motivations, strengths, and foibles. Ashe Magalhaes has a wholesome system with a compliments workflow, birthday reminders, a custom friend social feed, and gratitude journaling.

Vaughn Tan hits on this in Boring Tiny Tools: “Generative AI coding tools now enable high-utility, highly customised, but narrowly scoped software.”

A new genre of software is emerging. Maybe “Unicorn” will no longer refer to a billion-dollar company, but to rare, one-of-a-kind precision software, tailor-made just for you.

…if you can build them

But don’t expect a magic silver bullet. Despite what people selling AI courses tell you, I don’t know that Claude Code is for “everyone.” I’m not gatekeeping or acting superior, only setting expectations for what raising your rat looks like.

Do you have systems? Can you get them out of your head, breaking them into components with clear instructions, constraints, and success criteria? Sure, you can get a system up in a couple of hours, but larger gains take many, many rounds of iteration. Alex keeps a dev log of his assistant (or at least he did; this prompt implies his agent is now self-blogging). He’s at 96 days and counting.

I was already taking notes to a near-unhealthy degree and tracking tasks in markdown files. It helps that I have 15 years of experience as an engineer. Turning fuzzy business requirements into code is kinda my jam.

Could this eventually be a job I have? Acting as a translator and transcriber for people who can’t cross the brain-to-LLM bridge? Vaughn Tan thinks so. Again from Boring Tiny Tools:

What's missing is someone to bridge that gap. Someone who can help articulate workflow needs in ways that can be rapidly prototyped, who can evaluate where a Boring Tiny Tool would make sense, and who can help grow an internal organisational culture for doing this systemically.

This requires an unusual combination: understanding of product strategy, enough technical fluency to evaluate what's feasible, and deep appreciation for how work actually happens versus how organisations think it happens. It also requires not having a vested interest in any particular technical solution.

Could I build a system like this for someone else? Technically, yes, but I’m not convinced it would be good. It would be better to teach or collaborate with people and let them figure out what to build and how to get there. You have to cook with your rat.

This piece attempts to teach Claude Code for the non-engineer. If you’re the target reader, I’d love to hear if you found it valuable, or if it’s all still mind-boggling.

If you want someone to riff with on this stuff, shoot me an email or DM.

But for now, I’m off to do another few rounds of iteration on my agentic agent, whom I’ve christened Agentic Agent, because I hate anthropomorphizing AI. Next week, I’ll go into more detail about how I built my initial prototype.

Update: Read parts 2 and 3 here:

There’s a game at play here. Six, give you more content than you can handle, informed by all the personal information they’ve collected. They engage you, drain you, and monetize you. They make money by stealing your attention and making your life worse. That’s an asymmetric game. We can’t win.

There’s another game. One where we share with each other. The way the internet once was. Thoughtful, human-to-human recommendations. That’s our co-op game. We can all win that one.

I find the most interesting books through recommendations from interesting people. Conversations with friends. Or, references in books or recommendations from their authors. The Algorithm will only show me things it thinks I’ll like based on its profile of me. Only a person can show me something that’ll change me, that I’ve never seen before, based on who I am. For example, The Uncertainty Mindset fundamentally changed how I think about business. It’s criminally under read, and I never would’ve found it if someone hadn’t told me about it.

Good recommendation game

There’s an art to making good recommendations. If you want people to appreciate what you’re giving them, you need good recommendation game. You make recommendations valuable by making them specific and unique. Recommendations are something of a homework assignment. You owe it to the recipient to put in some effort on your end.

A recommendation is more likely to land if you:

• Explain why you’re recommending this thing in this context

• Summarize the value and explain why it’s worth their time

• Call out a specific feature or pull an excerpt of what you’re recommending

• Recommend one onboarding piece instead of an artist’s catalog or YouTube channel,

• Share a list of 3-5 items. Telling me you have “60 AI tools I should add to my dev workflow” tells me nothing

• Give them a ‘hook’ that explains how your recommendation connects to their interests or work

• Give a comment that helps the OP explore their original idea further, or asks an interesting question of them.

A couple of threads worth reading on recommendation game: 1, 2

Be a tour guide

We are smothered by infinite content. People are hungry for guidance on what’s worthy of attention. They want help finding the top 1% among the slop.

You can be a tour guide by sharing your best finds. You can help others navigate. Recommendations are a public service. Doesn’t have to be a comment or convo, can be a post, that helps people without you even realizing it.

The Call to Action

Send me your reading lists! Your playlists! Your books, articles, podcasts, songs, and videos that had a profound impact on you. The ones that changed rewired your brain. Made you feel alive.

Tell me why. Practice writing an impactful recommendation in the comments. 👇

I said AI would be transformative, not destructive. Jobs would ,change and people would change jobs. Has that come to pass?

## Where are people moving?

When old jobs ‘die’, people who make it through move one of three ways:

1. Upward, solving bigger problems at higher abstraction levels

2. Outward, moving laterally to related positions

3. Inward, working on the platform that does the work they were previously doing.

Like it did with WordPress:

There are many new opportunities in AI. Especially with all of the VC money flooding in. For better or for worse, engineers can’t afford to ignore the changes.

I said I wouldn’t be doing my job anymore. Technically, I was right. Computers are boring, people are interesting. I felt I couldn’t stay competitive with younger, hungrier developers in a new paradigm for another 10 years. Coding is a young person’s game. I’ve since moved from a senior frontend engineer role to an engineering manager role. AI wasn’t the cause of this change, but it was definitely an influence.

How can you reduce risk in your career moving forward? Do you think AI will replace more engineers or managers?

How you answer that question shows how valuable you think judgment is for engineers, how personal relations are for managers, and how capable you believe future models will be at having those skills.

AI is not “going to change” to field, it already has. So, to look forward, we must take stock of our current environment.

Where we are today

The biggest day-to-day change has been in *how* coding gets done. My workflow is entirely different now. I use CLI coding agents, primarily Claude Code. It writes code, runs scripts, and manages my version control. It’s a plain-text search engine of the codebase and its git history.

There’s also a shift in the wind of how companies are thinking about AI as a skill set. Zapier released an AI fluency matrix, and I think you’ll see more companies using rubrics like this.

The changes I’m seeing

1. The skill economics are shifting

The value of writing code is decreasing. The value of reviewing code, writing specs, system design, and defining processes is going up. Invest accordingly.

There’s also AI fluency as a job skill. If you’re on the job market, you need something on your resume about your LLM expertise.

2. It will only get tougher to break into the industry as a junior

It’s already tough out there for junior developers. LLMs are raising the bar on what’s expected. Whether LLMs affect productivity is irrelevant here. It’s whether people in charge of headcount budgets *believe* it can increase their value-per-developer-dollar. Companies will expect more from juniors for less, and I think they’re in for a rough decade. The industry could also face a shockwave of an expertise gap in 5-10 years because of this.

I could see a world where the job of a junior developer is to act as a mini-conductor, babysitting coding agents. The ones out there figuring out how to leverage new tooling will be in a great position.

3. It’s going to get harder to climb the ladder as an engineer

Even if you find a job, getting promoted isn’t going to get any easier. Previously, you could climb upwards by increasing either the complexity or the scope of your tasks. You moved from thinking at the ticket level to the feature level, and then to the multi-person project level. But with code being devalued, engineering skills are no longer enough to climb the ladder.

4. LLMs will improve the code quality of large codebases

LLMs reward good engineering practices: Well-organized code, automated tests, comprehensive tech specs, documentation, smaller, coherent files, and choosing standard technologies over shiny new toys. All of these will make using LLMs more effective in your project. Turns out when you make your codebase dead-simple to work with, you can get a lot out of a dead-stupid computer. LLMs can compound tech debt just like they compound productivity.

5. The quality of software will barbell

Creating slop is so fast and cheap now. Slop is not an AI-exclusive phenomenon. Slop means you didn’t try. People can tell when you don’t try. Now, not trying can produce more than ever before. I see this in writing already. Skilled writers can research more quickly and produce high-quality work faster.

There will be more crap. A lot of it. But there will also be people who understand the tooling and use it to create products at a quality that wasn’t possible before. LLMs will enable the best and worst of software.

6. We gotta stop saying ‘vibe coding’

‘Vibe coders’ are an evolution of ‘Code Monkeys, ’ a derogatory term for people churning out work with little thought to quality or craftsmanship1. There is a distinction between “vibe coding” by people who don’t know what a “tech stack” is and people who are implementing LLM-based practices into their software engineering jobs. Simon Willison tried to call that Vibe engineering. Great article, despite replacing the wrong word. This graph2 from Maggie Appleton sums it up nicely:

This is not to disparage vibe coders. It’s a lot of fun! I can’t hate a technology that enables more people to express themselves and make more things.

7. It’s gonna get weirder

Now that code is cheaper, and the tooling thrives on smaller projects, and more people can create more things, we’re gonna get weirder shit. Everyone can build a todo list how they like it. Everyone can make a game that caters to their taste. People with strongly attuned taste will build products they’ve always wanted. Companies will spin up internal tooling to solve their domain-specific problems.

These programs live behind VPNs and on people’s hard drives. A million dark matter applications.

Excited to see what happens next

I’ll check in with y’all in 2027, see how I did. Till next time 👋

In this piece, I go through a few of my favorite posts about agency and create my own mental model of agency, and how to practice it. Here goes:

Agency (n.) — the art of being yourself. Seeing beyond where you are today and journeying toward who you can become.

