Herb Caudill’s Lessons from 6 software rewrite stories is an extensive analysis of the rewrite projects of companies like Basecamp and Trello, why they succeeded or failed, and what we can learn from them:

Once you’ve learned enough that there’s a certain distance between the current version of your product and the best version of that product you can imagine, then the right approach is not to replace your software with a new version, but to build something new next to it — without throwing away what you have.

Eventually all product managers face a decision like this, so I found these case studies invaluable.

Kellan Elliott-McCrea has an excellent list of questions a team should answer before they decide to adopt a new technology in their software development process. For example:

If this new tech is a replacement for something we currently do, are we committed to moving everything to this new technology in the future? Or are we proliferating multiple solutions to the same problem? (aka “Will this solution kill and eat the solution that it replaces?”)

As he mentions in the post, these questions are not subtle… but I think they’re absolutely essential. It reminds me a little bit of Marty Cagan’s Product Opportunity Assessment questions.

This essay about the building blocks of the web by Rachel Andrew is really important. From HTML, CSS and our vanishing industry entry points:

There is something remarkable about the fact that, with everything we have created in the past 20 years or so, I can still take a complete beginner and teach them to build a simple webpage with HTML and CSS, in a day. We don’t need to talk about tools or frameworks, learn how to make a pull request or drag vast amounts of code onto our computer via npm to make that start. We just need a text editor and a few hours. This is how we make things show up on a webpage.

A lot of words are being written about AI and machine learning these days, so it’s sometimes hard to know what to pay attention to. M.C. Elish and danah boyd’s Don’t Believe Every AI You See is one of those essays that I would consider essential reading on the topic. On the ethics of artificial intelligence:

When we consider the ethical dimensions of AI deployments, in nearly every instance the imagined capacity of a technology does not match up with current reality. As a result, public conversations about ethics and AI often focus on hypothetical extremes, like whether or not an AI system might kill someone, rather than current ethical dilemmas that need to be faced here and now. The real questions of AI ethics sit in the mundane rather than the spectacular. They emerge at the intersections between a technology and the social context of everyday life, including how small decisions in the design and implementation of AI can create ripple effects with unintended consequences.

And on the supposed “neutrality” of machines:

[There is] a prevailing rhetoric around AI and machine learning, which presents artificial intelligence as the apex of efficiency, insight, and disinterested analysis. And yet, AI is not, and will not be, perfect. To think of it as such obscures the fact that AI technologies are the products of particular decisions made by people within complex organizations. AI technologies are never neutral and always encode specific social values.

As Kevin Kelly also pointed out years ago in his book What Technology Wants, technology is never neutral. It possesses the collective values of its creators. And that’s where things so often go wrong. A great resource on this topic is Sara Wachter-Boettcher’s book Technically Wrong: Sexist Apps, Biased Algorithms, and Other Threats of Toxic Tech.

In Filling the Silence with Digital Noise, Kate Moran and Kim Flaherty share some research-based findings on how people use digital background noise to make sure it’s never quiet around them:

While many participants reported feeling the need to have some sort of audio in the background during their silent moments, others reported a more intense version of this phenomenon: the need to fill all the empty moments in their lives with some activity to avoid boredom or downtime. This behavior fills the ‘silence’ in a figurative way — people use their devices to keep their minds constantly occupied.

I read this article with interest, because I also do this—albeit for a different reason. I have a condition called tinnitus, which is a consistent ringing in the ears. There is no cure for it—the only way to deal with it is to learn to manage and be ok with it. For those of us who suffer from tinnitus, silence is torture. Because there is no silence. Your only choices are (1) the sounds/noises you put on around you, or (2) a loud ringing in your head that comes from nowhere and everywhere and never goes away.

Guess which option we usually go for…

In The ‘Future Book’ Is Here, but It’s Not What We Expected, Craig Mod writes that after years of believing books will fundamentally change in the digital age, it’s simply not happening:

I think we can agree that, in an age of infinite distraction, one of the strongest assets of a “book” as a book is its singular, sustained, distraction-free, blissfully immutable voice.

What has changed, instead, is how books are created:

Instead, technology changed everything that enables a book, fomenting a quiet revolution. Funding, printing, fulfillment, community-building—everything leading up to and supporting a book has shifted meaningfully, even if the containers haven’t. Perhaps the form and interactivity of what we consider a “standard book” will change in the future, as screens become as cheap and durable as paper. But the books made today, held in our hands, digital or print, are Future Books, unfuturistic and inert may they seem.

Or, more succinctly:

Our Future Book is composed of email, tweets, YouTube videos, mailing lists, crowdfunding campaigns, PDF to .mobi converters, Amazon warehouses, and a surge of hyper-affordable offset printers in places like Hong Kong.

Karn Bianco asks What if video games could help fight climate change? No, really:

One of the first in a new line of climate change-focused games was survival game Eco. Developed by Seattle-based Strange Loop Games, this massively ambitious civilization simulator includes everything from detailed ecosystems and realistic climate modeling to player-driven government and economies. Players work together in a shared online world where every action impacts the environment around them. Laws to restrict or encourage almost any kind of behavior can be suggested and enacted to test their effects on the world.

