From Team of Teams by General Stanley McChrystal
Preface
Almost five years to the day of the COVID lockdown, America got rocked by another Black Swan, but it’s not as if everything was just fine between these two landmark moments. The past half-decade has been marked by perpetual uncertainty, so this newsletter aims to use this moment to try and learn more about it and how it can be positively harnessed.
Fewer Rocks to Which We Can Hold
“There is, then, the feeling that we live in a time of unusual insecurity. In the past hundred years so many long-established traditions have broken down—traditions of family and social life, of government, of the economic order, and of religious belief. As the years go by, there seem to be fewer and fewer rocks to which we can hold, fewer things which we can regard as absolutely right and true, and fixed for all time. To some this is a welcome release from the restraints of moral, social, and spiritual dogma. To others it is a dangerous and terrifying breach with reason and sanity, tending to plunge human life into hopeless chaos. To most, perhaps, the immediate sense of release has given a brief exhilaration, to be followed by the deepest anxiety. For if all is relative, if life is a torrent without form or goal in whose flood absolutely nothing save change itself can last, it seems to be something in which there is "no future" and thus no hope.
Alan Watts - The Wisdom of Insecurity
“Ayala-Hurtado found that the graduates from both the U.S. and Spain described themselves as stalled or stuck. She refers to these feelings as “perceptions of ‘expectational liminality’” arising from the disconnection between what the respondents expected their collegiate experience to lead to and what it actually did lead to. “Many respondents described the experience of being stalled or paused as a manifestation of the tension between their insecurity and their expectations of transformation and progress based on their status as college graduates,” Ayala-Hurtado writes. “Respondents understood themselves as having transitioned from being college students but without having attained the lives expected of college graduates.”
Princeton
Less Time with Current Employer
“The median number of years that wage and salary workers had been with their current employer was 3.9 years in January 2024, down from 4.1 years in January 2022 and the lowest since January 2002, the U.S. Bureau of Labor Statistics reported today.”
US Bureau of Labor Statistics
Choose to Do the Tougher Thing
“The big thing in my own experience is that the bravery is to not just go with a habitual pattern because it’s usually fear-based. Instead, stay present and open so you can connect with your underlying strength, which is called basic goodness. The seductiveness of habitual pattern is a false security, but we wouldn’t follow it if we didn’t think it was going to bring us some comfort or relief. Still, habitual patterns just keep us stuck in the same rut, so the courage is to actually realize you have a choice and choose to do the tougher thing.”
Pema Chodron
Soccer Moms Eliminate Trial and Error
“The biologist and intellectual E. O. Wilson was once asked what represented the most hindrance to the development of children; his answer was the soccer mom. He did not use the notion of the Procrustean bed, but he outlined it perfectly. His argument is that they repress children's natural biophilia, their love of living things. But the problem is more general; soccer moms try to eliminate the trial and error, the antifragility, from children's lives, move them away from the ecological and transform them into nerds working on preexisting (soccer-mom-compatible) maps of reality. Good students, but nerds--that is, they are like computers except slower. Further, they are now totally untrained to handle ambiguity. As a child of civil war, I disbelieve in structured learning . . . . Provided we have the right type of rigor, we need randomness, mess, adventures, uncertainty, self-discovery, near-traumatic episodes, all those things that make life worth living, compared to the structured, fake, and ineffective life of an empty-suit CEO with a preset schedule and an alarm clock.”
Naseem Taleb- Antifragile
Perhaps the above is another way to think about the “Dirt is Good” idea and how to inject more adventure into our lives and our children’s lives.
Kevin Kelly on the Future of Uncertainties
From impossible to inevitable. We can’t forecast them. But we can group our “knowns” using the Rumsfeld’s matrix (see below). Use Scenario Planning to plan for the future, so aren’t surprised and can prepare for them.
Frank Knight on Risk vs. Uncertainty
“Frank Knight was an idiosyncratic economist who formalized a distinction between risk and uncertainty in his 1921 book, Risk, Uncertainty, and Profit. As Knight saw it, an ever-changing world brings new opportunities for businesses to make profits, but also means we have imperfect knowledge of future events. Therefore, according to Knight, risk applies to situations where we do not know the outcome of a given situation, but can accurately measure the odds. Uncertainty, on the other hand, applies to situations where we cannot know all the information we need in order to set accurate odds in the first place.”
MIT
Risk has odds, uncertainty doesn’t, but Annie Duke below- suggests we need to apply effort to shift uncertainty to risk.
Don’t Accept Unknown Probability
“This knowledge of our incomplete knowledge should fire us up in two ways, Duke strongly believes – to carry out a “really good internal auditing” of what we do know, and to become more efficient at working out what we don’t. “One of the drivers here has to be a total unwillingness to accept that a probability is unknown,” adds Duke. “As soon as you do not accept a probability is unknown, that puts the quest for better knowledge in the forefront, because it is the better knowledge that will allow you to start narrowing down those probabilities. You just have to be comfortable with the fact – and this is true in poker as well – that there is almost never going to be a precise probability, that it is still going to be a range.”
