The Breaking Smart AMA, Part 2

Whew, that was exhausting, but I finally worked through the backlog of AMAs. I have a few straggler questions to respond to, but those seemed either repetitive in relation to the ones I'm sharing here, or not of broad interest. I'll respond in person to the remaining ones in a day or two.

Anyhow, thanks everybody for playing. This was partly a load-testing experiment to figure out the volume of Q&A I could handle, and I'm definitely not going to be doing this too often. Tackling 70+ questions in 2 sittings is quite the workout.

In other news, we just hit 100 sign-ups for the Breaking Smart Season 1 Workshop in the first week. Thank you all. I just uploaded the second session lecture videos.

For those of you still intending to sign up, last week's code EARLYBIRD will work till midnight (US Pacific) tonight and get you 50% off. If you miss the deadline, well, you'll have to use the code NOTSOEARLYBIRD and settle for 25% off. This will work till midnight next Friday (Feb 8). Then it will ratchet down further.

Now for the AMAs. And one TMS (Tell Me Something).

Finishing up the 2019 bout of Frasiering

In a non hierarchical, matrix oriented world, how should groups (teams, companies, countries) make a conscious decision to stop "kicking the can down the road" and proactively start to tackle a particular problem.  What are the signs and indicators that should tell a team to take action? -- Tom Broderick

I have never seen "groups" effectively solve a problem like this. It's a disguised form of a tragedy of the commons. The only way out is for an individual with enough political capital to make some "benevolent dictator" moves to break the gridlock. No amount of fiddling with structural aspects will solve the problem. When terms like "matrix management" and "cross-functional" become embedded in a stalemate conversation, it is no longer something that can be solved at a group level. An individual has to make some unilateral hard calls and then burn political capital to get others to follow their lead. Only individuals can precipitate the kinds of crisis that can break the stalemates that teams and groups can get themselves into. And vice-versa (though you didn't ask about that).

If someone gives you a decent amount of capital ($1Billion+) where only string would be to build resilience of the human condition / Global Social Computer in the Cloud against being bricked by a mass flippage of bozobits. What kind of team would you assemble and what would you build? -- Varun Adibhatla

I think this sort of thing is what people like the Kochs, Mercers, Soros think they are doing. I think it's dangerous to define and pursue challenges at this scale with bounding boxes defined by financial capital and "assembling people" into world-changing missionary tribes. Money is for the complex but more narrowly bounded problems of the sort that the Gates foundation for example tries to solve. If you're aiming for something as broad and ambitious as "build resilience of the human condition", money is the wrong starting point. Historically it has played a role in increasing resilience (basic research funding for say healthcare or food security). But for what you're talking about, I think "people assembled with money" is a part of the problem rather than the solution.

What’s the optimistic case for how software can eat climate impact and help win the war to decarbonize in time? -- Patrick Atwater

I think that ship has sailed. We are not going to "decarbonize in time." We're going to gradually normalize climate change, one bit of weirdness at a time. I think software will play a huge role in eventually decarbonizing and helping complete the energy transition (both directly, by enabling clean energy etc, and indirectly by substituting low-energy behaviors like video-conferencing for energy-intensive ones like travel) but it won't be "in time."  I think it is time to pivot to asking how software can help as many people as possible weather the unavoidable impacts. Mass migration is a big one. An example of the kind of idea I'd like to see pursued is this "Internet of Migrants" idea I did a twitter thread about.

Have you read any Tom McCarthy? Repetition, buffering, and being human in a software eaten world. -- Passepartout

No, thanks for the recommendation!

You've written in the past about the rise of cities. As larger state governments lose leverage, cities will break off and innovate. I'm the biggest business podcaster in Pittsburgh, PA. Am I unwise to try and "break out" of that box? Or should I double down on my geographic edge? -- Aaron Watson

Nice, congrats on your podcast success. I think the "city state future" hasn't been properly harmonized with the "digital future." It's like there are these 2 huge trends towards devolving geographic power to cities, and diffusing digital power via strong zeitgeist currents and vortices on massive global platforms. These are like the quantum mechanics and general relativity of sociology in our times. And just as physicists haven't figured out how to really put the two together in a grand unified theory, none of us has managed to put together the city-state future and the digital future in a compelling unified vision. I mean, the novels of Neal Stephenson are fun to read and all, but when you get right down to it, nobody knows how these two trends will interact.

