I am grateful — genuinely — for what Google and Apple and others did to make digital life easy over the past two decades. But too much ease carries a cost. I was lulled into the belief that I didn’t have to make decisions. Now my digital life is a series of monuments to the cost of combining maximal storage with minimal intention.

I have thousands of photos of my children but few that I’ve set aside to revisit. I have records of virtually every text I’ve sent since I was in college but no idea how to find the ones that meant something. I spent years blasting my thoughts to millions of people on X and Facebook even as I fell behind on correspondence with dear friends. I have stored everything and saved nothing.

This is an example of what AI, in its most optimistic state, could help us with.

We already see companies doing this. In the Apple ecosystem, the Photos widget is perhaps the best piece of software they’ve produced in years.

Every single day, I am presented with a slideshow of a friend who is celebrating their birthday, a photo of my kids from this day in history, or a memory that fits with an upcoming event.

All of that is powered by rudimentary¹ AI.

Imagine what could be done when you unleash a tuned large language model on our text histories. On our photos. On our app usage.

AI is only as good as the data it is provided. We’ve been trusting our devices with our most intimidate and vulnerable parts of ourselves for two decades.

This is supposed to be the payoff for the last twenty years of surveillance capitalism, I think?

All those secrets we share, all of those activities we’ve done online for the last twenty years, this will be used to somehow make our lives better?

The optimistic take is that we’ll receive better auto suggestions for text responses to messages that sound more like us. We’ll receive tailored traffic suggestions based on the way we drive. We’ll receive a “long lost” photo of our kid from a random trip to the museum.

The pessimistic take is that we’ll give companies the exact words which will cause us to take action. Our own words will be warped to get us to buy something we’ve convinced ourselves we need.

My hunch is that both takes will be true. We need to be smart enough to know how to use these tools to help ourselves and when to put them down.

I haven’t used Gmail as my primary email for years now², but this article is giving me more motivation to finally pull the plug and shrink my digital footprint.

This is not something the corporations did to me. This is something I did to myself. But I am looking now for software that insists I make choices rather than whispers that none are needed. I don’t want my digital life to be one shame closet after another. A new metaphor has taken hold for me: I want it to be a garden I tend, snipping back the weeds and nourishing the plants.

My wife and I spent the last week cleaning out our garage. It reached the point where the clutter accumulated so much that you could only park one car in it, strategically aligned so you could squeeze through a narrow pathway and open a door.

As of this morning, we donated ten boxes of items and are able to comfortably move around the space. While there is more to be done, the garage now feels more livable, useful, and enjoyable to be inside.

I was able to clear off my work bench and mount a pendant above it. The pendant is autographed by the entire starting defensive line of the 1998 Minnesota Vikings.

Every time I walk through my garage, I see it hanging there and it makes me so happy.

Our digital lives should be the same way.

My shame closet is a 4 terabyte hard drive containing every school assignment since sixth grade, every personal webpage I’ve ever built, multiple sporadic backups of various websites I am no longer in charge of, and scans of documents that ostensibly may mean something to me some day.

Scrolling through my drive, I’m presented with a completely chaotic list that is too overwhelming to sort through.

Just like how I cleaned out my garage, I aught to do the same to this junk drawer.

I’ll revert to Ezra’s garden metaphor here: keep a small, curated garden that contains the truly important and meaningful digital items to you. Prune the rest.

(Shout out to my friend Dana for sharing this with me. I think she figured out my brand.)

Because we’re social animals we tend to go along with the trend, and because we live under capitalist acceleration the trend is always one way, because our system only has one gear. We also have the ability to edit our memories, so can find ways to convince ourselves that this was all our own choice. That very same adaptability, though, prevents us from using the new tech to save time, because – under a system with a growth fetish – we’ll be expected to adapt to a new normal in which we have to do more stuff and get more stuff in the same amount of time.

