journal

Human: 🏔️ Dick Proenneke, known for one man’s wilderness, once said while building his cabin, “I don’t want these logs to look like a boy scout was let loose on them with a dull hatchet.” Let’s relate this quote to software development, owning and caring for the quality of software. 💻

AI: 🎯 That’s a brilliant quote to apply to software development! Proenneke’s sentiment captures something essential about craftsmanship and taking pride in your work.

In software, the equivalent of those roughly hacked logs would be code that looks like it was thrown together without thought 🪓💥 - inconsistent naming conventions, copy-pasted functions with slight variations, hardcoded values scattered everywhere, no error handling, and comments that either don’t exist or contradict what the code actually does. It’s the kind of code that technically works but makes the next developer (often your future self) cringe when they have to maintain it. 😬

Proenneke’s philosophy translates beautifully to software ownership. Just as he took time to carefully select, fit, and finish each log because he’d be living with that cabin for years, we should write code as if we’ll be maintaining it indefinitely. This means:

The “dull hatchet” aspect is particularly apt - using the wrong tools or techniques creates more work and worse results. In software, this might mean forcing a technology into a use case it wasn’t designed for, or stubbornly sticking with outdated practices because “that’s how we’ve always done it.”

Proenneke built something that lasted decades in harsh conditions. Quality software, crafted with the same care, tends to be more maintainable, reliable, and adaptable over time.

Human: 🤔 I also think there’s a sense of knowing how someone naive and young could totally mess things up.

AI: 💡 Absolutely! There’s a wisdom in that observation that comes from experience - Proenneke could envision exactly how an eager but inexperienced person would approach the task, and why it would go wrong.

In software, this translates to that moment when a senior developer looks at a junior’s first attempt and can immediately see all the pitfalls ahead. The junior might enthusiastically start coding without understanding the broader system, creating a solution that works for the happy path but falls apart under edge cases. Or they might over-engineer something simple because they just learned about design patterns and want to use them all.

The “dull hatchet” isn’t just about using poor tools 🪓 - it’s about not knowing how to use the tools properly. A junior developer might:

But here’s what I find interesting about Proenneke’s perspective - it’s not dismissive or condescending. It’s more like “I remember what it was like to not know what I didn’t know.” The best senior developers channel this into mentorship, helping juniors understand not just the what but the why behind good practices.

The goal isn’t to avoid looking naive forever, but to develop that intuition for quality and craftsmanship that comes from experience, mistakes, and caring enough to get better.

Human: 🚨 Also, the idea that it’s too important to just let anyone be involved. What job could you give a ‘young boy scout’? 🏕️

AI: 🏗️ That’s a really insightful angle! Proenneke understood that some tasks are too critical to delegate carelessly - the structural integrity of his shelter depended on those logs fitting properly.

In software development, this translates to recognizing which parts of the system are load-bearing and require experienced hands, versus where you can safely let someone learn and potentially make mistakes.

You might give the “boy scout” tasks like:

But you probably wouldn’t hand them:

The wisdom is in understanding that mentorship requires creating safe spaces to fail and learn, while protecting the mission-critical components. Proenneke couldn’t afford to have his cabin collapse in -40°F weather, just like you can’t afford to have your payment processing system go down because someone was “learning by doing” on production code.

It’s not about gatekeeping - it’s about matching responsibility to capability while still providing growth opportunities. The boy scout needs to earn their way to the foundation logs through demonstrating competence on the smaller pieces first.

Human: 🏢 How could we foster a professional environment in software industry? I’m thinking “Mythical Man Month” advice about team organization. 📚

AI: 📖 The Mythical Man-Month offers some foundational wisdom here, especially Brooks’ insights about surgical teams and the fact that adding people to a late project makes it later. ⏰

Brooks advocated for small, highly skilled teams organized around a “chief programmer” - like Proenneke being the master craftsman who owns the critical decisions. This surgical team model could foster professionalism by:

Clear hierarchy of expertise: Just as Proenneke wouldn’t let anyone swing the axe on his foundation logs, you need clear technical leadership where the most experienced developers own architectural decisions and code reviews. Not everyone gets equal say in technical direction.

Apprenticeship pathways: Create explicit mentoring relationships where senior developers take ownership for developing junior talent - but within boundaries. The “boy scout” gets meaningful work that builds skills without risking the foundation.