Practicing agency involves a four-part loop:

1. Seeing yourself

2. Exploring all possible options

3. Overcoming resistance

4. Taking action

I’ll go through these step-by-step. Also, I’ve sprinkled in some self-reflection questions throughout the piece you can use to pause and reflect if you like. Marked with 🤔

1 - Seeing yourself

🤔 What is the most capable version of me that I can imagine?

That’s the question by ‘Autotranslucence’ in Becoming a magician. They talk about “magicians:” people who are operating at a level that they cannot fathom. At first they were boggled by these people’s existence, then they realize they could become more like them. Someone different. That is, if they were willing to make the change.

It sounds like an empowering question. But if you’re like me, it also sounds frightening. Becoming someone else means, in some sense, the death of the current you. Habits, stories we tell ourselves, even relationships might disappear when we accomplish a metamorphosis. Butterflies have to leave their caterpillar form behind. There are new stories and friends on the other side. The butterflies are okay. But it’s hard to see that far ahead.

🤔 What emotional needs are not being met by your current life?

Being yourself is hard work

When I was a middle school outcast, I incessantly heard the refrain “just be myself.”

Terrible advice.

The implication was that I was perfectly fine as I was, and if people didn’t like it, that was their problem. “Myself” was the default state. Why should I have to put in effort to “fit in?” It was told with good intentions, but all I internalized is “why do I have to be myself if I hate how that feels?”

Later I discovered that “Being yourself” is hard work. It requires asking yourself hard questions. Curating your taste. Shaping your voice. Learning to enjoy your company. Living in accordance with your values. To be yourself you have to build yourself. Being yourself is a choice, a chore, a burden, a gift.

Understanding who you could be and who you are today are the same question. It’s Current You who wants to be New You. Why do you want it?

I feel slightly sorry for people who have never had the opportunity of a mental health crisis. Depression teaches that you are not your thoughts. Addiction teaches that you are not your desires. There’s no better way to learn that you can change who you are than by being in a situation where not doing so means your untimely death.

But once you’ve decided you want to move in a new direction, how are you going to take the next step?

2 - Exploring all possible options

I’ve really been enjoying Cate Hall’s recent work about agency on her Substack Useful Fictions. It started with her first post, How to be More Agentic, but the one I found most useful, and her top post, is Maybe you’re not actually trying.

Cate posits that we bring unequal amounts of rigor to different parts of our lives. Imagine a staff engineer who has a robust issue tracking system at work, but then when they go home to cook dinner, it’s chaos. They get hungry and have to make yet another DoorDash order, because after three trips to the store they still lack all the ingredients to make dinner. What if you applied maximum resourcefulness to every aspect of your life?

Think deeply about every option you have available. Ask yourself and others questions.

Making change means expanding our collection of all possible options. Expanding our possible options means expanding our definition of our own capability.

I’ll use myself as an example: I have written online since 2008. I have never managed to maintain a consistent content calendar. I could say it’s because I have a 9-to-5, a family, and an aging body to take care of. But have I explored every option? I could schedule and stick to more writing blocks. I could write and maintain a backlog. I could offer to donate $50 to a cause I hate if I don’t have at least one new post a week. I could lock myself in a cabin and not leave until I had a three-month backlog. I could schedule a draft post to go out and then it’ll ship whether I’m done or not. There are more strategies I’m sure. I could ask other writers how they do it. I could do more research on strategies that have worked for others.

Truth is, either consciously or not, I don’t want to.

If you don’t know what to do next, then you have to take a step back and realize that you can do something about that. Start anywhere, or do some light strategizing.

🤔 Have you spent a five-minute timer generating options?

I guarantee whatever problem you’re facing, you have more options than you realize. Is it possible you committed to one option too early and wrote off other options? Things you’re allowed to do is a fun list to scroll through for inspo. Sometimes we need a reminder that we’re allowed to ask for help or throw money at the problem.

🤔 Who do you know who you could ask for help from?

3 - Overcoming resistance

In The War of Art, Steven Pressfield describes the internal battle taking place inside all creatives between the Muse and the Resistance. The Muse pushes you to create, to grow, to venture into new frontiers. But the Resistance tries to stop, scare, over analyze,distract,deflect, and demoralize.

The more you take on, the more Resistance you find. This is the challenge of agency. It’s often less about “taking more intentional action” and more about “getting out of your own way.”

The trick is to learn to fight through the resistance, no matter how difficult it feels. Like a video game, the fights get harder the further you progress. I try tp develop a taste for battling Resistance. It’s a sign I’m moving in the right direction.

If you’re not careful, you can fall prey to Resistance Psychosis and start confusing Resistance’s words for your internal monologue.

These aren’t your thoughts and they are not valid.

If you hear any of these in your head, attack them and question their validity. Resistance dies in daylight.

• I can’t do this.

• I shouldn’t do this.

• I don’t have permission to do this.

• I don’t deserve to do this.

• I’m not the kind of person who does this.

• This is too risky.

• This isn’t my fault.

• This isn’t my responsibility.

• I have to do something else instead.

• I don’t have the {time, money, energy} for this.

• I’m not {good, smart, rich} enough for this.

• I’m scared I’ll never achieve this.

• I’m scared of what would happen if I did achieve this.

Obviously, You cannot and should not do anything. There are physical limitations and moral codes. But when you run into a limiting belief, it’s worth examining. What’s stopping you here?

One way to tackle these objections is to act as if the opposite were true. Looking at the problem differently can unstick you.

• What if you can do this?

• What if you are the kind of person that does this?

• What if you did have the time, the money, the resources?

• What if you made time for this?

• What if it’s worth the risk?

• What if you got started right now?

• What if it’s actually easy?

• What if it was your responsibility?

• What if you’re already enough?

But sometimes it doesn’t feel like a fight. Instead it feels like being stuck in a bog. In So you wanna de-bog yourself, Adam Mastroianni lists out several anti-patterns of feeling “stuck.” A quick summary:

You shouldn’t have to work on this problem anyways. It’s not your fault. Or it’s too big to handle. And even if you want to tackle the problem...

You can’t get started because you haven’t found the perfect solution. Or you don’t understand the problem enough yet. You’re waiting for the day you tap into that magical well of discipline you’re sure you’ve stowed away somewhere. And even if you did know what to do...

You have enough obligations on your plate already. Or you’re too concerned with the state of the world. (Solutions, in this economy?) Or it’s too scary to get started.

🤔 How am I the problem?

All of this comes from your ego’s survival instincts. If you change, it dies. Resistance is that lesser part of you, having an extinction burst. It’s doing everything it can to prevent you from acting different and becoming someone else. Resistance is the part of us that would rather stay as we are than be who we want.

🤔 What am I afraid of doing, and what would my life be like if I wasn’t afraid of doing those things?

4 - Taking action

Introspection is fun, but useless if you don’t put it into action.

There’s a distinction between exercising agency and biasing towards action. Agency is about effecting change, which means taking actions that get results. “You can just do things” does not mean “go do anything.”

It’s not a bias towards action, it’s a bias towards results.

Agency compounds

Action is key. Action produces information. Pay close attention while you’re doing the work. The work will teach you about yourself, about who you want to be. It’ll open more options, build your confidence, and help you get unstuck.

The only way to learn is by playing. The only way to begin is by beginning. - Sam Reich

The more you do this, the stronger you become, and the easier it gets. You will gain more capabilities, more self-knowledge, and more confidence, and move closer to the next iteration of you.

And now, a moment of Zen

Just beyond yourself
It’s where you need to be
Half a step into self-forgetting and the rest restored by what you’ll meet
There is a road always beckoning
When you see the two sides of it closing together at that far horizon and deep in the foundations of your own heart at exactly the same time,
That’s how you know it’s the road you have to follow
That’s how you know it’s where you have to go
That’s how you know you have to go
That’s how you know
Just beyond yourself, it’s where you need to be
— David Whyte

Bibliography

• Becoming a Magician - Autotranslucence

• Stanford encyclopedia of Philosophy entry on agency

• Musings on teaching agency - Chana Messinger

• Thread: High Agency Questions - Chana Messinger

• How to be more Agentic - Cate Hall

• Are you even really trying? - Cate Hall

• Things you’re allowed to do - Milan Cvitkovic

• So you Wanna De-Bog Yourself - Adam Mastroianni

Core elements of a menagerie game

1. A varied pool of interlocking game pieces. Cards, weapons, items, anything. You draw from a random subset each game.

2. Interlocking mechanics that influence one another and generate emergent interactions and strategies

3. Combos and nonbos. Some pieces are synergistic, others antagonistic.

4. Infinite extensibility. There's always room to add new pieces and mechanics.

Being dealt a pile of random pieces and figuring out how to put them together is the core hook. The mix of puzzle-solving and discovery keeps me coming back. The randomness adds to the addiction; each run is a fresh puzzle to solve. A new space to explore.

Menagerie archetypes: roguelikes and deck-builders

Two genres of games fit into this: roguelikes and deck-builders.

Roguelikes are games inspired by the 1980s video game Rogue. In Rogue, you navigate a labyrinth of randomly generated dungeons, with random item and monster placement. While other fantasy games are 30-60 hour epics, Roguelikes are built around 30-60 minute runs. One life, you either finish the dungeon or start over with a new one.

Deck-builders are what they say on the tin. You have a deck of cards you can modify, either before or during the game. You are drawing from a random pile, but you get to have agency in the design of the pile.

