colin f lane

Failing in the New Year

create: 20230214

modify: 20230216

thoughts on failure as aspirational exploratory feedback mechanism

Chasing Failure

My company brought in motivational speaker Ryan Leak. He was really good, I recommend him. Despite the too-slick aesthetic.

His basic imperative is to "chase failure". He maintains that only by chasing failure do we realize more opportunities than we ever would by playing it safe. This is an inspiring message. He was on the Queen Latifah show. He met Kobe. He tried out for the Phoenix Suns.

"Nothing ventured, nothing gained"; "If it doesn't kill you, it'll make you stronger"


I was discussing the Ryan Leak talk live with my teammates, and one of them linked to this post of Taleb's. He suggested that we enshrine "maximizing positive convexity" as a team goal. How cool is that?

Creating Luck

In his opening paragraph, Taleb writes, 'The discourse and controversies focus on the role of luck as opposed to teleological programs (from telos, "aim"), that is, ones that rely on pre-set direction from formal science. This is a faux-debate: luck cannot lead to formal research policies; one cannot systematize, formalize, and program randomness.' The word "luck" struck a chord.

Earlier that same morning, I had stumbled upon, via hn, this post. First sentence: 'My entire worldview changed when I realized that luck can be created.'

swyx summarizes thoughts of James H Austin and others, in laying out Four Kinds of Luck:

Life Strategies

Something about the representation of these different lucks (which conceit itself recalls The Long Ships) in a classic quadrants schematic immediately called to mind Scott Alexander's discussion of fast & slow life strategies. And, of course, Albion's Seed.

Can we productively map {Antagonistic / Exploitative; Seductive / Creative; Caregiving / Prosocial; Skilled / Provisional} life strategies against {Dumb; Active; Prepared; Extreme} lucks?


Getting back to Failure. My company's CEO emeritus used to like to say, "Fail Fast". Iterate, innovate. Try things out and move on.

Possessing wider currency is the SV hacker ethos, "Move Fast and Break Things".


Pseudo-randomly, I stumbled upon a since-forgotten post, linking to a post of Gwern's, about socks. (I was not disappointed. Gwern does reference the scene from Harry Potter in which Dumbledore tells Harry he envisions himself receiving socks for Christmas.) Gwern has unexpectedly run out of socks. This triggers a typically far-ranging and multi-faceted discussion. What caught my attention was the section on Exploration, in which Gwern writes, 'Underuse of System II particularly manifests as over-exploitation/​under-exploration, where large potential improvements are foregone because of a lack of a habit or other systematic factor which would trigger exploration.' Gwern was over-exploiting and under-exploring the sock drawer.


We went to the grocery market for dinner ingredients and to eat lunch. On the way home, in the car, we listened to NPR. The story was about popular music, and research into why some musical artists realize no "hits"; others are "one-hit wonders"; and those few whom our culture most celebrates possess an ability to consistently generate "hits".

The business professor whose book was being advertised maintains that the secret to success in popular music boils down to "explore first, then exploit". Be creative, realize initial success, then double down, and milk it for all its worth.

Organizational Science

Subsequent digging turned up what I believe to be the ur-paper, March: Exploration, Exploitation. It was mentioned in passing on NPR.

I read March's 1991 paper in down moments at work over the course of several days, and it helped crystallize a lot of "thoughts" I was having. Particularly around convexity, and diversity. Around striking off into the jungle in search of fabulous treasures. You stay here, guard the pack mules.

Mega Projects

The Journal carried a piece one weekend about a[nother] business professor whose expertise is "mega" projects. Works costing >$1B. Big deal. Evidently, most big projects fail. The professor has made a career studying these big projects, consulting on them, and divining why they are apt to fail.

A teammate of mine happened to also read the piece, and he shared with me his major takeaway: "Think slow, then act fast."

see also: mise en place

Be Prepared

A couple years ago Julie Galef's The Scout Mindset was making the rounds. I read Scott Alexander's review.

Galef argues that we ought to stop acting like Soldiers, and start acting like Scouts. Rather than zealously fighting to defend what we believe, broadening the horizons of what we know.

My question is: can we map this Scout-Soldier schematic to that of Explore-Exploit? Can we say that Scouts Explore, and Soldiers Exploit?

Exploration and Leadership

Finally, Derek Sivers writes that 'explorers are bad leaders'. What about Ponce de León and de Soto?!

Pick Up The Phone

Steven Jobs on Failure

But also, Alan Watts: 'If you get the message, hang up the phone.'