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Summary of How to Have Impossible Conversations

This is raw outline of Peter Boghossian and James Lindsay’s fantastic book on how to have tough conversations that potentially change minds.

Focus first on instilling doubt rather than changing beliefs.

Basics

  1. Goals – why are you having the conversation?
  2. Partnerships – be a partner, not an adversary
  3. Rapport – build the relationship
  4. Listen – talk less, listen more.
  5. Delivering messages does not work. Conversations are exchanges, not debates. Deliver a message only on explicit request.
  6. Intentions – Socrates Meno dialog. People don’t knowingly desire bad things.
  7. Walk Away. If your primary emotion is frustration, it’s time to quit. Breathe.
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The Tough Problem for Glass

As you may have seen, there’s a new photo sharing app called Glass. You pay $5/mo or $30-$50 dollars a year to use the app. it has no ads, no tracking, and no mysterious algorithms. It’s a great looking app and has a lot of hype that was generated by some vood0o-genius marketing.

In a sense, the mood around Glass feels the same as Clubhouse a few months ago. Given Clubhouse’s spiral, that’s an ominous comparison to make, and I’m only making it because photo sharing apps are very hard to bootstrap. Especially paid apps.

Photo sharing apps are very hard to bootstrap. Especially paid apps.

Instagram works because it successfully caters to two groups:

  1. Casual consumers: people who mostly want to look at other people’s photos and videos while occasionally sharing something themselves.
  2. Photography pros: people who are promoting something. They’re promoting their own photography, their business, or products they share as influencers. They may not be trying to make money, but self-promotion is still promotion.1

To make a photo sharing community sustainable, any app that wants to compete with Instagram needs to successfully attract people from both groups.


If an app’s community is missing users from the casual consumer group and only has the photography pros, it ends up being a bunch of people who mostly only engage with other people’s photos because they’re either hoping for reciprocal engagement or they’re trying to get ideas for how to make their own photography more competitive. In short, without casual consumers, engagement solely from other photography pros will not be genuine, it will only be comparative and competitive.2

Without casual consumers, engagement solely from other photography pros will not be genuine, it will only be comparative and competitive.

On the other hand, if the community is missing people from the photography pro group, for starters, it won’t truly be a photography app. It may be another social network, and that’s fine, but here we’re specifically talking about photography apps. More importantly, it won’t work as a paid app. There are simply too many free alternatives. The model of paying for privacy and fair feeds with no algorithms has sadly failed over and over.

So, what’s to be done? What’s the alchemical concoction that will compete with Incumbentgram without sacrificing the privacy of its users and integrity of its founders?

The Solution

To succeed, Glass needs to be free and attractive to casual consumers while offering features compelling enough for photography pros to pay for. It’s a hard balance to strike and no one does it well right now. Flickr is probably the closest, but they seem to have given up on being anything other than a niche community for photographers.

Casual consumers almost certainly won’t pay $50/year for Glass when they can use Instagram for free.

If I was a product manager at Glass, I’d focus on attracting users in the casual consumer group. I’d make their experience viewing, discovering, and sharing of photos excellent and free. Glass currently has no #hashtags or categories of any type and has no location based discovery features. Finding photography that appeals to your tastes is currently much too difficult.

I’d also focus on providing an experience for photography pros that’s good enough to pay for. An experience that showcases their work beautifully (luckily, Glass already does this) and gives them tools to successfully promote themselves to the niche audiences that are looking for the type of content they provide.

It’s tough to do that without going the Instagram way where pros have to either pay for views or blindly struggle to reverse-engineer the ever-changing algorithm but I think it can be done.

Glass doesn’t need to offer premium placement or algorithmically controlled feeds. Instead it can offer photography pros paid tools to enable them to compete among each other for the views of casual consumers in a free-market type environment. Not everyone will win all the time, but if pros sense that the competitive environment is fair and unbiased, the community will grow and pros will be willing to pay for it.

I don’t know if that’s what Glass is going for. Maybe they have a different vision or different goals and would find all this silly and completely missing the point. My response to that would be that in order for the business to be sustainable, this is The Way.

I hope Glass succeeds, but from what I’ve seen so far, I feel they need to make some changes to stay relevant and competitive. Today photography pros are joining Glass because with Instagram’s shift to video, they’re feeling the pressure to find what’s next. But this endless loop of competitive self-promotion can only last so long before good photographers realize that they can’t build a truly engaged audience on Glass.


1 You may be tempted to disagree with this simplistic dichotomy, but the fact is, high level photography is a commercial endeavor. Good photographs are expensive and time consuming to make. There will always be people (like me) who just want to share their photos and not make any money, but with the amount of time and equipment photographers have invested into gear and travel, good photographers are almost always promoting something.