Roguelikes give you a lot of different game pieces to randomize: dungeons, monsters, player stats, equipment, and consumables. Deck-builders have cards, an endlessly extendable game piece.

The three menagerie games I've had an obsession with, in chronological order, are Magic: The Gathering (the OG deck-builder), The Binding of Isaac (An absurdly funny and grotesquely horrifying roguelike), and finally Balatro (a deck-builder and a roguelike, drool).

To Magic: The Gathering, and Beyond

As of this writing, there are 30,367 unique Magic: The Gathering cards. Magic has been releasing new cards for 32 years. It doesn't get more extensible than that.

Magic cards have always represented a variety of concepts: spells, places, things, magical devices, weapons, battles, vehicles, and even reuniting with a long-lost old friend.

Magic wove extensibility into the lore. Magic takes place in a 'multiverse' with an infinite number of alternate universes called planes. This way each set can explore a new theme. Over the past 30 years they have had planes inspired by, but not limited to:

• Greek mythology

• Japanese mythology

• Indian mythology

• Fairy Tales

• Tolkien-inspired worlds

• Hell

• A world with a 600-year-long day/night cycle

• A 15th-century ecumenopolis

• A plane Gothic + Lovecraftian horror

• A plane of campy 80s campy horror

• A return to that Japanese mythology world but it's 2000 years later and now it's all cyberpunk

• Pirate dinosaur world1

• Cowboy world. Yee-haw!

Executives at Hasbro recently had a very profitable realization: Magic's system could support not just any world, but also any IP. They could play the same game as Lego and Fortnite. Why make a Tolkien-inspired set when you can just print the Lord of the Rings set? Magic released a Final Fantasy set, and it's their biggest seller ever. making more money than many other video games and movie releases this year. $200 million. If it were a movie, it would be tied for no.8 at the box office beside Captain America: Brave New World

They are seriously trying to become the everything trading card game. The Amazon of sci-fi fantasy. 30 years and 30,000 cards later, their rate of producing new cards is actually increasing.

The Binding (and duality) of Issac

Edmund McMillen gained notoriety with his breakout hit Super Meat Boy: a platformer that dared to ask the question: "What if Super Mario Bros. was batshit insane?" His follow-up, The Binding of Issac, a top-down roguelike that dared to ask the question: "What if The Legend of Zelda2 was batshit insane?"

The loop is simple: Like Legend of Zelda, there are dungeons, each with an item and a boss. But instead of an overworld, you move from dungeon to dungeon.

The lore is a little more complicated. It's an allegory to Genesis 22. The one where God asks Abraham to sacrifice his son Issac, then at the last minute says 'jk' and merks a ram instead. In the game, Issac's mother believes a televangelist ordered her to kill her son. Isaac flees to the basement, which happens to be a cascade of procedurally generated dungeons.

Power-ups are all over the place. McMillien includes references to anything and everything, including:

• in-game lore

• His previous games (Super Meat Boy, Time Fcuk3)

• His favorite games (Magic: The Gathering)

• The Bible

• His dead cat (RIP Guppy)

It's whiplash. The game swings from funny to tear-jerking. Horrifying yet goofy. While playing, you reflect on how Christian upbringings can fill children with a deep sense of guilt and shame, then collect a power-up that's a fart.

Balatro, the genius of Joker Poker

In Balatro, you play sets of poker hands and must hit a minimum score to advance to the next round. Every round, the minimum increases. Between rounds, you earn money and visit a shop where you can spend money to acquire jokers (permanent modifiers), one-shot items, new cards for your deck, or planet cards that increase the point value of specific hands.

Just like in poker, hand strength matters, but it's a small factor. Balatro's randomly generated dungeons are not the rounds; it's the shop. The shop gives you a limited number of options and 5 joker slots, which is your primary way of building your strategy and increasing your score.

Then there's also the deck-building. You start with a standard 52-card deck, then add, remove, and modify cards in it. If you have a joker that rewards hearts and another that rewards flushes, you can bias your deck towards hearts. If you have a joker that punishes face cards, you cut as many of them as you can. One of the most optimal decks is often 40 enhancement-packed kings of a single suit.

Building my menagerie game

In my last post, I mentionwed how another Substack post inspired me to build my own roguelike. Menagerie games are ideal learning projects. There are always new mechanics and pieces you can invent.

Add weapons. Then add elemental damage. Then status effects. Then triggers tied to player actions. Each layer asks new questions of me and of the game.

This creates an addictive, multi-tiered iteration loop:

1. I iterate on the game, adding new items, tweaking and balancing.

2. Then, I iterate on the engine. Adding new mechanics, refactoring code as the system grows.

3. Finally, I iterate on my build process. How can I leverage Claude Code to build more interesting gameplay faster?

I don't know when I'll stop iterating on this game. There's plenty else I want to build, but it's nice to have an evergreen playground that can be anything and everything. Just like Magic keeps adding expansions, there is always another weapon, monster, or mechanic to toss into the pot.

Devil's Den on Github

Playing game design with my son

I've co-designed a board game with my son, titled Dinosaur Breakover4. At the start, you pick which of four dinos you think will win a drag race. Then, players take turns drawing cards from a deck until one dino crosses the finish line. Former college drunks like myself might recognize this as a family-friendly riff on the drinking+gambling game Horserace.

What it lacks in complexity, it makes up for in how much watching my son draw his new card idea warms my heart. The deck contains various references that I put in and his ideas.

As he grows, maybe we can extend the lore and the mechanics. Make our own expansion packs.

One time, we sat down to play, and he asked:

"What if it had dinosaurs AND dragons?"

Great question, big guy. What if it did?

And don’t just take my word for it. Ludology, the science of play, was pioneered by Dutch historian Johan Huizinga in his 1938 book Homo Ludens: A Study of the Play-Element in Culture. In it, Huizinga examined what play is and why it matters.

He saw play as so essential that he described humans as fundamentally creatures of play—hence the title. Video game designer Hideo Kojima loved this idea so much he created a mascot called “the Luden” for his studio.

So what is play?

Huizinga defined play as free, unstructured activity that exists apart from ordinary life and creates its own order. He also introduced the idea of “the magic circle”—a specific space and time where the game exists which dissolves when the game ends.

For example, when I play pretend with my son, Magna-Tiles become houses, cars, and sushi restaurants. When we stop, they go back to being colorful connectable polygons in a bin.

The forms of play

Huizinga observed that play manifests in many forms:

1. Joking & jesting - Humor bends expectations and opens up shared space.

2. Child’s play: What Maria Montessori called “the work of the child.” Also observed in animals.

3. Competition: such as sporting events and board games.

4. Pretend play: Improv, acting, & mimicry.

5. Rhythmic play: dance, music, poetry.

6. Imaginiation: Mythmaking & storytelling.

The benefits of play

Huizinga viewed play as foundational to the human experience. It gives us so much:

Play builds community

Play isn’t a part of a culture — it creates it. Take professional sports for example: teams compete for a win, but also for the right to be celebrated. Fans join in too, sharing in joy or heartbreak with friends and strangers alike. (Fun fact: “praise” and “prize” share the same latin root.)

Play increases flexible thinking and problem solving.

As Visakan Veerasamy points out, people often come up with their cleverest ideas when they’re joking around.

Play teaches emotional regulation and perseverance.

Setbacks don’t sting as much when you have a lighthearted approach. And when you’re enjoying what you’re doing, you’re more likely to stick to it.

Play increases engagement

When you approach things as play, it’s easier to stay engaged, bringing more attention and energy to your craft.

Weaponized Play

Play is powerful, so obviosuly people will twist it for profit—and the results aren’t always good.

One common example is making work more “gamelike.” But play and games aren’t the same thing. Games are just one form of play—they have rules, goals, and structure. Sometimes game-like ideas are useful, like when we “level up” our skills or follow a “skill tree” to build knowledge. But they can also be harmful.

Gamification considered harmful

Gamification is adding game mechanics to systems with the element of play stripped away. Think leaderboards, quests, achievements, unlocks, and XP to drive behavior. It is psychologically manipulative. Uber rolled out a “quest” feature for drivers, offering bonus cash for hitting milestones. But as drivers got close to their goal, Uber would feed them lower-paying rides, keeping them behind the wheel longer. They are out driving, eyes burning, concentration fraying. Uber is helping driver’s have fun it’s putting them and others at risk to increase profits.

Gamification can have positive effects too. I used to go to a CrossFit gym, fully aware that CrossFit is just gamified workouts. But it worked: it kept me coming back and got me in better shape.

When you see gamified systems, you should stop and ask: What behaviors is the system pushing? Who benefits most from them?

Why gambling breaks some people

Gambling is another example of play gone awry. It’s subject to the overjustification effect—when external rewards crowd out internal enjoyment.

Gambling can be fun, but when done compulsively it can be destructive. Playing for stakes removes the intrinstic joy of the game, makign it worklike. In college I paid rent “playing” online poker for two years. It was miserable. It turned an activity I used to enjoy with my friends around a table into four-suited Excel hell.

Mandatory fun

At my first job, I received an email (remember those?) inviting me to the company picnic on Columbus day. It informed us that attendence was “mandatory and fun”.

Play cannot be a top-down directive. You cannot force your reports to play and have fun. Play, by definition, is free. As soon as it is put on your calendar with an objective of team building or building trust, it’s no longer play. It’s a a meeting with an above-average level of cringe.

So, How to we achieve this?

