Hi! Welcome to this week's digest. This is a very special Podcast edition of the digest, sharing hours of audio delight and insight that is then haphazardly dragooned into a handful of quotes. You are welcome :D

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This week's topics include social experimentation, discerning the essential, digital capitalism incentives, venture capital nuances, sleep cycle options, and meditation mastery. Enjoy!

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"It's not being unhelpful to the world for you to say No to something that is less important... Your obligation is to the highest point of contribution that you can make." ~ Greg McKeown
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Genesis: My girlfriend has EQ super powers (I do not =/). I was 'in the blue' this weekend talking about my various social rituals, and she called me out for being both "High Energy and High Effort", i.e., exerting tremendous effort in creating social interaction and in the social interactions. She advised that I switch to a "High Energy and Low Effort" social strategy, i.e., invest less in reaching out so I can invest more in my closest, reciprocal relationships and not be spread so thin. I have been running on auto-pilot with "High Energy and High Effort" for so long (2+ years) that I want to take a break and see how it feels.

Hypothesis: Conserving social energy for close, reciprocal relationships will be more effective and efficient, and build stronger bonds.

Specific Action(s): Do not proactively, incrementally reach out for social interaction to anyone where there is not currently a reciprocal relationship.

Specific Outcome(s): Qualitative feelings of connectivity and value of effort invested into social.

Results from Prior Week's Experiment, TEA TIME (TAKE TWO): Partial success! Tea time had a very positive impact on my emotional state headed into bedtime, creating feelings of relaxation and readiness for sleep. My performance on getting to bed on time improved meaningfully, but my performance on journaling and meditation before bed did not improve much. That said, I am patient and believe that the tea time trigger can be more firmly linked to these PM rituals over time.


PODCAST - The Tim Ferriss Show #355: How to Master Essentialism with Greg McKeown by Tim Ferriss - As some of you already know, Greg's book Essentialism is basically my bible (see my TD Digest summary). In this podcast, Greg uses himself and Tim as guinea pig case studies for implementing the key principles of Essentialism into your life. A wonderful explainer for those new to Essentialism, and a practical guide for those excited to engineer Essentialism into their lives.

One-Sentence Takeaway: We can learn to choose choice in every area of our lives, so that we can focus on our highest point(s) of contribution.

Answering The Drucker Question: Identify one large 'to-do' in your life that feels like an 'I have to...', and re-frame it into a 'I choose to [do X] because...' hypothesis that you can investigate and confirm (or disconfirm ;D).

My highlights:
  • The very nature of success is that you will have this basic problem. You will be stretched too thin - at work, at home. You will feel often busy but not productive... You just have more that you want to do than you can do. That is the normal scenario for successful people... Even if you don't feel very successful, as soon as you have more options and opportunity than you can pursue, you need a new way of handling it.
  • You used to think this was the thing, but you are pursuing it because you have it, you are caught onto it, you feel a sense of this Endowment effect. This sense of this is my opportunity, my thing, my goal. And it's not serving me anymore... It's about the stuff that really we need to get past and let go so that we can pursue the right things now, not just the things that we are pursuing because at one time we wanted to pursue them.
  • This is what Essentialism is. It's to figure out what is essential, to eliminate what is not essential, and to then build a system that makes execution as effortless as possible.
  • Your lack of planning does not constitute my emergency... It sometimes falls by the wayside in practice due to fear of social repercussions.
  • Essentialists embrace the reality of trade-offs. Of course there are trade-offs. Of course there will be people that are frustrated. Think about somebody like Oprah. How many requests go in that she can't possibly answer?... Warehouses full are going that way, and she had to get somehow to get to a level of peace... It's not being unhelpful to the world for you to say No to something that is less important... Your obligation is to the highest point of contribution that you can make...
  • The question is, if I do this thing, what doesn't get done? What else gets pushed out? If [responding to requests] is at the cost of something that is actually more important, that makes a higher contribution, we have an obligation not to do it.
  • To every request, whether the request comes from somebody else or from within ourselves..., there are only three options. You can say Yes, you can say No, or you can negotiate. And people default Yes because they are so fearful of the rude No and its effects... Sometimes, the best No is a Yes. It's saying I'm doing this, so I just couldn't do anything beyond this.
  • The generation that has forgotten me, what impact do I want to have on them?... The impact outlasts memory. This perspective helps reveal for us the difference between good things and essential things... It's not about getting more stuff done, it's about getting more of the right things done. And it's not about efficiently doing what's on the to-do list, it's realizing that the most important thing isn't even on the to-do list.
  • What we're saying when we say 'I have to' is there is nothing else that could be done. 'I have to' means there's no agency involved, there's no choice involved... We could have said, 'We have to do it', we don't want to, but we have to. And we almost did make that mistake. And then we changed the language. We said, and this is important, 'I choose to have a son in baseball because...' and we had to fill in the blank... If you say 'I have to', it's the end of your reasoning, end of your thinking, you can't prosecute the hypothesis... By saying 'I choose to do this because...', now we could test it.
  • The one choice you can't make is to get rid of your ability to choose... It's good news, this discovering I am choice. Whatever has happened to me, I can make a different choice going forward.