Schroders Podcast Interview with Annie Duke- Poker player
The Knowns Matrix after Rumsfeld
Kevin Kelly mentioned this in the video above as a way to organize the future
“Play around with the things that you’re interested in to see what direction to take next. Begin by delving into your interests and passions, whether they’re hobbies, side projects or areas of curiosity. Take the time to play around with different possibilities and avenues, allowing yourself the freedom to discover new opportunities that resonate with your values and aspirations. On top of that, be open to serendipitous discoveries along the way. While it’s essential to have a general direction in mind, don’t limit yourself by preconceived notions or rigid plans. Embrace the unexpected and be receptive to opportunities that may arise unexpectedly. Whether it’s attending unusual networking events, volunteering to gain new knowledge, or exploring exciting hobbies that you’ve always wanted to try, each experience contributes to your journey of career reinvention.”
Herminia Ibarra- London Business School
Being open to the unexpected and playing with possibilities is a way to break free of the limits and limitations you place on yourself.
Thriving in Uncertainty
“The leader who thrives in uncertainty doesn't eliminate it—that's impossible—but transforms it from a paralyzing force into a navigable landscape. By creating islands of clarity in seas of ambiguity, they give their people something solid to stand on while facing the unknown. In doing so, they don't just help their organizations survive uncertainty—they position them to capitalize on the opportunities that uncertainty inevitably creates.”
Rita McGrath
What are the islands of clarity that your leadership provides to help give people something solid to stand on while facing uncertainty?
Bezos on Two Types of Decisions
“Some decisions are consequential and irreversible or nearly irreversible – one-way doors – and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that – they are changeable, reversible – they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups. As organizations get larger, there seems to be a tendency to use the heavy-weight Type 1 decision-making process on most decisions, including many Type 2 decisions. The end result of this is slowness, unthoughtful risk aversion, failure to experiment sufficiently, and consequently diminished invention. We’ll have to figure out how to fight that tendency.”
Letter to Amazon shareholders 1997
Is your organization capable of making fast decisions that can be reversed?
“We need to be doing strategy much more real-time. It needs to be more dynamic, guided by audacious questions at the top level, but also actualized by people working much closer to the front line. It’s a question of how we pursue our objectives. Rather than a plan that looks like a game of chess or linear programming, we have to accept that the way we progress will be more like rugby: a series of forward, backward, and sideways moves, and accepting that a number of the moves we make will fail—this is where the term imperfection comes from. It’s also actually being okay with that, and making sure that we don’t punish teams for failure, especially where those failures are modest in terms of the total outlay, and are reversible.”
Charles Conn- Author of “The Imperfectionists- Strategic Mindsets for Uncertain Times”
Are we OK with failing as long as we learn?
No Invention Without Not Knowing
“Without the scanning processes engendered by not-knowing, without the possibility of having the mind move in unanticipated directions, there would be no invention. […] The combinatorial agility of words, the exponential generation of meaning once they’re allowed to go to bed together, allows the writer to surprise himself, makes art possible, reveals how much of Being we haven’t yet encountered.”
Daniel Barthelme
Go Somewhere New
“IN LIFE, we’re often pushed to see mistakes as failure. to see uncertainty as as bad thing. and control as a good thing. But in art… uncertainty and error are the only PATH to get to somewhere you’ve never been before.”
Brian Eno
Open the Door to the Unknown
“Leave the door open for the unknown, the door into the dark. That’s where the most important things come from, where you yourself came from, and where you will go.”
Rebecca Solnit
The most interesting and important things start in a state of unknown
“Keats coined the term negative capability in a letter he wrote to his brothers George and Tom in 1817. Inspired by Shakespeare’s work, he describes it as “being in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.” Negative here is not pejorative. Instead, it implies the ability to resist explaining away what we do not understand. Rather than coming to an immediate conclusion about an event, idea or person, Keats advises resting in doubt and continuing to pay attention and probe in order to understand it more completely. In this, he anticipates the work of Nobel laureate economist Daniel Kahneman, who cautions against the naïve view that “What you see is all there is.” It is also a good idea to take the time to look at matters from multiple perspectives. Shakespeare’s comedies are full of mistaken identities and misconceptions, including mixed-up genders. Keats reminds us that we are most likely to gain new insights if we can stop assuming that we know everything we need to know about people by neatly shoehorning them into preconceived boxes.”
The Conversation
Anthony Gormley’s “Passage” - A sculpture that invites people to test themselves with the unknown
“So why try to predict the future at all if it’s so difficult, so nearly impossible? Because making predictions is one way to give warning when we see ourselves drifting in dangerous directions. Because prediction is a useful way of pointing out safer, wiser courses. Because, most of all, our tomorrow is the child of our today. Through thought and deed, we exert a great deal of influence over this child, even though we can’t control it absolutely. Best to think about it, though. Best to try to shape it into something good. Best to do that for any child.”
Octavia Butler- A Few Rules for Predicting the Future
Our thoughts and predications about the future, shape the future.
