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How to Live a Life of Pure Meaning — Essentialism by Greg McKeown (BOOK OUTLINE)

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About Essentialism

In this personal development book by Greg McKeown, the author focuses on, as the subtitle states, “the disciplined pursuit of less.” McKeown discusses the importance of cutting out non-essentials to distill the most purposeful, targeted lifestyle, focusing on depth, intensity, and quality of life over broad, unfocused, unproductive living.

McKeown separates people into two categories: Essentialists and Non-Essentialists, and in each chapter goes through what makes Essentialists different from their Non-Essentialist counterparts. Topics the book covers includes: choice, sleep, discernment, play, saying “no,” small wins, and more.

CHAPTER 1: The Essentialist

The wisdom of life consists in the elimination of non-essentials — Lin Yu Tang
  • Evaluate requests using a tough criteria: Is this the MOST important thing I should be doing with my time/resources right now?
  • People can respect you MORE for your refusal than less.
  • Then you can focus, have more creativity
  • Give yourself permission to stop trying to do it all, saying yes to everyone, so that you cann make your highest contribution toward what really matters.
  • The Way of the Essentialist: He is driven by the idea that almost everything is noise. Few things are essential. His job is to filter noise to get essence. Live by design, not default.
  • Less, but better. I choose to, not have to. What are the trade offs? Pause to discern what matters. Say no to all but the essentials. Choose carefully, do great work. Feel in control. Joy.
  • The Way of the Nonessentialist: If you don’t prioritize your life, someone else will.
  • Another book by McKeown: Multipliers: How the Best Leaders Make Everyone Smarter
  • Paradox of success:
  1. Clarity of purpose = success
  2. Success = reputation for always being there for folks
  3. Increased opportunieis = more demands = spreading thinner
  4. Distraction from highest contribution = undermine original clarity = fail
The pursuit of success can be a catalyst for failure
  • Jim Collins: How the Mighty Fall examines how big companies fall
  • Why is nonessentialism rampant?
  1. Too many choices. Peter Drucker: this age is special not for technology but substantial choices available to the greatest number of people.
  2. Too much social pressure
  3. The idea “you can have it all”
  • Decision fatigue: The more choices we’re forced to make, the more the quality of decisions deteriorates

Become an essentialist:

  1. Explore and evaluate: all your coices. Ask “Do I love this?” Not “Is there a chance this is useful?”
  2. Eliminate
  3. Execute: you need a routine
  • Sunk-cost bias: We value things we already own more highly than they are worth
  • Highest point of frustration: Everything x Popular things x Now
  • Highest point of contribution: Right thing x Right reason x Right time
  • Ask yourself 3 questons:
  1. What am I deeply inspired by?
  2. What am I particularly talented at?
  3. What meets a significant need in the world?
Nothing is more powerful than an idea whose time has come — Victor Hugo
Photo by Greg Rakozy on Unsplash

PART I: ESSENCE: WHAT IS THE CORE MIND-SET OF AN ESSENTIALIST

I can do anything, but not everything

CHAPTER 2 Choose: The invincible power of choice

It is the ability to choose which makes us human — Madeleine L’Engle
  • McKeown’s school days: straddled strategy of attempting invest in all at once. Not failing in anything, but not succeeding either.
  • If you could do only one thing with your life right now, what would you do?
By refusing to choose “not law school,” I had chosen law school — not becauase I actually…wanted to be there, but by default…when we surrender our ability to choose, something,,,will step in to choose for us.
The ability to choose cannot be taken or given away, only forgotten
  • learned helplessness: Seligman and Maier’s experiment on dogs showed that over time, dogs stop running away from pain when they think they can’t.
  • People often believe they “have to do it all.”
  • Choice is the core of being an Essentialist. Nonessentialists forfeit choice.
My first act of free will is to believe in free will — William James

CHAPTER 3 Discern: The unimportance of practically everything

  • Getting used to “less but better” may be harder than it sounds.
  • Nonessentialists think almost everything is essential. Essentialists think almost everything is nonessential.

CHAPTER 4 Trade-off: Which problem do I want?

