Greg McKeown changed the way so many leaders think about life with his New York Times Bestselling book, Essentialism. He is the founder and CEO of McKeown Inc, an organization that helps leading companies like Apple, Google, Pixar and more reach the next level of growth. In addition to Essentialism, Greg is also New York Times bestselling author of Effortless and The Essentialism Planner, a world-renowned keynote speaker, and the host of the Greg McKeown Podcast.
Greg joined host Robert Glazer on the Elevate Podcast to talk about how he prioritizes the essentials in his own life, living a life by design, seeking and implementing feedback, and much more.
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Essentialism Author Greg McKeown On Designing Your Life Around What Matters
Our quote for this episode is from Virginia Woolf. “Only have time for essentials.” Our guest, Greg McKeown, is the leading advocate for doing only the essentials. He’s the Founder and CEO of McKeown Inc., an organization that helps leading companies like Apple, Google, Pixar, and more reach the next level of growth. He’s also the New York Times bestselling author of Essentialism, Effortless and The Essentialism Planner, which I have in front of me here. Greg’s a world-renowned keynote speaker and the host of The Greg McKeown Podcast. Greg, it’s great to have you back on the show. Welcome to the three-time club.
It’s great to be here again. Thank you. I like it. Three-time club. That sounds great. Thanks for having me again.
The Core Principles And Origins Of Essentialism
We started a conversation on AI. I’ll hold that off since we’re at 400 now and you are episodes 100 and 132. I encourage people to check those out. Can you just give new readers, and we have a lot of new readers, a brief overview of the principles of essentialism and your history developing the concept?
Essentialism is the disciplined pursuit of less and has three parts to it. You need to explore what is essential. You need to eliminate what is non-essential and then you need to make it as effortless as possible to do what matters most. That is an ongoing discipline pursuit. The story that is most associated with the origin of essentialism was that I left my hours-old baby with my wife and in the hospital because I’d been invited to go to a client meeting and was trying to do it all in order to I suppose have it all.
What I learned from that was if you don’t prioritize your life, someone else will. I found that that while most people haven’t done what I did, that a lot of people can relate with the challenge. You can feel busy but not productive. You can feel stretched too thin at work or at home. You can feel like people are hijacking your day with their agenda. That’s non-essentialism and both Essentialism and Effortless, now the planner, are all attempts to be able to help people to break out and to be able to design a life that really matters.
The Paradox Of Success: Navigating The Pursuit Of More
In that statement is something that most achievers would consider an oxymoron, the word pursuit and less. I think we tend to correlate pursuit with more and there tends to be this false perception. I’ve been discovering a lot of this in some of the research and reading since we spoke last, that more will provide more satisfaction. Arthur Brooks wrote an incredible book, From Strength to Strength particularly for high achievers. They think that getting to this pinnacle of a mountain is going to create all this fulfillment and satisfaction and they look down for ten seconds and then start climbing the next mountain anyway.
Yeah, so many ways one could go from that observation, but yes, it’s a success trap. That’s what you’re describing. I don’t remember the citation for this, but I remember somebody describing how they had saved and worked really hard and they’d achieved this moment of driving off the lot with the BMW that they had aspired to have. Literally in the moment of driving it off, they thought, “I should have just waited longer and got the nicer one.”
The satisfaction literally didn’t last beyond the blip of being in the car before they already wanted something else. This is part of a success trap because we can fall. You have focus, you have some clarity, it leads to success. Success breeds options and opportunities. Those very options and opportunities can undermine the very clarity that led to success in the first place.
Success can become a catalyst for failure if it leads to what Jim Collins’s called the undisciplined pursuit of more. That’s really the contrast here. The undisciplined pursuit of more is something that to be aware of because there’s no end to that. There’s no natural end to that. However, you can, of course, wake up one day and find that you are making trade-offs you didn’t intend to pursue.
Success can become a catalyst of failure if it leads to the undisciplined pursuit of more.
Nobody intentionally pursues what I call non-essentialism. Nobody says to themselves, “By the end of my life, the thing I don’t want to regret is that I should have spent more time on Instagram.” Nobody pursues that as an intent and yet you do of course end up pursuing a strategy you don’t mean to. That’s the success trap you have to be careful of. Success traps are harder to get out of than failure traps.
It seems a big part of it is the internal versus external locus. I want to talk a lot about kids and what they’re exposed to these days because I think it’s hard for them to figure this out. I’m curious too with your old kids, but it seems like true essentialism would be an internal viewpoint of what makes me happy and what’s enough. That’s really hard in this external world of social media and news and more. You need to be paying attention to this and do this and you’re missing out on this. It just seems like it gets harder every year that there’s more noise, more stress, more distractions.
Essentialism In The Age Of Distraction
I think that we are buried in noise now. When I ask audiences that question, which didn’t appear in the Essentialism originally, but when I ask people I’ll say, “This is true for you. Who here feel buried in noise?” Everybody agrees to that. That’s a very particular type of experience in life. You’re absolutely right. As the technology becomes more advanced, the risk is that we become a node in it rather than it in our service. That happens, again, not by our own design, but having worked with Silicon Valley companies for certainly the last fifteen years, but a little longer than that now, a lot of that is by design and it is not by default for them. The device in our pockets is whatever it is, it’s not a phone.
As the technology becomes more advanced, the risk is that we become a node in it rather than it being in our service.
That’s the last thing that it is. What I think is closer is it’s a $3 trillion military grade device, that disorienting machine, in one sense, no match for it. It’s adapting constantly to us. It’s adapting effortlessly. One more thought about this to throw out there, my wife Anna was sharing some new research that she was reading about that shows the first part we probably have all heard, which is that there’s this really strong correlation between depression in youth, especially adolescent girls.
