Chapter 1: The power of mindfulness and meditation

SAM HARRIS: I had at that point virtually no wilderness experience. So I was really just totally green and not in good shape. And I bought a new pair of boots that I had never hiked in. I mean, they admonish you to break in your boots, so I got just prisoner-of-war-level blisters the first days hiking, right. It was just, it was awful. And then the trip just unraveled from there.

REID HOFFMAN: That’s Sam Harris, describing an Outward Bound trip he took at the age of 16. Those blisters on his feet would heal. But there was another trauma from that excursion that left a more lasting impression on him.

HARRIS: One of their signature maneuvers on these trips was to put people on what they call the solo, which was three days of solitude where you were just camped out, in my case, by a lake, very high up, maybe at around 11,000 feet or so, and told to do more or less nothing other than write in your journal. You were given no tools by which to distract yourself there, you didn’t have any books, and you fasted. So it was three days of just drinking water, which also was something that I think I had never done before.

So my mind just became totally unhinged. I wouldn’t say I went mad, but I was mad with unhappiness, with longing to be back to my life in the world. The degree to which I was missing family and friends and ordinary distraction – it was a revelation to me how unhappy I was merely being placed in my own company without any other outlet. And I was in, objectively, one of the most beautiful spots on earth. This was just a gorgeous alpine lake with more stars than I’d ever seen in my life overhead. And I did not discover in myself the resources of a contemplative or a naturalist or a budding scientist or anything other than a miserably lonely and distracted person.

HOFFMAN: But when Sam finally came down off that mountainside and rejoined his fellow Outward Bounders, he found the rest of them had had a very different experience. 

HARRIS: I was seeing people who had been made apparently radiantly happy by the experience, right? Like this was the most important thing that they’d ever done. They were so effusive with just what a transformation it had been, and up until that point, I had never, it never occurred to me that there was any other way to be in the world, much less a way that could be systematically investigated or trained.

I mean, the notion of living an examined life or following any kind of contemplative path, that was a meme that had never gotten into my brain at that point. And if you’d asked me what I thought about meditation or spiritual life or anything, I think I just would’ve had an empty file there. So I had no prior associations with any of these concepts. And I was seeing people who had not found their own company oppressive in any way – to the contrary. And so that planted a seed for me, where I realized, “Okay, there’s something I really don’t understand about the possibilities of human wellbeing here.” 

HOFFMAN: That seed grew over the years, and Sam became a renowned voice of reason – and wisdom – on the power of mindfulness and meditation. 

But if you’re a founder, then Sam’s wilderness experience might resonate in a different way. Because the old adage of leadership is still brutally true: It’s lonely at the top. The ever-present danger for you as an entrepreneur is becoming lost on a wild mountainside of your own making. It’s a wilderness that can easily engulf you and make you start second-guessing not only your decisions, but the very reason you set out on the journey. 

That’s why I believe managing your emotions is as critical as managing your business. You need to cultivate the ability to think and act with clarity.

[THEME MUSIC]

Chapter 2: How to master your emotions

HOFFMAN: I’m Reid Hoffman, co-founder of LinkedIn, partner at Greylock, and your host. And I believe that managing your emotions is as critical as managing your business. You need to cultivate the ability to think and act with clarity.

I want you to think for a moment about carpentry. I’m no woodworking expert, but I do know that when you’re making something – from the lowliest bird box to the most ornate armoire – you need to use the right tool for the job at hand.

Sure, you could smooth the edges off your hardwood table with a scrap of sandpaper – but it will take you days. Far better to use an electric sander – the job will take a fraction of the time, and the finish will be more consistent. And you could secure the handcrafted dovetail joints of the cabinet you just built with an anvil. But for a less destructive approach, a standard wood clamp is probably a better bet.

The world of leadership is full of tool metaphors. And we often talk about how important it is to have a variety of them in your metaphorical toolbox. But we seldom talk about the actual toolbox itself. The container that these tools are in. 

I’m talking of course about your mind. Now we often speak of the mind with reverence. Its mysterious capacity to learn. Its awe-inspiring ability to innovate. But Sam Harris has a different view. 

HARRIS: Your mind is the most rambling, chaotic, needling, insulting, insufferable person you will ever meet. It’s like having some maniac walk through the front door of your house and follow you from room to room and refuse to stop talking – and this happens every day of your life.

HOFFMAN: This description of the mind struck me as very funny and very true. It leads to a profound lesson: For any other business tools to work, you have to improve the toolbox that is your mind. 

I wanted to talk to Sam Harris about this because his podcast “Making Sense,” his app “Waking Up,” and his many books have drawn a devoted audience among entrepreneurs, in Silicon Valley and beyond. As an author, neuroscientist, and philosopher, Sam’s known for his exceptionally rational, often hilarious, and sometimes controversial approach to life’s big questions. 

I should add that Sam is also known for his views as an atheist, but those don’t play any part in today’s episode. We’re laser-focused on what Sam’s learned about how you can manage your own emotions, and master your own runaway thoughts. 

HARRIS: Real relief comes when we recognize thoughts for what they are: mere appearances in consciousness, images, bits of language. The fact that a thought has arisen does not give it a necessary claim upon your life. It need not have any implications, psychological or otherwise. Of course, you’ll continue to think and to be moved to act by thoughts, but meditation gives you a choice: Do you really want to follow this next thought, wherever it leads?

HOFFMAN: Every founder engages in a battle with their own thoughts and emotions. From the outside, it can be hard to grasp just how challenging and lonely the entrepreneurial journey is. You’re tested at every turn. The true challenge for founders isn’t winning the strategic game – it’s winning the mental game. 

