Chelsea Troy

Chelsea Troy

A lot of people have a nagging feeling in the back of their minds that they should “learn to code” or undertake some other sort of technical self-education in order to improve their carer or become more effective at what they’re doing.

Chelsea Troy has a background in international relations and wanted to be a spy – but has self-educated and informally learned to code in more than a dozen languages and has also self-educated in machine learning and data science.

While this is impressive in and of itself, Chelsea also blogs regularly and shares her experiences and advice on coding and professional “leveling up” at

Check out the full conversation with Chelsea to hear:

  • Why feeling stuck and frustrated is where you will spend most of your time when learning software development – and why learning more tools to get “unstuck” is how you level up
  • >How to make the decision-making process of artificial intelligence less opaque and “human legible” – and what the future of machine learning means for human work
  • How technology companies can improve diversity in their workforces and handle the associated internal friction and discomfort that comes along with increased diversity– both in terms of tangible actions for employees and managers as well as higher-level organizational changes to improve viewpoint diversity

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Chelsea here:

Show Notes:

  • [0:07] Self-educating in software development and data science through a project-based approach – and the strengths and weaknesses of project-based learning vs a formal academic model
  • [08:48] Almost all of your time in software development is spent at the margin of what you know how to do, so you have to be comfortable with being uncomfortable. Improvement often comes through bettering your ability to solve the inevitable problems that you will run into.
  • [19:12] Reduce the feedback loop as much as possible and create testing scenarios in order to rapidly iterate on software. One weird trick to learning software development: copy the changes that more experienced developers make to their code by hand
  • [30:30] The best learning comes from realizing that you’ve made a mistake. Having a generalist approach and understanding multiple programming languages enables solving problems in non-traditional ways.
  • [37:42] Should we believe the hype on machine learning? What will be the future of machine learning and how will humans work with this technology as we are able to automate more and more tasks and better recognize patterns in data?
  • [48:02] The dangers of algorithmic recommendations and the amount of resources going into increasing advertisement clicks through machine learning. Can we have machine learning algorithms make their decisions and categorizations “human legible”?
  • [1:03:07] How can tech companies move the needle on diversity in hiring? What actionable communication and management behaviors can individuals employ in terms of making technical companies more welcoming to underrepresented folks?
  • [1:14:07] How do we get more viewpoint diversity in the upper echelons of technology companies? Viewpoint diversity seems to clearly help companies improve performance, but can be painful and create more conflict within the organization.

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Bowling Alone and the Decline of Social Capital

In my continuing quest to better understand the desire for social connection that afflicts most people (this is a partial joke about my own disagreeable nature), I recently read a book called Bowling Alone based upon multiple recommendations from disparate sources.

In this book, Robert Putnam makes a pretty compelling case that American social capital has been steadily declining for decades. The two main culprits, he argues, seem to be longer commutes and television. (Keep in mind that this book was written before the explosion of social media).

As someone who has repeatedly written with concern about the effects that social media has had on the way that we relate to both other human beings and the ideas that other human beings have, I found it very interesting to read something written just a few years before Facebook was created and long before algorithmic curation and newsfeeds became the norm for social networks and content aggregators.

With any complicated phenomenon, it’s extremely challenging to create causal explanations through epidemiological data and survey responses, but Putnam is fairly careful in terms of how he explains things – offering many caveats and alternative explanations for his conclusions, as well as some more detailed explanations of his statistical processes in the appendix.

While each innovation in media seems to bring out Luddites railing against the potential unintended consequences – from the printing press, to radio, to television, to e-mail, to social media – that doesn’t mean that each of those groups haven’t had valid critiques. We often find, though, that the juice is in fact worth the squeeze when introducing new technologies. The introduction of the printing press probably did impact the overall ability of the population to memorize important cultural stories and it probably did introduce a sense of information overwhelm that resulted in people going “wide” on a lot of topics rather than “deep” on a few culturally agreed upon classics. But, we’d rather have a lot of different ideas from different authors than sitting around reciting the Iliad yet again – and that’s a fine trade-off to make.

If I overlay Putnam’s arguments with my experiences both as a relatively anti-social person and as a person with a leadership position in a small-ish organization in which I’m trying to create higher degrees of social capital, I can say that I’ve seen and felt an overall decline in engagement and willingness to “participate.”

In Putnam’s arguments, he blames commuting – both due to the time spent traveling as well as the fracturing of the community that one engages with, since an individual can now belong to three geographical communities for home, work, and hobbies/children’s activities as opposed to all of those taking place in the same region – as well as television – due to the very low transaction cost ability to stay home instead of engaging in the broader community – as the two major causal factors for the decline in social capital.