2 This is, in some ways, where Flickr is now. There are some genuine communities on Flickr, but for the most part, it’s primarily populated by people who think of themselves as “photographers,” with very few photography aficionados. It’s closed and stagnant.

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Creative Cauldrons

Sometimes when the right circumstances evolve or are intentionally created, an environment is where creativity can run free appears. I don’t know if there’s a name for this already, but I call these special times and places “creative cauldrons.” Here are a few of them along with some very brief descriptions:

The Harvard Psychedelics Club

In the 1960’s Steward Brand, Andrew Weil, Richard Alpert (Ram Dass), Timothy Leary, Huston Smith defined psychedelic culture (for good and ill) for the next 50+ years. Read more about it in Don Lattin’s book The Harvard Psychedelic Club.

Vienna at the turn of the 20th Century

Painters Gustav Klimt, Oscar Kokoschka, Egan Schiele. Writer Arthur Schnitzler. Sigmund Freud. Read more in The Age of Insight by Eric Kandel.

Gustav Klimt – Fir Forest I, 1901

Compton, CA. 1980’s and onward

A relatively small town with a population of about 100 thousand was the starting place for a disproportionate number of of great and influential rappers. Among them, MC Ren, N.W.A., YG, Coolio, Eazy-E, Dr Dre, Ice Cube, Tyga, Kendrick Lamar.

Paris in the Late 18th, Early 19th Century

The movie Midnight in Paris does a great job of imagining the vibe: Cole Porter, F. Scott Fitzgerald, Josephine Baker, Ernest Hemingway, Juan Belmont, and Gertrude Stein.

The University of Utah in the Late 1960’s

John Warnock, Alan Kay, Jim Clark, Ed Catmull. These computer science luminaries all came from an environment that specifically catered to fostering innovation.

University of New York at Buffalo English department in the 1960’s

As described in Evolution of Desire, a book by Cynthia Haven about René Girard, this English department, through the intentionality of Albert Cook, attracted critic Leslie Fiedler, playwright Lionel Abel (whom Sartre called the most intelligent man in NYC), novelists John Barth and Raymond Federman, posts Robert Creely and Robert Has, and of course René Girard himself.

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Photo: Short-Eared Owl

This is one of my favorite image of a Short-Eared Owl that I’ve captured. I love the background, the grasses perfectly sweeping over to frame the owl. I love the wedge shape of the bird, its intense gaze.

This image reminds me of long, early mornings spent sitting quietly on a log, surrounded by tall grasses, looking out over the Puget Sound and waiting for these beautiful creatures to arise from hidden perches and began their utterly silent flights over the fields.

Short-eared owls are one of my most awaited treats of winter in the Pacific Northwest.

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Quoting Montaigne

I am very ignorant about what I am. I marvel at the assurance and confidence people have of themselves—while there is hardly anything I know for sure and that I could guarantee being able to do. I do not possess a checklist of my abilities; I learn about them only after they have done their job.

No matter how many times I go over my own writings, rather than please me they disappoint and irritate me. I always have an idea in my mind, a fuzzy image, of a far better expression than the one I used, but, like in a dream, I can neither grasp nor develop it.

I know how neither please, delight, nor titillate the best tale in the world dries up in my hands and drones on. I know only how to talk seriously. I am quite devoid of that facility, which I see in several of my acquaintances, to chat away with every newcomer, keep an audience on the edge of its seats, or engage a prince on all outs of topics without boring him.

From Essays, as quoted in The Art of Solitude by Stephen Batchelor

Montaigne is a great example of how someone who isn’t a natural storyteller, isn’t a born self-promoter, or a raging extrovert can, through careful introspection and honest self-appraisal, resonate with so many people for so long.

I find that in most of my writing I studiously avoid including “me” and instead write about “stuff” I’m interested in. Maybe revisiting Montaigne will change that.

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Bring Solutions

When you don’t know what to do…

Organize your best ideas and present them to your manager or leader and let them choose from your list of 2 or 3 proposed solutions or suggest one of their own.

If you don’t have any good ideas, before you complain or ask for help, use whatever resources you have to get some ideas or at least next steps. If you can’t figure anything out, have a concise list of steps you’ve already taken ready to go before you ask for help.

Your manager will almost certainly notice and appreciate this and, when it comes time for choosing a leader, they’ll remember who always comes to them with answers.

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Entertaining Outside the Box

Despite having almost1 never hunted, two of my favorite podcasts, Meateater and Bear Grease, are about hunting. They’re both hosted by talented storytellers and both consistently get interesting guests from walks of life that I am unfamiliar with.

