I’ve been reading ‘self-improvement’ books for the last five years. Some of those books dealt with financial and life management, where you leverage the money you earn to create more value for yourself. But until you reach that point in your life, it’s only a theoretical exercise to engage with – there is no point in thinking deeply into investing options or buying your way into freedom until you have money to buy options. I’m sure there are self-improvement adherents who will vehemently disagree with this, but the reality is you aren’t going to gain access to the game by saving money not buying lattes or avocado toast unless you are playing a really long game with a lot of good luck.

I’ve now hit a point in my life where options have opened up for my family, and we can make choices and trade-offs to build out a lifestyle that works best for our goals. This is not to say that all options are available to us – we have to carefully look at the tradeoffs and determine whether the downsides of any option are something we are comfortable living with (e.g. to pay for a given option, should we, say, reduce from two cars to one).

Part of this exercise is critically examining each of our assumptions and systems to determine if they are moving us towards what we want, or if they need to change to better align with what we want. This is where the concept of leverage has entered my mind, because when evaluating costs or expenses, it’s important to note that not all expenses are net negative. Some expenditures end up buying more value than what we spend on them.

This is the game in a nutshell – you trade your time for money. Money represents quantified time and effort that can be exchanged in markets with mixed goods. I spend time at work and my employer gives me money in return. I then take that money to purchases goods or services.

Until now, most of the way I thought about the game was surface-level transactions of 1:1 value transfer – I work x-hours for y-dollars. I then trade y-dollars for a good or service with a transactional value of y-dollars. I haven’t really given much thought to the value (that is, how much I value it subjectively) of the good or service provided back to me, and whether that value is higher than what I’m spending. I suppose I’ve thought about it in an abstract way, such as I receive more enjoyment from the thing than the money I spent on it; the opportunity cost is not higher than the value I’m getting from it.

By focusing on the surface-level transactions, the only metric that was critical was to ensure the revenue was not exceeded by the expenses, that I wasn’t spending more money to buy value than I was getting in exchange for my labour. It’s worked up until now, but the direction my family wants to head requires me to think more deeply about what those expenses are buying us.

Ideally, I should be seeking to engage leverage – I trade time for money, then use the money to buy time in greater quantities. What might this look like?

  • With my wages, I can lease or own a car. The money I spend on the car frees me up to commute to work on my own terms. I could get to work more cheaply, such as public transportation or cycling (ignoring environmental costs in this calculation), but then I’m trading cost for time. Having my own vehicle is more convenient, more comfortable, and faster, allowing me to maximize time at work and time at home.
  • With my wages, I can pay for cleaners to clean my house. This frees up more leisure time and cuts down on bickering in the house. It is cheaper for me to buy the supplies and do it myself, but I value the leisure and time with my family more than the cost.
  • With my wages, I can pay for daycare for our child. My spouse or I could quit our job to care for our child at home full time and save the money. However, the money we spend on childcare frees us up to earn multiples of what we spend for the childcare – e.g. at $1,000/month, we would spend $12,000/year for daycare so that we can make north of 5x of that in our jobs.

This is not an easy exercise as many of our expenses feel necessary on the one hand, or scary large in context. However at this point in our lives, we have to accept that our raw effort will only diminish (I can’t work all-nighters like I used to without significant physical cost), and there are no more hours in a day we can squeeze out through discipline and efficiency. We must now turn to leverage and force multipliers to translate what we have into higher value.

Stay Awesome,


The Beachhead

A friend who recently was appointed CEO of a company called me this week looking for a soundboard to sort out ideas he had in his head about how to proceed with company operations and strategic direction. The company is looking to shift strategic priorities, and he was looking for an outside voice to make sense of the new direction in relation to the legacy systems he’d need to grapple with.

One of the topics that came up reminded me of a concept I learned about while reading Susan Eisenhower’s book about her grandfather’s time during World War 2 and his subsequent Presidential years.

