JB

In 2018 I wrote “A New macOS”, since then every new macOS version that comes out, I reference the post to see how close they’ve come to meeting my imaginary ideal. It’s been over eight years now, so I thought it’d be good to see where I stand on my original requests, and how well the Mac is doing at it’s core job of managing information.

My original post made four requests:

• Raise relevant information associated with the currently selected item in a new view in the “Today View” swipe-over sidebar.
• True system-wide tags, so tags in Finder, Mail, Reminders, Notes, Calendar, etc… that are all from the same source.
• Rule-based file actions à la Hazel.
• End-to-end encryption for iCloud.

Of those, only end-to-end encryption in iCloud (via Advanced Data Protection) has actually been implemented. Nothing else has been looked at sideways. Instead we’ve got:

Mojave

• Dark wallpaper in dark mode
• Desktop stacks
• Dynamic Desktop

Catalina

• Replaced iTunes with separate apps
• Redesigned Reminders
• Redesigned Books
• New Find My app
• Sidecar for using an iPad as a second screen
• Removed Dashboard

Big Sur

• ARM support
• New icons
• UI Redesign
• Rosetta 2

Monterey

• Universal Control (control two Macs with one keyboard and mouse)
• AirPlay
• Shortcuts app (Nice, but limited. Not nearly as powerful as Keyboard Maestro)

Ventura

• Stage Manager (what the heck?)
• Redesigned Settings app (for the worse)
• Continuity Camera
• Handoff

Sonoma

• Redesigned Widgets
• Redesigned lock screen
• Video wallpaper/screensaver feature (actually pretty cool)

Sequoia

• Apple Intelligence (lol)
• iPhone Mirroring
• Passwords App (well done.)

Tahoe

• Liquid Glass
• Updated Spotlight (very nice)
• More Shortcuts capability
• Image Playground (ugh…)
• New Phone app
• New Games app

Reference: Wikipedia

There were obviously lots of smaller updates to the OS over the years, but I’ve highlighted what Apple highlighted. From what I can see, Apple has focused more on what macOS looks like than what it can actually do. And when they do take a look at upgrading what it can do, it’s for ridiculous AI garbage like Image Playground. Maybe that’s too uncharitable. They have done fantastic work on Notes, Reminders, and Shortcuts, and the improvements to Spotlight have made my day to day working life better.

From the outside, it seems like Apple doesn’t have a coherent vision for where they want the overall operating system to go. They’ve been putting engineering effort into making sure everyone’s icons are squished into a squircle, but haven’t given a thought to consolidating tags system wide. We can make a custom emoji in Messages, but we can’t associate a file in Finder with an email in Mail and a task in Reminders.

People use the Mac for work, every day. Yes, sure, they also use it to watch movies, keep in touch, and browse the web. But the Mac can add the features I’m talking about without interfering at all with those day to day, home computer tasks. If Apple spent less time trying to use AI to organize my Safari tabs and more time looking into ways to make the system better at managing the information we trust to it, the Mac would be a better, more useful, machine overall.

Revisiting the Request

So, here’s what I’m looking for every summer when the new macOS is released. I have thousands of files, some I’ve created myself, some I’ve scanned, and some I’ve saved off the web. I have thousands of emails going back decades, hundreds of notes, lots of Calendar events, etc, etc… how is Apple going to help me make sense of all this? How are they going to use the privileged access they have to all my personal information to help me organize my work and my life?

If the answer is “yet another redesign!”, my response is a deeper sigh with every revision.

There should be one single source of tags in the system, probably in System Settings, that apply to all first-party applications. Also in System Settings, there should be a way to set rules for new and existing information contained in the OS and first-party applications. Not some ‘AI-eNhaNcEd’ malarky, but a set of deterministic rules that let me say “when this event happens, do that, that, and then that”. For example, if I set create a new Task that says “create a project” and tag it with a project name, create a new Note with that tag, a new Folder with that tag in my Projects directory, and a new Smart Folder in Mail searching for that tag. That’s just off the top of my head, but it should be trivial for macOS to be able to do that, assuming the centralized tag repository described above.

Then, macOS could use that consolidated information, along with the existing Spotlight search index and, sure, even Siri’s AI, to show a list of documents that are associated with whatever I happen to have selected. If I have a task selected, it could show associated Calendar events, Emails, Notes, and Files that are relevant, maybe sorted by confidence in how closely they match. That list doesn’t have to be visible all the time, but the Today View would be a great place for it to live. Select a file, swipe left on the trackpad, see a list of related items.

A Concession

Admittedly, this is most likely a pipe dream. Even though it makes sense, even though it’d make the OS better, even though there’s clear reasoning, I don’t think Apple will do anything I’ve outlined above. There would need to be significant engineering effort into tying all the apps together, and it would be difficult to open the system up to third parties. Not to mention what happens to the tags and other data on iPhone or iPad? My answer is that I don’t actually care, since I don’t use an iPad and my phone is not used for work. My focus is on the Mac, which is why I can have this daydream to begin with.