  • Straddling: keeping your existing strategy intact while simultaneously trying to adopt a competitor’s strategy (Ex: Continental tried to copy Southwests’ essentialist strategy of trying to cut costs, and failed)
A strategic position is not sustainable unless there are trade-offs with other positions — M.E. Porter
  • We must make hard choices for ourselves, or allow others (boss, colleagues, customers) to do it.
  • When you craft a value statement, forget “passion, innovation, leadership, etc” who doesn’t value those things? Focus on what you value MOST. What should you do when those values are at odds?
  • By definition, trade-offs involve 2 things you want. Nonessentialists: “how can I do both?” Essentialists: “which problem do I want?”
There are no solutions. There are only trade-offs — Thomas Sowell
  • Jim Collins, Good to Great: Peter Drucker said, you can build a great company or great ideas, but not both.
  • Don’t ask “what do I have to give up,” but “What do I want to go big on?”
  • Cumulative impact of this small change in thinking can be huge.
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PART II: EXPLORE: HOW CAN WE DISCERN THE TRIVIAL MANY FROM THE VITAL FEW?

  • Paradox: Essentialists explore MORE options than Nonessentialists before committing.
  • Nonessentialists get excited by almost everything, react to everything.
  • Productivity is NOT busy, overextended

CHAPTER 5 Escape: The perks of being unavailable

Without great solitude, no serious work is possible — Pablo Picasso
  • If you’re too busy to think, you’re too busy, period.
  • We need space to discern essential few from trivial many.
  • We don’t get space by default but by design. Essentialists create space.
  • By abolishing the chance of being bored, we’ve lost time to think/process
  • You can take a week of, or do McKeown’s ex: read something from classic literature (something written before modern era) for first 20 minutes per day (avoid email, broaden perspective)

CHAPTER 6 Look: See what really matters

  • Journalism: the lead: contains why, what, when, who. Covers esesential info.
  • Ex: Journalism class, professor reads “Principal X announced entire faculty will be gone on Thurs to learn about education…” what is the lead? Ans: “No school Thurs.”
  • Don’t just regurgitate info, figure out the POINT
  • Not just who/what/when/etc, you need to know what it means and why it matters
  • In every set of facts, something essential is hidden.
  • Be a journalist of youor own life. Don’t hyper-focus on minor details. See the big picture.
  • Filter: we can’t explore every info we encounter. Discern what’s essetial to explore/scan
  • Listen for what isn’t explicitly stated
  • Nonessentialists listen in order to say something, get distracted. Essentialists hear what isn’t being said.
  • Keep a journal. People are shockingly forgetful.
  • Review every 90 days or so, but not focusing on the details. Look for patterns/trends. Capture the headline, lead of your day, week, life. Small incremental changes are hard to see in the moment, but over time they accumulate!
  • Keep an eye out for abnormal/unusual details — get a different perspective on the story, fresh light.
  • Exercise: use role play, put yourself in the role of each of the main players in a story to understand motives/reasoning/POV
  • Ask yourself: What question are you trying to answer? Ask it over and over until you are clear.
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CHAPTER 7 Play: Embrace the wisdom of your inner child

  • The word “school” comes from Greek “schole” meaning “leisure.”
  • Play: anything we do for joy, not as a means to an end
  • Stuart Brown: National Institute for Play: Play can significantly improve everything, personal health to relationships.
  • Play is necessary in a world with constant unique challenges and ambiguity
  • We’re built to play and built through play.
  • Play = purest expression of humanity, expands mind, generates new ideas, see old ideas in new light, broadens options, see connections, antidote to stress
  • Stress increases amygdala activity, suppresses hippocampus (cognitive function) = can’t think clearly
  • Dick Costolo, Twitter CEO, promotes play through comdey improv classes
Play doesn’t just help us explore what is essential. It IS essential itself.

CHAPTER 8 Sleep: Protect the asset

  • The best asset we have for contributing to the world is ourselves
  • Sleep: driver of peak performance
  • Essentialists see sleep as necesssary for high level contribution. 1 hr of sleep = many hrs of productivity. Sleep is a priority.
  • K Anders Ericsson study on violinists: 1st most important factor separating good from best is deliberate practice. 2nd is sleep.
  • Sleep helps with problem-solving ability.
Our highest priority is to protect our ability to prioritize
“A pug wrapped in a blanket on a bed” by Matthew Henry on Unsplash