At two times during Dwight Eisenhower’s tenure in significant leadership roles, he had to create a beachhead to establish his forces (literal and metaphorical) to push towards his objectives. During the war, Operation Overlord’s first phase was to establish a beachhead in Normandy to create a defensible position to allow Allied Forces to work their way into Europe to push back Germany’s army. Establishing a beachhead is critical to success, but is often difficult for offensive forces to complete as the defending force usually has the upper hand in terms of resources and strategic positioning. While the offensive forces need to both set up a foothold and protect its lines to allow more troops to arrive, the defending forces merely have to reinforce it’s occupying positions to clamp down on fresh troops from joining the beachhead. Once the effects of first-mover advantage wears off, the offensive force must contend with protecting supply lines, fighting active defense from the opponent, and pushing past inertia to avoid grinding to a halt in order to win. Once established, a successful beachhead serves as a ratchet for the offensive force – the location of which all future offensives are launched from, and from which the troops need not backslide past. Traction is gained, and the army moves forward.

Similarly, during Eisenhower’s presidency, he saw the importance of passing civil rights legislation, but saw the difficult uphill battle that would needed to both move the country towards accepting civil rights AND enshrining those rights in law (turning both hearts and minds of the nation). While he would have aspired to complete civil rights equality in his time, he knew that if poorly planned, then history, culture, and opposing interests would ensure that forward progress towards equality would halt. Instead, he sought to establish a kind of metaphorical beachhead for civil rights, working on government programs and legislation that would lay the foundation for future leaders to take up and ratchet their work – allowing the movement to progress forward without worrying about losing traction and backsliding.

In listening to my friend, I noted that he also needed to take this lesson from history and focus on his own beachhead. While we think that a CEO is all-powerful in terms of exerting their will over the company, we must also face the reality that comes with working with legacy systems and people. Change is difficult and slow, and when poorly executed either stalls from inertia or alienates your workforce. And so I suggested he take a leaf from Eisenhower’s example and focus on what his core objective is that is reasonable within the timeline he’s being given, and focus on establishing a beachhead to deliver value back to the company president.

Since reading about Eisenhower, I’ve thought about my own beachheads – what are the areas of my life that I must focus on to ensure I’m moving forward with my goals, whether they are family, work, health, or passions. It is still very much a work in progress, but I want to find those areas that I can carve out and secure so that when it’s time to take risks towards my goals, I have a safe space to launch from.

Stay Awesome,


World Limits

I’ve been thinking about the limits of my world, specifically as it relates to my ability to understand it. Much of the time, I operate as if I have access to capital-T Truth, that I have some connection with facts about the world. It’s easy to fall into this kind of thinking – when I can predict and explain events, it gives me feedback that I know things about the world in a meaningful sense.

But I also know that this confidence in my knowledge is not as strong as I assume it to be. I have to remind myself to adjudicate the claims I encounter, or to remind myself of the difference between history and the past. It’s also good to listen to others who have learned about issues from multiple vantage points (see this amazing conversation on the Tim Ferriss podcast with Noah Feldman, and his experiences with constitution building in the Middle East).

Generally speaking, all of our experience in life has presented us with a mostly successful set of interactions with the world, but those interactions are subjective and limited. Taking the long view of world events, learning new languages, and empathy provide the Archimedean point beyond ourselves to attempt to stand on some point of objectivity (if this is even possible).

As Wittgenstein says, “the limits of my language are the limits of my world.” This shouldn’t be literally taken to mean language (though I’m assuming that’s what Wittgenstein meant), but we should apply this to our understanding vis a vis experience. The limits of my world are constrained by the limits of my experience and the mental framework I use to make sense of it. If I want to seek to expand my worldview, it’s important to both prune out the dead branches of knowledge while cultivating new seeds of wisdom.