I recently started watching and enjoying Clarkson’s Farm which, say what you will about Clarkson, is a great look at what it takes to run a real farm.

I’ve seen most episodes of Forged in Fire, enough to speak the lingo of a blade smith. I’ve also enjoyed 3 seasons of Alone, a best-in-class wilderness survival show.

I’ve watched a full season of Hermitcraft with my son. It’s a fascinating youtube series about a world that about 20 Minecrafters build together and the storylines they invent inside it. This despite almost never playing Minecraft (anymore :)) myself.

Most of my favorite entertainment has nothing to do with my actual work or hobbies. I’m not exactly sure why this is the case.

It’s probably some combination of:

  • Excellent storytelling
  • The pleasure of taking mental break from things that Matter
  • Enjoying watching others in a flow state
  • The natural appeal of expertise and confidence

The point of this is that if you’re looking for something new to enjoy, look outside of your already-established hobbies and career and try something new. You’ll probably be pleasantly surprised.

1 I once hunted woodcock in Wisconsin

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Dahlias Up Close

Macro photography – Sony A9 with the Sigma 105mm f2.8 Macro lens.

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Huxley on the Consolations of Philosophy

Fifty per cent of the Consolations of Philosophy in seven words. And the other fifty per cent can be expressed in six: Brother, when you’re dead, you’re dead. Or if you prefer, you can make it seven: Brother, when you’re dead, you’re not dead.

Aldous Huxley, The Genius and the Goddess

Tongue-in-cheek and delivered through one of his fictional characters, but clever 🙂

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Inter-categorical: Here there be Monsters

To make sense of the world we naturally group things into categories. Categories aren’t scientific or fixed, they’re simply generalizations we use to lower the amount of mental processing we have to do when we encounter something new.

For example, tables are a familiar category of things that usually, but not always, have four legs and you can place things on them. When we see something table-like we immediately and unconsciously categorize it as a table.

What happens though when something defies our normal categories? John Vervaeke, relying on the work of Mary Douglas, discusses this in his 34th episode of Awakening from the Meaning Crisis. He says:

Inter-categorical are things that don’t fall into our ready-made categories and therefore we typically regard them as ‘weird’.

What do we do with inter-categorical things? Here’s an example from Mary Douglas (in Vervake’s words):

…in the Bible, the book of Leviticus, all the animals that are unclean, they’re very weird! It’s a very weird collection! If you tried to find some sort of essence, like why owls are unclean and crocodiles are unclean, and certain birds are unclean… It doesn’t make any sense! And then she argues, “Well, no, what happens is there’s ways in which people have categorized things and those categories have a certain pattern. And when that pattern is being broken, then these things challenge our grip on the world!

Then:

Douglas argues that you should have an interconnection between a creature’s shape–it’s morphology–its means of locomotion and its location–where it lives. So if it lives in the sea, it should swim and therefore it should have a fish shape. So you have things that are in the sea that don’t seem to be swimming, like the crawfish, shellfish, and therefore they’re kind of weird and they turn out to be unclean.

This type of thinking may seem outdated, but Vervaeke points out that we too have our own purity codes.

Jonathan Haidt has written quite a bit about this, notably in The Righteous Mind. There he talks about how, even today, the strength of someone’s sense of disgust plays a strong role in determining political beliefs. As summarized by David Potts:

Disgust is the emotional foundation of the moral ideas of pollution, stain, miasma. It is also (according to Haidt), paradoxically, the ultimate source of our sense of the sacred. For, the idea of pollution suggests its contrary, purity. The sacred is the pure, that which must be kept from pollution and degradation at all costs. It is the infinitely valuable. When we speak of the sanctity of human life, the Sanctity/Degradation foundation is in action. Sanctity talk is in decline in the West. There are still Westerners who think of virginity as sacred, for example, but they are outliers. However, as Haidt points out, we can still see Sanctity/Degradation at work in biomedical debates over abortion, physician-assisted suicide, and stem cell research.

Inter-categorical is similar to, but not quite the same as, disgusting. Vervaeke uses horror creatures as another example:

So if you take a look at many horror creatures, they’re prototypically inter-categorical. The Wolf man is inter-categorical between the beastial and the personal. The ghost is into categorical between the living and the dead. The vampire is also inter-categorical between the living and the dead and also between being alive in the sense of consuming and being alive in the sense of being able to be generative.

Something that’s simply disgusting can gross us out, but something that’s inter-categorical can have a much stronger effect, it can cause us to lose “grip on reality, and intelligibility, because of the deep connectedness between realness and intelligibility.”

(Thanks to Chris, JD, Benica, and Nica for the transcription of the lecture!)