Essentialism by Greg McKeown

Rating: 9/10

Best Line #1: “If you don’t prioritize your life, someone else will.”

Best Line #2: “It takes discipline to apply tough criteria. But failing to do so carries a higher cost.”

Essentialism is a book you read when you feel you need it. For me, that was in 2016. It was at a point in time where I felt a great need for focus. Trivialities and straddled half-measures were taking too much time, in work and at home, and all the effort with little output made me feel  useless. The condition, I’ve come to understand, is something we call “busy”. I was quite “busy” in 2016. This book helped put me on the road to recovery.

One of the best lines encapsulates a major symptom of “busy”. The instant you read this line, you’ll know if you are suffering the condition:

“Have you ever felt overworked and underutilized?”

Everyone, right? It’s a very surreal combination but this was 2016 for me and it’s no one’s fault but my own. I’ve reread the book earlier this year and understand that it’s a condition that affects me in any place, any time, if I allow the discipline to slide. Speaking of discipline, it’s a core piece that defines the eponymous term:

“Essentialism is a disciplined, systematic approach for determining where our highest point of contribution lies, then making execution of those things almost effortless.”

The best part of this concept is the notion that you must determine your highest point of contribution and make what you do, through that channel, an easy and immediate thing. But what, pray tell, is your highest point of contribution? It’s a very hard question to answer. It’s also the only thing that prevents this book from being a “perfect 10” for me because there isn’t nearly enough on this very point.

The vast majority of the book serves as a wise reminder of truths we should hold as self-evident. The mental models at the end will show that. And practically all of this book helps to reinforce the notion of “striving strategically”. Working harder gains very little. The most respected investor in the world, Warren Buffet, is quoted with one of his best lines on this point of focus:

“Our investment strategy borders on lethargy”.

Pick a few good companies, invest heavily, say no to the rest. This is a simple description of Berkshire Hathaway’s “lethargic” strategy but replace the word “companies” with “projects” or “endeavors” and you can apply this Essentialist idea to anything.

But if you say no to the rest, doesn’t that mean you miss out on opportunities?


The strongest chapter in the book gives a necessary introduction to the reality of trade-offs. We all face them and yet we don’t. Trade-offs are the natural by-product of the natural world. Mass cannot occupy two spaces at once and you can’t either. As a reminder, McKeown writes the following unavoidable truth that, again, we try to deny:

“Saying yes to any opportunity by definition requires saying no to several others.”

Am I overreading this? Or is it really just that simple? I think it’s really just that simple. If you choose to get waffles, you have also chosen to not get pancakes. Got it. The difficulty with this comes in the second and third level of decisions that cascade from the first. It’s not the trade-offs of your first decision that matter. Those feel obvious. It’s the cascading trade-offs that are, or aren’t, accepted afterward.

Consider Netflix. They sent you DVDs in the mail. Then they switched to streaming. Both have trade-offs but which path is the most essential? Which allows you to deliver at the highest point of contribution? A person or a company goes along one path, with one set of trade-offs, and then sees a new path and essentially discards everything they had done to accept a new decision with what are expected to be lesser trade-offs. This is called a “pivot” and the absolute most important aspect of a pivot is that you leave your old path behind.

If you don’t leave your old path, you essentially maintain one foot in one direction and the other foot pointing the other way. This results in the “straddle”, a concept Michael Porter coined to describe companies that try to do multiple divergent things at once. McKeown illustrates with the example of Southwest Airlines and its competitors.

Under Herb Kelleher, Southwest became one of the most successful airlines in history. The strategy was simple and serves as the pinnacle of Essentialist practice. 1 Herb said it best himself:

I can teach you the secret to running this airline in thirty seconds. This is it: We are THE low-cost airline. Once you understand that fact, you can make any decision about this company’s future as well as I can.”

It worked almost immediately. To such a degree that many airlines started to emulate the strategy. Partially. Continental Airlines began to run certain aspects of its service in the Southwest style but the partial step created operational nightmares and an identity crisis of sorts. What are they? A standard airline? A deluxe airline? A budget airline a’la Southwest? We’re all three, they would say, which invariably meant they were none. Millions were lost in their bid to compete because they only took the half-steps while Southwest was already well on its way to forging a new corner of the market.

It reminds me of an adage high school football coaches use all the time: “Going half-speed is what gets you hurt.”

Essentialism, then, is about fuller commitment to fewer things. The trade-offs can feel expensive but the avoidance of trade-offs carry a higher price. Continental is one of many companies to face such traps.

The Things We Leave Behind

It goes beyond companies, of course. The straddling trap is something we all face. So the third part of the book is focused entirely on elimination. Letting go. Developing a minimalist habit to get rid of everything you don’t need that doesn’t help you contribute at the highest point. It lends itself to a timeless quote from Ralph Waldo Emerson:

“The crime which bankrupts men and states is that of job-work, declining from your main design to serve a turn here or there.”

“Job-work”. A fascinating description. It does seem like our jobs are often designed to serve a turn here or there instead of driving towards your main design. Anyway, how does one eliminate the clutter of too many tasks straddled across too many directions?