We must do what Johan called “Embodying the spirit of play”. It has to come from within. It’s about choosing to bring an attitude of play and lightness to everything to do.

Because Play in the human engine of creation. **From it, we create culture, poetry, jokes, stories our communites . Being playful brings our own best, most creative, most. engaged, more powerful selves to the world. That’s why joking about the outcomes you want, bringing the character of play, enables you to be authentic, open to new possibilities, “yes and” reality, and meme your dreams into existence.

"We are all capitalists’…and therefore, we all have to take risks."

Franco "Bifo" Berardi, After the future

My first experience with self-employment was freelancing. I quickly realized I had to seek out work, invest in my personal brand and network, and use my time and resources efficiently. It wasn’t the “freedom” promised by lifestyle podcasters—it was more responsibility and autonomy.

Eventually, freelancing dried up. The only gigs I could find were 6-12 month, 40/hour week contracts. Those are just jobs with no benefits, no PTO, and an expiration date.

I retreated back to the world of full-time employment.

At first I thought I left my 'indie mindset' behind. But then I realized: succeeding as an employee is a lot more entrepreneurial than it seems. You have to take ownership, exercise agency, and run your career like a business.

You, Inc.

“If you’re an employee, your most important job is to think like a principal”
— Naval Ravikant

I am a company of one with a whale client responsible for 100% of my revenue.

Here’s what that mindset looks like in practice:

You work for yourself first

Of course you want to deliver great service and results for your client. But you do it because it boosts your revenue, strengthens your reputation, and builds proof of work like case studies. Selfish motives don’t make for sustainable businesses, and companies that don't take care of their customers or employees won't last.

You have a defined strategy, vision, and definition of success

This is the biggest difference between a 'You, Inc.' and a big corporation: You are not bound by shareholder doctrine. Increasing revenue is great but it can't be the ultimate aim.

You hunt for opportunities instead of waiting to be picked

You actively seek opportunities that align with your strategy. You don't say, "That's not in my job description." You work for yourself, you wrote your job description. You find work that moves you closer your goals. You craft your job in a way that plays to your strengths.

You gotta sell

No way around it: Selling is mandatory.

If you build it they will not come; They are too busy with their own work, wants, problems, and algorithmic feeds. You have to make yourself visible. You need to clearly and persuasively present your ideas. You have to push through that awkward feeling, straighten your shoulders, and toot your own horn. Learning to write & speak pays huge dividends in any knowledge work1.

Beyond reframing what I do, I also reframe why I do it. It’s about more than a paycheck.

Building career capital

“Prefer to work on things you can show. Prefer to work where people can see you. Prefer to work on things you can own.”
— Patrick MacKenzie, Don’t end the week with nothing

If we’re all capitalists, then even employment is a game of building capital, not just earning income.

I define career capital as any non-monetary value you add to your balance sheet.

Examples of career capital:

• Skills & expertise - what are you good at, and how well can you deliver?

• Specific knowledge- What secrets and insights have you gained that can't be found in any book?

• Network - How many people know you and what you offer?

• Reputation - Do people view you as someone that is trustworthy, reliable, and can get the job done?

• Proof of work - What evidence can you point to of what you've done?

• Side projects - What have you created that you own?

What ways have you acquired career capital, and how did it pay off?

Leave a comment

The most important aspect of career capital is liquidity. Prefer to build capital that you can take with you. The days of working 40 years for a pension and a gold watch are over. I’m not advocating constant job-hopping (though in early tech careers it can be strategic), but all jobs are finite. Plan accordingly.

If you take away one idea, it’s this: expand your investment mindset beyond index funds and retirement accounts. Start thinking about all the other forms of capital you can build.

Collaborating with your client

“You work for a week, collect your paycheck on Friday, and then you and the company are even.” — Jack Welch

I worry this attitude may be seen as antagonistic to your employer. In reality its the opposite.

When your customer/employer succeeds, you succeed. You want to be in a position where helping your employer aligns with your goals—and where it’s in their best interest to invest in you because you’re a safe bet with strong ROI.

But like recognizing the finitude of employment, it’s also important to understand the true nature of the relationship. Your employer, from an economic standpoint, is exploiting your labor. Their goal is to extract maximum value from your work. In exchange, you receive steady pay, benefits, and (hopefully) healthcare. For many, this is a fair deal.

Keeping this in mind reminds me that the relationship is symbiotic, transactional, and devoid of loyalty from either side.

I once worked at a company that, after an Amazon policy change, laid off a third of its staff overnight. I watched good colleagues—who’d done nothing wrong—get called into the office, return quietly to pack boxes, and walk out the door. It was a cold reminder: employment is never guaranteed.

Don’t live in fear, but have a Plan B.

You don't get ahead working hard for others. You get ahead working hard for yourself

I’m grateful I spent my early years self-employed. I didn’t earn as much as I could have in a salaried role, but I gained specific knowledge that’s paid bigger dividends. Mainly, it taught me that it was up to me to decide what I wanted, and what work I’d do to get it.

It taught me that in today's environment, I'd always be an entrepreneur, whether I like it or not.

AI is undeniably changing how people write. While some are excited by a future with less writing, I’m a little concered about a future with less thinking.

It’s plausible that most people won’t need to write in the near future; we might even celebrate the triumph. But writing and arranging words is the process of careful thinking. By offloading it, will we not atrophy the muscles of thought? We’ll each gain the illusion of competence, without even being aware of our cognitive amputation. We might lose our personal sovereignty in an age where we need it the most. — Micheal Dean, Essay Writing as Personal Sovereignty

The threat of technology reshaping our brains, permanently, is real. If you over 30 like me, you’ve noticed how you remember fewer phone numbers. You reach for the GPS every time you drive to Home Depot, even though you’ve lived here for almost six years, shouldn’t you know the way by now?

David Perell, creator of the now defunct Write of Passage course, holds a pessimistic view. He recently shared that he quit teaching the course because AI has made him bearing on online writing.

However, I still think Gen AI has a place in the writing process. They are language models after all. I also disagree with Parell, I still think there is a ton of leverage and alpha in writing online. If I didn’t, we wouldn’t be here right now.

Here are my guiding principles for leveraging AI:

DO: Use AI for research

ChatGPT Deep research is the new Wikipedia page. A starting point, not an answer. They are tapas menus of resources to pick and choose from. A great first stop when you delve into a new topic.

DON’T: Use AI for summarization

Summarizing isn’t just condensing information—it’s deciding what matters, how to structure it, and how to reframe it. Summarization is how you build retention and understanding. It’s a creative, intentional act. Delegating summarization is like sending an android to your CrossFit class.

DO: Use AI as reference

I urge my students to get a usage dictionary… To recognize that you need a usage dictionary, you have to be paying a level of attention to your own writing that very few people are doing… A usage dictionary is [like] a linguistic hard drive… For me the big trio is a big dictionary, a usage dictionary, a thesaurus — only because I cannot retain and move nimbly around in enough of the language not to need these extra sources.

As a teacher, about 90% of my job is getting the students to understand why they might need one. — David Foster Wallace, Quack This Way: David Foster Wallace & Bryan A. Garner Talk Language and Writing

Writers have always relied on tools—there’s no shame in using them to improve your work. When I’m stuck on a word choice, I’ll ask ChatGPT or Claude to give me 5 options to fill in the blank. Sometimes it’s faster than reaching for the dead tree tool a whole 15 feet away.

Don’t: Let AI strip your writing of personality

Don’t shove text through the AI mill and uncrtically publish what comes out the other side. Instead, use AI for suggestions. Pick the ones that work best or use them as inspiration to go in another direction. AI gives you options, you provide perspective and taste.

Do: use AI as a line editor

AI won’t make creative word choices, but it can suggest clearer alternatives, like replacing “talk about things” with “communicate.” Here’s a prompt I’ve been experimenting with to do this:

Act as an experienced writer with a focus on improving the clarity and readability of text. You are responsible for reviewing a piece of text. Break down the sentences into simpler forms without losing the original meaning or nuance. Implement appropriate punctuation, streamline the language, and remove any unnecessary jargon or filler words. Ensure that the content adheres to a consistent style guide and retains its original purpose while becoming easier to read and comprehend.

Go section by section, and give me the original version, the revised version, and a list of changes made

Don’t: Rely on AI as proofreader

AI cannot replace human feedback. It can fix a sentence, but it can’t tell you if it’ll resonate with someone. Writing is still for readers, and we need readers to help us figure out what’s interesting and what’s dull. What’s mind blowing and what’s confusing.

AI is an assistant, not a replacement

AI cannot replicate personality, perspective or taste. It cannot build human connection or express a deeply held belief. It can only help humans do so. It can replace my thesaurus, but it can’t replace my mind or my soul.

To wit, if your paycheck is contingent on pumping out thoughtless, soulless content, then yeah, I’d be concerned.

Maybe you’re wondering if it’s worth it, if you should, if it’ll backfire, or if it’ll be any good. Totally understandable. Happens all the time. Don't worry—these concerns are completely normal and common. Fortunately, there are proven strategies to overcome these obstacles. Let’s meet the villain of your journey: Resistance

Battling the Resistance

In his book 'The War of Art,' Steven Pressfield identified this phenomenon as 'the Resistance.' The Resistance is the antithesis of the Muse. Instead of inspiring you to create, Resistance tries to stop you.

Creativity requires doing something others won’t do, to an audience that might not materialize, without a guaranteed reward. It requires vulnerability. The feeling of resistance is normal and unavoidable.