The more they use social media, the unhappier they’ll be, the more likely they’re allowed to be depressed. This is not the news is that an even stronger correlation to depression in children is the degree to which their parents are using social media and on their phone. The term they used was tech interference. If a parent is hooked in the child or the teenager feels that disconnection and so that actually has a bigger impact than them being consumed with social media. I thought that was an interesting new update to this problem.
There’s a study for the book researching now, it’s called the Space Program. It’s a program to treat kids with debilitating anxiety. The really interesting thing about the program is they don’t treat the kids at all. They treat only the parents for 3 to 6 months. The kids seem to improve as a rate as if you’re giving them drugs or medicine. I think it’s right. It’s this overload.
I was going to ask you, some of it is circles. If you take anyone and you put them on a farm or a camp for a month and you take away their technology, you say, “It was a good day. We had a good meal. I got some exercise. I did some work. It’s super easy.” When you start pulling in all of this stuff and knowing about all of the worst stuff going on anywhere in the world, it becomes very hard to tune that out and say, “What’s a good day for me and my family?” You’re worried about stuff, you’re just not sure that we’re adapted to handle this. You historically grew up and you were in your little pocket and you never knew about any of this. I think it’s a more easy circle to essentialism. It’s a small circle from your day and your community and your mile radius.
Technology’s Impact: Disorientation And The Question Of Control
The difference is difficult to first to even really imagine. That’s not to say that I think we should romanticize the past because prior to let’s say 1865, it was extremely difficult to even survive. That’s the vast majority of the people alive at that time.
Your essentialism was your hierarchy of needs. Maslow.
Survival is like, in one sense, almost all of it because the number of options available to you is so limited. That’s the downside. The idea of the undisciplined pursuit of more, it’s like even if somebody’s listening to this conversation right now and they’re like, “I don’t really feel that successful in my life. There’s other things I’d like to achieve,” that’s not the same as not having the problem of the paradox of success. The optionality is like, what’s the number? It’s hard to pick a number that is large enough without producing hyperbole. Of course, we have 1,000 times the options of someone living in 1865, but is it a million? Of course it’s a million times. You could keep going. Of course, now that we’ve moved into the AI era, that’s at a whole different level and capacity on all sorts of levels.
One, because we’re just going to be in red brain most of the time because every app we use is updating constantly. That’s different than feeling distracted. If we say the information age was like a distraction was the downside, I think that this age we’re in now, it’s disorientation that is the downside. If every morning you woke up and someone had moved around all your furniture or just in the middle of the day, suddenly you turn around and all of it is gone, think of how disorienting that would be.
Think of how strange that would be. Yet that is just what’s happening with our apps every time we use them almost now. AI is speeding that process up. That’s of course only one use of how AI is disrupting and impacting us. It’s non-trivial problem that these AI bots are so sophisticated and impressive that you can have an endless conversation with them tirelessly.
It’s pervasive.
It’s so engaging. It’s the most I’ve ever felt about this question of who’s using who. To what degree is this an exchange of value with AI? Social media, we all felt that. We still feel it to some extent right away, like who’s using who? With AI, it’s like, it’s even more. We are getting the value, but pretty quick, it’s actually operating us and telling us how the rules go. All of these technologies, I’m no Luddite, but they make a good servant and a poor master. We have to assert ourselves in that. Otherwise, I think we will be, in a sense, a prisoner within the system.
All these technologies make a good servant and a poor master. We have to assert ourselves, otherwise we will be a prisoner within the system.
Societal Pressures And The Importance Of Internal Reflection
It’s one thing for adults to do this. You’re wearing a Cambridge shirt. I have two kids in college now, and they go to decently competitive schools. This is what it looks like when you go to a decent competitive school. You work for 3 or 4 years, you get into said school, welcome to school. It’s not just classes. You’ve got to join the business fraternity or this club, or you need 3 activities, or you’ve got to start on your interviewing process for the job in 3 years. It just constantly overwhelm.
I took my daughter and her friends out and they were stressed about applying abroad and that was competitive. It seems like a huge impediment to essentialism, this societal pressure of like, when it’s just okay to be there and just be enjoying what you’re doing without this next. Next is so built into university these days. We hear about the quarter life crisis but I understand it. I understand watching it why people are having a midlife crisis at 25.
There’s a term for this and there’s three levels. You can think about this. You can say, “What do I want?” You can say, “Okay, maybe want is actually what the neighbor wants. I’m just trying to keep up with the neighbor, keep up with the next student in college,” and so on. It isn’t really what you want anymore, but it’s what they want. You’re chasing it because they’re chasing it.
This is that external factor versus internal.
Right. External validation and the sense that they’re defining it for you. What’s really happening is actually removed from that and it’s heuristic is that we want a thing because we believe that somebody else wants a thing. It isn’t even what somebody else wants. It’s just what we think that they want.
You have no idea whether it will make you content or happy.
That comes back to the question that you’d asked a moment ago about is this external versus internal? Is that the way to think about this? I do think it is a helpful way to think about it. The noise outside of you and the noise inside of you. Try to find a signal in the noise to be able to create enough space to think. I’m just thinking about this, that I keep a journal faithfully. As in I haven’t missed a day in years and years. That doesn’t mean that there aren’t days that I don’t journal. I’ll just go back and catch up for a few days. I realize I haven’t done it for the last three days, I think it was something like that, but then it was a bit spotty for the last week before that. I can feel the difference.
That was an anchoring thing for you.
What you are missing is the connecting of the dots. If you’re not careful, you don’t even know what you’re pursuing. You’re just running and moving and technology’s allowing that to happen. It’s the having the too many tabs open, but literally too many tabs open. You’re busy and you’re doing things and it, but it’s such counterfeit. It’s counterfeit productivity. It’s counterfeit agility.
Counterfeit productivity like there’s lack of silence.
Yeah, because it feels fast, but it’s not.