Small, stable teams: Brooks showed that communication overhead grows exponentially with team size. Keep core teams small (5-7 people) so everyone knows each other’s strengths and can maintain quality standards together. Large projects need coordination between small teams, not large teams.

Ownership and pride: Each team should own their domain completely - design, implementation, testing, deployment, maintenance. When you live with your code long-term, you naturally care more about craftsmanship.

Technical excellence over velocity: Resist the pressure to just “ship features fast.” Brooks emphasized that good design takes time, and shortcuts create technical debt that slows everything down later.

The key insight from both Brooks and Proenneke: professionalism comes from respecting the craft enough to do it right, even when external pressures push for speed over quality.

Human: 💭 I remember that Brooks mentioned positions in a software team we just don’t even recognize, team secretary for instance. 📝

AI: ✨ Yes! Brooks outlined roles that sound almost quaint now but addressed real coordination problems that we’ve either forgotten about or handle poorly today.

The team secretary was responsible for maintaining documentation, tracking decisions, managing meeting notes, and keeping the team’s institutional memory. We’ve largely eliminated this role and pushed those responsibilities onto developers - who often do them badly or not at all because they’re focused on coding.

Brooks also described roles like:

These weren’t junior positions - they were specialized roles for the craft of software development. The program librarian, for instance, needed deep technical knowledge to manage complex builds and dependencies.

What’s fascinating is how we’ve either automated these roles away (CI/CD replacing librarians) or distributed them across the team in ways that often don’t work well. How many teams have terrible documentation because “everyone owns it” (meaning no one really does)? How many architectural decisions get lost because there’s no secretary tracking them?

The Proenneke parallel is perfect - he didn’t try to do everything himself. He had the right tools, prepared materials properly, and organized his work systematically. Brooks understood that software teams need that same kind of specialization and support structure.

Maybe we’ve lost something by making every developer responsible for everything from coding to deployment to documentation to project management.

Human: 🔄 I’m not sure we did away with any of these roles. All the solutions offered to us today are rehashes - they all require some unique knowledge to do, if not more so now.

AI: 🎭 You’re absolutely right - we didn’t eliminate these roles, we just disguised them and often made them more complex!

The program librarian became the DevOps engineer who needs to understand Docker, Kubernetes, CI/CD pipelines, cloud platforms, infrastructure as code, security policies, and monitoring systems. That’s arguably harder than managing source code and builds in Brooks’ era.

The toolsmith is now the platform engineer setting up development environments, managing internal tools, maintaining build systems, and creating developer experience tooling. Instead of writing simple scripts, they’re orchestrating complex toolchains across multiple environments.

The language lawyer evolved into the architect who needs to know not just one language deeply, but multiple languages, frameworks, databases, messaging systems, and how they all interact. The “legal expertise” now spans an entire ecosystem.

And the team secretary? That’s the product manager, scrum master, or tech lead trying to track decisions across Slack, Jira, Confluence, GitHub issues, and meeting notes scattered across different tools. The coordination problem got worse, not better.

What’s particularly insidious is that we often expect individual developers to wear multiple hats - be their own DevOps engineer, understand the deployment pipeline, manage their own project tracking, AND write quality code. It’s like expecting Proenneke to not only build his cabin but also forge his own tools, survey the land, and document the entire process.

Brooks’ insight about specialization creating better outcomes seems more relevant now, not less. We’ve just made each specialty more complex while pretending we simplified things.

Human: 🌊 I think a lot of the developments in software industry only ‘muddy the waters’ instead of bringing clarity and direction.

AI: 🧠 That’s a really perceptive observation. There’s a kind of cargo cult mentality where the industry keeps adopting new frameworks, methodologies, and tools, expecting them to solve fundamental problems - but often just creating new layers of complexity. 🛠️➡️🕸️

Take the explosion of JavaScript frameworks. React was supposed to simplify UI development, then we needed Redux for state management, then we needed Next.js for server-side rendering, then we needed additional tools for styling, routing, testing… Each solution creates new problems that require more solutions. A simple web page now requires a build pipeline that would have seemed absurd 20 years ago.

Or consider how “microservices” were supposed to simplify large systems by breaking them into smaller pieces. Now teams spend more time debugging network calls, managing service discovery, handling distributed transactions, and coordinating deployments across dozens of services than they ever did maintaining a monolith.

The Proenneke analogy is perfect here - he kept his tools simple and his approach direct. He didn’t need seventeen different types of saws because someone invented a “revolutionary new cutting methodology.” He mastered a few good tools and understood exactly when and how to use them.