Understanding that resistance is normal and expected should help prevent it from stopping you. Being creative is supposed to be uncomfortable. It’s like going to the gym — discomfort signals growth.

What’s the point of publishing online? Is it worth the time?

I can promise you it is.

You have value worth sharing. Helping even one person justifies the effort. If you frequently get the same questions, Publishing an answer saves you time and helps others more efficiently.

Writing also crystallizes your thinking. While our minds are fuzzy, unreliable webs of thought, writing is concrete and linear. The page stares back at us. It begs for examination. And knowing that other people will see it now encourages us to raise the bar on the effort and quality of our thinking.

Publishing can spark meaningful conversations. I’ve reconnected with old friends (Hi Cory and Jeremy!) through writing. I didn’t anticipate that, but I’m grateful for it. Sharing your ideas has a way of attracting like-minded people. You’ll also be a more engaging conversationalist since you’ve refined your thinking and opinions more than most.

Writing online can create opportunities. The right person reading one of your pieces at the right time can open doors. Based on my articles, I’ve received job offers, invitations to give talks, and opportunities to lead initiatives at work. The internet is an infinite leverage machine.

Finally, humans are built to create, not just consume. I want to see more people putting their ideas out into the world. I’ve read articles and essays that have permanently altered the way I think, and changed my career path for the better. What if you could make that happen for someone else?

Okay, I see the value in publishing. Do I have to go build a whole website now?

This is a common sticking point, especially for engineers. They want a personal website to pull double duty as a platform to share work, and a playground to mess around with shiny new technologies. Do not turn your personal blog into an engineering project at the start. Single responsibility principle applies here.

If you can’t spin up a new website in four hours or less, you’re doing it wrong. Making a website is easier than it’s ever been. Use SquareSpace or WordPress or Ghost. It doesn’t even have to be a website! You could use newsletter-based publishing tools like Substack or Beehiiv.

Okay, I have a site, but I don’t want to be a “blogger”

You don't need to build an audience, commit to a schedule, or maintain a content calendar. Forget about creating a "personal brand," crafting a "positioning statement," or developing a "content strategy." Resistance is trying to make the problem sound bigger than it is.

What I am advocating for is an entirely different game. Tom Critchlow calls this ‘Small-b blogging.’ You aren’t writing for a massive audience. You are writing for your network.

Don’t write just to hit some frequency some hustle blogger said you should, or to maximize pageviews. Instead, strive for writing that has specific appeal, at a comfortable pace, aiming for meaningful engagement over empty metrics.

Don’t borrow trouble from future articles no one is forcing you to write. Focus on what’s interesting now. Who can you help, and what can you publish today?

I don’t know enough

You have more expertise than you realize. Years of experience becomes so familiar we take it for granted — like water to a fish. Ideas that are obvious to you could be a revelation for someone else.

Here’s a secret: experts don’t write because they have expertise. They have expertise because they write.

Writing is a method for building expertise more than sharing it. The root of the word "essay" means "to attempt." You ask yourself a question and attempt to answer it, going on an intellectual journey and bringing others with you.

My writing is smarter than be because I can rewrite it.” Susan Sontag

There’s an episode of the Simpsons(Spelling as Fast as I can) where Marge is trying to figure out how they are going to pay to send Lisa to college. They have this exchange:

Lisa: Mom I'm having a crisis of conscience. Can you and Dad afford to send me to college?

Marge: Oh of course. I mean, not on your father's salary, but I could and give piano lessons.

Lisa: But you don't play the piano.

Marge: I just gotta stay one lesson ahead of the kid.

There’s real value in being one lesson ahead of the kid. Your recent time in the trenches gives you an accurate memory and shared context with the reader. The fresh perspective of someone who just learned something enables you to communicate in a more relatable, high-fidelity way.

To discover what you know, you have to get it out of your head. Jot down a rough outline of supporting points for your idea. Try doing a 10-minute free write on the topic. You can try to fill it in with other notes, ideas, and links. You might surprise yourself with how much you come up with.

From there, targeted research can fill any remaining gaps.

An idea I value is intellectual activism: The art of taking existing information and making it more accessible, understandable, useful, or enjoyable to others.

Finding information in books, papers or online videos, or threads and distilling and sharing it in a way that’s accessible to others is a public service. Curating and combining resources generates new value from existing material. You can draw from multi-disciplinary knowledge. Warren Buffet says he learned about how markets evolve by reading The Origin of the Species.

This is why I take notes compulsively and collect information and links like Pokemon: When I sit down to write I don’t face a blank page. Instead, I can draw from my bank of ideas and evidence.

I have nothing original or interesting to say

Isn’t that cheating though? How is building off of others' work not plagiarism?

The concept of “originality” in writing is a myth. Can you name a writer that is truly “original”? Everything is a remix — we all build on existing ideas. The image of an author pulling inspiration from the ether is fantasy. It's all old hats through new lenses.

No one is original, but everyone is unique. Your personal perspective matters and is worth sharing. Anyone can share facts or links. Combining them with your experiences, skills, context, and stories creates something worthwhile.

Uniqueness is combinatronic. For every experience, memory, skill, and story you have, there are intersections between them all. These give you even more unique places to draw inspiration.

Your network is also unique to you. If you share something with someone, they will see something that otherwise wouldn’t have. Don’t feel bad because it isn’t original “enough.”

Once you have an outline, you can add color to it by adding bits only you can: your stories, experiences, memories, observations, and perspectives. Consider how these elements intersect with each other and with your topic.

This piece was inspired by other books and articles I’ve linked to. They all have one thing in common: All these authors have had much more writing success than me. I had to get over Resistance telling me I didn’t “deserve” to write this. I’m betting there is some value in someone saying, “Look, I don’t have impressive subscriber numbers to show you. My readership is tiny. I still think it’s worth showing up and putting my ideas out there.” Maybe you will too.

You can also remix your own work. Every piece does not need to be 100% brand new. Previous notes, comments, conversations, or documents might have material that can be reused. I call this stuff “grist” material that is ready to be refined into something useful.

By using the existing grist, you can craft version 2s and version 10s of your ideas. These are bound to be better than the original. Venkatesh Rao calls this The Calculus of Grit. If I had written it first, I probably would have called it “The Calculus of Grist.”

The idea that you aren’t smart enough or original enough is also a myth. It can be safely ignored. Take the path of least resistance. There is an abundance of work out there from yourself and others, ready to be refined, referenced, and remixed.

The twin anxieties of readership

People can have opposite reactions to the same stimulus. Some people lose their appetite when they get stressed. Others reach straight for the fries and Girl Scout cookies.

As you approach hitting “publish,” Resistance gets stronger. His final move manifests in one of two opposing fears: Either you are afraid that no one will read what you write, or are you afraid they will.

I’m afraid no one will read what I write

Even if no one reads your piece, there is still inherent value in writing and publishing. You refined ideas and have more material for next time. You have an asset that may pay off later. You have one more rep hitting publish. Maybe you needed to write this piece so it could tell you what you should write next.

Everybody can benefit from the result. You get to benefit from the process.

If you want readers, be proactive. Put your link out on all your socials. Sure, that’s table stakes. But also, if you wrote a piece that you think could help someone you know, send it to them directly.

Here’s an offer: If you’re scared you can use me to practice. Send me your published piece or even a draft in Google Docs. I promise I’ll read it and share some feedback. You are guaranteed to have at least one reader.

I’m afraid someone will read what I write

What if the end result isn’t “good enough?” What if we’re misunderstood or misrepresented? This is a classic move of the resistance. It’ll never turn out exactly how you pictured it. Vision is ahead of execution, as it should be. Just remember that so long as you try, whatever you were able to put out was, in that moment, your best work. That’s all anyone can ask of you.

You can’t be perfect but you shouldn’t be sloppy. It takes practice to find the correct amount of effort to put into a piece before hitting publish. In my experience, the quality of a piece is a function of the number of revisions, not some spark of genius.

What about negative feedback? If you ever have an article that gets any traction, you will get some haters. This is a good thing. It means someone thinks your piece is worth engaging with. Some are trolls that can be ignored. Others will give you the precious gift of feedback.

This is a valuable part of the process. You can only refine your ideas and perspective so much internally. The real magic is in when you use them to interact with others. Feedback counts as grist.

Internet writing remains malleable—you can always edit or delete content. The internet has a goldfish memory, and it remembers successes more than failures.

Anything you publish is a UI for the reader who wants to be entertained or informed. They want the piece to be good. They are rooting for you. Everyone is on the same side; The relationship between reader and writer is ultimately positive.

Godspeed

Don’t be afraid. Countless others have published blog posts and lived to tell the tale. In a world overrun by vertical videos and AI slop, online writing is one of the best asymmetric bets opportunities for knowledge workers. You can create a lasting, high leverage asset in a few hours, for free. By writing and publishing, you refine your thinking, create a shareable asset you own, and expand your luck surface area. How many other activities offer this much upside with such minimal investment?

All you have to do is get over capital-R Resistance and do some small-b blogging. I’m excited to see what you come up with!

It’s both work-centric and work-negative. It assumes the default priority in your life is your 9-to-5, giving work equal billing with literally everything else. What are more effective ways to frame where work fits into our lives?

1

Work-life balance is off-balance. What people mean when they say “work-life balance” what they want is work-life boundaries.

You don’t want to be answering emails at 7 pm. You don’t want to hear screaming kids or yapping dogs when you’re trying to debug a PR. That’s fair.

