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tech
Super Thinking
by Gabriel Weinberg and Lauren McCann
CURATED BY GUILLERMO FLOR
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The Book in One Sentence
• Super Thinking is about the frameworks and
shortcuts top performers rely on the cut through
complexity and separate good ideas from bad
ones.
Favorite Quote
• “When you don’t use mental models, strategic
thinking is like using addition when
multiplication is available to you.”
Super Thinking Summary
1. Being Wrong Less
Carl Jacobi once said, “Invert, always invert.” What Jacobi
meant by that, was thinking about a problem from an
inverse perspective can unlock new solutions and
strategies.
“The central mental model to help you become a chef with
your thinking is arguing from first principles. It’s the
practical starting point to being wrong less, and it means
thinking from the bottom up, using basic building blocks
of what you think is true to build sound (and sometimes
new) conclusions. First principles are the group of self-
evident assumptions that make up the foundation on
which your conclusions rest—the ingredients in a recipe or
the mathematical axioms that underpin a formula.”
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“When arguing from first principles, you are deliberately
starting from scratch. You are explicitly avoiding the
potential trap of conventional wisdom, which could turn
out to be wrong. Even if you end up in agreement with
conventional wisdom, by taking the first-principles
approach, you will gain a much deeper understanding of
the subject at hand.”
“To be wrong less, you need to test your assumptions in
the real world, a process known as de-risking. There is
risk that one or more of your assumptions are untrue, and
so the conclusions you reach could also be false. Once you
identify the critical assumptions to de-risk, the next step is
actually going out and testing these assumptions, proving
or disproving them, and then adjusting your strategy
appropriately.”
“Ockham’s razor advises that the simplest explanation is
most likely to be true. Look at your explanation of a
situation, break it down into its constituent assumptions,
and for each one, ask yourself: Does this assumption
really need to be here? What evidence do I have that it
should remain? Is it a false dependency?”
“Overfitting occurs when you use an overly complicated
explanation when a simpler one will do. It’s what happens
when you don’t heed Ockham’s razor, when you get
sucked into the conjunction fallacy or make a similar
unforced error. It can occur in any situation where an
explanation introduces unnecessary assumptions.”
“One approach to fighting overfitting is to ask yourself:
How much does my data really support my conclusion
versus other conclusions?”
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“When crafting a solution to a problem, whether making a
decision or explaining data, you want to start with the
simplest set of assumptions you can think of and de-risk
them as simply as possible.”
“If you’re trying to be as objective as possible when
making a decision or solving a problem, you always want
to account for your frame of reference. A frame-of-
reference mental trap is framing. Framing refers to the
way you present a situation or explanation. You will of
course be influenced by your perspective, but you don’t
want to be unknowingly influenced. Therefore, if you
think you may not have the full understanding of a
situation, then you must actively try to get it by looking
from a variety of different frames of reference. When
someone presents a new idea or decision to you, take a
step back and consider other ways in which it could be
framed.”
“A related trap/trick is nudging. You can be nudged in a
direction by a subtle word choice or other environmental
cues.”
Another concept you will find useful when making
purchasing decisions is anchoring, which describes your
tendency to rely too heavily on first impressions when
making decisions.
The availability bias occurs when a bias, or distortion,
creeps into your objective view of reality thanks to
information recently made available to you. Further, the
availability bias stems from overreliance on your recent
experiences within your frame of reference, at the expense
of the big picture.
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Consequently, to be wrong less when thinking about
people, you must find ways to increase your empathy,
opening up a deeper understanding of what other people
are really thinking.
In any conflict between two people, there are two sides of
the story. Then there is the third story, the story that a
third, impartial observer would recount.
“Forcing yourself to think as an impartial observer can
help you in any conflict situation, including difficult
business negotiations and personal disagreements.”
“If you can coherently articulate other points of view, even
those directly in conflict with your own, then you will be
less likely to make biased or incorrect judgments.”
“Another tactical model that can help you empathize is
the most respectful interpretation, or MRI. In any
situation, you can explain a person’s behavior in many
ways. MRI asks you to interpret the other parties’ actions
in the most respectful way possible. It’s giving people the
benefit of the doubt.”
“Hanlon’s razor invites you to never attribute to malice
that which is adequately explained by carelessness.”
“The third story, most respectful interpretation, and
Hanlon’s razor are all attempts to overcome what
psychologists call the fundamental attribution error,
where you frequently make errors by attributing others’
behaviors to their internal, or fundamental, motivations
rather than external factors.”
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“The veil of ignorance holds that when thinking about
how society should be organized, we should do so by
imagining ourselves ignorant of our particular place in the
world, as if there were a veil preventing us from knowing
who we are.”
“The human tendency to gather and interpret new
information in a biased way to confirm preexisting beliefs
is called confirmation bias.”
“Confirmation bias is so hard to overcome that there is a
related model called the backfire effect that describes
the phenomenon of digging in further on a position when
faced with clear evidence that disproves it. In other words,
it often backfires when people try to change your mind
with facts and figures, having the opposite effect on you
than it should; you become more entrenched in the
original, incorrect position, not less.”