CHAPTER 9 Select: The power of extreme criteria

  • Derek Sivers TED talk: No more Yes. It’s either HELL YEAH! or no.
  • If the answer isn’t a definite yes, it’s a no.
  • Ask: Do I absolutely LOVE this?
  • The 90 Percent Rule: If a decision doesn’t score 90 or above on a scale of 0–100, automatically reject it
  • Assigning numerical values to options forces us to think logically, consciously, rationally instead of impulsively, emotionally
  • Make criteria selective and explicit
If it’s not a clear yes, it’s a clear no
  • This can get hard when opportunities come to us. Don’t say yes for an easy reward.
  • Jim Collins: Good to Great: If there’s something you’re passionate about, do JUST THAT ONE THING
  • How to decide whether or not to take opportunities:
  1. Write down the opportunity
  2. Write down list of 3 minimum criteria it needs to pass to be considered
  3. Write down 3 ideal/extreme criteria to pass
  4. If it doesn’t pass all 3/3 from #2 and 2/3 from #3, answer is no
  • Don’t just search for “good career opp” you will have too many options. Ask the 3 questions: passion, talent, world need, and choose from those answers.

PART III: ELIMINATE: HOW CAN WE CUT OUT THE TRIVIAL MANY?

  • Don’t just deide what isn’t worth your effort — get rid of those things actively.
  • Find the discipline to say NO
  • Every time you fail to say NO, you are saying YES by default
  • The question to help you uncover true priorities: Of your list of priorities, what will you say NO to?
“A pair of scissors with a black background.” by Matt Artz on Unsplash

CHAPTER 10 Clarify: One decision that makes a thousand

  • Mission statements are supposed to inspire you with a clear sense of purpose. Forget vague inflated, indistinguishable statements
  • Motivation and cooperation deteriorate when there’s a lack of purpose. Leading to 1) playing politics, and 2) fail to achieve essential mission
  1. ESSENTIAL INTENT: inspirational + concrete
  2. Vision/mission: inspirational + general
  3. Values: bland + general
  4. Quarterly objective: bland + concrete
  • some inspirational-sounding things sound so general, they are ignored (ie “I want to change the world”) Whereas concrete goals lack inspiration (ex “increase profits 5% over last year”)
  • Essential question: If we could be truly excellent at one thing, what would it be?
  • Rhetoric isn’t the only thing that inspires: Concrete objectives can too
  • Interesting exercise from Stanford Business school: evaluate vision and mission statements of nonprofits to see which are LEAST inspiring.
  • MOST inspiring ex: Make It Right “build 150 affordable, green, storm-resistant homes for families in the Lower 9th Ward”
  • It must answer the question: How will we know when we have succeeded?
A true essential intent is one that guides your greater sense of purpose, and helps you chart your life’s path.
  • Ex: Nelson Mandela’s dream to eliminate apartheid in S. Africa kept him going through decades of imprisonment
  • It takes courage, insight, and foresight to create an essential intent. Ask tough questions, make real trade-offs

CHAPTER 11 Dare: The power of a graceful “no”

  • A powerful no at the right time can change history (Ex: Rosa Parks. A normally timid person, she said “No” because it came from her deep values)
  • Courage is a must for Essentialists. Otherwise the disciplined pursuit of less is just skin deep/lip service. (Ex: Steven Covey said no to an old friend’s impromptu invitation to dinner to honor a commitment made long ago with his daughter)
  • It is hard in the moment to choose what is essential over what is nonessential because we are unclear about the essential = we are defenseless.
  • We also fear social awkwardness. We must learn to say NO resolutley, gracefully.
  • Peter Drucker: art of the graceful no.
Productivity in my experience consists of NOT doing anything that helps the work of other people but to spend all one’s time on the work the Good Lord has fitted on to do, and to do well — Peter Drucker
  • Note to self: I would amend that quote to read: …NOT doing other people’s work for them, but…
  • Separate the decision from the relationship. Saying no to a request is not denying the person
  • You don’t have to use the word NO to say no. “I’m flattered you thought of me, but I’m overcommitted” works too.
  • Focus on the trade off, the opportunity cost,
  • Remember everyone is selling something. (Idea, viewpoint, opinion) in exchange for your time. Don’t be cynical, but be aware of what is being sold to be deliberate about whether or not you buy.
  • Saying NO can mean trading popularity for respect. NO can impact the relationship short-term, but when the annoyance wears off, the respect kicks in.
  • Ex: Steve Job wanted designer Paul Rand to come up with some options for NeXT, but Rand said “I specialize in one option. Take it or leave it.” Earned Job’s respect, and Job hired him.
  • It’s better to get a firm “I’ll pass” than “I’ll see/I’ll try to make it work”
  • Essentialists don’t say NO occasionally — it’s part of their regular repertoire
  • Repertoire of NOs:
  1. Awkward pause: Don’t be afraid of it. Control it. Let the other guy fill the silence.
  2. Soft “no”/No, but: “I can’t now, but let me know after_”
  3. Let me check my calendar and get back to you: Gives you time to think/consider
  4. Yes, what should I deprioritize?: Sometimes you cannot say no. If your boss asks for help with one project, say Yes, and what other project should I deprioritize?
  5. Use humor
  6. You are welcome to X, I am willing to Y: Say what you are not willing to do in terms of what you ARE willing to do. Ex: “You are welcome to my keys, I am willing to lend you my car so you can drive yourself, but I will not drive you.”
  7. I can’t do it, but X may be interested
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CHAPTER 12 Uncommit: Win big by cutting your losses