It’s a challenge when working remotely, and you can’t escape to the office (or vice versa)

You can build boundaries around time or space to help. Have a dedicated office space; Let your family know when your focus hours are. In my office I have a ‘do not disturb’ door hanger, hotel-style. It lets my wife and kid know when I am heads down or on a Zoom call. I Walk the dog around the block at the start and end of every work day - a “commute” between work mode and life mode. He is still struggling to respect the door hanger.

But boundaries aren’t the only way.

2

Why must work be decoupled from life? What if work was something that enhanced your life rather than take away from it?

Hayao Miyazaki made The Boy and the Heron when he was in his 80s. He didn’t do it because he needed the money.

There’s work that interests you, that you are uniquely skilled to do, that you find compelling and enriching. Paul Millerd explores this idea in his book Good Work. There are ways to find work-life integration.

Or maybe it could mean separating vocation (work you do because you are compelled by the inscrutable exhortations of your soul) and occupation (work you do to pay the bills). This path is the most logical and fruitful for most I suspect, as it allows you to keep your art “pure” and your career optimized towards supporting you and your work.

I recognize that I do not contribute to world peace or solving hunger working in the financial services industry. I won’t pretend I enjoy it every day. But I find ways to make it work for me. I remind myself that our product helps people run their businesses with less friction. I find purpose in mentoring and coaching less experienced employees. My mandate also includes building and writing things that I’m proud of.1

3

What about the life half of the equation? What an oversimplification of our strange and beautiful existence. It can be broken down further with work-life decomposition.

Instead of a binary, many others have thought of life as a collection of several facets. Models include:

• John Maxwell’s Daily Dozen2

• Zig Ziglar’s Wheel of Life3

• Tony Robbins’ 6 human needs4

• Martin Seligman’s PERMA model5

• The 5 Fs Framework6

Take your pick or roll your own. Instead of balancing two things, these all frame life as a prism of physical health, personal relationships, financial security, spiritual fulfillment, emotional well-being, personal growth, making an impact, and sparking joy.

4

You can’t draw clear lines between the different facets. Each segment feeds to the others. I’ll, for consistency’s sake, call this work-life interdependence .

Career impacts money. Health increases productivity. Your passion for your job directly influences how fun you are to hang out with after work.

The separation only comes when you want to zoom in on one to make optimizations or improvements. But even then, you can’t do so without considering how it would impact the others.

Wrapping up

There are so many more interesting ways to frame how you prioritize your time and energy, set your intentions, and live your life. Thinking about “work-life” balance is limiting and guaranteed to make you off balance and bored.

There’s that Lincoln quote:

Give me six hours to chop down a tree and I will spend the first four sharpening the axe.

I would spend all six hours sharpening the axe. I would watch axe swinging technique videos on YouTube. Then I would shop different axe models on Amazon. Then I would second guess myself and wonder if chopping down a tree is what I should be focusing on right now.1

I don’t think I’m alone here. Does anyone else take a moment to look back at their 2024 resolutions and goals and notice that they barely got out of the gate for some? You wanted to track calories, but the last time you opened MyFitnessPal was January 21st.2

Planning as recreation

Past a certain point, planning ceases to be useful and can unwittingly become a form of play. Planning is no longer about mapping a course of action, it’s about the fun of drawing the map

There’s a dopamine hit with “a ha” moments. You get them when you write plans, learn new ideas, and fantasize about reaching your goals.

@digitallybaffledDoing the plan #animation #animationmeme #productivityanimation #entrepreneurmeme #productivityfail

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My goal is to minimize map drawing and maximize exporting. Less ruminating, theorizing, and noodling. When thinking, I try to keep it as action-oriented as possible. Here’s my framework for my internal dialogue3:

Sometimes, the “next thing” is doing research, and that’s fine. Research is collecting information with intent. You ask questions, you get information to answer that question well enough, you move on.

With this mindset, when you see a piece of content, you can quickly filter it:

This rubric helps you avoid the infotainment trap.

How infotainment traps us

Learning is fun. Our brain gets a dopamine hit when we learn something new, even if never put that information to use. Infotainment is a whole genre of content based around people who enjoy this kind of engagement.

TED talks, Malcolm Gladwell books, Planet Money. All examples of infotainment.

I’m not hating on this content. Hell, I’ve produced plenty of it myself. What I’m hating on is the false sense of productivity this content can create.

Enjoying infotainment is fine so long as you recognize it as leisure **not work. It took me a while to make peace with the fact that I would read about copywriting for fun. But that’s just the kind of nerd I am.

But I have to be mindful of my information diet, because I’ve fallen into this trap before.

My time in the trap

When I was a freelancer4, I listened to indie biz podcasts on runs, doing the dishes, and driving in my car. I felt like I was doing something. I was fooling myself. I was simply looking for those “a ha” dopamine jolts. In truth, outside of the cardio, the clean dishes, and getting where I needed to be, I accomplished nothing.

I spent too much time theorizing about my ‘business’ and not enough on billable hours.

I went to conferences and even spoke at one of them. I made some great friends, had fun, and left feeling energized. But very little changed in my day-to-day work.

Eventually, my freelancing businesses folded after a client offered me a full-time position with a salary that was higher than any revenue year I had had previously.

I learned how to write persuasive proposal & how to stand firm on my fees with stingy clients. But now I realize I substituted too much of my judgement with that from various “experts.”

Not this time.

Perfection’s never possible, progress always is

For 2025, I’m paying close attention to how I spend my time. When I know a directionally correct next step, it’s time to close the notebook, shut the Kindle, and get to work.

But unlike Leeroy Jenkins, I’m sticking to the plan and coordinating with others. And unlike his pals, I won’t stand around number-crunching my chances of survival anymore.

So much is '“off” about the new one—the animal’s faces jitter. Lighting and perspectives are off. A bottlecap flies unbounded by Earth’s gravity. It has that AI slop gloss sheen. There are so many camera cuts because AI can’t yet generate convincing video over three seconds long.

It is noticeably worse than in previous years. Compare this to the 2020 commercial. The animals move. They emote. They have personality.

Speaking of a loss of personality, let’s talk about this year’s Spotify wrapped.

Spotify Wrapped was worse writ large this year.

Generated genres were nonsense. We didn’t get lists of our top genres like last year. Everyone’s top artist #4 was weird. I had to DuckDuckGo1 to figure out who mine was. Spotify lost the thread; it’s not about showing us a list of songs, it’s about diving deeper and showing us something about ourselves that we didn’t know.

They kept the artist messages, little targeted commericals you get from your highly played artists, letting you know about their upcoming tours and albums. Some people speculate that these were also AI-generated content, specifically Mariah Carey. You can watch it here and judge for yourself.

The verisimilitude of Mariah Carey has always been in question. I’m not fully convinced this is AI, but it’s definitely not 100% organic.

I’m not an AI opponent. I think it has utility as a creative tool but not as content. When I use AI to write here, it’s used as a thesaurus, an editor, and an improv tool to riff with. I wouldn’t put out pure AI-generated words because if no human cares to write them, why should any human take the time to read them?

Corporations seem to be testing the boundaries of how much AI slop consumers will tolerate.

Hopefully, a shiny, slightly morphing Ghost of Christmas Yet to Come will pay a visit and show them what the future looks like if we keep going down this path.

But then, sometimes the game changes.

Whether it's becoming more fun, or more bleak and disheartening, it changes.

We may not want the change, or resist it. We try to play the game the way we used to, back when it was how we enjoyed it. When we thought we had it figured out. But that's not up to us.

We can't control the games, only how we play them

Some win conditions may change, while others are immutable. Strong bonds with family, friends and community are always a solid play strategy. Before it may have been about thriving, and now it may be pivoting to surviving or merely existing.

## Adapting with OODA Loops

Strategies have to change. Military strategist and former Air Force colonel John Boyd came up with the OODA loop model for making high-stakes decisions under duress: Observe, orient, decide, then act.

The faster you can complete these loops, the better your chances of success.

1. Observe: collect data. Get the best information you can and try to get to the most accurate interpretation of it. Understand the rules, constraints, and contours of the situation.

2. Orient: understand your position. Where are you at in all of this? What options are available to you?

3. Decide: form a new strategy. A hypothesis on how you can move towards your win conditions. What gives you the best chance of success?

4. Act: Test your strategy by taking action. Action provides information, usually the best information for you in your current situation and orientation. Observe. Now we're back to the beginning.

Sometimes OODA loops are small, sometimes they are large. They take the form of annual reflections, quarterly business reviews, or split-second decisions in a match of a Street Fighter 3 tournament.

It’s your move. Move forward

When the rules change, it's time to scrap or adjust old ideas. You may be frustrated or terrified into paralysis.

But that is never a winning strategy.

When the rules change, you may not like the new system but you may not have a choice in whether or not you play.

In these cases, the only was forward is to observe, orient, decide, act.​​​​​​​​​​​​​​​​

Especially act.

Before we traveled across the country to a glamp in the desert with our 10-month-old, the best advice I received was to have no expectations. Worst case scenario, you are just parenting in a beautiful new location.

The next best advice I received is don’t panic.

You can always bail. This has been my motto throughout the first year of parenthood, and I readily applied it to our biggest trip. It would be harder to bail, but there is always a way out. If baby can’t handle the dinner, leave. There is no reason to stay with a screaming baby because you can’t enjoy it anyway.