If I think about the difficulties of trying to either get myself to attend a social event or to get others to attend something like a gym outing or a heavy metal concert, I think that the low transaction cost of staying home coupled with the high mental transaction cost of going out (despite some improvements in transportation efficiency due to ride-sharing, etc.) may be a key factor in terms of the continued decline in engagement.

Note that this is all wild speculation and I have no business talking about any of this stuff with any authority since I’ve basically read one book on it lol.

Increased at-home entertainment options – from things like Netflix, smartphones, and social media – make it really easy to elect to stay home. And, in fact, staying home is often a much more engaging experience – even if it may not provide us with the same level of retroactive fulfillment as heading out into the world.

Imagine going to an amusement park.

Most of the time, you’re hot, waiting in a line, surrounded by obnoxious people, feeling crowded, and overpaying for snacks. But, the brief thrills that you get from the rides (the “peak experiences” of the trip) are exciting enough and salient enough in your memory that it’s worthwhile for many people to make the trip.

However, your moment-to-moment experience would be much more positive staying at home and watching Netflix rather than waiting in line for 30 minutes to spend $15 on a terrible piece of pizza at Great America. Sometimes, we seemingly prioritize the satisfaction of our future self’s memories over the immediate comfort of our current selves.

The options and connectivity presented to us by the internet also create a sense of overwhelm with the various obligations, FOMO and event invites that we all receive. We also receive fewer individual invitations to participate in social activities, since a lot of outreach occurs through Facebook event invites, group texts, and e-mail blasts.

Additionally, we are also concerned with curating our digital image on social media, and we know that almost everything we do will be documented in some form or another through Instagram stories and group pics. This creates a pressure for everything to be “extra fun” – which can also make things overwhelming since we may not feel up to dressing up and putting on a show for the cell phone.

This all combines to create a high mental transaction cost for engaging in social commitments, since we have to make dozens of decisions to filter through all of our options and prepare ourselves to be documented – even though the physical transaction cost getting somewhere has likely been reduced through the omnipresence of ride-sharing.

On an individual level, then, it’s easy to see how the access to easy, low friction entertainment that promises a steady level of comfort in Netflix and social media can overwhelm the high activation energy needed to attend a social gathering, a concert, or an optional community meeting.

Putnam discusses TV watching and categorizes individuals into those who either passively turn on the television whenever they are home versus those who only watch TV when they have actively chosen to follow a specific show. It seems that the negative effects on social engagement of television are more pronounced in the first group of passive television consumers.

The causality of something like this is likely complicated – and I would hypothesize that behavior here potentially tracks with a personality trait like conscientiousness – meaning, those who tend to be organized, structured, and better at controlling impulses are much less negatively affected by the presence of a low-friction entertainment option like television. (See also: junk food)

Still, I think that we are likely to see a bifurcation of negative effects on engagement that is further exacerbated by things like smart phones, social media, and Netflix.

Those who are better able to organize their time and control their attention are likely to disproportionately reap the benefits of easy access to information and culture facilitated by the internet – and others are more likely to end up disengaged from their communities, engaging in flame wars on Facebook, and deciding not to vaccinate their children because of YouTube.

To be clear, I also don’t think it’s totally fair to “blame” social media per say for this bifurcation or this continued trend of decreasing social capital.

This was very clearly a trend that has been in place for decades.

That, however, doesn’t mean that new innovations aren’t integral to the continuation of that trendline.

Think of something like Moore’s Law: “the number of transistors on a circuit doubles every two years.” In order for the trend to continue, researchers and companies need to keep on innovating and keep on packing in those transistors. This isn’t some natural phenomenon that plods along indefinitely – and the rate of doubling has in fact slowed in recent years.

Similarly, the decline in social capital likely requires continued innovation that further facilitates people staying home feeling overwhelmed – and further disconnected from their communities.

Survivorship Bias & Bad Advice

xkcd on survivorship bias

If there’s one thing that drives me crazy, it’s terrible advice from successful people.

If there’s another thing that drives me crazy, it’s magical thinking.

A lot of the advice thrown out there on podcasts and articles comes from successful people offering post hoc rationalizations for why they were successful.

And, believe me, as an avid consumer of online content, I often want to hear what successful people have to say about how they accomplished what they accomplished.

However – particularly in business and athletics – listening to the stories of those who have “made it” can give a pretty twisted perspective on why they were in fact successful.

The concept of “survivorship bias” is used when only those who have made it past some sort of threshold are considered – without taking into account the entire cohort of people who started a process.

So, for example, there are literally thousands and thousands of people who want to work hard in training, push themselves day in and day out in the gym, and make tremendous sacrifices to their personal life and their career in order to maximize their physical potential.

And a huge number of them will never qualify for anything.

So, when you hear elite athletes saying that they outwork everyone and they just “want it more” – they are not taking into account all of the other individuals who worked just as hard and wanted it just as badly who didn’t make it.