There’s also this lack of silence and quiet and introspection. We’ll come back probably multiple times to the AI, but there’s this great paradox in ai which is that if you start relying on AI for everything and you lose your own reasoning, critical thinking and human skills, you’re going to lose the one thing that you have a chance of being better at for the next 10 or 20 years. You’re almost going to give up your competitive advantage.
One way to think about AI is the competition, this war and to what extent we can collaborate and to what extent it actually them versus us. That’s one way to frame it. Another is just what percentage of the pie of my life do I want to be in an AI conversation in an AI relationship? What percentage do I want to be having a conversation with myself with the people that matter most to me?
That’s one of the reasons I was raising the physical paper and pen experience, because that’s a technology too. It’s the technology that’s lasted the longest. It’s most likely to be with us for the longest in the future as well. Physically getting back to it is key. A really important part of why I created The Essentialism Planner and why I created it in the way that I created it was through trial and error of how to deal with this level of noise.
Noise comes from the same Latin word as nausea. When we have that sense of drowning and noise, that’s quite literally how the word came to us with this. This nauseous, we feel nauseous. We’re just constantly in a digital world, we will feel nauseous through that experience even if we’re addicted to it. The physical act of coming away from that and having a paper and pen, it was so nice.
I was at a library in Cambridge, which I only really point out because I already had that opportunity before. I’m here studying, I’m here doing research, I’m here writing, but suddenly I was writing paper and pen and digital noise is gone. I can suddenly feel my surroundings and I can start to make connections of what’s happening in my life. Those are three questions that appear in the daily process in The Essentialism Planner.
This is the journal. This is the structure.
Also in my own life too, which is what, so what, now what those three questions. Those are so helpful to me now. I don’t do it every day but at the moment I start writing, the moment I start getting that noise out so I cannot be a prisoner to the noise but an observer of it, “Okay, what am I going to do about this? What’s the news for me? What does it mean for me? Therefore, what’s the right important next action for me? When it’s missing, I can feel it when I have it. I can feel it.
I’ve got a new book coming out and we’ll talk a little about core values. It’s a parable about understanding your personal core values. I’m building the keynote talk to go with it. My plan was to work on that and my OneNote and we got on the plane and the battery was drained and the Wi-Fi didn’t work.
Actually, I had all this paper in my bag and I just sat down for an hour and I was in the zone and the whole presentation came out. I couldn’t read my handwriting, but I honestly think it was better than anything I’ve designed. I don’t know, there was something about that old fashioned pen to paper and I laid out the whole thing because I was in the moment emotionally too thinking about it.
I so relate to this because in the moment it’s easy to be tempted by the sense of progress you have if you’re in a digital environment, especially now in an AI everywhere, AI-first environment. You can produce an entire presentation on this subject instantly.
Lots of quantity.
You have a sense of, “Look at that.” You can be in the iterative process. It’s not like I think there’s no value to that because I think there is some value to that. However, if you are going in the wrong direction, AI will never help you with that. It has no sense of that. It won’t say, “Should you really be talking to me right now?” It has no conscience. It doesn’t have a sense of guiding you. Unplugging of that and thinking yourself, you have a far better chance that you are making progress if it doesn’t necessarily feel like you’re moving as fast. Obviously, you said that you’ve both, which is a great experience.
It was a feeling in the zone thing and a flow thing. A lot of my friends have these devices now because it’s obviously helpful, the capture and sorting digitally. I can’t remember the company that makes one, but there’s knockoff, but it looks like a notepad and you write and you take the notes, but then you get digital copies of all of them. That seems like the win-win device in today’s world.
Technology As A Tool: Navigating Influence And Assumptions
I think it’s Paper, isn’t it? Isn’t that what it’s called, Paper? I think that’s the tool. I myself have never bought one, but I’ve seen people using them and I do know what you mean. As I said before, I’m not a Luddite. I don’t think there’s anything inherent about essentialism that says technology shouldn’t be a part of your life. What I think is worth remembering is that technology is never neutral. It’s always built on assumption. Those assumptions, if they are non-essentialist assumptions, then the technology will default to non-essentialism. I’ll give you a perfect example of this, which is email. Email, the most used productivity tool in the world and has been, arrived a little over 25 years ago.
What is worth remembering is that technology is never neutral. It’s always built on assumption.
Cal Newport wouldn’t argue it’s a productivity tool.
He wouldn’t, of course. I chatted with him about that when he was writing what is a little less read of his work that but is a really bold visionary book and treaties, A World Without Email. Even if you put aside all of the arguments he’s making in that, if you just observe the email as to this day next to no prioritization function built into it. That’s very strange.
Other than Apple’s very poor first Apple Intelligence thing, which made my email harder to follow and I can’t figure it out.
There we go. We could riff on Apple Intelligence for a while.
Apple lack of intelligence so far, it seems like.
How do you still have Siri working so badly it when all of the technology is now there for it?
Siri seems pretty in a world of AI now.
Actually, Siri has never really become intelligent. We put up with it in various ways and we know that there is voice interaction, but it’s been limited. What I think is amazing is that it exists still. You already have the technology now available and it’s still obviously miles behind based on its assumptions. How did we get there? Email. The idea that the latest thing that came in should get your priority attention, which is default assumption of the email, the last thing.
It’s accounting principle. Last in, first out.
It is, and I just think it’s an evidence of a broader point. We have to act upon our lives because the default setting in most digital products and then maybe in lots of other ways in society is to default towards the non-essential reacting.
Essentialism In Leadership And Communication
I’ll give you an example in leadership. One of the things I always talk about and I have a presentation on delegation is that particularly if you’re someone who’s visionary and you have a lot of ideas and you’re talking, you have an assistant or you have people on your team and there’s a little bit of a power structure, they’re constantly responding as if the last thing you told them is the most important.
They should be saying, “Greg, thanks but is the ticket for the conference and whatever more important than your speaking engagement tomorrow?” People really struggle to prioritize if you don’t say to them, “I know I’ve been giving you all this stuff. Feed it back to me and I’ll tell you which ones are important,” because they forget the five things they asked before that.
