How do people make decisions? What persuades them, what doesn’t, and why? What are the implications for a free society?
This site collects essays and notes exploring those questions, drawing on my work in marketing and fundraising. (About me.)
How do people make decisions? What persuades them, what doesn’t, and why? What are the implications for a free society?
This site collects essays and notes exploring those questions, drawing on my work in marketing and fundraising. (About me.)
It’s an article of faith among many fundraising executives: Keep it short. Nobody reads anymore.
It’s not wrong, exactly. The direct marketers who tried to send fundraising emails as long as their letters — these letters can run eight pages or more — learned the hard way that email is a different medium. That people consume email differently than mail.
(Consider Jeff Brooks’ image of Aunt Ruth settling into her comfy chair to read her mail. Nobody settles into a chair to read email.)
But the people who took “keep it short” as the whole lesson often found their short fundraising emails equally ineffective. Not because they were short, but because they were only short. They’d edited out the emotional argument — the part that actually moves someone to give.
Direct mail wasn’t long because readers were more patient in 1985. It was long because building a case for why someone should care — and care deeply enough to write a check — requires space. The length wasn’t a feature of the medium but a reflection of human nature.
Email changed the form. The reader remained the same.
What AI is doing to writing in education looks similar to what email did to direct mail.
Teachers who’ve spent years assigning take-home essays are watching students produce polished work they didn’t write. The form — the overnight research paper, the five-paragraph essay — is being disrupted.
Some educators are banning AI entirely, doubling down on old forms and hoping enforcement holds. This misses the point.
The take-home essay was never really about the essay. It was about forcing students to think through the material and demonstrate they’d learned it.
The most interesting educators aren’t the ones fighting AI. They’re the ones asking what writing is actually for and redesigning their lessons around that.
That’s what disruption does. It strips away the form — the multi-page letter, the essay — and leaves intact the problem the form was always trying to solve.
Gmail taught us to be digital hoarders. To save every email, every chat, every search. Because it might come in useful someday.
All that data might feel like a security blanket. But it creates real mental load.
Do you really need that email from 2010 coordinating movie plans? The shipping notification from 2014? Backed up files you’ll never actually look at again — files that could be a liability in a breach?
This digital clutter can have the same effect as physical clutter — overwhelm, the sense you can’t quite move on since you’re worried about what if.
I recently cleaned out years of digital detritus — tens of thousands of emails dating back more than 20 years, gigabytes of data in online storage.
One account now holds 45 total emails — just those that were particularly meaningful. Everything else? No longer a weight.
Turns out nothing I deleted was ever needed. It never was.
Twenty years ago, posting an article to the website I managed took 30 minutes. Not 30 minutes of writing but 30 minutes of work after the writing was done.
Creating the raw HTML page. Updating the HTML on every page that linked to it. Fighting with Internet Explorer 6.
And that was after I’d already paid for Dreamweaver to simplify site management and spent months learning ASP and HTML well enough to not break everything.
It was handcrafted. And it was awful.
Last week I built an entire web app on my commute. My family has been watching films together for years, and I wanted something that would track what we’d seen and suggest what to watch next.
From idea to working app: 30 minutes. The whole train ride was spent on the thing I actually cared about — the feature set and the experience. Not painstakingly centering divs, or debugging a CSS error, or digging out solutions from the snippiness on Stack Overflow.
At one point, I asked my AI collaborator to add a custom date picker. At another, I asked it to create an import-export function for the database. Each change took 20 seconds to type and only slightly longer to execute. Almost magical.
The cost of entry? Twenty dollars a month.
Some people will say it doesn’t count if you didn’t write the code yourself. My kids, discovering a film they love on a Friday night, would disagree.
The tools used to eat your time. Now they give it back. That’s genuine progress.
I’m not good at home repair. I don’t enjoy it. When something breaks, my first instinct is dread.
For a long time I thought the solution was willpower — grit my teeth, get through it, reward myself after. The task was something to endure.
But that framing made the problem worse. On top of my broken toilet, I had to deal with my resistance to fixing it.
Here’s what shifted things: realizing that the toilet doesn’t care how I feel about it. It needs fixing whether I’m frustrated or not. The frustration isn’t doing any useful work — it’s just a second unpleasant thing running alongside the first.
The solution wasn’t learning to love DIY, or steeling myself more firmly against discomfort. The solution was recognizing that my frustration was optional, and setting it aside.
Just noticing it wasn’t helping and moving on.
Step out for a one-hour meeting and you come back to dozens of project notifications.
Status updates. Comments. @mentions. Automated alerts telling you a due date changed on a project you’re barely involved in.
You weren’t gone long. But the tools kept churning out noise without you — and now they want your attention.
This is the hidden cost of systems built for transparency. They show everyone everything. All the time.
In theory, that makes coordination easier.
In practice, it means you’re always a little bit behind.
Worse, none of it tells you what to actually do next.
An inbox full of updates tells you what’s happening — not what matters, not what’s required of you, not what should happen today. Figuring that out is its own work, layered on top of the actual work.
The fix I’ve landed on: one list, maintained separately from the project tools my team uses. A filter that sits on top of the existing tools.
I treat the notifications as inputs. When something actually requires action, I pull it out and add it to the list, alongside everything else competing for my time. Then I decide what to work on next.
The project management tools tell me what’s happening. My list tells me what to do.
Only one of them should be in charge.