This can lead to a form of magical thinking, where the idea of pushing yourself and “wanting it” becomes the key variable that dictates success.

In reality, there are a few key things that probably make the difference between businesses and athletes who “achieve” – and other variables are either marginal or noisy.

And listening only to advice from those who made it without considering the others who didn’t is a recipe for confusion.

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

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Consolidating Fitness Markets

As a high school leftist, I would have looked down upon my current self with contempt based upon the fact that I give significant mental energy to the dynamics of markets and how they improve the quality of life for both business owners and consumers.

The market for CrossFit gyms has been consolidating over the last few years in the United States – meaning that many original gyms are closing or being purchased by other groups, and many of the gyms that started after the wave of initial success circa 2012 are limping along and occasionally shuttering their doors.

What’s going on here?

Some gyms are collapsing under the weight of the debt that they took on to finance their growth, others are noticing members churning out faster than they can replace them – resulting in a settling point of monthly cash flow that is below what makes it worthwhile to continue operating, some have pivoted business models to focus on Facebook marketing and 6 week challenges as opposed to “forging elite fitness,” and others have owners who have badly burned out from years of stress and chaotic hours with minimal financial reward.

While this happens, some of the gyms that “do things well” are getting stronger based upon flywheel effects where they are able to leverage their membership and cash flow to reinvest in their business and their staff – thus making the gap between them and the rest of the market even greater.

So, gyms that are coming on the market now are competing with even more established businesses with a significant head start – which makes the start-up costs to get involved in the market much higher since the expectation of the consumer has been elevated significantly.

Since boutique fitness in a brick and mortar location is a pretty low margin business, taking on significant debt to finance the growth of a new location is a pretty risky proposition (I should know since we did this at SLSC).

However, the introduction of these well-financed competition creates some interesting dynamics, since these businesses compete away marginal clients from pre-existing gyms – often while operating with business models that are not sustainable over the long term.

This is not something like the battle between Uber and Lyft where venture capitalists placed huge bets on the eventual profitability of each fraction of a percentage point of marketshare in a future with autonomous vehicles and layers of businesses built atop the logistical infrastructure developed to facilitate ride-sharing.

Instead, many of these folks are amateur investors who enjoy fitness and think it would be fun, cool and fulfilling to own a gym. (No knock on these folks, since I totally get it – we took money from some of them, as well).

I do have concern for the future of the boutique fitness industry, though, since so many gyms are operating with unsustainable business models.

What happens to the “big players” in the market that eventually close down since they’re unable to generate enough of a margin due to constant competition from competitors who aren’t subject to normal market dynamics based upon significant investments of amateur capital?

What happens to the new gyms that take on huge debt to get going but will never generate enough of a margin to pay it back?

How does this serve the clients who want to be coached by professionals – but the structure of the fitness industry doesn’t allow for enough revenue to support paying a living wage to coaches?

How do owners of boutique fitness businesses set up their businesses to be stable over time when they have to coach classes and work with clients for 30+ hours per week to generate enough revenue to pay themselves and keep the lights on?

I wish this problem statement was leading to some sort of clever and insightful solution, but all I can do for now is frame the problem.

Marcus Filly (Revival Strength)

Marcus Filly (Revival Strength)

“The next level of growth is going to come from letting go and taking more risks. You’re trying to control things and you’re good at that, but the next level isn’t going to arrive with that mentality.”

This is what James FitzGerald told Marcus Filly before Regionals in 2017. Marcus ended up qualifying for his first CrossFit Games as an individual that year after “letting his hair down” so to speak and pushing the pace harder than he was comfortable with in the final workout.

Since then, Marcus has popularized the concept of Functional Bodybuilding and a more measured approach to intensity in fitness training – especially for people whose goal is to look good, feel good and move well.

Marcus owns multiple businesses including an online coaching company, a brick and mortar gym facility in San Rafael, and a supplement company called Revive-Rx.

Check out the full conversation with Marcus to learn:

  • How Marcus thinks about content creation – and how to approach writing to have a record of what you’ve done, writing to self-reflect, and writing to solve a problem for an audience
  • The difference between systemizing and going with the flow – and how to decide when a system is helpful and valuable, and when it should be ditched for being overly restrictive
  • How being overly analytical can cause roadblocks – and why the behavior that got you to where you are now won’t always get you to the next level

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Marcus, Revival Strength & Functional Bodybuilding here:

Show Notes

  • [01:51] The differences between posting training on a WordPress blog and posting training on social media – and the differences between posting to have a record of what you’ve done, posting to self-reflect, and posting to share for an audience.
  • [11:17] What was the tipping point to move from the personal fitness blog to social media?
  • [15:20] The difference between systemizing and going with the flow – and how to decide when a system is helpful and valuable, and when it’s overly restrictive.
  • [20:04] “Letting your hair down” – how being overly analytical can cause roadblocks, and why what got you here won’t always get you there
  • [31:53] Training with Danny Nichols – and strapping him to the pull-up bar with lifting straps to teach him kipping. And tales of folly and intensity from the Grid League including a broken hand from touch-and-go power snatches.
  • [42:59] Tying multiple different businesses together – and the challenges of running an in-person gym when you’re running a successful online business.
  • [52:38] How to create content for a large audience – and how to think about people misunderstanding the message
  • [01:03:25] How to handle and react to negativity on the internet – and how handle the opportunity cost of helping everyone who reaches out for advice while still being grateful for the fact that people are paying attention.