I think the best strategy for somebody with a foot in both worlds, as a city-focused podcaster like you would be, is to pay attention to both worlds independently and not try to force a false synthesis. Where something makes sense both as a bet on Pittsburgh and a bet on digital futures, it's easy. When the two are in conflict, I don't think you can expect to find general grand-unified theory answers. Maybe Pittsburgh becomes the 2nd biggest city in the world for some weird new global online business sector like fidget spinners. Should you bet on that development in a Pittsburgh-first way or a fidget-spinners first way (which might mean focusing on city #1)? There won't be one right answer. You'll have to take it case by case.

Any good tips on how to make relationships with interesting people? I'm living in a new city and in need of mentors and friends with interesting philosophies of work and life to learn from. Not just smart people with similar interests--interesting people. -- Drew Schorno

I am the worst person to ask this question when it comes to meatspace, since I've managed to live in half a dozen cities with an unbroken record of being spectacularly bad at this. If you're talking online, however, I'm a blackbelt at that. My answer for the online version is to simply produce and publish interesting things yourself. Interesting attracts interesting. Maybe you can focus it to be more relevant to the city you're in, but I have no idea how to do that. My own style of producing stuff doesn't seem to stay within any such nice boundaries.

Your Brain-Bicycle-(Rider-Fit) article resonates with me! I'm stuck in an uphill ride wobbling along (the bicycle that I've chosen may not be suitable for me) how do I get competent in negotiating and structuring deals? -- Weiyi Yang

I'm blanking on where I wrote about that metaphor, but am happy to take credit for it :) I assume you're doing the obvious things relating to your challenge, like finding books and classes on negotiations and deal-making. So let's go beyond that a bit.

When it comes to loose touch-and-feel type skills like negotiating and structuring deals where you're trying to add some hard structure to squishy stuff, I've found that the only way to really learn is to watch a more seasoned expert do it live, and pick up on their tricks. It's a form of close observation. What conversational tactics do they use? How do they break out of predictable objections? Do they use specific phrases? And of course you have to get good at studying the "hard" side -- parsing deals and contracts, learning to read legalese well enough to not let lawyers bullshit you, etc. There's plenty of literature and training available on this subject. Paradoxically, the more complex it gets -- huge billion dollar M&As for example -- the easier it is in some ways, because the sheer size and risk of the activity forces a lot of professionalism, well-defined role boundaries, formal protocols, and emergence of best practices. It can be harder to negotiate and structure a deal about play time with a 5-year-old.

How do you know when your "bicycle" doesn't fit? When you sense that your natural "literacy" in reading what more experienced people are doing is lacking, like there's whole levels of the conversation you're missing or misreading, and can't predict outcomes. It seems like black magic. Normally, any non-technical skilled practice should slowly become legible to an intelligent observer with the right aptitude, with time. But if it doesn't, you may not have aptitude for it.

Are you consulting for any projects that involve crypto/blockchain/Bitcoin? Do you have insight into which parts of the cryptosphere are cargo cults?  -- Stefan King

I've done a small amount of consulting on crypto projects where there are aspects that don't have much to do specifically with crypto itself, but am by no means particularly well-versed in how the sector is shaping up. I have no particularly good instincts for picking the winners and sniffing out the cargo cults. I'm not particularly bad at it either. In general, I don't trust myself to do the required thinking here myself. Instead, I rely on good friends who know a lot more than me at both the technical and business levels.

Have you ever played a JRPG? If so, which one, and what did you think of it? -- Ellen Kaye-Cheveldayoff

No, I'm afraid I don't even know what a JRPG is. I had to look it up :)

What was the most significant piece of advice you received early on in your career? Did it have a "eureka" like effect or were its benefits realized over time? For context, I am a recent college graduate working full time at a nonprofit where I interned in college, but am dissatisfied and trying to plot out my next move. -- Anonymous

I'm bad at asking for, and taking, advice in general. I'm much better at dishing it out confidently :) I did recently write a post about my PhD advisor who recently passed away, and the things I learned from him. No eureka effects, however. I don't trust advice that causes that kind of sudden red-pill effect. I prefer deceptively simple-sounding advice that takes years to sink in.

How do you think you would've handled the modern dating app culture, had you been dating today? -- Nicolas Lawler

Probably horrifyingly badly. I have no idea how young singles manage to navigate that world.

What’s your personal recommendation on blogs & books for self development on financial literacy? -- Seun Awoyele

I don't think I've consciously worked on "self-development" in like 15 years. David Allen's Getting Things Done was the last significant bit of self-development literature I internalized, and that was 2002-04. I don't trust the idea of "developing" yourself, especially past 30. Before 30, it kinda doesn't matter what self-development ideas you consume. Pick what resonates with you, internalize what feels right, trust your gut. It's not as important as it seems at the time.