“You may also succumb to holding on to incorrect beliefs
because of disconfirmation bias, where you impose a
stronger burden of proof on the ideas you don’t want to
believe.”
“The pernicious effects of confirmation bias and related
models can be explained by cognitive dissonance, the
stress felt by holding two contradictory, dissonant, beliefs
at once.”
“A real trick to being wrong less is to fight your instincts
to dismiss new information and instead to embrace new
ways of thinking and new paradigms.”
“There are a couple of tactical mental models that can
help you on an everyday basis to overcome your ingrained
confirmation bias and tribalism. First, consider thinking
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gray. You may think about issues in terms of black and
white, but the truth is somewhere in between, a shade of
gray. A truly effective leader, however, needs to be able to
see the shades of gray inherent in a situation in order to
make wise decisions as to how to proceed.”
“A second mental model that can help you with
confirmation bias is the Devil’s advocate position.
More broadly, playing the Devil’s advocate means taking
up an opposing side of an argument, even if it is one you
don’t agree with. One approach is to force yourself literally
to write down different cases for a given decision or
appoint different members in a group to do so.”
“Another, more effective approach is to proactively
include people in a decision-making process who are
known to hold opposing viewpoints. Doing so will help
everyone involved more easily see the strength in other
perspectives and force you to craft a more compelling
argument in favor of what you believe.”
“Sometimes you may want something to be true so badly
that you fool yourself into thinking it is likely to be true.
This feeling is known as optimistic probability bias,
because you are too optimistic about the probability of
success.”
Key Takeaways
• To avoid mental traps, you must think more
objectively. Try arguing from first principles,
getting to root causes, and seeking out the third
story.
• Realize that your intuitive interpretations of the
world can often be wrong due to availability bias,
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fundamental attribution error, optimistic
probability bias, and other related mental models
that explain common errors in thinking.
• Use Ockham’s razor and Hanlon’s razor to begin
investigating the simplest objective explanations.
Then test your theories by de-risking your
assumptions, avoiding premature optimization.
• Attempt to think gray in an effort to consistently
avoid confirmation bias.
• Actively seek out other perspectives by including
the Devil’s advocate position and bypassing the
filter bubble. Consider the adage “You are what
you eat.” You need to take in a variety of foods to
be a healthy person. Likewise, taking in a variety
of perspectives will help you become a super
thinker.
2. Anything That Can Go Wrong,
Will
Key Takeaways
• “In any situation where you can spot spillover
effects (like a polluting factory), look for an
externality (like bad health effects) lurking
nearby. Fixing it will require intervention either
by fiat (like government regulation) or by setting
up a marketplace system according to the Coase
theorem (like cap and trade).”
• “Public goods (like education) are particularly
susceptible to the tragedy of the commons (like
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poor schools) via the free rider problem (like not
paying taxes).”
• “Beware of situations with asymmetric
information, as they can lead to principal-agent
problems.”
• “Be careful when basing rewards on measurable
incentives, because you are likely to cause
unintended and undesirable behavior
(Goodhart’s law).”
• “Short-termism can easily lead to the
accumulation of technical debt and create
disadvantageous path dependence; to counteract
it, think about preserving optionality and keep in
mind the precautionary principle.”
• “Internalize the distinction between irreversible
and reversible decisions, and don’t let yourself
succumb to analysis paralysis for the latter.”
• “Heed Murphy’s law!”
3. Spend Your Time Wisely
Key Takeaways
• “Choose activities to work on based on their
relevance to your north star.”
• “Focus your time on just one of these truly
important activities at a time (no multitasking!),
making it the top idea on your mind.”
• “Select between options based on opportunity
cost models.”
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• “Use the Pareto principle to find the 80/20 in
any activity and increase your leverage at every
turn.”
• “Recognize when you’ve hit diminishing returns
and avoid negative returns.”
• “Use commitment and the default effect to avoid
present bias, and periodic evaluations to avoid
loss aversion and the sunk-cost fallacy.”
• “Look for shortcuts via existing design patterns,
tools, or clever algorithms. Consider whether you
can reframe the problem.”
4. Becoming One with
Nature
Key Takeaways
• “Adopt an experimental mindset, looking for
opportunities to run experiments and apply the
scientific method wherever possible.”
• “Respect inertia: create or join healthy flywheels;
avoid strategy taxes and trying to enact change in
high-inertia situations unless you have a tactical
advantage such as discovery of a catalyst and a
lot of potential energy.”
• “When enacting change, think deeply about how
to reach critical mass and how you will navigate
the technology adoption life cycle.”
• “Use forcing functions to grease the wheels for
change.”
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• “Actively cultivate your luck surface area and put
in work needed to not be subsumed by entropy.”
• “When faced with what appears to be a zero-sum
or black-and-white situation, look for additional
options and ultimately for a win-win.”