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When to take down Chesterton’s Fence

At a recent “nerd meet-up” that I attended, one of the participants asked how we explain what we are doing to peers, co-workers, girlfriends, etc.

I responded that I tell people I am going to a “nerd meet-up.”

Anyway, I’ve recently forced blog reading (and guitar-playing) back into my schedule after neglecting both for years, and, by reengaging with online content, I’ve also found myself attending real-life events based upon people who engage in online content. Funny how that works out.

The topic of the most recent Chicago Rationality meet-up was the Chesterton’s Fence principle – which is not only defined on Wikipedia, but is a key aspect of the regulation of wikis across the land:

The quotation is from G. K. Chesterton’s 1929 book The Thing, in the chapter entitled “The Drift from Domesticity”:

In the matter of reforming things, as distinct from deforming them, there is one plain and simple principle; a principle which will probably be called a paradox. There exists in such a case a certain institution or law; let us say, for the sake of simplicity, a fence or gate erected across a road. The more modern type of reformer goes gaily up to it and says, “I don’t see the use of this; let us clear it away.” To which the more intelligent type of reformer will do well to answer: “If you don’t see the use of it, I certainly won’t let you clear it away. Go away and think. Then, when you can come back and tell me that you do see the use of it, I may allow you to destroy it.”

Another piece of reading for the discussion was from Scholar’s Stage on the value of tradition and how many traditions have second and third order effects that are optimized for something that may not be obvious from a surface-level examination of the tradition. Couple that with James Scott’s Seeing Like a State (and the associated essay from the Cato Institute) – which chronicles all kinds of failures and unintended consequences as governments attempt to make the goings-on of their citizens “legible” to things like censuses, tax collectors, and urban planning commissions – and you’ve got yourself a libertarian stew.

As someone who tends to disregard tradition and conventional wisdom, I find it useful to be reminded of heuristics that value tradition and “the way things have been done” over simply wiping the slate clean and starting over.

I tend to default more to the “pot roast heuristic” – as stated on Mindful Mornings:

A mother was preparing a pot roast for her family’s Easter meal while her young daughter helped. Knowing her daughter was very curious, the mother explained each step. As she was preparing to put the pot roast in the oven, the mother explained, “Now we cut the ends off of each side of the meat.” As young children often do, the daughter asked, “Why?” The mother thought for a moment and replied, “Because that’s the way it’s done. That’s how your grandma did it and that’s how I do it.”

Not satisfied with this answer, the young girl asked if she could call her grandma. The young girl called and asked, “Grandma, why do you cut the ends off the pot roast?” Her grandma thought for a moment and said, “Because that’s the way it’s done. That’s how my mom did it and that’s how I do it.”

Still not satisfied, the young girl called her great grandma, who was now living in a nursing home. “Great grandma,” she said, “Why do you cut the ends off the pot roast?” Her great grandma said, “When I was a young mother, we had a very small oven. The pot roast wouldn’t fit in the oven if I didn’t cut the ends off.”

So, how are we to make decisions? If we encounter a fence, how shall we decide its worth? Do we take it down? Go around it? Identify as “fence people” and hate all people who don’t have a fence? Or, sit upon it – forever neutral and uncommitted?

Based upon our discussions during our “nerd meet-up” and my own impulses, I would propose asking several questions and weighting the responses to decide what to do with the fence (or tradition).

Is the tradition an iteratively created response to a complex system? There’s a big difference between a rule or tradition that is top-down created by a state or government agency (like the confusing mess of dietary recommendations related to cholesterol levels and heart-disease risk that have created all kinds of negative consequences such as people replacing traditional foods with the even more dangerous trans fats) vs traditions that are iteratively arrived at over time through some sort of selection process (like the complex cassava preparation process detailed in the Scholars Stage article that removes the cyanide from the food and makes it edible). If a tradition or rule is “evolved” – meaning it was iteratively created potentially in response to selection pressure in a complex system, we should weight it more positively.

Is this a one-way door or a two-way door? This concept was popularized in one of Jeff Bezos’s letters to shareholders:

Some decisions are consequential and irreversible or nearly irreversible—one-way doors—and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that—they are changeable, reversible—they’re two-way doors.