I trust the idea of least-effort paths and enlightened mediocrity much more. I think it's a mistake to "optimize" the self. The older I get, the more wisdom I see in letting life happen to you, with your self evolving in a more natural way, as a result of actually dealing with the specific challenges you face. Your life does not have to be a development project. It's not a developing country or an iPhone with versions. Instead of trying to "develop" my "self", I try to navigate situations in hopefully imaginative ways. Solve your problems, not your "life."

All my financial literacy is second-hand and not worth either bragging about or turning into advice for others. Ultimately, finance does not interest me. I try not to be too dumb about it, but it's not a game I feel like getting more literate at.

Hume's problem of induction, Godel's incompleteness theorems, the free-will/determinism paradoxes, the lack of explanations for emergence - Do they all point to the same thing? (that consciousness is expressed through brains but not created by them and that our current language systems don't know how to fully study it). -- Zat Rana

Kinda cute how you snuck in a presumptive consensus explanandum there, begging your own question to some extent :) I don't know if they all point to the same thing, but language systems certainly seem like an inadequate tool for studying any of these imponderables or their "pointing" propensities. I don't know that "study" is even the right verb to apply, since these things you're gesturing at precede epistemology. Similarly "pointing" assumes a relationship of reference between two distinct things, which is assuming a lot at this level of philosophy. To study or point is to "do" something. Some would argue that our relationship to these things is a matter of being rather than doing. There are mystics around who are confident that their private experiences qualify as truer ways of being with these things than "studying" them per se.

To cut to the chase, I used to have beliefs and positions about these things. Now, mostly I don't, since I find that holding positions doesn't actually change anything for me in relation to these imponderables.

How do I become a member of the cryptobourgeoisie? -- Steven Miller

Buy some crypto, HODL and pray. You've got as good a chance as anyone else. The only way to make it more than a passive casino bet for yourself is to learn the technology and get involved in building the stuff.

How do you decide how much money you need? Also, how do you know how much you must get paid? -- Tejesh

I've managed to get through nearly 45 years of life without ever asking either of these questions, so my answer is, you don't need to decide or know. I've never liked asking finance questions in the abstract. If there are concrete numbers I need to think about, they generally fall out of other considerations like rent or retirement savings or stuff I want and have to pay for, like sandwiches or a car. I like the saying "money is a problem to be solved." I take it to mean that in the process of deciding what to do in other parts of life, inevitably money comes up as a variable in the mix, and you need it to do certain things. "Solve" the money problem one instance at a time. Unless you're in finance or want to get rich for the sake of getting rich, money is not something that's productive to think about front-and-center for most people. If you want to take on money more directly, you should be in finance.

If the purpose driving the last era was growth, would you agree that the most beneficial purpose for our next (and current) era is health or balance, or do you believe it is something else? And what do you believe is required to shift society to this new purpose? -- Katie Levine

I don't believe in such collective "purpose" conversations because that's never been how the world has worked. And I certainly don't believe in trying to "shift" society. Thar be toxic ideological tarpits. The "purpose" of an era is something that's evident with hindsight with tasteful historical perspective. And it's always something of a fiction imposed on the emergent motivational patterns of billions of people acting at various levels of coordination. Right now, in 2019, each of us will do what we think best at whatever scale of coordinated agency we act at, and we'll know what it all means when we are unfrozen from our cryostasis chambers in 2234 and the history orientation guide tells us what the 21st century was all about.

How many 2x2 matrices do you make before you stumble across one that is insightful? Or - do you have insight, then see if you convert it to a 2x2? -- Todd Nief

It's the latter 99% of the time. And generally, it's not an explicit attempt to convert an insight into a 2x2, but the insight itself striking my awareness in a half-done 2x2 form that I then have to tweak to get it right. I suspect this is how it is for most people. Making random 2x2s in search of an insightful one doesn't seem like a workable process to me.

I am attempting to catch up on breakingsmart and ribbonfarm, do you have a "best of", most popular, or preferred reading order? -- Peter Williams

There's a New Reader page for ribbonfarm, but for Breaking Smart, besides the Season 1 essays, there's no curation of the newsletter contents. I should probably get on that.