The dark irony then, is that it is the introduction of the new tech that inspires the subsequent irritation at its absence. Twenty years ago nobody fidgeted in agitation if they had to wait ten minutes for a taxi. Now you’ll check your phone incessantly if the Uber is running three minutes later than you expected. And god forbid the driver cancels, because you’ve probably algorithmically planned everything down to the last minute. We increasingly live a ‘just in time’ life because, at a systemic level, there’s pressure to pack in as much stuff as possible at both a consumption and production level. We’re just as dissatisfied, only busier.

The more I dig into the reasons behind my anxiety and depression, I keep coming back to some form of “it’s the system, maaaan.”

And that thought often leads me down two paths:

The first path is wallowing in anger around our horrible healthcare system, our completely corrupt political system, and our inability to have a rational conversation around solutions to all these problems (often with people whom I actually deeply care about).

The second path is spinning around solutions for these problems. How can I tone down the heat in conversations with my loved ones? How can I push back against a culture hellbent on incessant and mindless consumption?

How do we all just slow down?

Here is how platforms die: First, they are good to their users; then they abuse their users to make things better for their business customers; finally, they abuse those business customers to claw back all the value for themselves. Then, they die.

I call this enshittification, and it is a seemingly inevitable consequence arising from the combination of the ease of changing how a platform allocates value, combined with the nature of a "two-sided market," where a platform sits between buyers and sellers, hold each hostage to the other, raking off an ever-larger share of the value that passes between them.

If you’ve spent much time in the same tech bubbles as me this past year, you’ve probably come across this article already.

At a bare minimum, I’m sure you’ve seen the phrase “enshittification.”

Once you understand the concept, you do start to see the pattern unfold around you constantly. ¹

While there are countless examples of this natural platform decay within our virtual world, what about the physical world?

Is enshittification simply human nature, an inescapable fate for any collaborative endeavor above a certain size?

And if enshittification is not inevitable, what are the forces that lead to it, and how can we combat them when building our own communities?

If, on the other hand, you view freelancing as a path to real business ownership, your first step is to recognize that the billable hour is a binkie that keeps you in amateur purgatory for the entire time you rely on it.  A kind of Hotel California with timesheets.

And that’s really my only call to action — the recognition as the first step.

I’m not suggesting you fire all of your hourly clients or do anything dramatic.  I’m not even suggesting any immediate change.  Rather, I’m just suggesting that you change your viewpoint.

If you want to be a professional business owner, you need to become an expert in delivering outcomes that add value.  And you’ll never achieve that without enough reps to flat price your work and enough skin in the game to feel it when you get it wrong.

I found it difficult to do “value-based pricing” when running my agency.

But I think it took a little time away to really understand my value. It was never about programming stuff. It was about making something that could turn $1 into $2.

And knowing what to spend that $1 on.

I gotta find the video from this and watch it myself, because essentially every single thing mentioned in this article is what I wanna build a podcast around.

Let’s start with this:

As Kwan first explained, modern capitalism only worked because we compelled people to work, rather than forced them to do so.

“We had to change the story we told ourselves and say that ‘your value is your job,” he told the audience. “You are only worth what you can do, and we are no longer beings with an inherent worth. And this is why it’s so hard to find fulfillment in this current system. The system works best when you’re not fulfilled.”

Boy, this cuts to the heart of the depressive conversations I’ve had with myself this past year.

Finding a job sucks because you have to basically find a way to prove to someone that you are worth something. It can be empowering to some, sure, but I am finding the whole process to be extremely demoralizing and dehumanizing.

“Are you trying to use [AI] to create the world you want to live in? Are you trying to use it to increase value in your life and focus on the things that you really care about? Or are you just trying to, like, make some money for the billionaires, you know?”  Scheinert asked the audience. “And if someone tells you, there’s no side effect. It’s totally great, ‘get on board’ — I just want to go on the record and say that’s terrifying bullshit. That’s not true. And we should be talking really deeply about how to carefully, carefully deploy this stuff,” he said.