When interfering with complex systems, we often want to make small, reversible changes based upon initial feedback. In a business, for example, it’s often better to gradually implement policy changes in small groups to test them out before rolling out to large cohorts of customers or employees.

In the case of a fence in the woods, for example, we could try going around it and see what happens before taking it down.

Are you hopelessly iterating to a local maxima? This is a common problem in A/B testing methodology. You can iterate on a website and squeeze every drop of conversion out of the button placement, headline, and bullet points – but you may have much more success by speaking to customers and figuring out how to solve a problem that they don’t even know how to articulate that they have.

If you think about the concept of “trying to find the highest peak,” you could come up with a decision-making algorithm that requires you to always take steps in directions that are either neutral or higher than your current elevation. If you were to get to the top of a small hill, the algorithm would require that you stay on top of that hill, since each step that you take would, in fact, decrease your elevation – even if there were a huge, mountainous peak just a few yards away from that hill.

Traditions and processes can sometimes lock us into local maxima and we need to be willing to discard them in order to find a higher peak.

Will there be second order consequences to removing the rule or tradition?

Sometimes it’s not just about the rule or tradition itself – there may be significant second and third order consequences to adjusting a significant part of a complex system.

I’ve put algorithmic social media feeds on blast before for not just hijacking our attention but also making us into the kind of people who have our attention hijacked. I doubt anyone designing those algorithms had a serious concern that they would be modifying the brain chemistry of billions of people as they tried to increase engagement on their platforms. But, nonetheless, here we are.

Benedict Evans has one of the best articles on the web on second order consequences in relation to the future of autonomous driving. It’s not just about truck drivers and cab drivers who may have their jobs replaced nor is it just about the people whose lives will be saved that would have otherwise died in auto fatalities – what happens to the auto insurance industry? What happens to the space currently used for parking? What happens to greenhouse gas emissions?

Not all of these second and third order consequences require or deserve a value judgment – it’s just crucial to recognize that adjusting part of a complex system will have a variety of unintended consequences that can be both positive and negative.

Is the rule or tradition caused by inertia and/or entropy?

I’ve set up and built a lot of different systems to operate South Loop Strength & Conditioning – and I don’t necessarily do a great job of maintaining them. We have e-mail nurture sequences, Zapier integrations, and data tracking and Airtable that have all gotten quite jumbled as we’ve fixed bugs, added software, and scaled our business. There’s a lot of duplications of previous work or things that used to make sense based upon the scale that we used to be operating at and simply need to be removed or cleaned up.

There’s also redundancy layers added to account for likely errors and to create a sort of ad hoc QA/QC process as we’ve added more employees.

As we work on cleaning up our systems, it’s not always obvious what is essentially inertia and overgrowth and what is a functional stopgap or QA/QC process – especially since I often don’t remember how or why I set things up, nor did I used to do a very good job of documenting our processes.

Is the rule or tradition a spandrel attached to a more valuable rule or tradition?

Many times traditions or rules are created and other things come along for the ride. Religion (to this skeptical atheist – just putting my cards on the table, not intending to create value judgment) seems to be full of cultural spandrels.

It seems obvious to me that the social rituals, moral codes, and sense of transcendence that most religions create for people are an adaptive trait. To give an extreme example, it seems that taking phenobarbital and wearing sick Nikes may not be a tradition worth saving.

I’m sure there are other questions to weight when deciding whether or not to remove a traditional fence, but these are the ones that come to mind for me in my decision-making processes. Any others that I missed?

Should you work on your weaknesses?