One not fix is to have levels of importance with your messages so that you say, “This is a strong opinion,” or, you say, “This is a very light opinion,” or you can say you like signaling when you communicate because all of that context gets cut out, again, I think, partially because of technology. A text is just a text. An email is just an email.
Applying Essentialism: The Four-Day Work Week And Team Dynamics
You don’t have a sense of the voice and the urgency and like, “This is driving me crazy, but yeah, I don’t care about it right now.” There isn’t that interplay. I think you have to really try to be deliberate in signaling the strength and the genuine urgency about what you are saying. A case study about this that I thought was interesting. We got the tenth anniversary of Essentialism.
How has it been a decade? That’s crazy.
That’s what almost everybody says to me and myself included. Isn’t that something, isn’t it? A whole decade?
I think that’s because the whole COVID couple of years is like a Bermuda triangle in the middle of that.
It doesn’t help, but it also, it is a strange thing about time.
How many copies have sold? Is it 2 million?
I think we just put 2 million on that. It was more than that. We’re certainly past 3 million now and it just keeps going, which is of course a blessing and a surprise.
People still find it essential. That’s good.
It seems to have hit a zeitgeist type feeling. I hear from people all sorts of stories and ways that they’ve applied it and so on. One of the people that I wrote about in the new introduction to it was Banks Benitez, who was the CEO of a company who had read Essentialism himself. He’d found it life changing for him personally in trying to evaluate all the things he should be saying no to that he was saying yes to currently, stripping away and building what he felt was a really essential personal private life.
At some point, he has this tipping point question in his mind about what would it look like, this organization, not just as a passing you should read it, it should be interesting, but like as an operating system to rewire the brain of his organization. He brings in everybody, like all the executives first and they, they all have to read it like a book club. They’re getting together and one of the executives, I remember him saying, “I want to throw this book across the room,” which I love that little line because I thought this person was reading it, they’re actually getting it.
It’s stoking something within you. Someone once told me if you give a speech and no one hates it, then no one loves it. If it’s a warm cup of tea, it doesn’t mean anything to anyone.
I felt like why he wanted to throw it, it wasn’t because he hated it, but because the ramification, like the reality that it was trying to bring to the fore was you can’t do it all. You have to make tradeoffs and he doesn’t want to make these tradeoffs. That’s really painful as the executive of this company.
He doesn’t want that clarity.
Here’s the reason I’m sharing the case study all is because they say, “If it’s true, if this is real. We should really have a testable hypothesis. We’re going to measure our output today and we’re going to move to a 4-day work week for 3 months and we’re going to test at the 6-week mark and at the end of it, what is our output? Can we achieve in 32 hours of work, 40 hours of output?”
They brought in an external firm to do the measurement and they conclude at the end that they could do that. The whole company became a four-day work week. As official policy, they’d increased their productivity of their important work output by 20%. That’s the big story. One more piece of it that I think is so relevant to what you said before.
The real change internally, like four-day workweek, the policy change, but what the behavioral shift was inside of the organization was people being willing to have the conversation you just were describing that you need people to have. It was when his executive assistant basically comes to him and says, “This whole like essentialism thing and that’s fine.” We’re saying like, “What are we saying no to?” We can say yes to the things that really matter most. Does that apply to me with you?
I gave my assistant the ability. I gave people my team, “If I give you 10 things, bring it back to me and force me to pick the 5, that’s not your burden to bear.”
He’s like, “Yes, it does apply to you,” but suddenly they were having conversations about prioritization that they had simply not been having before. That was my own wakeup call with this because there I have, I’ve been teaching it all over into literally hundreds of organizations and learned so much or at least I thought. Suddenly, I realize it’s not the people aren’t having enough prioritization conversations. They’re not having them at all.
The default setting in the technology that people are using to have their communication does not initiate prioritization conversations, so they don’t have them. That was the wake-up call. It’s emotional, it’s challenging, but by having these priority conversations they were able to increase output by 20% plus have more time in their own life for other things. To me, that is pretty impressive.
Let’s double click on this. Cal and I talked about this. This is the thing. The four-day work week is really dangerous because if you flip to it, you can never go back. You need to make sure it works. One thing I found is it’s very hard for professional service companies to say we’re not working these. If you manufacture, you want to do whatever you want to do. There’s a client’s like, “You just can’t reach us on Friday. It’s a little difficult.”
What’s interesting, and you illuminated this so clearly, and Cal and I had this conversation I think on this podcast, it was like, what were the things that you did? That’s the learning. How did we get down to four days? We started going through and saying. You don’t have to cut out the day or do that whole thing, but the only way you were able to do that was clearly removing stuff that didn’t matter. You should be doing that irrespective of how many days a week people are in the office.
Prioritization: The Inverse Law And The 1-2-3 Method
The four-day work was just a forcing function for them. I completely agree with you on the premise. The point of the story isn’t the four-day work week. That’s just such a tangible element of it. At least for me, it helped me to say this is a whole organization that demonstrate a proof point that essentialism can work at an organizational level, not just, “This is a nice idea or you can use it here and there.”
You are absolutely right. The mindset is much more important than that particular policy application. Can you get a sense of your life? Where am I spending time? What am I saying yes to? Eliminate enough of it that you create space to invest in the things you are not even getting to. A new idea for me, but that I’ve recently been able to articulate, it’s like the inverse Law of Prioritization, which is basically this. The most important thing in your life today is the least likely thing that you will do.
The most important thing in your life today is the least likely thing that you will do.
Urgent and important paradox, too.
I stay with important, though. That’s the cut. The most important, and there’s a few reasons for that, but to, two main ones are that you don’t know what the most important thing is because you are just busy reacting to other things, urgent things or just the trivial things or just the proximate things that are just coming at you or the technology. All of those things just make it so you never even define your most important thing.