I’ve literally said the words, “I don’t want to make rich people richer” no fewer than a hundred times since January.

There is so much to unpack around this article, but I think I’m sharing it now as a stand in for a thesis around the podcast I am going to start in the next month.

We need to be having this conversation more often and with as many people as possible. Let’s do our best right now at the precipice of these new technologies to make them useful for ourselves, and not just perpetuate the worst parts of our current systems.

I love the hottest take. 😂

(For what it's worth: I am starting to come around on pineapple on pizza, especially if it's part of a really spicy pizza.

A couple years back, I tried to watch all the MCU movies in release order. I gave up after Winter Soldier. It was just too much. I'm glad superhero movies exist, but they're not my cup of tea these days.)

In my explorations of “sustainable business”, I'm often wondering what these two words really mean. I've previously shared some ponderings about the meaning of the word “sustainability”, but what about the word business?

It turns out that it is exactly what it sounds like. The word business originates from Northumbria where the old English word “bisignes” meant care, anxiety or occupation. This evolved into “busyness”, meaning a state of being occupied or engaged. In other words, a state of being busy.

This puts a whole new perspective on the term sustainable business and makes it feel like even more of an oxymoron. If sustainability is the ability to sustain something over the long term, then sustainable business would be to stay busy indefinitely.

Is that viable?

And more importantly, is that what we really want?

As always, Tom’s on point with this essay.

I’m working hard to reduce my wants. Sounds a bit like an oxymoron (no pun intended here), but we’ve all been so conditioned to chase after the shiny thing that we hardly ever stop to ask if the shiny thing is worth coveting.

And it’s really hard to not want to go after the shiny new thing. Getting laid off made it easy to not insta-buy a Vision Pro, but the hype leading up to its release sure got me intrigued.

I’m glad I didn’t, in retrospect, because the reviews aren’t exactly lighting the world on fire.

But this is just one of many examples I can give about being bit by the conspicuous consumption bug.

Another thought: nothing drives me more batty about a job than when you need to track your hours.

The hardest part for me is the obligatory feeling to maximize the time you are claiming you worked.

Let’s say I write down that I spent 8 hours building your website. One of those hours included a meeting where we spent half of it talking about how our weekends went. Ethically speaking, is it wrong for me to charge for an hour of that time, or should I actually say I worked 7.5 hours on your website that day?

Of course, writing this down, it feels silly. Everybody writes down 8 hours.

But if everybody does it, then why do we do it? What gain do we get by tracking our hours? Shouldn’t the final output matter more than how much effort went into building the thing? Is time a useful representation of effort?

I dunno… every time I read Tom’s posts, it feels like there should be a better way to orchestrate our economies. It’s probably time we figure out what symphonies we should be playing before we burn our planet to the ground in the name of growth.

The French priest Pierre Teilhard de Chardin famously said that “We are not human beings having a spiritual experience. We are spiritual beings having a human experience”. In other words, our minds and souls are having a material experience here on Earth. You would imagine that a healthy society would therefore cherish both sides of this duality - the non-physical and the physical. The strange thing about our modern culture though is that we have rejected almost all concept of spirituality and, according to Watts, we have also forgotten the value of the material world, leaving us with nothing that we truly value.

I just finished bringing 12 full boxes of baby clothes outside for donation.

Twelve boxes of mostly mediocre fabrics stitched together to be worn, what, ten times at the most? And in some cases, never worn at all.

Twelve boxes that contained thousands of dollars worth of labor to purchase them initially, not to mention the thousands of hours of labor to stitch them together in the first place.

And while placing every single item inside those twelve boxes, I hardly felt nostalgic or wasted any time lamenting the loss of anything I was discarding.

I kept thinking of a quote that says, “Look around you. All that stuff used to be money. All that money used to be time.”