5. Lies, Damned Lies, and
Statistics
Key Takeaways
• “Avoid succumbing to the gambler’s fallacy or
the base rate fallacy.”
• “Anecdotal evidence and correlations you see in
data are good hypothesis generators, but
correlation does not imply causation—you still
need to rely on well-designed experiments to
draw strong conclusions.”
• “Look for tried-and-true experimental designs,
such as randomized controlled experiments or
A/B testing, that show statistical significance.”
• “The normal distribution is particularly useful in
experimental analysis due to the central limit
theorem. Recall that in a normal distribution,
about 68 percent of values fall within one
standard deviation, and 95 percent within two.”
• “Any isolated experiment can result in a false
positive or a false negative and can also be biased
by myriad factors, most commonly selection bias,
response bias, and survivorship bias.”
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• “Replication increases confidence in results, so
start by looking for a systematic review and/or
meta-analysis when researching an area.”
• “Always keep in mind that when dealing with
uncertainty, the values you see reported or
calculate yourself are uncertain themselves, and
that you should seek out and report values with
error bars!”
6. Decisions, Decisions
Key Takeaways
• “When tempted to use a pro-con list, consider
upgrading to a cost-benefit analysis or decision
tree as appropriate.”
• “When making any quantitative assessment, run
a sensitivity analysis across inputs to uncover key
drivers and appreciate where you may need to
seek greater accuracy in your assumptions. Pay
close attention to any discount rate used.”
• “Beware of black swan events and unknown
unknowns. Use systems thinking and scenario
analysis to more systematically uncover them
and assess their impact.”
• “For really complex systems or decision spaces,
consider simulations to help you better assess
what may happen under different scenarios.”
• “Watch out for blind spots that arise from
groupthink. Consider divergent and lateral
thinking techniques when working with groups,
including seeking more diverse points of view.”
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• “Strive to understand the global optimum in any
system and look for decisions that move you
closer to it.”
7. Dealing with Conflict
Key Takeaways
• “Analyze conflict situations through a game-
theory lens. Look to see if your situation is
analogous to common situations like the
prisoner’s dilemma, ultimatum game, or war of
attrition.”
• “Consider how you can convince others to join
your side by being more persuasive through the
use of influence models like reciprocity,
commitment, liking, social proof, scarcity, and
authority. And watch out for how they are being
used on you, especially through dark patterns.”
• “Think about how a situation is being framed
and whether there is a way to frame it that better
communicates your point of view, such as social
norms versus market norms, distributive justice
versus procedural justice, or an appeal to
emotion.”
• “Try to avoid direct conflict because it can have
uncertain consequences. Remember there are
often alternatives that can lead to more
productive outcomes. If diplomacy fails, consider
deterrence and containment strategies.”
• “If a conflict situation is not in your favor, try to
change the game, possibly using guerrilla warfare
and punching-above-your-weight tactics.”
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• “Be aware of how generals always fight the last
war, and know your best exit strategy.”
8. Unlocking People’s
Potential
Bill Bradley once said, “Leadership is unlocking people’s
potential to become better.”
It’s sometimes said, “Culture is what happens when
managers aren’t in the room.”
Key Takeaways
• “People are not interchangeable. They come from
a variety of backgrounds and with a varied set of
personalities, strengths, and goals. To be the best
manager, you must manage the person,
accounting for each individual’s unique set of
characteristics and current challenges.”
• “Craft unique roles that amplify each individual’s
strengths and motivations. Avoid the Peter
principle by promoting people only to roles in
which they can succeed.”
• “Properly delineate roles and responsibilities
using the model of DRI (directly responsible
individual).”
• “People need coaching to reach their full
potential, especially at new roles. Deliberate
practice is the most effective way to help people
scale new learning curves. Use the consequence-
conviction matrix to look for learning
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opportunities, and use radical candor within
one-on-ones to deliver constructive feedback.”
• “When trying new things, watch out for common
psychological failure modes like impostor
syndrome and the Dunning-Kruger effect.”
• “Actively define group culture and consistently
engage in winning hearts and minds toward your
desired culture and associated vision.”
• “If you can set people up for success in the right
roles and well-defined culture, then you can
create the environment for 10x teams to emerge.”
9. Flex Your Market Power
Charlie Munger once said, “Mimicking the herd invites
regression to the mean.”
Key Takeaways
• “Find a secret and build your career or
organization around it, searching via customer
development for product/market fit (or another
“fit” relevant to the situation).”
• “Strive to be like a heat-seeking missile in your
search for product/market fit, deftly navigating
the idea maze. Look for signs of hitting a
resonant frequency for validation.”
• “If you can’t find any bright spots in what you’re
doing after some time, critically evaluate your
position and consider a pivot.”
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• “Build a moat around yourself and your
organization to create sustainable competitive
advantage.”
• “Don’t get complacent; remember only the
paranoid survive, and keep on the lookout for
disruptive innovations, particularly those with a
high probability of crossing the chasm.”