This is a really neat development. I also like the ideas about how this could translate to long-running simulation games like SimCity:

Imagine a SimCity that puts people (not cars) and sustainability (not endless growth) first. Where designing a city that’s easy and safe to navigate on foot or by bike is not just possible but rewarded, with lower pollution and healthier citizens. Where constructing energy-efficient buildings provide long-term in-game benefits like lower energy demands, as well as a chance to learn about real world trends like passive housing.

Jonathan English’s article on mass transit in America starts off sad, and just gets worse from there:

One hundred years ago, the United States had a public transportation system that was the envy of the world. Today, outside a few major urban centers, it is barely on life support. […]

At the turn of the 20th century, when transit companies’ only competition were the legs of a person or a horse, they worked reasonably well, even if they faced challenges. Once cars arrived, nearly every U.S. transit agency slashed service to cut costs, instead of improving service to stay competitive. This drove even more riders away, producing a vicious cycle that led to the point where today, few Americans with a viable alternative ride buses or trains.

It’s important to note that this is not an accident. It is a direct result of urban design:

The story of American transit didn’t have to turn out this way. Look again at Toronto. It’s much like American cities, with sprawling suburbs and a newer postwar subway system. But instead of relying on park-and-ride, Toronto chose to also provide frequent bus service to all of its new suburbs. (It also is nearly alone in North America in maintaining a well-used legacy streetcar network.) Even Toronto’s suburbanites are heavy transit users, thanks to the good service they enjoy.

Likewise, in Europe, even as urban areas expanded dramatically with the construction of suburbs and new towns, planners designed these communities in ways that made transit use still feasible, building many of them around train stations. When cities like Paris, London, and Berlin eliminated their streetcar networks, they replaced them with comparable bus service.

Some further reading that digs into pedestrians and cars a little more:

• The Hell of Being Carless in America’s Suburban Sprawl
• There Are Better Ways to Get Around Town
• American cities are designed for cars—which makes life worse for everyone

Nicholas Carr discusses the importance of using the right terminology when we talk about how companies use our data in his essay I am a data factory (and so are you). On the problems with the “data mining” metaphor:

Data does not lie passively within me, like a seam of ore, waiting to be extracted. Rather, I actively produce data through the actions I take over the course of a day. When I drive or walk from one place to another, I produce locational data. When I buy something, I produce purchase data. When I text with someone, I produce affiliation data. When I read or watch something online, I produce preference data. When I upload a photo, I produce not only behavioral data but data that is itself a product. I am, in other words, much more like a data factory than a data mine. I produce data through my labor — the labor of my mind, the labor of my body.

On extending the “data factory” metaphor to the platform companies:

The platform companies, in turn, act more like factory owners and managers than like the owners of oil wells or copper mines. Beyond control of my data, the companies seek control of my actions, which to them are production processes, in order to optimize the efficiency, quality, and value of my data output (and, on the demand side of the platform, my data consumption). They want to script and regulate the work of my factory — i.e., my life — as Frederick Winslow Taylor sought to script and regulate the labor of factory workers at the turn of the last century. The control wielded by these companies, in other words, is not just that of ownership but also that of command. And they exercise this command through the design of their software, which increasingly forms the medium of everything we all do during our waking hours.

The factory metaphor makes clear what the mining metaphor obscures: We work for the Facebooks and Googles of the world, and the work we do is increasingly indistinguishable from the lives we lead. The questions we need to grapple with are political and economic, to be sure. But they are also personal, ethical, and philosophical.

This brings up a point I haven’t given much thought to. It’s not just that platforms use the data we create to further their business interests. It’s that they are also invested in having us create a very specific kind of data. Data that can be as useful as possible to advertisers. That changes our behavior and gives rise to the prevailing wisdom that people are not being authentic on social media.

Clive Thompson digs into software that aims to add friction to our lives in his Wired essay We Need Software to Help Us Slow Down, Not Speed Up:

It’s certainly possible to slow our software, and thereby ourselves. But it’ll happen only when we become too unsettled by the speed of our journey.

His post reminds me of some other ideas I’ve read about this in the past. Chris Palmieri in A Practice of Ethics:

But some friction is borne of respect, when we present information about the choices available to users and help them make better decisions. An emailed invoice could remind a customer they were paying for a service they no longer use. A checkbox could assure a user of their current content privacy settings before posting a sensitive photo. Recognition of a past purchase can save a customer the hassle of having to return a book they already have, or confirm that they are re-buying exactly the same shampoo.

And here is Andrew Grimes in Meta-Moments: Thoughtfulness by Design:

Meta-moments can provide us with space to interpret, understand, and add meaning to our experiences. A little friction in our flow is all we need. A roadblock must be overcome. A speed bump must be negotiated. A diversion must be navigated. Each of these cases involves our attention in a thoughtful way. Our level of engagement deepens. We have an experience we can remember.

Not all friction is bad…