Been thinking about Cal Newport’s idea of ‘career success comes from having rare and valuable skills’ recently. (a) What are your thoughts on this idea? (b) What skills will be rare and valuable in the future? -- Daniel Thomasan

It's certainly one way to have career success. It's not the only way. There's Scott Adams' idea of having two relatively not-rare skills that are rare in combination for example (in his case, drawing skill and a sense of humor). And then there are non-skill-based approaches to thinking about career success. And then there's thinking about life in terms other than "career success." In general, I'm not exactly the greatest fan of Cal Newport's advice, tbf. It sort of works for people on strongly credentialist life paths, but is of limited value outside such paths. I wrote a newsletter issue riffing off of (my skepticism of) his thinking a while back:

_I've been thinking about this bit from "The Key to Act Two":

"Then there is a bit of an intermission of about 2 years, which for most people is a very confusing, unscripted time, like an inter-airport transfer in a strange foreign city with sketchy-looking shuttle buses that you are reluctant to get on, and long queues at the bathroom."

Question: What specific advice would you have for someone in this intermission who is pretty thoroughly traumatized but not sure if she's learned enough from it, more made the right connections, to become a key? -- Anonymous_

I think the best thing to do if you really are in this stage (and it's easy to mistake a bout of depression for an Act I to Act 2 transitional intermission), is to lower your standards, embrace enlightened mediocrity, and focus on living well rather than "learning." Don't close your mind to learning, and accept the challenges and new experiences that life will continue to throw at you, but "learning" and "preparing" for life is no longer task #1. Task #1 is actually just surviving with grace and living life. Stop trying to win, work on continuing the game. Sometimes that's one day at a time, sometimes it's one year at a time. The life-long learning, hustling, stress-driving pressure we get from society is somewhat necessary (at a cost) in Act 1, but if you let it keep riding you into Act 2, it's mostly masochism. There's a point past which it makes more sense (and better mental health) to inhabit the life you've built for yourself as gracefully as you can, rather than trying to keep raging and storming to extract more from the universe.

One thought I've found useful for this lately is: you don't need permission to exist.

Why don't people think big enough? Where do your large scale thoughts expressed in your writing come from? As an ambitious thinker, how can I better express my big ideas and get started building them when I find it difficult to see the small, more actionable beginner stuff? -- Elijah Claude

Hmm. I don't agree that people don't think big enough or that it's a particularly good thing to try and do. You should think about interesting things, with enough imagination and courage to let a thought take you as far as it wants to take you. Some thoughts want to take on huge galloping rides across the universe, other thoughts want to take you 3 steps to pay attention to one small thing. I think it is important to not get attached to the scale of thoughts or actions. One trick to do this is to imagine thoughts and actions as having all the agency, and you having none. The thought decides how it wants to be thought. The action decides how it wants to be performed. Your job is to get out of the way and let the thought or action "use" you as its instrument. Be the medium, not the message or the agent.

Ambition is not bad per se, but it can exhaust itself. It is like running on fossil fuels of the psyche. It can also work into a box it cannot work itself out of. In a way, ambition itself is one of the thoughts/action patterns that can possess you, and in my experience, not one that takes you on particularly interesting rides. Things we often describe as "ambitious" from an outside perspective are often the result of being possessed by thoughts and actions that feel necessary and natural rather than "ambitious" to the people who serve as their mediums. The thoughts and actions I find myself most fascinated by (both my own and those of others) are those that are the result of the human ego stepping out of the way and letting the thoughts and actions flow on their own. I suppose I'm a Taoist or something.

Do you use randomness for any of your processes (e.g. dice, decks of cards, or anything else)? What about contrarian thinking? Oh also, I believe you visited Boyd’s papers at Quantico. What did you think? Which papers and books did you read? -- Chris Butler

No. Life is plenty random enough for me, and contrarian thinking for its own sake seems kinda dumb to me. Think interesting thoughts, and sometimes they are contrarian, other times they are not.

I didn't spend much time at the archives. We were there for like half an hour as I recall. I browsed several papers on Network-Centric Warfare (NCW) with Boyd's critical annotations in the margins. As I mentioned in an old newsletter, one thing I took away was the idea that he didn't like tight synchronization.

How would you innovate public restrooms? Improving cleanliness metric -- Anonymous

It's actually among the most important problems in the world. I have Rose George's book The Big Necessity, on my to-read pile. No clever thoughts besides the assessment that it's a very important problem.

TMS from Matt Maier

I co-founded the humanist church
All of the meaning and community, none of the supernatural.
My co-founder Andrew does regular sermons on how to be better

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