Stay Awesome,


Evidence, Credibility, and the Homunculus Courtroom

We should think of our beliefs and the evidence we engage with as if we had a little homunculus tv courtroom in our brain adjudicating whether to admit evidence into the record. Obviously, this is incredibly difficult to pull off in real time, but it’s a nice thought experiment to pause and consider the weight of a claim being made.

This idea came to me while watching a YouTube video covering the recent downfall of a famous hustle influencer, where the presenter made an observation that she (the presenter) would normally not take people’s personal lives into consideration when judging their professional work, but the case that the influencer sold conferences and products marketed as relationship coaching courses under the pretenses of having a great marriage was swiftly undermined by her (the influencer) getting a divorce approximately two years later.

I was impressed with this statement by the presenter – she was right! Under normal circumstances, the personal life of a person shouldn’t bear weight on something like this, but given the fact that the evidence under consideration was whether someone was misleading about their personal life and getting others to pay for her “expertise,” it would be grounds to consider this piece of evidence as relevant or bearing weight. My homunculus courtroom judge ruled that the testimony was admissible.

This is a silly thought experiment to anthropomorphize cognitive thought-processes that are otherwise just a black box to me. I suppose it’s a little farfetched to think that we have this much control over our beliefs, but maybe the next time I listen to a claim (or gossip, or something that doesn’t jive with my experience… or claims that I want to be true…), I will remember my homunculus courtroom and think twice about the claim’s believability.

Stay Awesome,


My Best Interest

If you want a good newsletter, you should check out Arnold Schwarzenegger’s newsletter. I signed up a few months back and have thoroughly enjoyed each update. I find him such a fascinating and inspiring person, not just from his bodybuilding work, his acting career, or even his time in politics, but above all because he strikes me as a fundamentally decent person.

He made two interrelated observations in the latest issue that stuck out for me. A significant portion of the email dealt with his clarifying and elaborating on his viral “screw your freedoms” moment during an interview talking about why people should get their vaccines. In his expanded comments, he urges his readers to pay attention to the motivations of people trying to give them advice, and discard those opinions which are not in your best interest (including his own). By this, he means fitness influencers and politicians, whose motivations are clicks and ad revenue in the former, as well as outrage, donations, and votes in the latter. When it comes to your health, these people are not giving advice based on your own health and wellbeing.

The second related comment is that if you can’t trust government or social media, who should you trust? To that, he says you should trust your doctor because your doctor took an oath to protect you. Your doctor is paid with only one expectation in return – the promotion of your wellbeing and health.

Talk to your doctor, not people who don’t have your health as their main responsibility. The Instagram and Facebook accounts you follow that give information on vaccines are not concerned about your health. They are concerned with getting more followers and making money.

I have seen way too many stories about people who listened to politicized information about the vaccine instead of their doctors, and then changed their minds when it was too late.

At the end of the day, everyone has to make their own decision about getting vaccinated. But if I can inspire even a few of you or your friends or family to avoid another one of these tragic stories that tore families apart, I want to do it.

He urges us to trust the experts and take wisdom from their experience. When presented with advice, we should ask ourselves what the advice-giver gets in return for our compliance. Do they benefit from our participation? What do we lose by their gain? These are important checks that we should make when deciding what’s in our best interest.

Stay Awesome,


Initial Assumptions

I was reflecting on Seth Godin’s musings about the number of moons in our solar system. The initial assumptions we use to make predictions about our world can sometimes be orders of magnitude off from truth.

We as humans don’t like to be wrong, but we shouldn’t be overly concerned with our initial assumptions being off the mark. After all, if we knew the truth (whatever “truth” happens to be in this case), there would be no need to start from initial assumptions. It is because we are starting from a place of ignorance that we have to start from an assumption (or hypothesis) in order to move forward.