After eight years, I’m not expecting anything spectacular from Apple anymore. Not when it comes to macOS. I suppose I should be happy when they just don’t make anything worse year over year.

Maybe I should look closer at Shortcuts.

I’ve written before about getting my start in the tech industry, and my experience with security since. What I haven’t written about is my experience with the “Certified Information Systems Security Professional”, or CISSP, certification, and what it means to me. This is a story 25 years in the telling.

It’s only fair to acknowledge that 25 years ago I was a stupid young guy in his early 20’s with the responsibility of a young family and the immaturity of a college kid. I also thought I was much more clever than I actually was. Looking back on that guy now all I can say is that I had a lot to learn. So, if anyone who knew me back then sees this post at some point, well, I have indeed learned a lot. Some lessons were very hard indeed.

One thing that guy had on his desk back then is a massive three-inch book titled the “CISSP Study Guide”. Our boss, Senior, had said that it was the only certification that he thought was worthwhile. It was also the only certification that none of us at the time could get, because one of the requirements for it then was, and remains now, that you must have five-years of security experience before you can be certified. But I was cocky and figured I could get it soon as I had the experience.

Time went on, I’d page through the book sometimes. We moved, I got out of the military and we moved again, I brought that book with me and it sat on the shelf. I did continue to work in both security and sysadmin, and later programming and devops, but my aspirations for passing the exam went by the wayside. It was hard, I mean hard, and expensive. So it was a gamble that I never felt confident enough to take. Eventually, I think the book was sold to a second-hand bookstore. I don’t have it anymore.

But then there was AI. ChatGPT, Claude, and the like turned the tech industry on its head, and it doesn’t look like there’s any going back. The genie is out of the bottle. I’ve been watching as thousands of jobs have been lost in the tech industry over the past few years. Some of that’s due to over-hiring during COVID, some of it’s due to economic pressure, and some of it is at least claimed to be due to “efficiencies” from AI. So, I saw a confluence of pressures pointing towards security being a safe bet.

For one, I’m an old-school sysadmin at heart. And the number one rule of being a sysadmin is “always have a backup”. I feel very confident in my current position, and I’m optimistic about the future of the company. However, that doesn’t mean that I don’t also need to prepare for things taking an unexpected turn.

Secondly, I’m turning 50 this year, and regardless of what should be, ageism is a very real thing in the tech industry. I’m still looking at 10-15 years of work ahead of me before I retire, so I wanted to make sure that whatever direction I went in would be far enough removed from dev work that age wouldn’t be an issue, and close enough to it that my decades of experience would make a difference. I’m an engineering manager now, of a very small (but awesome!) team. I think that’s a pretty good place for me, all in all, but if worse came to worse, could I rely on only my experience as an engineering manager to get me to whatever comes next? I didn’t feel quite comfortable yet.

So, I started thinking about my security experience again. I realized that a significant number of deployed applications were built using AI. Some developers even claimed that they didn’t even look at the code anymore, just let the robot deploy to production. Between using AI to both find security holes and create them, it seemed like a good idea to be right in the middle.

So, about six months ago, I sat down with my wife and explained my reasoning. We looked at the signup page for the CISSP exam, pondered the $750 price tag, discussed the commitment in time that I’d be signing up for, and decided to go for it.

I initially thought I’d only need three months to study. Every morning I’d load up the Udemy course I’d signed up for, watch the lecture, and take notes by hand in my notebook. I went through the entire course, and started taking all of the practice exams. As the date grew nearer, I got more and more uncertain that I was ready. So, I made a call and pushed the date back another three months, to July 9th.

I continued to study, though not as often. I spent many mornings taking practice exams, and many nights after dinner transcribing my notes from hand into the computer. When I got a question wrong in the practice exam I’d write the question and answer down on a notecard. I learned a lot. The place of policy in an organization, how to think about risk management, how to prioritize work in different environments, and how to accept risk when the cost of the system being attacked is less than the cost of protecting it. The CISSP requires a deeply technical background with a lot of breadth. That background is necessary, but not sufficient. The CISSP requires you to change the way you think, more like a manager, less like a technician.

The day of the test finally came. I made my way to the Pierson testing center in Des Moines, and was cleared by their security to go in the room to take the test. The process to enter the room was surprisingly thorough. I had to provide two forms of ID, get my picture taken, rather unflatteringly, and get both palms scanned. I had to take everything out of my pockets and put what I had in a locker which they gave me the key to. Finally, I got scanned three times by different wands, looking for metal, video, or any signals being sent out. Finally I was able to sit down for the test.

After the first five questions I was certain that I had made a mistake. The questions all seemed to have no good answers, or all good answers, or two answers that were entirely equal in possibility. I felt my pulse rise. After the first 15 or so I got into the rhythm and started ignoring every previous question and focusing entirely on the one in front of me. When I answered a question I moved on, no looking back, no second guessing. When I hit question 85 I started wondering how many questions past 100 I was going to have to go.

