I think about this a lot, both in IT and civil infrastructure. It looks so trivial to “fix” from the outside. In fact, it is incredibly draining to do the entirely crushing work of real policy changes internally. It’s harder than drafting a blank page of how the world should be.

I’m at a sort of career crisis point. In my job before, three people could contain the entire complexity of a nation-wide company’s IT infrastructure in their head.

Once you move above that mark, it becomes exponentially, far and away beyond anything I dreamed, more difficult.
And I look at candidates and know-everything’s who think it’s all so easy. Or, people who think we could burn it down with no losses and start over.

God I wish I lived in that world of triviality. In moments, I find myself regretting leaving that place of self-directed autonomy.
For ten years I knew I could build something and see results that same day. Now I’m adjusting to building something in my mind in one day, and it taking a year to do the due-diligence and edge cases and documentation and familiarization and roll-out.
That’s the hard work. It’s not technical. It’s not becoming a rockstar to peers.
These people look at me and just see another self-important idiot in Security who thinks they understand the system others live. Who thinks “bad” designs were made for no reason.
Who wasn’t there.
And somehow I think this is the mental unburdening conceit of Authoritarians.

Everything is possible, tomorrow, when you don’t care about endemic complexity of real-world problems and the humans already architected to try to solve them.

More from Tech

A common misunderstanding about Agile and “Big Design Up Front”:

There’s nothing in the Agile Manifesto or Principles that states you should never have any idea what you’re trying to build.

You’re allowed to think about a desired outcome from the beginning.

It’s not Big Design Up Front if you do in-depth research to understand the user’s problem.

It’s not BDUF if you spend detailed time learning who needs this thing and why they need it.

It’s not BDUF if you help every team member know what success looks like.

Agile is about reducing risk.

It’s not Agile if you increase risk by starting your sprints with complete ignorance.

It’s not Agile if you don’t research.

Don’t make the mistake of shutting down critical understanding by labeling it Bg Design Up Front.

It would be a mistake to assume this research should only be done by designers and researchers.

Product management and developers also need to be out with the team, conducting the research.

Shared Understanding is the key objective


Big Design Up Front is a thing to avoid.

Defining all the functionality before coding is BDUF.

Drawing every screen and every pixel is BDUF.

Promising functionality (or delivery dates) to customers before development starts is BDUF.

These things shouldn’t happen in Agile.
Ok, I’ve told this story a few times, but maybe never here. Here we go. 🧵👇


I was about 6. I was in the car with my mother. We were driving a few hours from home to go to Orlando. My parents were letting me audition for a tv show. It would end up being my first job. I was very excited. But, in the meantime we drove and listened to Rush’s show.

There was some sort of trivia question they posed to the audience. I don’t remember what the riddle was, but I remember I knew the answer right away. It was phrased in this way that was somehow just simpler to see from a kid’s perspective. The answer was CAROUSEL. I was elated.

My mother was THRILLED. She insisted that we call Into the show using her “for emergencies only” giant cell phone. It was this phone:


I called in. The phone rang for a while, but someone answered. It was an impatient-sounding dude. The screener. I said I had the trivia answer. He wasn’t charmed, I could hear him rolling his eyes. He asked me what it was. I told him. “Please hold.”

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"I lied about my basic beliefs in order to keep a prestigious job. Now that it will be zero-cost to me, I have a few things to say."


We know that elite institutions like the one Flier was in (partial) charge of rely on irrelevant status markers like private school education, whiteness, legacy, and ability to charm an old white guy at an interview.

Harvard's discriminatory policies are becoming increasingly well known, across the political spectrum (see, e.g., the recent lawsuit on discrimination against East Asian applications.)

It's refreshing to hear a senior administrator admits to personally opposing policies that attempt to remedy these basic flaws. These are flaws that harm his institution's ability to do cutting-edge research and to serve the public.

Harvard is being eclipsed by institutions that have different ideas about how to run a 21st Century institution. Stanford, for one; the UC system; the "public Ivys".