Using this motto as a failsafe, I knew we could take on anything. 

So, how did we take on this trip? Planning. Weeks leading up to the trip, I paid close attention to all the items we used daily.

• Are there toys or books that he asked for regularly?

• Which spoons is he the most successful with?

• Even though we weren’t tracking diapers anymore, I started to pay attention to how many diapers we used a day (mind you, on most trips, you can ALWAYS run out to get more diapers, but for us, the closest big box store was at least 40 mins away so we had to take it all… and then some). 

At first, I felt a little silly about the number of bags we brought, but in the end, we used almost all of it (and flew Southwest, so we might as well use the free checked bags!). So let’s chat through the gear and how we got it there:

Checked in a large suitcase:

• Pack and Play—We have a basic Graco pack and play, and it has served us well. It assembles quickly and provides a clean, safe sleep space at night. I know a lot of folks recommend getting one from the place you’re staying or possibly renting one when you get there, BUT I cannot tell you the peace of mind I had knowing that he had a place to sleep and containment area during the day. I also packed a sheet for the mattress that comes with the PnP. 

• Slumberpod— I thought I was being extra when I ordered this. Who needs a tent in a tent? But let me tell you, we did. We have used this for every trip since it arrived and it is a game changer when you are room sharing with your baby/toddler who is used to their own space. It allows me to move around hotel rooms and go to bed after baby. 

• Sleep gear— We got a travel white noise machine, the baby monitor, though we couldn’t use it in our yurt, sleep sacks, and PJs. We also took everything we normally use for our bedtime routine—soaps, lotions, etc. We tried to make it as familiar as we could for him.

• Extra Food— He was nursing and eating several meals a day, but we weren’t sure we could always order something for him so we made sure to pack extra pouches and crackers. 

• Extra diapers— After figuring out our average number of diapers, I packed those plus 50% more and man did they take up a lot of room.

Second large suitcase:

• Clothes for me and baby. 

  • Packed a onesie for each day and then added 50% again. Onesies are the best- it’s a shirt, a sleeper, or a whole outfit if needed. Something is going to happen- food, poop or dirt, and it was wonderful having easy back ups.

  • Adventure specific items: we were hiking so I packed some sun shirts. And I always take a bathing suit! (Just a life rule)

  • PJs- packed a sleeper for every night- we ended up not using these due to the weather and relied on the onesies but it was good to have the option if it had been cold

Car Seat:

We purchased a second seat that was FAA-compliant. Even though we opted to travel with him in our laps, we wanted a seat that we could strap into a plane when the time came. It’s lightweight, seems to be comfortable, AND is super easy to install! We also bought a backpack carrying bag for the airport since we opted to gate check it on the way to our destination. You can rent a car seat, but for the cost of the rental, we now own a second seat for our cars, AND we know it’s clean and never been in an accident.

NOTE: we fully checked the car seat on the way home. We had a seat installed in the car at the airport at home so IF it didn’t make it back, we would be ok. However, I didn’t want to take any chances on the way to vacation. 

Baby Carrier

Little man loves being in the carrier, and we tested his limits on this trip! This was amazing for getting around the airport and around town. We use the Ergo Baby Omni Breeze, which helped with getting on and off the plane as well!  Since we only have a large stroller, we didn’t bring it, but will be trying a travel stroller on our next adventure!

Carry on # 1, under the seat: The diaper bag:

This was stuffed to the brim with extras. What if we got delayed??? So I had too many diapers AND overnight diapers. We had a 4-and-a-half-hour flight, so along with boarding and deplaning we would be on the plane a little over 5 hours. I decided to change baby into an overnight diaper for the trip. We had no leaks and no solids, so we didn’t have to change on the plane!

TOYS: We packed some easy-to-reach toys and books for him that we could access when needed. 

Snacks and water- we packed him a water bottle and tons of puffs and crackers to help keep him happy.

Carry on #2, overhead:

We packed additional toys and snacks in here. I wanted enough with us that IF the checked bag didn’t make it, or we were super delayed we could make it through at least double the meals we were missing. In hindsight, this was excessive. There are tons of options to purchase fruits and cheese at the airport. But for a first-time flight it did give me a sense of security.

On arrival

Yes, we were that family at baggage claim, two large suitcases, one small, one car seat, two backpacks, AND a baby strapped to us.

BUT, we also were the family that hiked Zion, slept in the yurt, and had an amazing family trip with a 10-month-old baby.

We had to bail on one dinner, but we knew we were pushing his limits as naps were thrown off, but that’s ok. I took him back to the yurt and watched the sun set over the mountains with a glass of wine.

Want to hear more from Kim? Let her know in the comments!

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1. The Uncertainty Mindset : Innovation Insights from the Frontiers of Food

By Vaughn Tan

3 key takeaways

1. Innovation and efficiency are at odds with one another. Innovation requires experimentation and making mistakes, while efficiency requires removing these in favor of efficiency.

2. People conflate uncertainty and risk, but they are two different things. Risk always has an unknown element, but just because something is uncertain does not mean it is risky.

3. If organizations want to encourage innovative behavior, they should give people open-ended job titles and roles

2. Developer Hegemony: The Future of Labor

By Erik Dietrich

3 key takeaways

1. You get ahead not by working for other companies but by working for yourself. Even if you are employed and happy, you should invest resources in building your body of work and your network and be looking for new opportunities.

2. Even though it’s lucrative labor, writing code for a living is still labor. There is no leverage in slinging code for someone else.

3. Eventually, you should strongly consider moving away from development work in your career, into something higher leverage.

3. Four Thousand Weeks: Time Management for Mortals

By Oliver Burkeman

3 key takeaways

1. Time just happens— You don't own it, you don't have it, and you aren't really spending it, wasting it, or losing it. Enjoy the ride. If you are always future-focused and trying to instrumentalize time, you are never truly living.

2. Work is infinite; you are finite — There will always be more to do than you have time and energy to do. There is no moment of completion to race towards. There is no point where you will feel you "have it all together and figured out."

3. Serialization — Tackle fewer things simultaneously, and instead, start ordering your projects. If you can't do everything, doing fewer things to completion is better than having several half-assed, half-finished projects.

4. Die With Zero : Getting All You Can from Your Money and Your Life

By Bill Perkins

3 key takeaways

1. Think about the whole game — It's possible to guesstimate when you will die. Insurance companies do it all the time. Doing this, along with looking at the seasons, helps you think about your life more holistically. It also enables you to make the most of your time when you realize how much you have left.

2. Decumulation — at some point, the net worth number has to go down instead of up. Typically between the ages of 45 and 60. Huge psychological shift

3. Seasons of life —Your life has different seasons, and some experiences are enjoyed more during certain seasons. Some experiences are locked out of specific seasons. Big life choices like marriage, parenthood, and retirement also define seasons.

5. Working Identity: Unconventional Strategies for Reinventing Your Career

By Herminia Ibarra

3 key takeaways

1. Your working identity is something that does not reside internally. Instead, you have multiple possible future selves. The only way to discover these selves is by performing experiments that involve interaction with others.

2. At first, you will have several small possibilities. As some of them grow, they will begin to push out other identities. This includes your current self.

3. Act your way into a new way of thinking and being. You cannot discover yourself by introspection.

6. Tempo: timing, tactics and strategy in narrative-driven decision-making

By Venkatesh Rao

1. Tempo — Has three elements: rhythm, emotion, and energy. It’s not about conveying speed. It’s about conveying emotion.

2. Rhythm — Decision-making, business development, and life all have different rhythms. Changing these tempos takes energy. Staying at one tempo for too long can lead to boredom.

1. Narrative rationality — every decision is telling part of your life story. Your life will have rising and falling action and liminal passages. Make the choices that tell the most interesting story.

If you have any other books on similar themes, I’d love to hear about them in the comments below. I have a big flight coming up, and I need to load up my Kindle.

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If you go forward 24 months from now, or some amount of time — I can't exactly predict where it is — it's possible that most developers are not coding
— Matt Gorman, CEO of AWS

Gorman’s prediction is extreme but directionally correct. I know AI is going to change my field. What will I be doing in two years? Five? Ten?

Here’s how I know there is truth to this:

AI is already changing coding

I use AI every day. It needs to be carefully prompted, questioned, and reviewed, but it’s a productivity increase. I’d estimate it’s a 15-20% improvement. Does this mean that a company could cut headcount by 15% at scale without sacrificing velocity? Depends on the developers.

Here’s why it won’t put developers out of work

Technological advancement doesn’t destroy jobs; it mutates them. We’re adding more abstraction. If you are an engineer and want to keep it that way, start cultivating skills at a higher level of abstraction, like product skills.

Here’s what Gorman got right:

Product thinking skills are valuable now and will appreciate with time.

"Coding is just kind of like the language that we talk to computers. It's not necessarily the skill in and of itself … It just means that each of us has to get more in tune with what our customers need and what the actual end thing is that we're going to try to go build, because that's going to be more and more of what the work is as opposed to sitting down and actually writing code

I’ve always believed in product thinking skills.

Instead of fretting about AI, spend that energy learning about usability, research, and business.

Knowing how to identify problems, clarify them, and develop solutions is an evergreen that will always be in demand.

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P.S. If you’re a dev who wants to level up their product skills, hit me up here, on LinkedIn, X, or email. I’m working on something you might be interested in. 😉

There’s no shortage of TikToks and travel blogs that talk booking first-class ticket to Bali for $17. These stories are often bullshit, and if they’re not, they require booking flights with lots of flexibility about where you go, when, and how long your layovers are. Booking these kinds of ‘rewards flights’ aren’t realistic for people who have spouses, kids, and jobs with limited PTO.

