Warnings against “efficiency” and “optimization” date back millennia
What started as a birthday reflection on living less “optimized” has turned into a rabbit hole: a cross-century search for who else has challenged the cult of efficiency. This post gathers those voices -from Sappho to the Luddites; hooks to Doctorow- into a living bibliography of unoptimization, an ongoing project I’ll keep expanding as new resonances and missing voices emerge.
A Reading List for Aspiring “Unoptimizers”
I went to my bookshelf, my previous coursework, Bibliographies in a few treasured books, and ChatGPT to design a reading list if I were to teach a class or take a class on the topic of the history of “Unoptimization”. Here’s what I have so far - comments open for anyone to add / tweak what I’ve compiled.
What does it mean when meaning evolves?
Along the way we begin to think. We try on, reject, and are inspired by the thoughts, words, gestures, and expressions of others. We are rewarded, punished, and surprised by how we put shape and texture around our thoughts in a variety of scenarios: with coworkers, in romantic relationships, for online "communities".
Unoptimized
Why is everyone in such a hurry to remove the friction out of every task, every aspect of human life? For much of life, it’s the friction that keeps it interesting.
Scale yourself while developing others
If you never step back and create a gap, there will never be real space for someone to step up.
Behind the request for speed lies the physics of first going slow
The first pull off the ground is the hardest. You are working against an object at rest. It will never be heavier than in the beginning.
How Farming Can Help You Frame the Solution
A lively, metaphor-packed conversation with the NYC Salon community.
Do Leadership is the new Thought Leadership
Success will come, I promise—but it’s not the vehicle. It’s the outcome. And if I’m honest, it’s not nearly as awesome as you think it is. The most fun I’ve ever had is when I am materially and positively impacting people and the world.
Intuition, Ingenuity, Small Data
The noisier the world becomes with notifications, emails, spreadsheets, link bait, things you should (and shouldn’t) be watching, reading, eating, drinking, and just generally doing… the more I find myself reaching for things that allow me to be focused, go deep, and get lasting results.
Beyond Data Science: Advancing Data Literacy
My dream, though, is a future of More Meaningful Data. And for that, we need: the data gathered and parsed; the data analyzed, interpreted, and contextualized; and the data visualized, narrated, and made accessible.
Rent, Stream, Experience.
In addition to basic human psychology driving a preference for experiencing over owning, the Internet age has produced accessibility, impermanence, and rapid change like no other moment in time.
I’m Joining a New Venture in 2013!
But before I look forward, I want to pause and reflect briefly on a few of the many amazing things that this chapter has contained.
![We won AdAge Small Agency of the Year Gold for the Southeast Region [2012]](https://images.squarespace-cdn.com/content/v1/671e92dea779f563ce684aac/1755376923471-B2RE5ZXD0VL4WYHOJXIQ/JESS3+-+AdAge+Small+Agency+of+the+Year+-+Southeast+Region+-+2012.jpg)
We won AdAge Small Agency of the Year Gold for the Southeast Region [2012]
So many years in the making and so many have contributed to this moment -- makes the victory a sweet one.
The Entrepreneur's Dilemma
Overcoming obstacles, haters and challenges is hard. Biting your tongue when all others are flapping theirs is hard. Keeping your head about you while all others are losing theirs and blaming it on you is hard.
I will be talking Big (Beautiful) Data at Stanford
My topline POV: the investment to date in the big data space has been "under the surface"… [this] focus means that the financial, recruitment and even cultural emphasis on engineers comes at the cost of top designers.
Leaving D.C.
I shared things in the comments in 2025, above, that only a few people knew at the time in 2012. I have enough distance from the experience that I can share this information neutrally - whereas before, it would be highly charged (for me and likely for others).
Awarded Washington Life’s “Young & The Guest List” (2012)
And to my family, thank you for teaching me the value of not just hard work, but also teamwork — and for putting up with not hearing from me for weeks on end while j3 and I were building in the early days, and again in the later days when things started to catch fire [in a good way].
Grace under fire
If I can find comportment and calm in these fiery times, if I can keep my head about me while all others are losing theirs, then I can live to gracefully fight another day.
A Different Kind of Occupation of Wall Street
The SA 500 companies are building businesses that are disrupting the marketplace and, therefore, the stronghold that the “old guard” has on things like information, data and communications.