PODCAST - Making Sense #146: Digital Capitalism with Douglas Rushkoff by Sam Harris - Sam and Douglas do a thorough job highlighting the pernicious incentives and downstream consequences of our current digital economy. This is definitely the more cynical lens, and does not spend much time highlighting the benefits of technological improvement. That said, I would love to see the technology sector's incentives re-aligned towards metrics like (long term) human happiness and time well spent, rather than metrics like engagement and spending. That desire stems from my own cynical take on our ability to navigate well-known cognitive biases and ridiculously high levels of hyperbolic discounting (i.e., severely discounting the benefits of anything in the future vs. present moment).

One-Sentence Takeaway: Our digital technology ecosystem has some pernicious incentives which lead to bad practices in innovation and growth.

Answering The Drucker Question: Identify one digital technology product you use frequently, and take a minute to understand what its creator's incentives might be, and how those incentives led to choices that impact your behavior with and benefits of using the product.

My highlights:
  • The one difference between speech, text, radio, television, and digital technology today, is that the algorithms that we are building, the artificial intelligences that we are building, continue on, they change themselves as they go... The companies that are building these technologies don't quite realize what they are setting in motion. The technologies end up doing what we tell them, but by any means they see fit. We are not even privy to the techniques they are using to elicit whatever response they want from us.
  • In certain contexts, we have trained ourselves to expect things for free. And yet, the only way free is possible, is this increasingly insidious ad model that is gaming people's attention... This is the problem we want to figure out how to solve. And yet, if we put everything behind a paywall, then we have a real problem of people not being able to get access to content that we really do want to spread as widely as possible.
  • The idea that someone could take months to write the best piece that has been written in a decade on the threat of nuclear war, and that could just sink below the noise of Kim Kardashian's latest tweet, or our President's latest tweet, and just disappear from a news cycle and therefore earn comparatively little ad revenue. And the net message of all of that is that those kinds of journalistic efforts don't pay for themselves, and that we really don't need people to hold those jobs because we can't figure out how to pay them.
  • I don't believe that the vast majority of people who are developing these technologies are doing it with my best interests at heart. They are propelled by business plans that are looking at how to extract value from me rather than how to enhance me.
  • You can't really establish true rapport in a way where your mirror neurons are going to fire when you are using something like Skype... You can't see the micro movements in their face, you can't see if their pupils are getting larger or smaller, so all of the subconscious cues that we use to establish rapport, they don't really work. But what they find happens then, if the person on the other side is agreeing with you and nodding, but your mirror neurons aren't firing and you're not really feeling it, then you leave that conversation feeling like that person wasn't really agreeing with me, they were lying. And you don't blame the technology, you blame the other person.
  • The construction of it, when they say "Humane Technology", it makes me think of cage free chickens. As long as we are going to be taking them to the slaughter, let's treat them as humanely as possible while we extract their data and their money. I no longer feel like the user in these situations, I feel like the used. The political economy of these media platforms supports that, that we are here to deliver value to the shareholders of these companies. And that's not the best relationship to have with the technologies that we are bringing into our lives in such a personal and profound way.

PODCAST - The Knowledge Project #50: Inventing the Future with Josh Wolfe by Shane Parrish - Shane's conversation with Josh Wolfe of Lux Capital, a well-known venture capital firm, is mostly about VC investing and parenting. But during this discussion, they also smuggle in a variety of interesting principles on broader subjects like intellectual humility, processes, and communication. Josh also has a highly probabilistic view of the world (as most investors do, especially in VC), so if that is a new lens for you, you can learn a lot from hearing his perspectives.

One-Sentence Takeaway: Intellectual humility and curiosity enables better questions and, ultimately, a more refined and accurate map of what the future may hold.

Answering The Drucker Question: Identify one thing that you absolutely know for certain, and hunt for disconfirming evidence. See how it feels to process that data, and see if you update your beliefs based on what you find (for example, counter-intuitively, becoming more entrenched in your original belief).