One way is to consider the endowment effect. We endow special value to things we own. A coffee mug we buy for $5 will now cost $7 for anyone else to buy it from us. This is sensible in some ways if you wish to make a profit somehow or if this happens to be the only coffee mug you own. But the endowment effect fuels so much of our hoarding. Not only hoarding of physical things but the non-physical stuff too. I overvalue stuff that no one else cares about and I honestly don’t know why. 

McKeown offers us a great question to break this tendency. “If I did not own this item, how much would I pay to obtain it?”

Excellent question. When applied to your overstuffed closet, you start to understand that these precious garments are not-so-precious after all if you had to reacquire them. So maybe get rid of them. And in the workplace, the question can take a different shape:

“If you didn’t have this task or project already, how much would you work to try to obtain it?” Many of us ambitious, high performer types look to grab everything we can. It’s a desire for control, prestige, advancement, or perhaps a battle against our insecurities. We can’t do it all and yet we want to so badly until it’s month seven for all those projects and nothing makes sense anymore.

Once acquired, these projects or jobs or tasks never feel as worthy. The pursuit of new stuff to do allows us to avoid the stuff we’re already doing. It’s novelty. The psychology applies at all sorts of levels. I suspect Continental straddled against Southwest because they felt a little bored with their current strategy and wanted something new. Just not completely new.

A final concept from the book that’s worth considering: the reverse pilot. I really love this idea and am convinced that it would yield massive insights in the workplace. What is it exactly? The reverse pilot is a technique used to fly airplanes backwards.

Jokes aside, the reverse pilot is a test to see what happens if you REMOVE an initiative or activity. So often, our pilot projects are a test to see what happens if we start something new. The reverse is to see what happens when we stop something old. Something we’ve always done.

I’m reminded of a somewhat dismal but truthful quote in the book from John Maxwell: “You cannot overestimate the unimportance of practically everything.”

An honest reverse pilot will probably yield an 80/20 result that tells us we’re just wasting time of everything. It’s as if the movie “Office Space” could be validated in this one exercise. Who has the courage to do a reverse pilot? Who has the courage to stop being “busy” for a minute and see what matters and what doesn’t?

An Essentialist will have an eye for waste and unimportance. They will cut and redline like a good editor. Why? Because removing the fluff enhances what remains. In the words of Dieter Rams, it allows us to find the state of our design that gives us “Less but better”.

A reverse pilot leaves you with the vital 20%. It’s less but better. For everyone.

Conclusion: Essentialism In Action

Consider this website that I stubbornly call a service. I use the term because a service will modify itself for the user whereas a blog will modify itself for the author. This service currently strives to produce content five days a week. Four posts are small bits on a singular concept. One post is a book review. It’s a lot for one person to do and I’m quite certain that a lot of it is completely unessential.

But what should I do? It would be absurd to cut things indiscriminately. So I’m spending six weeks 2 developing the content. I’ll then reassess on a number of criteria to decide what the next six weeks will be.

It’s part experiment, part search. A search for what my highest point of contribution can be. This is a pilot. It leads to a reverse pilot. An 80/20 analysis. Elimination. Pivots. You get the idea. The ideal end-state is a service that produces regular useful information with as little waste as possible. It will likely take five years to get remotely close to that goal. And what’s essential, within that time horizon, will likely change from one six-week period to the next.

The point, ultimately, is that Essentialism is an active practice. Because the things that are essential change from time to time. It isn’t a static philosophy one uses to posit their thoughts. It’s a discipline that is used every day.

You should be warned, though. This practice will create a tiresome paranoia. I often look around and think of all the things that are completely unnecessary and it plunges me into a nihilistic race to the bottom. I’M GOING TO GET RID OF EVERYTHING.

John Maxwell is right. Practically everything is unimportant in a detached, objective, life-goes-on sort of way. Importance is a choice. Meaning is what we make it.  

Not everything can be meaningful. Not everything can be important to you. So be ruthless in finding what’s Essential. Only don’t fool yourself into thinking nothing is. As McKeown says in my favorite line: “If you don’t prioritize your life, someone else will.”

There’s much more to the book than this. The section on mission statements is worth three times the price of the book. I really appreciate that McKeown tees off on this absurd practice. More on that in future posts. It’s a fantastic work that everyone can benefit from. Buy it on Amazon.

Mental Models

  • Less but better
  • Essentialism is a disciplined, systematic approach for determining where our highest point of contribution lies, then making execution of those things almost effortless.
  • The endowment effect – we overvalue what we own
  • A counter to the endowment effect – If I didn’t already own this, how much would I spend to buy it?
  • Choose choice in every area of your life. Optionality produces upside risk.
  • A strategic position is not sustainable unless there are trade-offs with other positions.
  • The faintest pencil is better than the strongest memory.
  • The reverse pilot: test whether REMOVING an initiative or activity will have any negative consequences.
  • To attain knowledge, add things every day. To attain wisdom, subtract things every day.
  • We can’t know what obstacles to remove until we are clear on the desired outcome.
  • Done is better than perfect.
  • Minimal viable effort