Author Archives: Jeremy Wilkinson

Highlights & Iterations: Same as Ever (Housel)

“We are very good at predicting the future – except for the surprises – which tend to be all that matter.”

Iteration: At some point, it may be better to focus on the likelihood and impact of surprises instead of trying to improve my base-case model by a fraction of a percentage. 

“Invest in preparedness, not prediction.”

“People don’t really communicate on social media so much as they perform for one another.”

Iteration: View social media posts as performance art instead of non-fiction.

“With a large enough sample, any outrageous thing is apt to happen. That’s part of why the world seems so crazy, and why once-in-a-lifetime events seem to happen regularly.

…if an event has a one-in-a-million chance of occurring every day, it should happen to 8,000 people a day, or 2.9 million times a year.

Iteration: Another reminder of how bad we (humans) are at processing large numbers. The 24-hour news cycle now exposes us to more one-in-a-million chance events than ever. The world is not crazier than ever – its exposure has changed. As Housel put it a few pages later, “We just see more of the bad stuff that’s always happened than we ever saw before.”

“The best story wins. When a topic is complex, stories are leverage. Guiding people’s attention to a single point is one of the most powerful life skills.”

Some of the most important questions to ask yourself are: Who has the right answer, but I ignore it because they’re inarticulate? And what do I believe is true but is actually just good marketing.”

Iteration: Replace inarticulate with disliked, new, unknown, or any other bias. The best answer is often unfamiliar, unknown, or uncomfortable. 

Bezos once said, “The thing I have noticed is when the anecdotes and the data disagree, the anecdotes are usually right. There’s something wrong with the way you are measuring it.”

Iteration: I remember the day I told my boss I had data available to help him win whichever side of his argument he wanted to be on. He replied, “Congratulations, you just became a real analyst.” We love data and quantification, but it can be bent, abused, and manipulated. The real skill is peeling back the details of the data and providing thought. Data interpretation is the more impressive skill. 

“Most things have a natural size and speed and backfire quickly when you push them beyond that.”

Iteration: Sitting in a room and applying simple math or hurried thoughts on how to double a measurable item or event is easy. Experience teaches you that doing such a thing is more likely to be exponential than linear. 

Voting

Should I vote only with self-interest in mind?

Should I vote for short-term self-interest or long-term self-interest?

If I’m not voting for self-interest, should I vote to maximize the common good or for outcomes for those I believe are most in need?

Is my perception of “those most in need” rooted in fact or opinion?

Am I knowledgeable and experienced enough to understand what my votes will do to benefit the common good?

If I vote to improve the common good, do I vote to optimize short-term or long-term outcomes?

Am I knowledgeable and experienced enough to understand what my votes will do to benefit those I perceive to be most in need?

If I vote to maximize outcomes for those I perceive to be most in need, do I vote to optimize short-term or long-term outcomes?

Quick Notes from Tufte’s Visual Display of Quantitative Information

Use colors from nature

To clarify the point of a visual display, sometimes detail should be added, not removed.

Erase non-data ink

A longer graphic (width) is usually better than a taller one

The purpose of the graphic is to:
– Provide the greatest number of ideas
– In the shortest amount of time
– Using the smallest space (least amount of ink)

Iterations: Charlie Munger

I can’t say anything about Charlie Munger that has not been said already, but I can share my take on my favorite quote of his.

“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”

— Charlie Munger

When I’m stuck on a problem or trying to choose amongs options, asking myself, “Which option do I think I will regret less” is always find helpful.

Take actions that you think will prevent or minimize future regret vs. the other options available.

That’s it. In a way, it’s an iteration of Doing Favors for your Future Self.

Most people (rightfully) apply Munger’s wisdom to investing, finance, or business. 

It works just as well outside of business.

I’ve used it to optimize decisions about spending my free time, what to say to a friend in need, and thinking through how to handle interpersonal disputes.

Upon reflection, a second theme emerged.

If you are struggling with what to do in a given situation, the path of less future regret is the path where you do more, not less.

If a relationship is struggling, the “prevent future regret” action is to try harder, not give up.

If you are struggling with a plateau in your health or wellness, putting in the extra effort in time is the path of less future regret.

As I reflect on my regrets – and the regrets that others have been kind enough to share with me, “I wish I would have done more” is exponentially more common than “I wish I would have done less.”

If you find yourself frustrated with something, trying harder, doing more, or giving it one more shot is almost always the safer bet.

Here’s an excellent post about Munger and preventing regret: Charlie Munger: The Power Of Not Making Stupid Decisions

One thing I learned: The Subtle Art of Not Giving a F*ck

Here’s one of my takeaways from Manson’s award-winning book.

In the book, Manson talks about a test where people are put in a room with a bunch of switches and buttons. They are told that if they do something correctly, a light comes on.

People come up with incredibly creative and unique combinations to make the light come on.