The test is meant to be between 100 and 150 questions in an adaptive format, so if you get too many wrong in a particular domain it will ask you more questions in that domain. Also, if you didn’t get to the 75% correct needed to pass in the first 100 questions, you got more chances up until 150 questions or till it’s mathematically impossible. I answered the 100th question and, instead of the computer telling me I passed, it just kicked me over to a survey asking me what I thought of the test, where I took the test, and what studying was like.

My heart fell. I thought for sure I had failed at 100 questions. The proctor saw that I was done, escorted me out of the testing room, and started printing papers at the front desk. Finally, she handed me a printout. It said “Congratulations!” After 25 years of thinking about this exam, this certification, I’d finally passed.

I don’t know where this will take me. I know that right now, and probably for the next few years at least, I have no plans to leave my current job. I’m an engineering manager in charge of the cloud infrastructure at the TARA Group and it’s a fantastic place to work. I’ve got a great team, we’re part of a great team, and there’s certainly no lack of work to be done. But, like I said, I’ve always got to have a backup, and the CISSP can only help, no matter what the future brings.

More importantly, I feel like I’ve finally closed a loop that’s been open for a very, very long time.

The last lines of the poem “The Summer Day” by Mary Oliver go: “Tell me, what is it you plan to do with your one wild and precious life?”. I’m honestly not one for poetry most times, but that one hit me like a brick the first time I read it. The phrase has lived in the back of my mind since.

I’ve been thinking about the poem the past few days as I’ve been reading through various remembrances of Om Malik, the writer, photographer, entrepreneur, investor, and for many years, the inner voice of Silicon Valley. I didn’t know Om personally, my connection to him came from my early years of writing at the now defunct “The Apple Blog”. Om passed away from heart issues at 60, far too young. John Gruber knew him well, because of course John knows everyone, and when referencing Matt Mullenweg’s mention of Om’s appreciation of care and attention to detail he said:

If you’re going to get into something, you ought to pursue it to its full extent. If you’re not interested enough to do that, don’t bother getting into it. Find the few things you love; don’t waste your time on the many things you merely like.

I try to remind younger folks, especially those going through tough times that life is long, and when you’re young there’s so much time ahead of you that it’s important not to get too wound up about the immediate future. School, college, that summer job you don’t like… these things are all temporary and will be just a blip on the long timeline of life. But time is relative of course, and it goes faster the older you get. Life is long when you are young, but it’s far too short when you get old. What will you spend those precious seconds on?

What I’ve found, and what I think John is referencing here, is that a person will get far more satisfaction out of their work or their hobby if they can put their entire self in and get lost in it. Think about the last time you were so focused on a task that you had no recollection of the time passing. This is where the best work is done, and this is where a person can be the best version of themselves. From the outside it can look like obsession, maybe it is. Maybe it becomes that. Absolute focus is the demand of craft. That focus on the task is what makes paying for it with the time required worth it.

It really doesn’t matter what the task is. It only matters that you put your entire mind to work doing it. You could be a developer, a blacksmith, or a janitor. A mechanic, a systems administrator, a barista, an accountant, or a project manager… doesn’t matter. I once read about a company in Japan that made brooms, and that company employed a person who attached every bristle into the broom head by hand. To do that, day after day, sounds like obsession, but it’s also a person perfecting their craft.

I’m not saying that everything a person does should be perfect. On the path to expertise one will do many, many, many things wrong. Mistakes are made, things are forgotten, that plan you thought would work out great went poorly. Perfection for every task is not the goal, the goal is to complete every task with intention. Sometimes the best of what we can do right now isn’t good enough. That’s ok. Learn from it, remember it, and keep going.

What I am saying is that everyone’s life will be improved if more of us take the time to care. I began writing this thinking I’d agree entirely with John’s quote above, but that’s only part of it. John is talking about pursuing a hobby, and in that I do completely agree. But I also want to go farther, and say that whatever tasks you have in your life do them with care and attention to detail.

I’m currently in the middle of several projects, both at home and at work. My garage has been a mess for weeks as I’ve been doing some landscaping around the house. I finally started cleaning it up yesterday, but it’s got a long ways to go till I’m actually happy with it. Cleaning a garage doesn’t sound like the kind of thing where care and attention to detail would be required, but I’d argue that it’s exactly the kind of ordinary work where craftsmanship becomes a habit. Like mowing the lawn and then blowing the cut grass off the sidewalk and driveway. Little details matter.

Finding a home for everything worth keeping in my garage is difficult, and requires thinking through if the object is still good, if it still serves a purpose for me, and the manner in which I will use it in the future. Sometimes though, when I’m not paying attention, things just get swept into a plastic tote or some drawer. The next time I open that drawer and see a hodgepodge of junk, I’m reminded that there’s still work to do. Cleaning my garage can take hours, but it’s time well spent because it will be easier to work on other projects later, and it feels good to have spent the time on something worthwhile. Better than staring mindlessly at the TV, or doom scrolling through Instagram.

We live in a world of things and software, how many of those things are built by people committed to craftsmanship? I’d like to see more people care about more of the things they do. What we spend our precious time on matters, and while we may not always be able to define what occupies our day, we can always define how we will approach the work that needs done.