The problem lies with whether we realize we are making assumptions, and how committed we are to holding on to them. Assumptions made about the physical world can often be value-neutral, but assumptions that intersect with the lived experiences of people always come pre-packaged with history that’s value-loaded. It’s fine to make an assumption that your experiences are shared with others, but that assumption can only be carried so far. At some point, you have to acknowledge that there will be a lot missing in your initial assumptions that need to be accounted for.

The lesson then is this: when working from an estimation or prediction, be careful with your initial assumptions. It’s fine to begin with your own experiences, but always put an asterisks beside it because your experience is likely not universal. We must guess, then check. Test, verify, then revise.

Aiming at truth is a noble goal, but we should settle for asymptotically moving closer towards it as it more likely reflects reality.

Stay Awesome,


Friday Round-up – August 7, 2020

This was a light week for consuming content that stuck with me, so here is the sole round-up list for the week ending on August 7th:

đź’­Reflection – Citing our sources – How to Think for Yourself | Ozan Varol blog post and Don’t Quote. Make it Yours and Say it Yourself | Derek Sivers blog post

The Varol piece was new, and as I read it, it reminded me of the Sivers piece, so I’m pairing them together. I’m a little conflicted with the message. On the one hand, I agree with both writers about the sentiments they are expressing. In Varol’s case, often citation becomes a short-hand for original thinking. Rather than expression your own unique ideas, you regurgitate what you’ve consumed from others (whether you are citing it or not, as is on display in the Good Will Hunting example). Likewise, Sivers is on to something when he suggests that integrating facts into our mental apparatus should not require us to cite our sources when it’s no longer the appropriate context. It makes sense to cite sources when writing something that will be graded in school, but it is stilted while in informal settings.

Where I feel conflicted is when there is a need to trace ideas back to verify the content. I don’t think it’s a new phenomenon, but it has certainly accelerated in recent years that misinformation is being thrown out into the void at a rapid pace. The internet has optimized itself on three facts of human nature – we like sensation, we like things that are familiar (that accords with what we already believe), and we are less critical of our in-group. Therefore, information bubbles get set up online, which creates a digital environment that’s conducive to rapid spreading of memetic viruses. When you think about it, it’s a marvelous analogy: the online information bubble is a closed environment where people are like-minded, which amounts to a roughly analogical immune system. A memetic virus then latches hold on one person, who spreads it to people in their network. Since the folks in the network share similar belief structures, the homogeneous group quickly spreads the meme throughout the information bubble. The meme is then incorporated into the belief network of the individuals through repetition and confirmation bias exposure. It writes itself into the belief web, in the same way viruses incorporate themselves into DNA.

I’m using the example of a memetic virus, but I think this framework is equally applied to more benign examples. Scientists release findings in the form of pre-peer reviewed news releases, which gets amplified and distorted through the media, which is then amplified and distorted through information bubbles. See here for an example:

At each phase, part of the signal is lost or transformed, like a social media game of telephone. When one person in the chain misunderstands the data, that impacts how the idea gets replicated. Over time, it becomes the digital version of a cancerous mutation of the base information.

This is why it’s important that we take care of how information is communicated, because as soon as you print something like “the majority of people believe x,” or “studies showed a y% decrease in the effect,” without a proper context of what the data is saying (or its limitations), that gets incorporated into people’s webs of belief. If you are a part of the population that believes something and you read that information, it reinforces your prior beliefs and you continue on in replicating the idea.

And so I’m torn. On the one hand, I shouldn’t need to cite my sources when having a casual conversation (a la Sivers), and I shouldn’t be substituting original thoughts with the ideas of others (a la Varol), but at the same time, I want it to be the case that when I encounter something that it should be verifiable and scruitable. I don’t know what the solution to this is, other than to flag it and remind myself to be wary of absolutist language.

Stay Awesome,


Leadership Lessons – Individual Rights vs Expediency

Star Trek: The Next Generation – Season 3 Episode 7 “The Enemy”

As with many other people right now, I have chosen to go back and re-watch favourite television shows. I decided that with Star Trek: Picard’s recent release, it would be a great time to go back to the beginning (of the modern era, anyway) and revisit Star Trek: The Next Generation. I had probably watched every episode in my teen years, but I had always watched it in syndication, so this is my first time going through the show in order.

