It seems as though the opposite of “careless” ought to be “careful.” That the best way to avoid avoidable errors is to try harder, to put more care into the work. This means…
The Paradox of Perfection: When ‘Good Enough’ is Actually Better
Exploring the tension between engineering perfectionism and pragmatic delivery. Discover why striving for the perfect solution often prevents us from shipping valuable improvements and how to find the balance.
Ways people trying to do good accidentally make things worse, and how to avoid them
Even when you try to do good, you can end up doing accidental harm. But there are ways you can minimise the risks.
Laziness Does Not Exist
Psychological research is clear: when people procrastinate, there's usually a good reason
How to write error messages that actually help users rather than frustrate them
One of the most consistently neglected parts of today’s user experiences is our handling of errors. We’re so busy designing the happy paths through our products that we often forget to give the same care and attention to the times when things will go wrong
Pluralistic: Sarah Wynn-Williams’s ‘Careless People’ (23 Apr 2025) – Pluralistic: Daily links from Cory Doctorow
I never would have read Careless People, Sarah Wynn-Williams's tell-all memoir about her years running global policy for Facebook, but then Meta's lawyer tried to get the book suppressed and secured an injunction to prevent her from promoting it:
Pluralistic: Sarah Wynn-Williams’s ‘Careless People’ (23 Apr 2025) – Pluralistic: Daily links from Cory Doctorow
I never would have read Careless People, Sarah Wynn-Williams's tell-all memoir about her years running global policy for Facebook, but then Meta's lawyer tried to get the book suppressed and secured an injunction to prevent her from promoting it:
Careless love: the unmaking of Elvis Presley
Careless Love is the full, true, and mesmerizing story …
The Biggest Mistake I See Engineers Make
Throughout my career, the biggest mistake I see engineers make is doing too much work on their own before looping in others. I’ve experienced this mistake as both an IC and a manager. As an IC, it’s a mistake I made many, many times early in my ow...
Careless People: A Cautionary Tale of Power, Greed, and…
An explosive memoir charting one woman’s career at the …
Good and Bad Procrastination
Good and Bad Procrastination
Work Smarter: The Cocktail of Simplicity, Manageable Adversity, and Muntzing
Sometimes deliberate roadblocks can be a good thing to get more efficient and effective products and workflow. Here's how.
3 Cognitive Habits of People Who Get Things Done
High-achieving workers have these things in common.
How I stopped worrying and learned to love the easy fix
On the balance between perfect solutions and pragmatic fixes in software engineering
How to create software quality.
I’ve been reading Steven Sinofsky’s Hardcore Software, and particularly enjoyed this quote from a memo discussed in the Zero Defects chapter: You can improve the quality of your code, and if you do, the rewards for yourself and for Microsoft will be immense. The hardest part is to decide that you want to write perfect code. If I wrote that in an internal memo, I imagine the engineering team would mutiny, but software quality is certainly an interesting topic where I continue to refine my thinking. There are so many software quality playbooks out there, and I increasingly believe that all these playbooks work in their intended context, but are often misapplied.