I’m a dad pushing 40. I use a credit card. I like to travel. I love playing games and exploiting systems and all these different points are alluring to me. There has to be something I can do, right?

Turns out there is. It’s not as exotic as what you might see online, but you generate a few thousand bucks in travel equity a year with a few high-leverage decisions and a dozen hours of work.

This is my anti-viral, made of words not videos, travel hacking guide for the rest of us.

In this article, I’ll share the primary credit card, hotel, and airline brand I use. I don’t claim this is the optimal approach; I’m sure that it isn’t. But it’s one that is simple and works for me.

(Disclaimer: I tried to include specific numbers whenever possible, but these values change frequently. Values are accurate as of the last time I updated this article, which is August 2, 2024. Depending on when you read this your (airline) mileage may vary.)

Why is travel hacking possible?

Taken at face value, travel hacking seems too good to be true. Why would airlines just give flights away? Aren’t they losing money? What about credit cards offering $500 signup bonuses to customers who never carry a balance or pay interest?

Airlines and hotels are in a unique position where they have liabilities on their books (empty seats and rooms) they can position as assets for the consumer (free vacation woohoo!). They dole these out via points based on frequency of travel.

I used to think credit card companies made most of their money on interest and fees. Turns out they make more on the interchange(the percentage cut they take on every transaction, typically around 3%). High spenders are where they make their money, even if they don’t carry a balance.

They attract these high spenders by offering them a cut of the interchange, either in the form of cashback or points.

Credit cards also make money on partnership deals with other merchants. Put all of this together, and you get credit cards programs with travel portals where you can book travel, and transfer partners where you can exchange credit card points for points at airline and hotel points.

If you want to read more about how all this works, I strongly recommend Patrick MacKenzie’s piece Anatomy of a credit cards rewards program.

However, I would recommend not thinking too hard about the fact that these companies are still making money off of you, even when you’re travelling for “free.” Travel hacking is more fun from an iconoclastic mindset, and believing that you putting one over on major banks and airlines. I’m still sticking it to the man while I drink my piña colada on the beach, right? right?

In short, that’s the game here: pick a credit card, pick a preferred airline, pick a preferred hotel chain. Rack up the optimal amount of points on each, then exchange them to reduce the cost of trips you want to take.

Preferred credit card vendor: Chase

Many credit cards offer a signup bonus in the form of “if you spend X dollars in the Y months, we will give you some points.” These offers are your primary source of accuing value.

My current primary card is the Chase Sapphire Reserve1 card, though I use multiple cards in the Chase ecosystem. It has an annual fee of $550/year + $75 per authorized user, and it's well worth the cost. Signup bonus: 60,000 points have a rought “value” of for $4,000 of purchases in the first three months. Chase points are worth 1 cent2, so you could think of it as a $600 signup bonus.

Every year, you get a $300 travel credit and a 1.5x multiplier on points exchanged for travel(so that $600 bonus could be worth $750), among other benefits, such as access to airport lounges via Priority Pass. I will leave the valuation of free time-unbounded airport beer and mid food as an exercise for the reader.

Many people balk at the high annual fee, but if you’re using all the benefits, it pays for itself.

Other types of Chase cards will also earn ultimate rewards points and have a $0 annual fee.

1. Chase Freedom Unlimited - $0 Fee and 0% APR for 15 months. Useful if you want a card with no fee to earn ultimate rewards points. Chase actually two kinds of points, and you want to avoid the much less value Amazon rewards points.

2. Chase Sapphire Preferred—$95 fee, 1.25x travel multiplier. Also offers 60,000 points for $4,000 spending in the first 3 months. This is a cheaper alternative to the preferred with fewer rewards, but you can use both bonuses if you like (within Chase’s limitations; see below).

3. Chase Ink (business unlimited or business cash) —$0 fee, 75,000 points if you spend $6,000 in the first 6 months. Unlike other cards, there is no rule against holding multiple Chase Ink cards, and they don’t count against your 5/24 limit. They are for "business," but you can use an SSN and get one as a "sole proprietor.” One new card every quarter seems to be the safe spot.3

You can transfer points between cards and between household members, but you will need to call customer support to do the latter. You can get the 1.5x multiplier on all Ultimate rewards points, regardless of which card earned you the points. If you get 2 Chase cards, that's 150,000 points. With the Sapphire reserve multiplier and travel credit, that’s $2,550 in free travel bucks right there.

The biggest controllable factors for points accquisition is the number of signup bonuses you're willing to churn through and how frequently you’re willing to go update all of your payment settings.

How many credit cards can you open?

It depends. You should be aware of the 5/24 rule—if you open more than 5 personal credit cards from any issuer in 24 months, Chase will not let you open new cards. Opening 2 cards in a 30-day period could also get you flagged. Generally, one credit card every 4-5 months is safe.

These rules apply to individuals, not households. You and your spouse can double-dip and even send each other referral links.

Tips for managing multiple credit cards

1. Keep a spreadsheet of when you open every rewards card and when they expire. Set reminders to cancel credit cards with annual fees you don’t want to keep. I try to only have one annual fee active at a time.

2. Make a spreadsheet of every recurring bill you have and every online merchant you frequent, with links to their payment pages. This will make it easier to switch cards.

Games you can play with cash flow

1. This should go without saying, but don’t spend extra “for the points.” That’s how you lose this game.

2. If you have a large ($2,000+) purchase coming up, that’s a good time to open up a new card so you can get through the bonus quickly. You probably aren’t paying for 100% of your travel this way, so booking a trip can be a quick way to jump-start this process.

3. Time spending with opening new cards. Hold off on optional purchases for a few weeks, then make them all at once when you open a new card.

4. If you are approaching the end of a bonus’s time limit, buy gift cards for recurring spending you would make anyway, such as groceries and gas.

Preferred Airline: Southwest

Two free checked bags, CrowdStrike immunity, what’s not to love?

Southwest is a travel rewards partner with Chase, so you can transfer points 1:1 from Chase to Southwest.

I will say airlines are the place I’m the least picky. I will happily fly Delta or American4 if it means one less layover or a more convenient departure times. Another part of travel hacking is deciding how you want to balance quality of the journey vs. price.

Flight booking tips

1. I use the ITA Matrix search to compare flights.

2. Always have a frequent flyer number with every airline you fly with. Use it with business travel if your company allows.

3. If you have a child, be sure to set up an email address and frequent flyer number for them as well.

4. Always check the point cost of booking through Southwest direct and the Chase travel portal. You never know which one will be cheaper.

5. Do not buy points from Southwest. They have one of the worst rates, charging you 2-3 cents per point, and redeeming them at 1.

Preferred Hotel Chain: Hyatt

Hyatt has decent coverage, is a travel partner with Chase, and is the key to getting maximum value for your points.

Firstly, Hyatt values points at roughly 2 cents compared to Chase’s 1 cent, but you can transfer them 1:1.

Secondly, unlike airlines, which use an inscrutable calculus to determine point values for flights, Hyatt has a fixed system.

Here’s an example: As of this writing, I found a room at the Andaz Maui at Wailea Resort for $871 dollars/night, or 40,000 points. That means if you followed the Chase steps outlined above, you could have 3 nights in a Hawaiian resort for free.

• 40,000 points exchanged for cashback = $400, 1 cent per point

• 40,000 points spent in travel portal = $600, 1.5 cents per point

• 40,000 points on Hyatt resort = $871, 2.1 cents per point

If that sounds interesting, Hyatt also has its own rewards cards, which are good for another 60,000 Hyatt points5.

Booking hotel tips

1. I like TripAdvisor or the native Hyatt app for finding hotels, but I always book through Chase Travel (if spending points) or through Hyatt directly (if spending cash).

2. Hyatt will sell you points for 2.4 cents each. It might make sense to buy them if you trying to book a higher-end resort.

3. I like resorts, so I try to refrain from cashing in points on regular hotel stays and save them for nicer places.

What if I prefer staying in AirBnBs or short-term rentals?

Pay cash, sorry.

Preferred tertiary travel booking: Costco

Costco travel is legit, y’all.

There are no points games to be played here, but you can find good rates on hotels, vacation properties, and sometimes flights, especially if you get a package deal. If you have an executive membership, you’ll earn 2% cashback on bookings. Many will include a gift card as well, so it still feels travel-hacky.

Take the package below; it costs $3,197, but once you factor in the gift card and the 2% back, it’s effectively $3,0216.

If you have an executive membership, I’d give it a look when exploring trip ideas.

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Other things I don’t do that are also probably pretty good

There are only two credit card companies that are competitive with travel rewards, the other one being American Express. I haven’t messed with them, but they did just build the biggest Centurion lounge in Atlanta, so maybe I’ll try them in the future.

Hilton has a similar fixed point system to Hyatt, along with their own rewards cards.

Based on your nearby airlines and travel preferences, maybe those are interesting to you. But I haven’t tried them, so I can’t describe how well they work. However, the same general strategies outlined above should still apply.

Summary

In short, you find credit cards you like, chrun some offers, get some points, move ‘em around, save a few thousand bucks. Pretend you put one over on multiple mega corporations even though they made their money on interchange and in-flight beverages. Have fun! If this was helpful, I’d love to hear about it. tell me about your trip!

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