I recently listened to an episode of Adam Grant’s “WorkLife” called “When Strength Becomes Weakness.”
This got me thinking about how much – if any – time we should spend working on our weaknesses.
CrossFitters pride themselves on the amount of time that they spend working on their weaknesses – doing endless rowing intervals to try to improve their engine, constant EMOMs of strict handstand push-ups, and accessory sessions of banded pull-aparts and seated external rotations to try to improve their shoulder muscle endurance.
Lots of business advice, however, recommends the exact opposite.
Here’s a quote from Paul Brown’s Forbes article “Forget about working on your weakness, play to your strengths!”:
Yes, I got marginally better at all those things. But, I was still really bad and putting in all that effort for so little gain made me extremely cranky. And worse, I wasn’t having any fun.  Spending every day being reminded of what you are awful at is enough to make anyone depressed.
Eventually, I realized I would be far better off doing what I do well–solving business puzzles–and NEVER managing again.
So, how do you decide which advice is correct? How do you know when to work on your weaknesses vs work on your strengths? Am I talking about fitness or business?
Who can really say?
Anyway, I have some thoughts on how to decide whether it’s best to spend your time on doubling down on your strengths or shoring up your weaknesses.
To figure out where our time is best spent, we have to consider three things:
  1. What is the “unit of competition” or “unit of action”?
  2. Are playing a bounded or an unbounded game?
  3. What is your current limiting factor?
What do I mean by “unit of competition”?
In business, organizations compete with each other. So, while it may not make sense for an individual to spend significant amounts working on his or her weaknesses, the organization as a whole may need to do so.
What does this mean?
Well, if your organization struggles with management, it may not make sense to try to train a bunch of impatient people with poor social skills to manage. It ‘s obviously better to put those people in roles that require less interaction with others and allow them to play to their specific strengths (maybe something like strategic thinking or creating systems).
The organization as a whole will probably benefit from individuals within it focusing on their specific strengths and staying away from their weaknesses.
What about the “unit of action”?
However, roles within an organization don’t always allow for an individual to fully stay away from their weaknesses – and there are many situations where someone will need to improve a weakness since it becomes a limiting factor for them relative to their ability to execute on their strengths.
In some cases, it can make sense to simply delegate all of the tasks that an individual struggles with – I know several entrepreneurs, CEOs, law firm partners, etc. who are seemingly incapable of keeping a calendar or handling e-mail in a reasonable way, but they have assistants who essentially keep them on track.
But, what about a CrossFit coach who struggles with providing feedback without sounding judgmental? It doesn’t make sense for that coach to “delegate” giving feedback on movement to an assistant coach while they focus on their strength of providing clear explanations and demonstrating movements correctly.
In this case, the coach is a self-contained “unit of action” and will see the biggest gains in his or her capabilities as a coach through improving the ability to give feedback without triggering defensiveness in clients.
Are you playing a bounded or an unbounded game?
The possibilities of significantly outsized results can completely change the incentive structure for whether or not you should work on your strengths or work on your weaknesses.
We may as well use CrossFit competition as an example here, since I think this is a particularly salient example of this phenomenon.
In most competitions, one of two scoring structures is typically used.
You either receive a point total relative to your placing on an event (1st place gets 1 point, 2nd place gets 2 points, 3rd place gets 3 points, etc.) and the lowest point total wins. This is the scoring system used in the Open.
Or, you get points relative to your placing with some scaling in the interval between places (1st place gets 100 points, 2nd place gets 95 points, 3rd place…28th gets 24 points, 29th gets 22 points, etc.) and the highest point total wins.
This is a bounded game – meaning that you don’t get an advantage by winning an event by 10 minutes compared to winning an event by 10 seconds.
And, based upon the way the scoring works out, it’s much more important to not have weaknesses than it is to have significant strengths. For example, someone who finishes in 5th place across five events will beat someone who finishes, 1st/30th/1st/30th/1st.
So, CrossFit athletes respond rationally to the incentive structure and work hard to eliminate weaknesses.
But, what if you’re playing an unbounded game? (Or at least a game that allows for totally outsized results).
In that, case it would make a lot more sense to double down on your strengths. If, for example, the margin of victory mattered in CrossFit, we would see a totally different incentive structure for training. It would be possible to have people competing who would push the extremes on strength events and endurance events far past the middling numbers that CrossFitters currently put up relative to elite powerlifters or runners.
If we take an example from business, PayPal left millions of customer support e-mails unanswered while they were rapidly scaling in the online payments industry. Did that hurt them? Probably a bit – but they still sold to eBay for 1.5 billion.
Would they have been better served by focusing on their weaknesses in customer support or by doubling down on their strengths in fraud prevention and detection and serving the eBay users that provided their initial case of product market fit?
The answer seems obvious to me.
What is your current limiting factor?
If we think about the above factors, we should be able to come up with an understanding of what your current limiting factor is.
Is it possible that – by developing your strengths – you can achieve a significant and outsized reward? Are you playing a “winner-take-all” game?
Can you delegate your weaknesses? Or come up with a creative solution to get around them?
Or, are you yourself the unit of competition and your weaknesses are either holding you back (by preventing you from accomplishing a key and irreplaceable aspect of the task that you’re trying to complete) or they are potentially creating the possibility of a significant negative event in the future that could derail your success even if it is outsized (significant accrual of technical, management or cultural debt).
It’s not always obvious where the highest leverage activities lie, but it’s clear that blanket advice to “focus on strengths” or “fix weaknesses” doesn’t take into account the variability in the types of games that people are playing or the ways that they compete in those games.

Four Tendencies + Five Factors

I recently had an error with my Dropbox account that caused me to go through a bunch of my files in order to clean up a bunch of trash on my hard drive.
I found this little drawing that I made with the intention of creating a blog post, but I don’t think I ever actually wrote this thing up.
If you’ve been on this newsletter for a few years, you may remember me writing about Gretchen Rubin’s “Four Tendencies” framework.