I have a vision of the future that I just can’t shake. It’s shaped my politics and many of the choices that I’ve made. It’s a vision of human experience over corporate profits, a vision of abundance and community. It’s a vision that, sadly, feels farther and farther away, but not yet entirely out of reach. When the future is continuously portrayed as something negative, like The Matrix, Blade Runner, or Fury Road, it can be hard to imagine something better. Something positive. But to build the future, we first must imagine the future. Iowa is a mid-sized Midwestern state, but still similar in size to several European nations. There’s a lot we could do as a state. So, allow me a small indulgence and join me in this daydream of how things could be.

Imagine living in a small Iowa farming town, but it’s not run down and falling apart… it’s vibrant, alive. Imagine walking down to a local railway station, a beautiful, clean, and modern building next to the city square. Inside you’d stop at a coffee shop run by a friend’s daughter for coffee and a pastry, before riding the train to Des Moines, or Ames, or Iowa City in minutes. Imagine looking out the window at the farmland as it passes by, not growing corn for ethanol, but diverse crops of actual, real food. There’s still plenty of sweet corn, of course, we just aren’t growing corn to burn anymore. The smaller farms employ more people, and switching to food production has revitalized the traditional family farm.

You wouldn’t only see the food-growing farms as you pass by; you’d see wind farms as well, generating the clean energy that the state now runs off of. As you pass through the suburbs on the way to the city center, you’d see green lawns and solar panels on every roof, each home generating the electricity it needs and trading the excess to the grid. The transition to clean energy and sustainable farming has cleaned the air and the water; Iowa now has some of the cleanest water in the country, no more worrying about nitrates or other cancer-causing chemicals when you want to fish or swim.

When you arrive in the city you either walk, ride a bike, or rent a scooter to your studio. Your work in engineering is in great demand, balancing the economic boom from investments in renewable energy and railways with making the best environmental decisions for everyone. You spend the day engrossed in your work, breaking for lunch at noon, and heading home around four. You pass by thousands of workers who are also working in the clean energy industry, building, maintaining, or managing solar panels, wind turbines, and train components. Iowa’s history of manufacturing and culture of building and making dovetailed nicely with the demands of clean energy that’s not reliant on international suppliers.

You hop on the train and, in 20 minutes or so, get off in your town and walk to the local grocery coop to pick up some fresh produce and dairy for dinner. Passing by the local brewery you think about stopping by later tonight to meet up with friends, but for now dip into the bakery for a loaf of fresh sourdough. Instead of carrying all that home, you borrow one of the city bikes and put your groceries in the basket; they know you’ll ride it back tomorrow. When you get home, your house senses that you’ve arrived and turns on the appropriate lights, opens the windows, and greets you as you walk in the door.

When I envision the future I think about jobs in clean energy, farmland that grows actual food, and a sustainable way of life that doesn’t actively destroy the world we live in. How can anyone argue against a life where everyone benefits? I can understand being skeptical, but I invite you to imagine with me. If you think the best we will ever be as a society is in the past, what hope is there for the future? I think we all want to live well, to feel safe, to be hopeful. There’s a way forward, but we have to choose to go there together, none of us can make the world on our own.

I’ve been reading about, listening to discussions about, and exploring AI tools myself more and more over the past few weeks. While I still don’t think that my assertions were necessarily wrong, I can’t deny the effect the tools are having now and will have on the industry in the future. The conclusion I’ve come to so far is 1. the tools are not going away anytime soon. 2. there’s a very good chance that software development and devops will be forever changed by these tools. 3. If you’re planning on staying in this industry for the foreseeable future, this is one of those waves you either ride or get rolled over by.

I don’t like it, and I still think that craftsmanship, technical knowledge, and ability are extremely important. However, consider what’s being built right now, tools like a software factory by StrongDM where software is being churned out without human interaction at all. If the AI/LLM tools continue to advance and get better, where does this lead in 5 years? In 10? Will all software just be a prompt away? Will we be able to define custom software solutions for each individual or organization with a well designed prompt?

Most organizations move slow, especially the larger ones. Some banks still rely on COBOL and mainframes. The code that’s running in the world right now will continue to need to run for a long time, but things are changing fast.

My biggest complaint against AI is the power requirements, and how these big companies are building massive data centers drinking up all the water and energy in the area. They did that in Des Moines where I live. One of the Microsoft data centers out here required more water than the raccoon river had available. Looks like that trend isn’t going to change anytime soon either. So, from a values point of view, I’m disappointed and worried, from a professional point of view, I see the change as inevitable.

That’s my 2¢ on AI.

Sometimes it takes big organizations to do big things.

Apple exerts its power on it’s entire supply line to ensure that they are using renewable energy and environmentally sound principles. Additionally, they forward to after the sale and are committing to accounting for all of the power that their devices use once they are in the hands of their customers. Neither one of those things, looking back at their supply chain, and forward at their customers, is something that Apple has to do. But as one of those customers, I’m glad they are doing it.