“Our digital lives are mediated through words, whether the tumult of Twitter or the doom-scrolling of Reddit, the ever-present ping of texts and the flux of Facebook. Yet this is an estimably different experience than the immersion in Wuthering Heights or Moby-Dick, Mrs. Dalloway and Ulysses. What’s been sacrificed is not reading in the most prosaic sense, but the particular experience of a certain type of reading, perilously endangered among all of us attracted to the alluring siren-call of the smartphone ping. Readerly “flow” allows for a submersion in another way of being, an expansion of possibilities and consciousness.”
Ed Simon-Lithub
Book reading is an act of embracing uncertainty and being able to experience an expansion of possibilities
“….we absolutely need to allocate some effort towards pursuits that are simply interesting in their own right, even though we don’t yet know or can even try to predict what the payoff might be. In effect, by investing in some pursuits simply because they’re interesting, we are collecting stepping stones that may end up leading to something useful or valuable in the future. So collecting such stepping stones is its own virtue.
Kenneth O. Stanley writing in The Big Think
True Creativity is a Succession of Acts
“While on a family vacation to Santa Fe in 1943, Land took a photo of his 3-year old daughter. She innocently asked to see the picture he had just made, which of course was impossible. Her innocent question stuck with him, and as they walked around town, he set his mind to solving the problem. According to Land’s own recollections, within an hour he envisioned the camera, the film and chemistry required. That evening, he sat with a friend and described, “a dry camera which would give a picture immediately after exposure.” His decades of experience and knowledge in one area had led him to a revolutionary discovery in another. According to Land, “True creativity is characterized by a succession of acts each dependent on the one before and suggesting the next after. This kind of cumulative creativity led to the development of Polaroid photography.”
Musee Magazine on Edward Land- The Inventor of Polaroid photography
Cumulative creativity via stepping stones or a successions of experimental/interesting acts can take you to an entirely new place.
“This bleak vision of the present points though to the potential for a more progressive future. The longing for self-improvement reveals persistent and, yes, “desperate” desires for bettering our individual and collective existence. Further, the various experiments with self-improvement undertaken by Cederström and Spicer uncover how these radical desires can be pursued through local experimentations with different lifestyles. Rather than trying to save our souls, there are real opportunities to feel radically empowered through introducing radical principles of democracy and equality into diverse areas of our existence. While full-scale revolution may not be immediately on the horizon, it is never too late to try and “occupy” your own life. Doing so can provide people with the opportunity to feel radically empowered in an age where this may seem impossible or futile. Yet this small slice of revolutionary optimism requires jettisoning demands for optimization and instead embracing an ethics of openness and experimentation. We need to stop trying to be our best selves and instead find ways to improve how we live together.”
Peter Bloom’s Review of Desperately Seeking Self-Improvement by André Spicer and Carl Cederström in the LA Review of Books
Below is almost a response to the above.
“If we want to shift culture, we probably need to slow down and have some conversations we’re not having. We have to be willing to turn and face our practices, use what we’ve learned in our first and second spaces, and create a fun and creative space. I’ve been having game nights. I’ve been doing songwriting circles. All these people, trying to change the world, and I just invite them over and on random nights, usually no notice at all, to just come play some games. And it’s been so healing. To have that space, especially over the course of these last difficult years where it can be hard to get through the day. I know others are struggling as much as I am, in the existential swirl of it all, so it feels good to say, you know what we need to do? Laugh together. Letting ourselves play feels really important to me.”
Adrienne Maree Brown- Orion Magazine
How can we create space and invite others to play?
Whitney Museum
Sol LeWitt - Art wth Instructions
“LeWitt once said, “Each person draws a line differently and each person understands words differently.” Because of the human factor in the process of art making, essentially every “copy” of the wall drawing, even from the same set of the guidelines or the same hands, still differs from the ones before. This adds a layer of uncertainty and drift, as well as a possible divergence between the expected result and the eventual end product. It also distinguishes each “copy” from all of the other copies so every new exhibit of the wall drawings is still a unique one.”
Chroma- MIT Student Magazine
Le Witt’s brilliant idea of instructions ensures variance within an ordered theme
John Cage on Chance Operations
“In the early 1950s I began using chance operations to write my music, and after I became acquainted with the I Ching (The Chinese Book of Changes), I used it extensively. I apply chance operations to determine the frequency, amplitude, timbre, duration and placement of different elements in my music. The chance operations allow me to get away from the likes and dislikes of my ego so that I can become attentive to what is outside of my own psychology and memory. By using chance operations I am accepting what I obtain. Instead of expressing myself, I change myself. You might say I use chance operations instead of sitting meditation practice.”
Inquiring Mind
Cage finds a guide to creating chance.
Finally……
“Though we yearn for clarity, the universe whispers caution. If you listen closely to those who’ve made it, you’ll find what many of them want most is to return to the unknown. Kurt Cobain said he wished he could’ve stayed forever in the moment right before Nirvana got big. Virgil Abloh believed no piece mattered more than having the freedom to make the next thing.
The destination isn’t the goal. The unknown is.”
Yancey Strickler- Co-Founder- Kickstarter and founder- Metalabel
great format