Gretchen Rubin's Four Tendencies Framework

I’ve personally found a lot of personality psychology to be extremely helpful in working with clients and running a business since – well – most people are not like me and I don’t understand what the hell they’re thinking.
While there’s a lot of pseudoscience and frameworks that are really just about one step above a shoddy Buzzfeed quiz (“You know you’re a [INSERT TYPE OF PERSON] if you [INSERT SHARED GROUP EXPERIENCE]”), I’ve found it helpful to understand a variety of different frameworks and attempt to relate them back to the more evidence-based big five model of personality.
The big five model of personality is based upon the idea of five independent personality “knobs” that can be dialed up or down in individuals – these knobs are:
Openness to experience: Openness reflects the degree of intellectual curiosity, creativity and a preference for novelty and variety a person has
Conscientiousness: Tendency to be organized and dependable, show self-discipline, act dutifully, aim for achievement, and prefer planned rather than spontaneous behavior
Extraversion: Energetic, surgency, assertiveness, sociability and the tendency to seek stimulation in the company of others, and talkativeness
Agreeableness: Tthe six facets of agreeableness are: Trust, straightforwardness, sycophancy, AltruismComplianceModesty, and Tender-Mindedness
Neurotocisim: The tendency to experience unpleasant emotions easily, such as angeranxiety, depression, and vulnerability.
Gretchen’s model of four tendencies seems to be built one layer up  from the big five model.
She phrases things in terms of “meeting your own expectations” and “meeting the expectations of others” – which I view as proxies for traits conscientiousness and agreeableness, respectively.
I drew my own version of the Four Tendencies model below with the axes of the graph representing the percentile of conscientiousness and agreeableness.

Four Tendencies + Five Factors

So, what’s going on here?
I think that anyone above a certain percentile of conscientiousness would be an “upholder” in Gretchen’s model – someone who views tasks and expectations as duties that must be completed. These systematic people live to complete the tasks laid out before them – whether assigned by themselves or assigned by others.
I can personally speak to the Upholder mindset as someone who tests as very high on conscientiousness and very low on agreeableness in the Big Five model.
People below a certain conscientiousness threshold tend to be either Questioners (meet their own expectations but struggle to meet the expectations of others) or Obligers (meet the expectations of others but struggle to meet their own expectations).
These people don’t necessarily feel the overwhelming compulsion to complete tasks regardless of source that the high conscientiousness Upholder does, but they will either relentlessly pursue things that make sense to them and their own priorities (Questioners) or fight to never let anyone down who they care about (Obligers).
Below a certain threshold of both conscientiousness and agreeableness, we have the Rebel. These individuals struggle both to meet their own expectations and the expectations of others. “You can’t tell me what to do, and neither can I.” Rebels are interesting, since they often frustrate those around them as well as themselves with their seeming capriciousness and lack of follow-through.
I would also posit that we could include a Z-axis on the above graph with “% Openness” as the axis. I think the structure of the above diagram would remain similar, but the line of conscientiousness above which someone becomes an Upholder moves higher up the lower someone is in trait openness.
If I compare myself (very high openness and exceptionally high conscientiousness) with my mother (exceptionally low openness and very high conscientiousness), I think that openness also serves as a filter to which tasks we will “accept.” I can be too open to new ideas and new projects and allow myself to agree to too many different things or spread myself thin, while my mother behaves much more like a “Questioner” despite her very high conscientiousness since she is often mistrustful of new information and can seem “stubborn and set in her ways.”
Anyway, I read this Gretchen Rubin book kind of awhile ago and I still think about the practical takeaways from it consistently when working with clients and staff – so I would highly recommend it even if it may not be a perfectly evidence-based iteration of personality psychology.

Orion Melehan (LIFEAID)

Orion Melehan (LIFEAID)

“Being a Pollyanna actually works in your favor in business since you don’t really understand all of the obstacles.”

Orion had an intuition that he was onto something a few years back when he and business partner Aaron Hinde went on a domain registration spree for all things ending in “aid” and found that just about every iteration they tried was still up for grabs.

From hustling to get their first product into golf course pro shops (GolferAid) to rapidly scaling and simultaneously running out of product while broken computer systems left them unable to match inventory to customer orders, it turns out that original intuition was correct.

Orion and I talk about the challenges of managing a company growing so quickly that things start to fall apart, and LIFEAID’s mission to change the landscape of beverages outside of the fitness subcultures that got them their start.