Of course, not everyone sees things the same way. Cory Doctoro is a smart guy and a fun writer. I enjoy his podcast, and I’ve read a few of his books. There’s enough of a streak of rebellion in me that I find his worldview and calls for action particularly appealing. One area where I partially disagree with him though is his call to move away from Amercian tech. While I think it’s a no-brainer for foreign governments (or anyone else for that matter) to stop using Microsoft Office, I wouldn’t extend this idea to adopting European laptop vendors. At least not how they currently exist.

Apple, Google, and Microsoft have all committed to meeting certain environmental goals by 2030. In the case of Apple, their commitment is to be entirely carbon neutral. Microsoft’s commitment is to be “carbon negative, water positive, zero waste, and protect more land than we use.” Likewise, Google is pursuing “net-zero emissions across all of our operations and value chain by 2030, supported by a goal to run on 24/7 CFE on every grid where we operate.” I’m not a big fan of Microsoft or Google, but I have been following Apple as a hobby for over 20 years now. To be completely transparent, I find Apple’s commitment to and execution on their environmental goals to be astonishing.

Let’s get the caveats out of the way first. Yes, there are many, many things that Apple needs to do better at. Yes, they don’t need to be quite as big as they are. Yes, they need to treat developers better. And for the love of God yes, they need new leadership at the top, the Trump bootlicking and ring-kissing has to stop. But today I’d like to focus on what Apple is doing right, and what I hope they continue to do right.

A nerdy way to get an idea of how important a topic is to a big organization like Apple is to see how deeply they bury that topic in their information hierarchy of their homepage. For Apple, at the bottom of every page is heading titled “Values”, and under that is a link to “Environment”. I think it’s telling that the link points to https://www.apple.com/environment/, a top-level folder of their domain. A few bullet points from Apple:

• 21.8M metric tons of CO₂e emissions avoided
• 24% of materials shipped in our products came from recycled or renewable sources in 2024.
• 99% recycled cobalt in all Apple‑designed batteries.
• 3.6M metric tons of supplier facility waste diverted from landfills through our Zero Waste Program.
• 150,000 acres of sustainably certified forests restored
• 100,000 acres of native ecosystems protected through the Restore Fund.
• 14 billion gallons of freshwater savings through our Supplier Clean Water Program in 2024.
• Mac Mini manufactured with electricity sourced from 100% renewables.
• Mac enclosures made with 100% recycled aluminum.

One could argue that the metrics listed here are misleading, or that this is greenwashing and Apple is no more responsible than any other tech giant. There may be some truth to that, but I think overall Apple’s commitment to environmentally sound manufacturing and recycling principles is real. And, not only good for everyone in general, it’s good for their business. They could make their lower-end machines like the Mini or the Air out of cheap plastic. They could not be doing any of the things that they are doing, but it would cost them in raw materials, and it would cost them in reputation.

One argument I’ve seen from Doctoro is that Apple’s recycling program prevents good parts from entering the third-party market, which gives Apple more power because then only Apple can be the supplier of repair parts for their products. Fair enough, with a company the size and scope of Apple, there are a number of different lenses to look at any given topic through. I’m fully on board with making machines that are easy to repair. But I’m also fully on board with making sure e-waste stays out of landfills and dangerous third-world smelting factories.

Looking at Apple’s products purely through a repairability lense often leads to considering Framework. Framework is intentionally built with repairability in mind, every component in the machine can be easily ripped out and replaced with a new one, from the screen to the motherboard. My concern with Framework’s model is what happens to the components that are replaced? And how often are they being replaced? If we are honest about the consumption habits of most Americans, and probably most Europeans as well, those replaced parts will wind up in the trash. So… if the Framework model becomes widespread and commonplace, e-waste from replaceable Framework components grows exponentially.

Ok, so if we don’t want a world full of junk Framework components, and we want to get off American tech in general anyway, where do we go? There are a few small European laptop vendors making Linux laptops, like Germany’s Tuxedo, and Spain’s Slimbook. These vendors offer a seamless experience of Linux pre-installed on their machines, with all the components guaranteed to work, and even an extended warranty available to purchase. So far so good, but there is no environmental impact statement for these companies, because they don’t actually make the laptop. In general, these companies are white-labeling laptops from a Chinese manufacturer named Clevo, an ODM (Original Design Manufacturer).

Clevo, somewhat surprisingly, has an environmental report similar to Apple or Microsoft’s, but reading the report shows that the company is doing the minimum it can get away with, along with some very modest goals. A brief rundown:

• Apple achieved 60% carbon reduction since 2015, Clevo’s goal is 5% by 2030.
• Apple currently uses 100% renewable energy for it’s own operating, and is pushing suppliers to 100% by 2040, Clevo uses 12.85% with no supplier requirements.
• Apple has invested billions in renewable energy and recycling, Clevo does not disclose it’s investments.

Apple might be accused of greenwashing, but this report from Clevo actually is greenwashing. Among other things, it emphasizes replacing LED bulbs for Christ’s sake, but avoids making hard commitments to real environmental protection.

This is all to say that while it may feel good to support a small, European Linux vendor, the environmental impact of that choice is far from neutral. I’d be all for manufacturers in Europe to start building their own computers from scratch that were easily repairable, easily recyclable, and used environmentally friendly processes, but as far as I can tell that doesn’t exist. Not yet anyway. Maybe this current moment we are in can jumpstart the effort.