If you don’t define it, you can’t do it. That seems pretty solid logic. There are exceptions. The second reason is that because the most important thing is often to do with the very nature of how important it is makes it higher risk to you, higher vulnerability to you. It’s just something you want to avoid in that sense. You don’t want to start doing it and fail. You have that conversation with that most important person in your life and then it goes badly and so on.
There are these pressures against us. This is the 1, 2, 3 method that is in the planner. Of course, you don’t need the planner to do it and it’s to identify every day that one most important thing, the two things that are essential and urgent and the three things that are maintenance items, like the taxes of our life so to speak, or maybe we say laundry of our life would be a better example for that. The thing, if you don’t do it today, it makes tomorrow a lot harder.
I find that if you create that list of 6, those 6 items become your done for the day list. It’s not that you have to be done after those things, but you say, “That is a meaningful amount of important things of urgent things and of things that just maintain my life and make life smoother going forward. You have permission to rest after that, permission to give your mind a break.
Essentialism And Values: Aligning With Long-Term Vision
We were talking about this. There’s an interesting thing with a couple of things. One, you also can’t escape the Pareto principle at the end of the day, if you look at it in anything that we do, but there’s this also like when is it a liability that you should give to your future self? When will your future self be really annoyed? There was a story where these guys were trying to make this conference and the Toronto airport thing happened and they got stuck. They drove to Buffalo.
All their friends were at this conference, it’s a big conference, they paid for it. The guy’s like, “How are you going to get your car from Buffalo?” The other guy was like, “That’s a problem for my future self.” That’s actually a case where like the essential thing then was getting there and with your friends or otherwise, but there’s a whole bunch of other ones where we burden our future self with a huge debt of something that we could have done now.
I think it’s a great test to ask yourself like, “What’s my future self going to thank me for?”
Also be pissed about, right?
Yeah, I agree. I like the combination. Of course, you can go further and further not just as a thought experiment, but as a practical tool to try and decipher the vital few from the trivial many because that’s a pretty good rule of thumb for what’s most important. What’s most important is what lasts the longest. You say, “A hundred years from now, my great-grandchildren, what are they going to be ticked about or what are they going to be grateful for if it was done now?”
That’s been a non-trivial, helpful form way for me to try and think through this in my own life, like the 100-year vision. What really matters intergenerationally, you start to go, “A lot of this stuff doesn’t matter, but some of these things do. Let’s get going.” It’s the plant, the seed type stuff. It’s like, “It’s investment. We’re going to do it now. That’s the priority today. I wouldn’t otherwise do it, but I want to invest in something that lasts a very long time and I need to, therefore, start it sooner.”
How much of that comes back to understanding your value, your personal values, your family values? At the end of the day, I think those are the things that we’re trying to transmute or to pass along or that in theory should matter as to most, right?
Yeah. I certainly believe the value of values and I certainly think that it’s helpful to go through exercises. I’ve done it myself before and found it product to have like 100 values in front of me. You’re going through them, you’re effectively prioritizing them, but you’re eliminating, you’re saying, “If I could only have 50, if I could only have 10.”
I remember when I did it, it was to go down to three and in priority order. You have identified by the time you’re done. Those are the three things and it is. It’s much different to make a list of things you value. Maybe take like version 1 and then version 2 is, “Now put it in select.” You actually have to eliminate almost all of them and put in priority the last three. You actually know it’s one thing if I’m going to make tradeoffs in my life, that will be the thing.
If they’re in conflict or tradeoffs, I know which one I’m picking. I remember someone showing me they had two values and one was really about like telling the truth. One was telling the truth and the other was supporting people or making them feel better or something like that. I was like, “What happens if the truth hurts? Which one are you going with?” They had to really think about that. In that context, was the truth more important or was it more important not to hurt the person?
One of the ideas that Anne and I talk a lot about is the duality within every value, meaning the pairing of values. They’re only actually valuable together. The quintessential Western example would be justice and mercy. It’s like if you only have 1 of the 2, you don’t have wisdom. If you just have justice, that’s not wisdom. If you just have mercy, that’s not wisdom. It’s the combination of them that gives you a sense of what the right path forward might be.
You can do that with many other values. I think that that is a very helpful way to think about values and to think about that, the tension between them so that we avoid extremity. Even essentialism, I think, lends itself to this thinking because for example, the first two principles I mentioned it before it’s what is essentially exploring what’s essential. The second is to eliminate what’s non-essential. It’s like, yeah, you need them both.
Exploring And Eliminating: The Balance Of Essentialism
Sometimes people read essential is they only hear the elimination story and so they’ll almost turn it into say no to everything and everyone all the time without thinking about it. I’m keen to point out that that’s a different book. That would be a book called Knowism and this is Essentialism. The difference is not is really important because the goal is to invest in what is most important. One of the surprising findings I discovered when I was researching essentialism originally was that essentialists actually explore more options than non-essentialists.
They’re filters are just better, right?
Yes. Both are better. They are exploring more options and filtering more options. Whereas a non-essentialist is considering fewer options. They’re just already hooked to the first thing that they see. They’re already pulled in, they’re already distracted. They end up exploring far fewer options than an essentialist does. You can think about this like they think about for a visual of Steve Jobs and Jony Ive meeting every day for lunch, talking, what’s that conversation like?
We have a decent amount of insight into that, particularly with Jony Ive writings since Steve passed away. The way that those conversations went was constantly saying, “Here’s something crazy,” or, “This might just be the dumbest idea ever,” and allowing those ideas to breathe and not shooting them down. It’s such a sift from the media quintessential image we have of Steve Jobs being a big jerk about everything.