  • Sunk-cost bias: tendency to continue investing time/money/energy in something you know is losing becasue you already sunk in a cost you can’t get back
  • Essentialists ask:
  1. “If I weren’t already invested in this project, how much would I invest in it now?”
  2. “What else could I do with my time/money if I pulled the plug now?”
  • Essentialists are comfortable cutting losses.
  • Owning something causes you to value it more highly. Even if it’s not much use to you now. Same goes for activities you are involved in.
  • So: Pretend you don’t own it yet. And ask yourself: “How much would I pay to get this thing?”
  • Get over fear of waste (If you have a $50 ticket for Vacation A and a $100 ticket for Vacation B, most people choose B even if they would like A better)
  • Admit failure to begin success: Admitting mistakes means you are wiser now than you were
  • Get a neutral second opinion
  • Be aware of status quo bias (when people don’t question the way things work because it’s always worked that way). Use zero-based budgeting (accountants can base a yearly budget on last year or on zero/a clean slate)
  • Stop making casual comitments, pause before you speak, get over fear of missing out
  • Reverse pilot: test whether removing something will have negative consequences. Ex: stop doing some presentation, and if no one notices or cares, eliminate it.
  • This is opposite of prototyping: building a model to test if the idea will work, before investing a lot of money up front.

CHAPTER 13 Edit: The invisible art

I saw the angel in the marble and carved until I set him free — Michelangelo
  • Since 1981, no film that wins Best Picture has not also been nominated for Best Editing
  • A good film editor makes it hard NOT to see what’s important because he eliminates everything but what NEEDS to be there.
  • For an Essentialist, exploring is like being a journalist, discerning is like being a film editor
  • Editors don’t just say “no,” they also add things: use deliberate subtraction to add life to the story.
  • Book editor: job is to make life as effortless as possible for the reader
  • Cut out what confuses the reader, clouds the message
  • The Latin root of “decision” is “cis/cid” meaning “cut/kill”
  • Doing less/condensing is harder.
  • 2 questions: 1) are you saying what you want to say? 2) Are you saying it as clearly/concisely as possible?
  • Ex: See LifeEdited.com
  • Eliminate multiple meaningless activities, replace with one meaningful activity
  • Editors must have clear sense of overarching purpose of the work being edited. Make course corrections by coming back to your core purpose.
  • Edit less: you don’t have to change everything. Know when to show restraint.
  • If you don’t set boundaries, there won’t be any. Boundaries are empowering.
  • Don’t take other people’s problems. It doesn’t do them any good.
  • What are your dealbreakers? When do you feel violated?
  • Make a contract with others.
“Iowa man sits at a messy table while holding paint covered pencil and brush” by Alice Achterhof on Unsplash

CHAPTER 14 Limit: The freedom of setting boundaries

  • Clayton Christensen: The Innovator’s Dilemma If you make an exception once, you may keep making it. Boundaries are like dominoes. One falls down, all falls down.
  • Boundaries can come at a high price.

PART IV: EXECUTE: HOW CAN WE MAKE DOING THE VITAL FEW THINGS ALMOST EFFORTLESS?

  • Nonessentialists force execution. Essentialists cut so much out and have a system that execution is almost effortless.
  • Systems make neatness effortless and routine.