Apple is too big. Tim Cook needs to go. They have focused too much on profit and not enough on developer relations, code quality, and user experience design. I mean, good grief, have you looked at Apple News+ lately? Embarrassing. But give credit where due, Apple’s environmental efforts are second to none, and that’s partially because they decided to use their strength to push the industry in a more sustainable, cleaner, and greener direction. I think the world would be a better place if everyone else would follow suit.

To say that 2025 has been a hectic year would be an understatement. Even in my personal corner of the world, my work life has been chaotic, far more than I would have liked. I’ve lost one team member, brought on a new one, weathered changes and challenges at the company level, and overall become far more reactive than proactive than I’d like. Feels like I’ve been trying to steer a ship through the fog, with only the dimmest lighthouse to guide the way.

Part of that is my own confusion about where I wanted my professional life to go. Since being promoted from Staff Engineer to Engineering Manager (and seeing my old team dismantled and handed over to foreign contractors), I’ve been unsure about how much time I wanted to dedicate to maintaining my technical skills. Not only that, but the additional uncertainty present with the proliferation of AI tools and massive layoffs in tech has also caused me to question my place in the industry for the next part of my career.

Am I still an engineer? Was I ever? Am I now just a manager?

I think the answer for the foreseeable future is going to be both… and more.

I’ve been what I would describe as a competent programmer. My history with Objective-C, and experience with Python and other languages along the way, has given me a good foundation for understanding the concepts and syntax needed to build applications. However, most of my professional experience has been focused on scripting and DevOps-centric tasks. Building pipelines, setting up system automations, etc. From time to time, I’ve dabbled in other languages, but I haven’t gone all in on any of them. I’d like to change that. One of the things I’m going to focus on in the new year is learning Rust. I’m not one for making resolutions; instead, I create yearly themes, with a few ideal outcomes for the year. I’m not “resolving” to learn Rust this year, but I am focusing on it as part of my overall theme.

As a sysadmin, and later a DevOps engineer, I’ve always focused on deep technical expertise. That meant understanding filesystems at the kernel level, tracing TCP packets through the system, and occasionally spelunking through the Linux kernel source code. Over the past few years of cloud automation, though, a lot of that has fallen to the wayside to make way for learning the AWS APIs. I’ve missed the low-level operating system work. I haven’t had to manage a RAID array in nearly 10 years, nor have I had to track down why a deleted file still has an open handle. However, I do now have an opportunity to dig back into some hard low-level problems, and I’m looking forward to seeing what new skills I can learn.

Taking on a management role has been one of the most challenging things I’ve done in my career. Not because of my plans for where I’d like the systems we’re responsible for to go, but because of all the other interpersonal tasks that are now my responsibility. Last year I hired the first person on my team, and this year I had to let a person on my team go. Both decisions were difficult, and the second took far longer than it should have. That was a lesson learned, one that cost me months of productivity. There are other management tasks that are difficult, like deciding on metrics to gather, how to build reports that are worthwhile, and how best to accurately reflect the value of our team. Management has a lot of abstractions, time-consuming tasks that attempt to convey an idea, either to my team, to my boss, or to the rest of the company. Difficult, but interesting.

Thinking through these aspects of my career informs my position on AI. I’ve gotten to where I am by prioritizing expertise, technical knowledge, quick learning, and being able to get things done. What I’ve noticed using AI occasionally over the past couple of years is that it makes me intellectually lazy. When faced with a difficult problem, my first impulse isn’t to dig into the problem and discern a solution, it’s to hand the problem over to AI and see what it has to say. This unhealthy habit undermines the very thing my career has been built on, thinking clearly. When I offload a task to AI I’m offloading my own thinking, and that’s something I just can’t do. On top of that, AI has very real environmental problems and a questionable financial future, at least in its current form. I understand the usefulness of AI for many tasks, but for me, personally, I can’t risk my career on outsourcing my brain.

So, that’s 800 words or so on why I’m thinking my next yearly theme should be “The Year of Thinking Clearly”. My focus will be on building my expertise, communicating effectively, and, as an essential part of having a clear head, building and maintaining a consistent and challenging exercise program. Healthy body, healthy mind. I’m looking forward to 2026. I think it could be one of my best years ever.

I started an email thread with Jeremy Friesen, that we later roped Jack Baty into, discussing our relative computing choices. The thread has gotten lengthy, and honestly was probably always better suited for blogging, so I decided to post my next response here.

Jeremy and Jack have both switched at least part of their computing from macOS to Linux, continuing a decades-old tradition of getting fed up with Apple’s corporate malarkey and jumping ship to the open waters of open source. I don’t want to speak for them, but my impression is that Jeremy has had more luck making the switch than Jack has, but they’ve both wound up with one foot in each pool. I feel the pull of Switcher Season every few years myself, more powerfully in 2025 than in the past, but still not quite strongly enough to convince me that it’d be in my best interest.

There are a few practical reasons I’m still enjoying my walled garden.

