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