It’s like, no, the people that knew him best know that that’s not how the experience looked like. If I just can tie this together, this most famous quote from Steve Jobs, “You have to say no to 1,000 things to say yes to 1 thing.” Almost everybody, myself included, interpret that one way, which is, yeah, you have to say focus means saying no to everything. That’s what it means. It’s not that that’s wrong, but it’s a good example of getting only half of the value. The other side is, “I don’t think this is unimportant.” You have to create enough space to come up with 1,000 ideas. That’s really important.
What’s not implied in that is like when you said no, it doesn’t mean you said no at a hand. It means you evaluated, you looked at your lens and you said no.
Just so because you are letting them live and you’ve got to let them nurture a bit and you’ve got to see how all these ideas connect. You have to create a lot of space for exploration, a lot of brainstorming space. What if this? What if that? What if the other? I’ll share an idea that at first glance, I think people would think that’s a really non-essentialist idea. I don’t think it is at all. I think it’s completely consistent with the combination of explore and eliminate and the wisdom that you get when you balance them. I was invited by Steve Harvey. He has an annual conference that he does. This is comedian Steve Harvey of Family Feud. He brings together hundreds of single mothers and their at-risk teenage sons.
This grows out of his own experiences, not in exactly the same situation, but certainly being homeless at different times and being at risk in various ways. It’s a give back thing. It’s cool because you definitely get to see a different side of Steve. He is very raw. He’s funny still, but he is not on show as you normally imagine him to be.
He is a very driven person and there’s a sense of not messing around. Also, you get see a sense of his thinking, which is also different to the persona. One of the things he said, he’s got all the mothers in the room, so hundreds of mothers, and he says, “The problem is your problem is that you don’t ask God for enough.”
He starts to explain. He says, “I tell you what you pray for. You say, ‘Help me pay the rent.’ does he ever let you down? Something comes through some way, some way you’re able to pay that check. Somehow it sorts out. You’re just not asking for enough.” He gives this assignment. He says, “I want you to go home and write down 150 things you want.” Actually, his number is 400. He said that he started saying 400. He said, “That’s going to be totally overwhelming. You just do 150.”
Four hundred sounds non-essential, but yeah, go ahead.
Right. It does, doesn’t it? It’s not, because here’s the thing. I don’t believe it. It’s a literally consistent thing with the idea of 1,000 things. You’re saying no to 1,000 things. I started doing it myself. I took the challenge. What happened to me is just what he predicted would happen, which is you’re going to get to a certain number. For me it was maybe around 30 or 35 and that’s it. That’s everything I can think of.
Now these were huge things. There weren’t 35 small things. There were 35, I think, huge things, unrealistic things. It doesn’t matter. This is not a commit to list. This is an explore list, it’s a what if list. What I became aware of in the exercise was there are limits to my thinking I didn’t know were there. That’s the point of the exercise. You are pushing yourself way beyond the limits. I have kept on going and going.
You can then pull it back down afterwards.
Precisely. You need both extreme exploration, noticing the limits, pushing past those boundaries. Also, a far more extreme filter. The 90% rule of course is the language from essentialism, so that you’re saying no to 90% of things so that you can say yes to the 10% that are essential and really matter.
Essentialism In Processing Feedback
Another interesting area to apply this, you’ve talked about essentialism in the context of processing feedback. As you put it, you want to be open to feedback, but doesn’t mean you should internalize it doesn’t mean it all matters. Can you explain the distinction, how people can discern what feedback is essential and what feedback is not?
There’s a couple of things that just immediately come to mind about that. One is I just did a post which is like don’t absorb feedback from someone maybe that you wouldn’t ask for advice from. That’s like a good one for me just to keep remembering myself because it’s awfully hard to remember that in the moment of feedback.
Feedback, we can say, yes, we’re good at feedback and of course we can get better at feedback, but most of the time, it’s pretty uncomfortable to give and pretty uncomfortable to receive because is this a blind spot? That’s really the idea here and it’s another example of two extremes make you unwise because if you have the mode of, “I’m just rejecting all feedback,” somebody said that to me a while ago, they said, “When I do work for clients and companies, I never want the feedback.” That’s one version.
That’s a blind spot.
The other extreme I think is also not wise, which is okay, I’m just not just open, but like what you say is true.
Therefore, I have no grounding or perspective or point of view. “Okay, let’s do the presentation. I hated that part of your presentation.” I take it out and everyone else loved it.
Precisely. That sense of being able to figure out, I don’t mean your own truth as in each of our truth is all subjective, that there is no such thing as truth. It’s like I am going to pursue truth and as I find truth, I’m going to hold onto that truth. I’m not just going to be bandied about by every piece of every opinion, every piece of feedback.
One of the most helpful things that somebody shared with me in how to think about feedback and I think in a way that’s healthy is that when people give you feedback, of course they reveal something to you about you but they also reveal something about them. I really find that to be a helpful thing to say. It’s like, “I need to be open to what it can reveal about me, but I also need to be open to what it reveals about you.”
I call them narrative shoppers. I read an article and they respond to me way out of context for something that I really didn’t say. You can just tell that they’re bringing this narrative to every discussion. It’s almost like this is their fight and if they just get a hook somewhere, they’re bringing it in and I’m like, “I didn’t even say this.” You’re putting stuff together that wasn’t even there or they’re like, “You should really write an article about this.”
I’m like, “It sounds like you’re passionate about it. Maybe you should write an article about this.” I agree. The feedback that I take the hard and I got even some of the show like, “This is what you’re doing. This is the impact it’s having on the audience and on your guest.” That seems to be about me. Understanding that understanding not like their stuff, their baggage is clearly loaded into it.
I feel like I’ve had to learn layer by layer about feedback because I had learned and felt genuinely to ask for feedback. I still feel that to now. I want to know it because I want to improve. I’d be very open to the feedback which I think is right to ask for it and I think that’s right. I personally didn’t maybe grow up with a very clear sense of boundary about being able to filter. If somebody thinks, “I don’t need to persuade you and you don’t need to persuade me.” We can learn and I can absorb some but not all. It’s been good for me to have to develop over time a better sense of, “You revealed something about you too. I can do something with me.”