Sunk Costs

I’ve spent quite a bit of money on my Apple ecosystem over the years. An investment that I’d like to make the best out of. Most recently an Apple Watch Ultra 2, a decision I struggled over for weeks. I was very close to buying a Garmin Fenix, but in the end decided on the Apple Watch because, again, it was so well integrated with the rest of the Apple ecosystem.

There are also a number of third-party applications that I’ve paid for, most notably OmniFocus, an app for which there really is no equivalent anywhere else.¹ There’s also OmniGraffle from the same crew, as well as Transmit, Acorn, and DEVONthink. All in all, the third-party ecosystem might be the most compelling reason not to switch.

Hardware

Linux has an even more difficult time running on Macs since Apple switched to their M-series chips, and the PC world just doesn’t have anything close to the power, efficiency, and build quality of a Mac. Vendors like System76 and Framework each make compelling cases for their machines; in the end, you just won’t get the same battery life and performance as you will running macOS on a MacBook.

One only needs to feel the difference between any PC and a MacBook. Pick one up, set it down, and open the lid; close it again. Pick it back up. The Mac feels sturdy, well-built. Test the trackpad, the keyboard; feel the snap of the MagSafe power cord as it magnetically connects and lights up. The Mac hardware is once again that good.

Also, buying new hardware would be expensive. Especially if I wanted something that was at least close to the build quality and specs of a MacBook. It’d be several thousand dollars invested in a new machine that I’m not entirely sure I want.

Familial Obligations

Over the past two decades of using Apple gear, I inevitably bought some for my kids when they were ready. Starting with iPhones when they were teenagers, then Macs for college if they chose to go, and HomePods or Apple Watches for gifts. I pay for Apple One Premier, which comes with just enough accounts for everyone in our family to share iCloud Drive, Apple TV, and Apple Music. As our family has grown and moved farther away, we rely on FaceTime and Messages to keep in touch, sharing quick photos and videos throughout the day. We also share our workouts in Apple Fitness, so I often get pings from one of my daughters and reply with a quick encouragement.

If I were to start moving away from Apple, and macOS specifically, I’d miss out on some of those little interactions throughout the day. Maybe I’d be more focused at work, but I also wouldn’t have those little pings of connection that make me smile.

Will I Ever Switch?

Given all of that, even after sounding like a commercial for Apple in this post, I still want to switch. Apple’s declining software quality, their horrible design decisions over the past few years, poor treatment of developers, overall greed, and executive embrace of our authoritarian regime have all given me ample reason to move to a computing platform that I can own and control. There’d be so much that I’d miss though. I’m not sure when I’ll ever decide to do it. Maybe if Tim Cook gives Trump another gold trophy. Or if Apple abandons all good taste and decides to put ads in Finder like Microsoft. At that point I’d drop them like a hot potato.

One of the systems at work accepts data in csv format, which is essentially plain text with columns separated by commas. Occasionally a client will upload a file with mistakes in it, and while our applications are fairly robust and can handle most issues, sometimes one slips by that we weren’t expecting. When this happens, as it has twice in the past as many days, I’m called in to find out why.

The first issue was with a Python application that was pulling a file from S3, parsing it, and turning it into a tab-separated values file before uploading it back to S3 to be further processed by another system. The error given by Python’s csv package was:

_csv.Error: need to escape, but no escapechar set

Which was odd because we process many, many files during a day and this same code hasn’t needed to set anything else. After a bit of faffing around replicating the error locally, and isolating where in the code the error was occuring, I finally got it in my head to just grep the file for special characters. Sure enough, I found that the file contained tabs inside of the values, which given the logic of our program was causing it to have a bad time of it.

The command grep '\t' in.csv gave me the lines containing the offending tabs, and grep -n '\t' in.csv | cut -d : -f 1 gave me just the line numbers, which is what I was asked for. The cut command lets me select specific parts of a line, in this case I asked for -d : which set the colon as the delimiter, and -f 1 which asked for just the first column.

This morning I was asked to look at another task that had failed, this time using a custom Go binary that, again, parsed a csv file from S3. Thinking I might get lucky I ran the same search for tabs in the file but came up empty. After some looking around I found a Stack Overflow question that pointed me in the right direction, but I first had to install the GNU version of grep.

When Mac OS was merged with NeXTSTEP to create Mac OS X, the NeXT OS brought with it pure Unix underpinnings thanks to BSD¹. Thanks to that lineage, the Mac contains all the Unix tools we’d expect, but it does not include the Linux tools you’d expect. There are sometimes subtle differences between the tools, and I’ve found that the (ugg…) GNU/Linux version of grep to be more flexible. Luckily, Homebrew makes it trivially easy to install standard GNU tools, and running brew install grep provided me with the ggrep binary.

Equipped with the right tools for the job, I ran this command:

LC_ALL=C  ggrep --color='auto' -P -n "[\x80-\xFF]" in.csv

I’ve written about setting LC_ALL=C before, so I’ll skip that here. The rest of the command I’ll cover below.

--color='auto', this makes it much easier to spot the matching characters in a long string.