Approaching the series in my 30’s has been a real treat. I have more life and cultural experience to draw upon as I watch these incredibly written episodes play out. I knew the show was amazing, but I never appreciated how well it engages with moral issues.

I want to highlight one excellent episode from the third season – episode 7, “The Enemy.” The characters provide us with a moral issue about autonomy, and a good lesson in leadership.

The story centres on the conflict that arises when the protagonists rescue an enemy officer from an out of bounds planet. The officer, from a race of people called Romulans, is gravely wounded and requires a blood transfusion. There is only one member of the crew whose blood could be usable, but that crew member, Worf, has a history with the enemy’s peoples – Worf’s parents had been killed during a Romulan attack when he was a child. Worf, still carrying his anger for their death all these years, refuses to give his blood.

Meanwhile, a Romulan ship is en route to recover the officer. There is a tenuous peace treaty that prevents an all out war, but the Romulans have a history of subterfuge and deceit. It is believed they will cross the border and assume an antagonistic stance to provoke a war. Worf’s Captain, Jean Luc Picard, is seeking any means that would avoid an armed encounter, and decides to plead with Worf to reconsider his decision.

In this moment, it would be expedient to Picard and his crew to order Worf to donate his blood. He is about to contend with an adversary whom has no issue with breaking a peace treaty by provoking an attack (whether or not his side is initially in the wrong). Picard is seeking to recover a still-stranded crew member on the planet below, keep his ship safe, maintain the territorial sovereignty of the Federation, and maintain tenuous diplomatic relations with a rival group. This is all threatened because the one solution to his problem, keeping the enemy officer alive, is being blocked by a crew member whose personal history and honour motivate him to not help the enemy.

There is a beautiful scene where Picard appeals to Worf for him to reconsider:

Picard: So, there is no question that the Romulan officer is more valuable to us alive than dead.
Worf: I understand.
Picard: Lieutenant, sometimes the moral obligations of command are less than clear. I have to weigh the good of the many against the needs of the individual and try to balance them as realistically as possible. God knows, I don’t always succeed.
Worf: I have not had cause to complain, Captain.
Picard: Oh, Lieutenant, you wouldn’t complain even if you had cause.
Worf: If you order me to agree to the transfusion, I will obey of course.
Picard: I don’t want to order you. But I ask you, I beg you, to volunteer.
Worf: I cannot.

In silence, Picard slowly walks back around his desk and sits in his chair.

Picard: Lieutenant.
Worf: Sir?
Picard: That will be all.

We then learn from the ship’s Chief Medical Officer that the Romulan has died. Picard has lost the only bargaining chip he had to keep things peaceful with the approaching enemy ship.

Picard could have chosen to order Worf to allow the blood transfusion. Instead, he chooses to respect his crew member’s personal wish, and as a leader deal with the hand he’s given. He also knows that making an order against the personal rights of a crew member under his command sets a dangerous precedence – that anyone is disposable if the captain judges it. Instead, he accepts that this closes off options. He knows that this places him not just on the back-foot, but also with his arms tied behind his back as he prepares for the possibility that his ship will be destroyed. However, the burden of command requires him to take these realities as they come and make the best decisions that he can. Events are being shaped around him that are beyond his control, but he strives to make the best decision that he can. He’s not perfect, but he becomes a role model in striving to do the right thing.

Even if the right thing might mean the death of he and his crew.

It’s a wonder piece of science fiction that I’m glad to be discovering anew.