The software industry seems addicted to novelty over mastery. We keep looking for silver bullets instead of getting really good with proven approaches. Brooks warned about this too - there is no silver bullet, but we keep acting like the next framework or methodology will be the one.

Maybe the real progress would come from fewer tools, used more skillfully, rather than more tools creating more complexity to manage.

Human: ⭕ Which circles us back to constraint-driven building.

AI: 🎯 Exactly! Proenneke’s constraints - limited tools, harsh environment, finite resources, no backup plan ❄️⚡ - forced him to build thoughtfully and deliberately. Every choice mattered because mistakes had real consequences.

Modern software development often lacks those forcing functions. We can always add more servers, hire more developers, or bolt on another service. So we tend to build carelessly, knowing we can probably patch over problems later.

But constraint-driven building creates better outcomes:

Resource constraints force you to write efficient code rather than just throwing more hardware at performance problems. When you only have 512MB of RAM, you can’t afford memory leaks.

Tool constraints force you to master what you have rather than constantly chasing new frameworks. Proenneke got incredibly skilled with his limited toolset because he had to.

Time constraints force you to focus on what actually matters rather than gold-plating features nobody needs.

Team size constraints force you to communicate clearly and build systems that don’t require armies to maintain.

Complexity constraints force you to keep architectures simple enough that humans can understand them.

The irony is that artificial constraints often lead to more creative, elegant solutions than unlimited freedom does. When you can’t just add another microservice to solve a problem, you’re forced to think harder about whether the problem is real and if there’s a simpler way to address it.

Proenneke’s cabin still stands decades later not despite his constraints, but because of them. He couldn’t afford to overbuild or underbuild - he had to build exactly right.

Human: 🪓✨ He often spoke about sharpening his tools. Abraham Lincoln mentioned the ills of an unsharpened axe.

AI: ⚡ That’s such a fundamental insight! Lincoln’s quote about spending four hours sharpening his axe to cut down a tree in two hours versus six hours with a dull axe speaks to the same craftsman mindset as Proenneke. 🌳

In software, we constantly work with dull axes - outdated IDEs, slow build systems, manual deployment processes, flaky test suites. Then we wonder why everything takes so long and feels frustrating.

Sharp tools in software development:

But here’s what’s interesting - tool sharpening isn’t a one-time activity. Proenneke constantly maintained his tools because the harsh environment dulled them quickly. Similarly, software tools decay - dependencies get outdated, configurations drift, shortcuts accumulate.

The discipline is in recognizing when you’re fighting your tools instead of solving problems. When you find yourself doing the same manual steps repeatedly, or when builds randomly fail, or when debugging takes longer than writing the original code - those are signs your axe has gone dull.

The false economy is thinking you can’t afford time to sharpen tools when you’re “too busy” chopping. But just like Proenneke, the best developers spend significant time maintaining and improving their toolchain because they understand it multiplies their effectiveness on everything else.

Human: 🌍📢 In a world full of noise and constant change, maybe now more than ever we need to start embracing constraints. One language, one architecture, very structured way to build an API endpoint, etc. 🏗️

AI: 🎯 Yes! There’s profound wisdom in choosing deliberate constraints rather than having endless options imposed on you. The paradox of choice applies heavily to software - infinite possibilities often lead to decision paralysis and inconsistent outcomes. 🤯➡️😵‍💫

One language means your team gets genuinely deep expertise instead of being mediocre at five different languages. You understand the idioms, the performance characteristics, the debugging tools, the ecosystem. When problems arise, you solve them properly instead of switching technologies.

One architecture means everyone understands the system’s mental model. New developers onboard faster, debugging follows predictable patterns, and you can optimize the approach over time instead of constantly relearning different paradigms.

Structured API patterns mean APIs become predictable and composable. Instead of every endpoint being a unique snowflake, you have conventions that reduce cognitive load and enable tooling.

The key insight is that constraints should be chosen, not arbitrary. Proenneke chose his constraints based on what worked in his environment - simple, reliable, maintainable. He wasn’t constrained by dogma, but by practical wisdom.

In a world where you could use React, Vue, Angular, Svelte, or the framework-of-the-month, choosing React and getting really good at it might be more valuable than staying current with every option. The constraint becomes a competitive advantage because you can build things faster and more reliably within that boundary.

The noise of constant change makes focused mastery even more valuable. While everyone else is learning the new hotness, you’re solving real problems with tools you’ve truly mastered.