-P, tells grep to use Perl-compatible regular expressions

-n, print the line numbers

"[\x80-\xFF]", This searches the text for the extended ASCII characters ranging from hexadecimal code 80, or €, to code FF, the ÿ, or “Latin small letter y with diaeresis”, according to the ASCII table hosted at ascii-code.com.

Finally, in.csv is just the file name.

After editing the file, re-uploading, and kicking off the job again, it completed successfully. How in the world is it 2025 and we still have text encoding issues?

On August 6th, in the White House, Tim Cook announced that Apple is committing an additional $100 billion dollars in American manufacturing. If only he’d left it at that. If only Cook had simply announced the additional investment, bringing Apple’s commitment up to $600 billion over the next four years, and then politely thanked the president and walked out of the room, he may have held on to his integrity. But that’s not what happened. Instead, Cook kissed Trump’s ass and gave him a gold participation trophy.

The trophy is a glass plaque, “made in America”, and “designed by a former Marine” (probably while a bald eagle flew overhead singing “God Bless the U.S.A.”, wearing the American flag as a cape, with a gun in one claw and the Constitution in the other) that sits in a 24 karat gold base. The trophy itself is, honestly, kind of ugly. It doesn’t give off the “Designed by Apple in California” vibes I would expect from something that they actually put a lot of effort into. It looks like a high-school shop class project. However mediocre the actual object, Cook’s gift represented his, and Apple’s, subjugation. Bending the knee and kissing the ring. I nearly threw my iMac out the window.

But I didn’t, because my mind grinds slow and fine. I thought on it for days before reading Gruber’s take on Daring Fireball, where he says that Cook:

…is keenly aware that trust and reputation are only accrued slowly, but are always at risk of being squandered quickly, and that this applies both to how he is perceived personally and how Apple is perceived as an institution — a pillar of American ingenuity and industry. His life’s work. And that despite all of that, Cook concluded that debasing himself, selling some shares of his own dignity, was the best course of action — for Apple, for Apple’s customers (and, yes, shareholders), and perhaps even for the country. That ruthless practicality is necessary merely to stay afloat in a sea of abject graft, extortion, and cronyism. That’s dark. That requires considering that the problem isn’t the greed of a few billionaires and executives who ought to resist burgeoning corruption, but that Trump and his sycophants in the Republican Party have already succeeded in corrupting the system. That the corruption isn’t happening, but happened. The United States isn’t heading for existential trouble. We’re in it — and a pathway out is not yet clear. That’s not to say all is forever lost, but that we are, in our current political moment, beyond the point where the game can be played successfully on the level. You can choose to play a crooked game straight, but you can’t win. Business is competition. A loser who played above reproach is still a loser. You need to choose your battles. US manufacturing is Cook’s choice.

Once again, Gruber is faster to put into words what I’ve been mulling over.

To be clear, I fully support Apple bringing manufacturing back to the United States. In rural Iowa, small towns have been decimated over the past few decades by big manufacturers leaving the country and building overseas or in Mexico. Newton’s loss of Maytag is the poster child for describing how lives can be upended and entire ways of life lost due to the greed of corporations chasing the cheapest labor. The loss of identity and self-respect associated with losing a career is one of the reasons we’re in this mess with Trump and his ilk to begin with. But, one can both agree with bringing manufacturing back to the US and despise the bootlicking at the same time. With many things with the Trump administration, it’s not just what is being done, but how they are going about doing it.

Yes, bringing manufacturing back to the US is a good and nobel goal. I hope we can actually do it, but I also hope that we can do it in an environmentally clean way, leveraging renewable energy and sustainable materials harvesting whenever possible. The Republicans want to tout new investments in the US and new jobs, but they don’t believe in climate change, and their oil-drilling overlords won’t let them invest in clean energy alternatives. Since the MAGA cult is in charge of everythign for at least the next year and a half, if not till 2029, the United States is in a downward spiral that I don’t see a way out of.

The government is now blatantly, openly corrupt. Gifts like Cooks are now just the way things are done to win favor. The US is doing everything it can to roll back environmental protections, dissuade people from buying electric or investing at all in renewable energy. The health department is making it harder to get vaccinated. The Department of Education is being dismantled, which will make it easier to send public funds to private religious schools. There are literally masked gangs of thugs kidnapping people off the street in broad daylight and putting them in camps. And just to really own the libs, they give the camps fun names like “Alligator Alcatraz”.

Cook’s display of fealty has given me pause when considering future Apple purchases, but changing my computing platform of choice would be like cutting off my nose to spite my face. The answer isn’t in punishing individual companies (which would also be punishing myself and my family) that are playing by the current rules, the answer is to change the rules. To try to rebuild a fair, just, and civil society, free from the corruption of the MAGA movement. The only way we are going to do that is by making sure we vote out every Republican currently in office, so that not a single one of those sycophantic cowards ever get close to holding power again. Is that likely? Probably not. Not anytime soon anyway. The bad guys won. We’re living in their world now.

I hope Trump scratches the base of his little trophy someday to discover that it is only “gold plated”, and as fake as his orange tan.