You don’t want to take that on. I’ll give you an example. Grammar police. I’ve had some people over the years who write me about a typo in a thing telling me it discredits the whole thing and all that. I’m like, “I know you went to like some school and the nun beat you with a ruler when you made a grammar mistake.” The trauma around grammar that they have comes from a parent or school. It’s so interesting. I just learned to laugh those off.
There is something funny about it to me. I had a post that went up and it had a spelling error in the graphic. That’s worse because that’s so self-evident.
It happens. It’s not great, but it happens.
First of all, I didn’t take it down. For all the people still getting the value out it, they still are and it was actually getting really great responses and so on. I thought it was interesting when people messaged me about it. People I don’t know and have never messaged me before.
They lose their mind.
I like your example of sharing it because it just illustrates the point. It’s like, “You are obviously giving me some feedback that is true. There’s a piece of this that is true. That is misspelled and I didn’t know it before someone said it, but you are also revealing you, so you have been reading these things.” Let’s assume that the people that have been emailing have been receiving my all the other social media posts potentially for years and you’ve never reached out.
I’ve given value to your life.
This is what you’re reaching out about. It’s like, “That really matters to you. You’re happy to have found that wrong thing and need to tell me that. That’s right.” I don’t know quite what it reveals, but it reveals something.
It reveals some childhood trauma. It is someone who was never praised.
Do you think that’s what it is? I got another idea for you. It’s worse because this will sound like I’m saying that people that do this are like this and that’s not what I’m saying. The pointing out somebody’s misspelled something is a pretty trivial thing, but I think that there is something deep in the human psyche, the confessing somebody else’s sins thing.
I just got finished watching a premiere, I guess a preview of a new movie, which is based on a true story. I’m going serious and dark now to do this, but it’s called Bonhoeffer and it’s about this minister in Nazi Germany and about his experiences there. It’s an amazing story. It’s an unusual story. It’s a strange story in some ways, too, but it’s certainly a courageous story.
Someone who just isn’t willing to pretend that something’s okay when it’s not, and at personal risk willing to speak the truth even though that’s extremely dangerous and unpopular to do so. That’s very impressive to me. The only way that totalitarian societies can operate is based on people’s willingness to go along with the grand lie.
The only way that totalitarian societies can operate is based on people’s willingness to go along with the grand lie.
In this case, yes, furor is good and everything about the furor is good and if you want to add 2 commandments to the 10 commandment, which an institute at the time did, and one of them was honor, it’s people’s willingness to go along with that. It’s the other thing which I think is maybe among the nastiest parts of our human nature, and I think it is in all of us, is the willingness to report the person next door, to sit there in the church and to say nothing until they say something about Nazism at the time.
They’re like, “I’m going to be the one to tell on that.” There’s something about that, though. It’s very easy to think of myself, “I would’ve been the Bonhoeffer.” It’s like, “Statistically, not much chance of that. He’s 1 in 1 million.” Chances are I’m one of the other million and just trying to hopefully, try look after myself to end up to do any damage. When I think about there’s a lot of people in society who are willing to report you, that’s the little darkness in us.
I think that’s interesting. I’m going to go with a simpler. I believe that the grammar and typo abusers are the grammar and typo abused. If you dig into their past, there was a teacher, a parent, or someone who made them feel horrible about those mistakes and then they’re just paying it forward. That’s just been my experience.
Self-Awareness And Avoiding Extremes In Essentialism
Either way, even if you don’t go use dog like I just did, again, to be clear, I’m not saying this would be a very false equivalency, but that there’s something in us.
We all know the study where they go around with people and how big is the straw? Four out of the five people pick the wrong straw is the largest. The test person almost every time thinks that their logic must be wrong. They say that the smallest one is not the smallest. This is just human psychology.
There’s a dangerous part of us, though. We all have the shadow self within us and to just pretend we don’t. We’re just all good and all the bad is in others. That is a naive way to think about it. Maybe lightening it just a little bit, you can just go back to essentialism, non-essentialism. To pretend, which I certainly don’t pretend, but to pretend, yes, I’m a perfect essentialist. I’m always essentialist. It’s like, this is a nonsense. It doesn’t matter to try to be truthful about it like, “This is what I struggle with.”
In one sense, I think about it like this now with the journey to become an essentialist, that there’s two kinds of people in the world. There are people who are lost and then there are people who know they are lost. To get into the second category, I think, is actually a really big improvement because instead of being lost and you don’t want to admit it or you don’t know it, I think it’s more not wanting to admit it, to act like, “I’ve got it all sorted. I know what I’m doing.”
There are two kinds of people in the world: people who are lost and people who know they are lost.
Conscious incompetence versus unconscious incompetence.
Conscious is so much better than unconscious. I really think that’s true because then you can do something about it. Growing up, my dad was a bit directionally challenged, let’s say. My mother was worse than he was. This was not a strain. I remember one time leaving to go somewhere. I was really little at the time, but we went around for hours.
We never found a place we were supposed to. It wasn’t very far away, but we were new to the area and we never made it. It was really awkward. We came back home after like two hours of this nonsense. All along the way, and many other times, other times my dad would say, “I just feel it’s down here. I just feel it’s down there.”
You learn to not trust feelings.
Yeah, it’s like Inigo Montoya from Princess Bride. It’s like, “I don’t think those words mean what you think they mean.” I don’t believe those words. What you have to do is go, “I’m lost and I’m not good at directions at all. I’m going to stop and ask directions, but I’m going to ask for one direction because that’s what I can remember.” Do that one direction to stop again, then you’re fine.
This is just a metaphor back to being an essentialist. It’s like to not pretend that we know what’s essential and what’s important today, and I don’t want to pretend that, I don’t want to admit means that we get lost for longer. If we say, as I find myself doing maybe more often than the average person, waking up to being like, “There’s so many things. I don’t know what to do,” and being honest about that means you know what to do. That is just fault.