Stay Awesome,


A Modern Cartesian Demon

grey and brown concrete building close-up photography
Photo by Marius on Unsplash

During a throwaway thought experiment in his 1641 treatise, Meditations on First Philosophy in which the existence of God and the immortality of the soul are demonstrated, RenĂ© Descartes posited the idea of an evil genius or demon that systematically deceives us to distort our understanding of the world. Contrary to first year philosophy students everywhere (a younger version of myself included), Descartes did not actually believe in the existence of an evil manipulator that was holding us back from understanding the nature of the real world. Instead, he was using it as part of a larger project to radically re-conceive epistemology in an era of rapid advancements in science that was threatening to overturn centuries of our understanding of the world. He felt that knowledge was built upon shaky ground thanks to an over-adherence on the received authorities from Greek antiquity and the Church’s use of Aristotelian scholasticism. Similar to Francis Bacon twenty years earlier, Descartes set out to focus on knowledge that stood independent of received authority.

Through Meditations one and two of his book, Descartes considers the sources of our beliefs and considers how we come to know what we think we know. He wants to find an unshakable truth to build all knowledge from, and through an exercise of radical doubt he calls into question many of the core facts we hold – first that knowledge gained from the senses are often in error, that we often can’t distinguish the real from fantasy, and through the use of the evil genius, that perhaps even our abstract knowledge like mathematics could be an illusion.

AndrĂ© Hatala [e.a.] (1997) De eeuw van Rembrandt, Bruxelles: CrĂ©dit communal de Belgique, ISBN 2-908388-32-4.

When I teach this to first year students, they either don’t take his concerns seriously because of the force of the impressions the real world gives us in providing sense data for knowledge (a stubbed toe in the dark seems to forcefully prove to us that the external world to our senses is very real), or they take Descartes too seriously and think Descartes really thought that a demon was actively deceiving him. Regardless of which side the student falls on, they will then conclude that Descartes’ concerns are not worth worrying about; that this mode of thinking is the product of an earlier, less sophisticated age.

Unless you are a scholar delving into Descartes’ work, the real purpose of teaching the Meditations is to provide students with a framework to understand how one can go about thinking through complex philosophical problems. Descartes starts from a position of epistemic doubt, and decided to run with it in a thought experiment to see where it took him. The thought experiment is a useful exercise to run your students through to get them to think through their received opinions and held-dogmas.

However, in light of my rant a few weeks back about informed consent and vaccines, I’ve discovered a new contemporary use for thinking about Descartes’ evil genius. In some sense, the evil genius is *real* and takes the form of fear that shortcuts our abilities to learn about the world and revise our held beliefs. Descartes posited that the evil demon was able to put ideas into our heads that made us believe things that were completely against logic. The demon was able to strip away the world beyond the senses and even cast doubt on abstract concepts like mathematics.

Much in the same way Descartes’ demon was able to “deceive” him into believing things that were contrary to the nature of reality, our fear of the unknown and of future harm can cause us to hold beliefs that do not map onto facts about the world. Worse yet, the story we tell about those facts can get warped, and new explanations can be given to account for what we are seeing. This becomes the breeding ground for conspiracy thinking, the backfire effect, and entrenched adherence to one’s beliefs. We hate to be wrong, and so we bend over backwards to contort our understanding of the facts to hold-fast to our worldview.

In truth, we are all susceptible to Descartes’ demon, especially those whom believe themselves to be above these kinds of faults of logic. In psychology, it’s called the Dunning-Kruger effect, of which there are all sorts of reasons given why people overestimate their competence. But in the context of an entrenched worldview that is susceptible to fear of the unknown lurks Descartes’ Demon, ready to pounce upon us with false beliefs about the world. Its call is strong, its grip is tight, and the demon is there to lull us into tribalism. We fight against those we see as merchants of un-truth and in a twisted sense of irony, the weapons of truth we yield only affect those already on our side, while those we seek to attack are left unaffected. It becomes a dog-whistle that calls on those who already think and believe as we do.

If we hope to combat this modern Cartesian demon, we’ll need to find a new way of reaching those we see on the other side.

Stay Awesome,