My highlights:
  • Fitzgerald's famous quote was "The test of a first rate intellect is the ability to hold two opposing ideas in your head at the same time, and still retain the ability to function."... Most of the front page news for the New York Times, or the Wall Street Journal, or the FT, are Fitzgerald situations.
  • [Twain]'s famous dictum was "It ain't what you don't know that kills you, it's what you know for sure that just ain't so." And so what is the thing that everybody is predicting linearly is going to continue, and then boom there is informational surprise.
  • The Schopenhauer dictum, "Talent can hit a target that nobody else can hit, and genius hits a target that nobody else can see." And that goes back to the asymmetric information contained in the minds of the scientists who feel like they have the answer, or have a secret, that nobody else knows.
  • Another quote that we indoctrinate into [our kids] is finding the balance between fitting in and standing out. And there are times where you want to fit in, and there are times when it is really important to stand out.
  • When the team has total consensus, we typically make an investment, and we've typically been very wrong. When everybody agrees, we are missing something. If we pride ourselves as being contrarians, and we think that we are thinking differently from everybody outside the walls of the firm, but then internally we all 100 percent agree, then something is wrong, we are missing something.
  • The best thing we've done for better decisioning... the process of recording people's judgments, and perceptions, and observations at each deal is really important. Because what we observed, before we starting doing this in a very formal way, was that people had very selective memory. They would say, "Oh I always thought they were going to be wildly successful", and then somebody would be banging their head and be like, "No you didn't, you thought that they were total idiots". Being able to go back and refine our judgment has made everybody a little more nuanced and a little bit less absolute... It has reduced the extreme certitude, and that helps to make us a little bit more nuanced, and from that you get a diversity of viewpoints, and the diversity of viewpoints leads us to the best questions.

RESOURCE - Slumber Bear by Kieran Parker - A simple and highly practical resource for learning about different sleep routines and creating your own. I am currently on a Monophasic Cycle, but during higher stress periods I have become Biphasic. Learning to accept the various cycles (rather than feeling anxious about them) was incredibly important for me.

One-Sentence Takeaway: You have options for designing your best sleep routine.

Answering The Drucker Question: Learn about one type of sleep routine that you weren't familiar with before.


PODCAST - Making Sense #4: The Path and The Goal with Joseph Goldstein by Sam Harris - Sam's lengthy conversation with his meditation mentor, Joseph Goldstein, is a wonderful resource for both beginning meditators and more advanced meditators seeking guidance on the subtleties of extended practice. This podcast was tremendously important for me personally, as I experienced my own "corruption of insight" during my Vipassana retreat in 2015, but did not understand what that was until listening to this. By illuminating the core principles of meditation, as well as a variety of different practices and interpretations, Joseph and Sam make the practice "easier" than it can first appear, and also provide options for longer term practice.

One-Sentence Takeaway: Meditation is ultimately an exercise in greater awareness of the impermanence of all phenomena, which creates a path towards freedom from our monkey minds.

Answering The Drucker Question: Attempt to focus on your breath for ten breaths! If (when) you fail, congratulate yourself on successfully doing one "meditation rep" of awareness :D

My highlights:
  • I realized there was a way to look into the mind, as well as looking out through it... So it was like turning in place. Just that was so extraordinary to me.
  • Simply be aware or feel the sensations of each breath, as it comes into the body, as it leaves the body. It's not a breathing exercise, it's an exercise in awareness. So we simply use the breath as a vehicle for being aware.
  • What's unique about Vipassana, and I think the reason why it has been adopted by so many clinicians and now scientists who are studying meditation, is that it doesn't require that you add anything strategically to your experience... You don't have to develop an interest in, or sympathy for, historical figures, or imaginary figures, deities... It really is just paying closer attention to whatever happens to be happening in that moment in the mind and body. And the other very important feature of it is that in principle doesn't exclude anything. You don't need a quiet room, you don't need a comfortable body. In principle, anything you notice is a good as any other object of meditation.
  • If you want to know something more about that it's like to be you, and what could possibly be discovered through introspection, it makes sense to pay attention. And all this is, is paying attention... If you want to understand your mind, sit down and observe it.
  • It's a way of coming out of suffering. We become much more expert in terms of understanding our own minds and our own conditioning. Because we all have established habit patterns that are not helpful, that are not conducive to peace, or freedom. We need to learn about that, to see how all of that is happening.
  • People at a certain stage have experiences of tremendous rapture and clarity and concentration, and all of the things we are practicing to develop. At this particular stage, they are called corruptions of insight, because the tendency is for almost everybody, in one way or another to get attached to them. It's such a remarkable shift from anything that's happened before, that when you are experiencing that, it just feels you have arrived. It has the flavor of enlightenment... If freedom is dependent on conditions, it's not freedom.
  • In Vipassana, we begin to see this flow of impermanence on more and more microscopic levels, as the mind gets more refined and concentration is stronger. And as a result of that, we begin to see the unsatisfying nature of phenomena. The characteristic of things being ultimately unsatisfying... There are many things in life that are pleasant and enjoyable and we don't experience as suffering. The deeper meaning of the word dukkha is that things ultimately are unsatisfying or unreliable precisely because they are impermanent. Some of these things are pleasant, some are unpleasant, but all are equally dukkha in the sense of not capable of giving us a lasting satisfaction.
  • In the freedom from grasping, the mind is freed... Ultimately what we are freeing the mind from are various afflictive emotions, which the Buddha condensed into three unwholesome roots of greed, and hatred, and delusion, out of which all the others come. And that is really what we are freeing the mind from.
  • In seeing impermanence, the mind becomes disenchanted from the grasping. In the disenchantment, it becomes dispassionate. In the dispassion, it lets go. In the letting go, there is freedom.
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