Check out the full conversation with Orion below to learn:

  • How Orion learned to feed off the energy of the crowd – and adjust on the fly to keep them dancing – as a house DJ – possibly some carryover to the role as CEO of a rapidly growing beverage brand? Who can say?
  • How to prioritize as you’re scaling – and how to know what to allow to break as you grow and what needs to be a top priority
  • How LIFEAID plans to stay true to their mission as they expand outside of the fitness subculture into more mainstream markets in grocery stores – and why just helping already fit folks get fitter isn’t enough for LIFEAID

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Orion and LIFEAID here:

Show Notes

  • [01:43] Orion’s seemingly contradictory background as both a certified financial planner and a DJ, as well as his early entrepreneurial ventures (including a record store).
  • [08:30] The process of crafting a DJ set – and balancing your own desires with the desires of the audience. The differences between being a “technical” DJ and going off the feel of the crowd, and developing DJ skills in a time before comprehensive DJ software.
  • [15:25] Starting LIFEAID with multiple different SKUs, and figuring out how to prioritize the many different options. The benefits of understanding direct response marketing and split testing offers with different markets.
  • [24:33] How to manage ultra-fast growth – and how to figure out what you’re going to let break and what you’re going to stay on top of. And why being starved of capital during a growth phase is better than being flush with capital.
  • [33:18] Breaking into the very high barrier to entry beverage space through direct response marketing, understanding the long tail and subcultures, and hiring during rapid expansion.
  • [40:47] How LIFEAID plans to manage its expansion from a niche community (CrossFit) into mainstream areas like grocery and convenience stores while maintaining the vision for the company. Just continuing to create products for already healthy people doesn’t serve the mission of getting the population off of sketchy energy drinks.
  • [52:45] How to find the optimal balance between optimizing things that are already working while still being innovative and expanding into new markets. LIFEAID’s goal of solving different problems for their customers throughout the day – the goal is to have products for all the different “jobs” customers buy beverages to accomplish.
  • [01:00:32] How to think about the sequencing of growth in a company and do things in the correct order. Crafting new quarterly vision statements and creating alignment across the team based upon objectives and key results – as well as creating an environment in which the best ideas can percolate throughout the organization from the bottom up.

Links and Resources Mentioned

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A return to trust in expertise

I had some good responses to my last e-mail about finding the balance between critical thinking and a blanket mistrust of expert opinion.
As someone with a history of rebellious opinions and clashes with authority, I find it strange that I’ve found myself in the position of defending “expertise” and establishment.
However, I am currently much more concerned with the rise of crackpotism than I am with mindless obedience to authority.
By removing gatekeepers and democratizing the ability to spread information (especially through algorithmically curated social feeds), we seem to have accelerated the rate at which both autodidacts can take in and filter huge amounts of information as well as the percentage of potential crackpots that can be exposed to conspiracy theory.
I’m trying to parse out the difference between what I would consider to be healthy and appropriate skepticism versus what I would consider to be dangerous and foolhardy crackpotism.
If we use the example of CrossFit HQ sharing articles regularly calling into question the expertise of medical professionals, conflicts of interest in science, and potential corruption through pharmaceutical money that I discussed last week, I think I can clarify what I mean.
Let’s think through a rough Bayesian framework for trusting expert consensus on medical matters.
We can kind of bastardize the the details for the purpose of conversation without getting too into the weeds in defining our question appropriately, and say something like:
“The probability that expert consensus on matters related to health, wellness and prevention of long-term disease is largely correct is X%”
Or – to rephrase – “Of 100 consensus expert opinions on health and wellness topics, X of those opinions are largely correct.”
To list some specific examples, we can think of things like the following examples making up our list of expert consensuses:
•Recommend dosing of creatine supplementation
•Recommended daily allowances of various micronutrients
•Recommendations on total sleep
Then, if we happen to have additional information about a topic or reason to doubt expert consensus, then we can engage in Bayesian updating.
From the link:
Situation # 1:
Given: The median height of an average American Male is 5’10”.  (I don’t know if this is accurate; that’s not the point.)  You are on a business trip and are scheduled to spend the night at a nice hotel downtown.
Wanted:  Estimate the probability that the first male guest you see in the hotel lobby is over 5’10”.
Solution:  50%  (Well, that’s certainly self-evident.)
Situation # 2:
On your way to the hotel you discover that the National Basketball Player’s Association is having a convention in town and the official hotel is the one where you are to stay, and furthermore, they have reserved all the rooms but yours.
Wanted:  Now, estimate the probability that the first male guest you see in the hotel lobby is over 5’10”.
Solution:  More than 50%   Maybe even much more, and that’s obvious too.
I have no issues with updating off of expert consensus based upon new or more nuanced information.
However, I have a concern that a lot of the information that CrossFit is putting out is not intended just as information for updating a Bayesian prior, but as an attempt to downgrade our trust in expert consensus as a whole.
Meaning that – rather than clarifying the nuance on a specific issue – it’s meant to change our belief in whether or not we can trust expert consensus in general
My 17-year old punk self probably can’t believe I’m saying this, but I actually think that most people don’t trust experts enough.
Or, they potentially miscategorize experts and put someone like Dr. Oz on the same footing as lipidologists who have been studying the metabolism of cholesterol for decades.
Here’s to a return to true expertise!