CHAPTER 15 Buffer: The unfair advantage

Give me six hours to chop down a tree and I will spend the first four sharpening the axe — Abraham Lincoln
  • Life is unexpected, so create a buffer.
  • Nonessentialists assume best case scenario, but things always inevitably come up.
  • Essentialists use good times to create buffer for the bad
  • Life is going faster, there is no room for error
  • How to prepare:
  1. Use extreme preparation
  2. Add 50% to your time estimate. Don’t fall for planning fallacy (underestimating time of a task, even when you’ve done it before), or social pressures (wanting to look better in front of others)
  3. Conduct scenario planning: 1) what risks do you faceon this project? 2) worst case scenario? 3) social effects? 4) financial impact? 5) how to reduce risk/strengthen sociail/financial resilience?

CHAPTER 16 Subtract: Bring forth more by removing obstacles

  • Look for constraints: obstacles that hold the whole system back
  • Identify the thing that holds everything back, and find ways to make it better.
  • Ex: put the slowest hiker at the front of the pack, remove his burdens. That way the group stays together and goes as fast as possible.
  • 3 kinds of work: 1) Theoretical work (end goal is truth) 2) Practical work (action is goal) 3) Poietical work (bring forth more by removing more instead of doingmore)
  • You can’t know the obstacles to remove until you’re clear on the desired outcome
When we don’t know what we’re really trying to achieve, all change is arbitrary.
  • Identify your “slowest hiker” based on prioritizing your list of obstacles.
  • Even “productive activities” can be obstacles

CHAPTER 17 Progress: The power of small wins

  • Start small and celebrate progres instead of going for flashy wins
  • The more people are rewarded for doing something good, the more motivation they have to keep doing good
  • Adopt minimal viable progrerss: what’s the smallest thing you can do that will be useful and valuable to the overall task?
  • 2 ways to approach a goal/deadline: 1) start early and small or 2) late and big
  • What’s the minimum you can do RIGHT NOW to prepare?
  • Visually reward progress!
“A piggy bank on a white surface” by Fabian Blank on Unsplash

CHAPTER 18 Flow: The genius of routine

  • Michael Phelps has a mental routine of visualizing the perfect race every day before bed and after waking. For years. His habits take over.
  • Routines make the essential the default position.
  • Routines are a powerful tool for removing obstacles
  • Charles Duhigg: The Power of Habit the brain can almost completely shut down, which is an advantage, because you can use mental energy for something else.
  • The wrong routines are pallid/bland. The right routines enhance innovation/creativity
  • Creative people use routines to free up their minds
  • Charles Duhigg: Habits are made of 1) cue/trigger 2) routine/behavior 3) reward
  • To change behavior: find the cue that is triggering the nonessential behavior, and associate that cue with something else
  • Focus on the hardest thing first
  • Mix up your routines — different ones for different days
  • Many nonessential routines are deep and emotional
  • Start small. One step/small changeat a time.

CHAPTER 19 Focus: What’s important now?

  • WIN = What’s Important Now?
  • Being beaten = they were stronger than you. Losing = you lost focus, didn’t concnetrate on the essential
  • Do you get stuck replaying past mistakes?
  • Greeks have two words for time (Chronos — old man, ticking clock, quantitative. Kairos — qualitative. When we fully experience NOW)
  • See Jiro Dreams of Sushi by David Geld
  • We can do more than one thing at a time (eat and talk), but we can’t FOCUS on more than one thing at a time
  • Multitasking is not the problem, Multifocusing is.
  • Ask: What do I need to do to be able to go to sleep peacefully?
  • Get the future out of your head so that you can focus on what’s important now.
  • Pay attention for your own kairos moments, think about what triggers them. Try to recreate them.

CHAPTER 20 Be: The essentialist life

Beware the barenness of a busy life — Socrates
  • Think of Essentialism as something you ARE, not something you do
  • We all have a Essentialist and Nonessentialist inside us, which one are you at your core?
  • As ideas become emotionally true, they have the power to change you
  • Greek metanoia: transformation of the heart. Not just the mind. Bible/Proverbs 23:7 “As a man thinketh in his heart, so is he”
  • Essentialism: more clarity, control, joy, meaning

APPENDIX: LEADERSHIP ESSENTIALS

  • FCS: Fewer things done better + Communicate the right info to the right people at the right time + Speed and quality of decision making
  • If you can do only one thing, what would it be?
  • For leaders: 1) hire selectively 2) debate until you establish REALLY clear intent 3) go for extreme empowerment. No ambiguity over who’s doing what 4) communicate clearly 5) accountability and follow-up are easy and frictionless
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