Okay, what’s happening? What now? Build your list, the 1, 2, 3 list. You know what to do and you just keep coming back like the airplane master. You’re off track 90% of the time, but you keep coming back on track. It’s how quick can you admit to being lost. How quickly can you admit to being pulled into the non-essential is really the actual test of being an essentialist.
The Essentialism Cycle: Quarterly Review And Adjustment
I’m curious, as we wrap up here, how do these seasons of essentialism change? Is this a constant reevaluation? Is it something you look at over a year or five years or months or day? What’s the 80-20 rule around that?
It’s hard to answer that question without just directly speaking back to the planner, because these were the tools that I tried and tried again.
For you, how much of what’s essential for Greg in 2025 versus 2020?
This is the answer, though. The planner is a 90-day planner. This is a quarter tool and it starts with the personal quarterly offsite. That’s what I have found to be the magic amount. You’re still doing daily adjustments, but every quarter.
Basically what every company has figured out.
It doesn’t mean that you don’t then also do annual or five-year planning sessions. Those are different and rarer, but there is something about quarterly that you really get to reflect still, but the changes you start to implement or that you intend to implement still feel real. I think that’s important because if you get too much into the, “Here are my general values, or here are my general thing,” that’s fine. There’s nothing wrong with doing that, but it’s disconnected to what’s real now.
I just have found that when I do that, so I did it about two months ago. From the time of recording, we will be the quarter again. I just go through three questions. What’s essential that I’m under investing in, what’s non-essential that I’m overinvesting in, and how can I make what matters most as effortless as possible?
It’s consistent with the whole approach of essentialism, but it’s about investment, like almost a portfolio type approach. It’s like, “Where am I just getting that investment a little wrong?” That’s always really helpful to me because then I have the equivalent of an early warning system because I see, “That relationship, that’s not terrible. It might be a B-plus or even an A-minus, but I can see I’ve been under investing in it.
That relationship’s always important, but from quarter to quarter, it may be more important because you’ve neglected it. That’s what I was trying to ask. How much of the stuff, I know the recalibration, but how much is fundamentally new or how much stays the same in terms of what’s essential?
I think about trying to give you a direct and honest answer to that question. I think I would say that quarterly is more about adjustment, not rethinking. That’s how I would answer that question. My own temperament is such that I have a tendency to rethink in big ways all the time. Sometimes, people are at the other extreme, they’re not rethinking anything, so they’re into a normal, “This is my cycle, this is my routine and this is life and it can’t be anything different.”
I tend towards the other extreme, which is also not very helpful sometimes. You mentioned I’m wearing a Cambridge sweatshirt. I’m a literally in Cambridge right now and I’m literally doing a mid-career doctorate, an unusual move. There’s no real reason. There was no career imperative to do it, but there’s a willingness to rethink at deep levels that is also advantageous. You just can’t do that all the time. I think that’s a more like a 2, 3-year cycle can really think radically different.
Since you’re always focused on the future, tell people where they can get the book, learn about the podcast you’re writing, and also what the next book going to be or what current research might we learn about in a few years?
Understanding And Connection: The Essential Need
There was a lot of things there. I think if I were just giving people one thing to do one action, we created a tool, it’s completely for free. It’s called The Less but Better Course and people can sign up free. Go to GregMcKeown.com. It’s right there on the homepage. You can get it in ten seconds. You get really high-quality worksheets, printables series of emails over 30 days, every 3 or 4 days. It’s not overwhelming. It answers this question. Where do you start? With Essentialism and with Effortless, where do you start?
This is where you start. That’s my answer to that. The other question is an interesting question to ask, for me anyway, is like, what’s the biggest need in the world right now? What’s the biggest challenge and what’s the biggest need? I think the answer to that question, and this is a lot to why I think this, but is the challenge of understanding each other. I think it’s the biggest single phenomenon, and I think it’s the most important phenomenon of our lifetimes, is the polarization to the degree that people can’t understand each other, can’t talk to each other.
They don’t want to understand each other.
That’s the same thing, but worse because then, if you don’t want to, then of course you can’t. Trying to understand why can’t we do that anymore? What can we do about it? That is what am at Cambridge researching and trying to codify and trying to put together. It’s really important work.
We can solve that problem. The world needs that. Greg, thanks for coming back for the third time, sharing your story with us. The planner’s great. I encourage people to check it out. We’ll have you back for number four once you’ve solved the solution to why we can’t all be nicer to each other.
Robert, it’s really been a pleasure. Thanks for having me. Thank you.
Alright, to our readers, thanks for reading. If you enjoyed this episode or the show in general and you’re a longtime reader, I’d really appreciate if you could just leave us a review. It’s actually what helps new users discover the show and great guests like Greg McKeown. If you’re on Apple podcast, just hit the library icon, click on Elevate, scroll down to the bottom, and you can leave a rating and a review. Thanks again for your support and until next time. Keep elevating.
Important Links
- Greg McKeown
- Essentialism
- Effortless
- The Essentialism Planner
- The Greg McKeown Podcast
- Episode 100: Greg McKeown on Essentialism and What Really Matters
- Episode 132: Greg McKeown Returns With A New Book: Effortless
- From Strength to Strength
- A World Without Email
About Greg McKeown
Greg McKeown is a highly influential author, speaker, and social innovator, best known for his New York Times bestsellers “Essentialism” and “Effortless,” which have been translated into 37 languages and recognized for their impact on leadership and success. He’s a sought-after speaker for major companies like Apple and Google, and his podcast consistently ranks among the top self-improvement and educational shows. With a background including an MBA from Stanford, a certificate from Harvard, and ongoing doctoral research at Cambridge, McKeown combines academic rigor with practical insights, also contributing to social causes through board memberships and mentorships, and participating in global forums like the World Economic Forum.