And it made me think about my anxiety surrounding my job search. Needing to get myself back into the work force, just so I can keep consuming more stuff?

I think a lot of my anxiety stems from moments where I’m unable to make sense of a given situation (or, at the very least, make peace with it).

This is the system we’re in. There’s only so much I can change about it.

My kids got so much stuff for Christmas this year. Thousands of dollars of toys, books, clothes, games.

And yet, they don’t really care about any of it.

Their Barbie dream house? It’s in shambles, with stickers peeling off the walls and various marker doodles covering the floors.

Their PAW Patrol Lookout? Shoved in the corner along with two complete sets of each of the 7 (wait, 8? wait, no, they added a few more?) characters with vehicles in various states of destruction.

The best I can hope for is that they get a few hours of enjoyment from these toys.

Because someday soon, probably within the next two years, I’ll have to grab twelve more cardboard boxes out of the garage and start placing all of those toys into them.

And there is very little about this situation that makes sense to me.

I’ve never wanted to promote myself.

I’ve never wanted to argue with people on the internet.

I’ve never wanted to sue anyone.

I want to make my little thing and put it out in the world and hope that sometimes it means something to somebody else.

Without exploiting anyone.

And without being exploited.

If that’s possible.

Sometimes, when I use LLMs, it feels like I’m consulting the wisdom of literally everyone who came before me.

And the vast compendium of human experiences is undoubtedly complex, contradictory, painful, hilarious, and profound.

The copyright and ethics issues surrounding AI are interesting to me because they feel as those we are forcing software engineers and mathematicians to codify things that we still do not understand about human knowledge.

If humans don’t have a definitive answer to the trolly problem, how can we expect a large language model to solve it?

How do you define fair use? Or how do you value knowledge?

I really feel for the humans who just wanted to create things on the internet for nothing but the joy of creating and sharing.

I also think the value we collectively receive when given a tool that can produce pretty accurate answers to any of our questions is absurdly high.

Anyway, check out this really great comic, and continue to support interesting individuals on the internet.

Why do we hate bureaucracy?

Taken literally, a bureaucracy is just an organization tasked with ensuring some outcome. In the public sector, OSHA ensures worker safety, FDA ensures drug safety, EPA ensures environmental protection; in the private sector, HR ensures legal compliance, IT ensures trade secrets and data privacy, and so on. Yet even if people agree with the outcome, they often disagree with the implementation. Bureaucracies have an endless talent for finding wasteful and ineffective solutions.

Bureaucracies are ineffective due to a lack of accountability. If a bureaucrat imposes a wasteful policy, what are the consequences? Well, as long as they are achieving their desired outcome, they are doing their job, regardless of the pain they inflict on others. They can wield legal, technical, or financial penalties to force compliance. And paradoxically, when bureaucrats fail to achieve their desired outcome, they often get a bigger budget or a bigger stick to wield, rather than being fired for incompetence. The inability to recognize failure goes hand in hand with the inability to recognize success: competent and ambitious people avoid working for bureaucracies because their efforts go unrewarded. Bureaucracies end up staffed with middling managers, and we have learned to hate them.

I don’t know how to solve this problem in the public sector, but I think it’s solvable in the private sector, because there is theoretically a CEO who is incentivized to maximize the overall effectiveness of the company; they just need the right tactics. The solution is simple: hold bureaucracy accountable by forcing them to do the actual work.

I feel like there’s a counter argument to be made in here about the role of competition in the work produced for external entities to do.

In a functioning capitalistic system, you have several competing entrepreneurs who are testing all kinds of novel ideas against the rules established by the government to ensure a safe, fair playing field.

The role of a bureaucracy is not to get to the end goal faster. The role of bureaucracy is to make sure we get to the end goal without taking harmful shortcuts.

Regardless, there is something to be said about being thoughtful in imposing burdensome policies, and I think this concept of bureaucratic leverage is an interesting way to consider the role of the public sector in optimizing our systems.