Here’s the catch – the light comes on at completely random intervals. 

People exit the experiment with passionate conviction that they “solved” the sequence(s) that make the light come on.

Manson argues that our brains are constantly in search of meaning. Combine this with the prevalence of misinterpreting and misremembering, and people quickly develop conviction and passion around something which they have no understanding of. 

The more complicated, unknown, or difficult to explain a result is – the more we will falsely attribute our actions in order to explain it.

We don’t like not knowing, and deceiving ourselves is more comforting than attributing an outcome to randomness.

The distance: specificity ratio

Details are exponentially more important based on the length of the journey.

If you are in a restaurant for the first time and need to find the restroom, you will likely receive directions such as “around the corner and to the left.”

Odds are, you will end up where you need to be. 

The distance traveled is very short.

The destination is evident and recognized.

If you happen to get lost, the cost (time) to reset is very low.

Multiple sources can redirect you on your journey. 

Now imagine you are standing in Boston and asking for directions to Los Angeles. (Let’s just pretend GPS doesn’t exist for a moment.)

Would “travel Southwest” be enough to get you there?

What if you needed to get to a specific address or need to arrive by a certain time.

Being given the direction to “travel Southwest” is accurate.

The simplicity is also cruel.

With such little direction, the odds of a successful journey are near-zero. 

Leaders often provide far too little detail when asking others to make significant developmental journeys.

It is their fault that the travelers end up lost. 

If you are managing, mentoring, or coaching someone through a significant change, your directions need to be incredibly specific. 

Short-term feedback can lack detail and still be helpful.

Long-term feedback cannot.

Specificity, waypoints, details, and notes are critical.

GPS systems warn you of traps along the way and regularly update you on how much more time is needed before you arrive. 

If you are coaching someone towards a significant, long-term, or developmental hurdle, it is your responsibility to provide:

  1. Turn by turn directions
  2. Warnings about traps, confusing parts of the journey, and areas where slowdowns are likely to occur
  3. Notifications when the traveler makes a wrong turn – including directions on how to get back on track.

Three Thoughts

“Going with your gut” should be a statement reflecting your preparation, not a willingness to gamble. (Inspired by Annie Duke.)

If you are committed to growth and improvement, spend time exploring how you are wrong and things you do not understand. Be aware that the pull to spend time confirming our beliefs and verifying what we already know is strong and persistent.

Waste no time thinking about the harmless actions of others.

The Adults Who Cry Wolf

Most of us know the childhood story of The Boy Who Cried Wolf.

Most of us could quickly recall the moral of the story. Once people brand you as a liar, they won’t believe you, even when you tell the truth.

The boy traded trust and goodwill for attention and entertainment.

Despite general acceptance of the lesson, most of us are still “crying wolf” more than we realize every day.

If you are constantly a contrarian, the value of your words decreases over time.

A moment may come when your contrarian viewpoint is correct, but the cost of being overly contrarian limits the impact of your words.

If you latch on to every available conspiracy theory, many of those around you consciously and unconsciously put less value on your words.

These beliefs come at a cost – and those that own these beliefs grossly underestimate the cost of owning them.

Until they cry wolf, and no one listens.

To teach, or not to teach

I’ve been learning to play disc golf this year. It’s a great way to get outside and move around. I also like anything where you can keep score and measure results and improvement.

I had an interesting decision to make when my brother joined me for a game.

A few things to know:

  1. I’m very new to the game. I’m two months and maybe 5-6 rounds into the sport.
  2. I’m not very good. On a scale of 1 to 10, I’m maybe a 3. That might be generous.
  3. My brother is a natural athlete.

My struggle was regarding my obligation to teach or advise my brother.

Although I was the more experienced player, should I be offering any tips?

What if, due to his natural athleticism, my brother would be a 4/10 without any input from me?

Would my advice, while coming from a good place, technically make him worse?

I’ll share what I did in a moment, but after some reflection, here are my takeaways:

The third bullet is the tough one, especially considering the pull of the first two. 

Here’s where I landed:

  • As a teacher, I need to be at least two levels of competence above the student to be worthy of teaching them.
  • If I’m unsure about whether or not I am a worthy teacher, the answer is no.
  • The measure of a potential student’s competence should be based on an observed result, not an assumed one. 
  • If you don’t meet the criteria of a worthy teacher, but someone asks for your advice, repeat the advice of someone even more experienced than you. Resist the urge to offer your take. Better yet, use technology to ensure the clarity of the message.
    • Even when our intentions are good, we may taint an expert’s message through our inexperience and incompetence.
  • If you must give advice, heavily discount it.
    • “I’m still learning myself, and this might be wrong, but here is what I am doing/trying” is a much better way to share tips than an overconfident, “This is how I do it.”

I resisted the urge to teach, only offering verbatim tips I had learned from others far more experienced than me.

(We tied.)