So this episode is designed as a Masterclass in mastering your emotions. It’s the first of several Masterclasses we’ll release over the course of this year, each with a different approach. Our format here will be different than usual. Instead of following Sam through the arc of his career, we’ll lead you through the arc of his ideas around meditation as the tool for mastery. 

You can think of each step as a waypoint on your metaphorical journey up the mountainside. We’ll draw from my interview with Sam, as well as excerpts from his “Waking Up” app. At the start of our journey, I wanted to ask Sam about how he describes the activity of “meditation.”

Chapter 3: Meditation — its meaning and its goal

HARRIS: The word “meditation” can mean several different things. And in one framing, it does mean calming the mind. It means growing more concentrated on a single object, whether that’s a mantra or the breath, or any arbitrary object, in fact. And in some traditions, that’s considered a profound practice that is really the only thing worth doing. 

But in other traditions, it’s recognized that that kind of concentration is just a tool for having insights into the nature of mind that, ultimately, don’t have anything to do with quieting the mind. It’s not to say that the mind doesn’t become quiet when you practice in this way ever, but ultimately, it’s about recognizing the nature of thoughts themselves, not having a mind without thoughts.

So the goal of meditation, in my view, is – you know if you can call it a goal, it’s not quite a goal – is to recognize that which is intrinsically present in even ordinary waking consciousness that is a more durable basis for wellbeing and psychological freedom.

HOFFMAN: As an entrepreneur, your success is directly linked to your ability to tune out the noise and focus. Not just when external fires burn, but also when internal worries blaze.

Once you have the ability to take a more detached view of your thoughts, you’ll also be able to see them more clearly. And therefore act more swiftly. A metaphor might help you picture how this works.

Imagine you work in a foundry full of molten metal – it’s blazingly hot, you’re constantly surrounded by a cacophony of noise, and your movements are limited by your protective gear. It’s disorienting and stifling.

Now imagine your job is to move through the foundry, quickly reading off precision gauges. Lives depend on you getting your readings right every time. Imagine how much harder this would be if your protective goggles were constantly fogged up.

Meditation is the equivalent of anti-fog goggles. It’s not going to improve the situation around you by making the foundry quieter or your protective suit less restrictive. But it will bring you clarity. And this will help you make clearer gut-checks and faster decisions. 

And with that, we’ll begin our journey with Sam at waypoint number one: Why meditation is worth your time.

Waypoint number one: Why meditation is worth your time

HARRIS: Many people who are at first skeptical about the benefits of meditation, find their skepticism relieved when they hear that meditation changes the brain. But the truth is virtually anything you do changes your brain. The fact that you had breakfast this morning, and that you can remember it, changed your brain, and, of course, learning any complex skill requires that your brain physically alter its structure. That is what learning is at the level of the brain.

HOFFMAN: As an entrepreneur, you have a bias for action, and you’re a pragmatist. So maybe you are among the skeptics Sam speaks of. Or, more likely, you haven’t dismissed meditation – you’ve just filtered it out for now as you focus on more pressing concerns.

But when time is your most valuable commodity, any method that can increase your efficiency should be investigated. Especially when it could have a multiplier effect. Meditation is one such method, because time lost chasing or identifying with negative or spurious thoughts that appear in our minds is time squandered.

HARRIS: The quality of your mind determines the quality of your life. Happiness and suffering, no matter how extreme, are mental events. The mind depends upon the body, of course, and the body upon the world, but everything good or bad that happens in your life must appear in consciousness to matter.

HOFFMAN: And that brings us to waypoint number two: Recognize what’s in your control.

Waypoint number two: Recognize what’s in your control

When it comes to your control, there will always be more factors outside of it than within. Actions by your competitors, movements in the market, stymied supply chains, spooling red tape, global pandemics or even something as basic as a burst water main can all throw you off track.

Dealing with these neverending challenges is tough – especially when the buck stops with you as the leader of your team. But it can be made far tougher if you are also struggling with stress, disappointment, embarrassment, and self-doubt.

Rather than trying to control what is by nature out of your control, you can look more closely at what you’re doing with your own mind, and cease to respond to sabotaging thoughts that hurt your ability to lead effectively, and that impact valuable relationships with your team.

HARRIS: Rather than trying to change the world in each moment, there’s another move open to you. You can look more closely at what you’re doing with your own mind and actually cease to respond to life in ways that produce needless suffering for yourself and those around you. When we’re lost in thought, there are certain things we tend not to notice about the nature of our minds. 

For instance, every thought or feeling you’ve ever had, good or bad, has arisen and then passed away. The anger you felt yesterday or a year ago isn’t here anymore, and if it arises in the next moment, based on your thinking about the past, it will once again pass away when you’re no longer thinking about it. This is a profoundly important truth about the mind, and it can be absolutely liberating to understand it deeply.

HOFFMAN: There’s a wonderful parallel here with the constant, nimble fire-extinguishing you need to excel at as an entrepreneur. When a new problem rears its head in the clutch of crises you’re dealing with, you can’t waste time bemoaning your fortune. As an entrepreneur, you will rapidly take stock of the situation and reassess what needs to be done – which fires to put out, which to let burn, and which are nothing more than distractions. You know from experience that the problems before you now need your attention, but at the same time that they are just fleeting occurrences – this time next week there will likely be a whole host of new problems. Sam sums this up well.

HARRIS: In some basic sense, meditation is the act of doing less than you normally do. It’s the act of being less distracted in the midst of everything that is already happening on its own. And once one is less distracted, one finally has a tool with which to notice truths about one’s mind that otherwise would never be discovered directly.

[AD BREAK]

Waypoint number three: An antidote to suffering and stress

HOFFMAN: Welcome back! Before the break, we got a grounding in how Sam Harris thinks of meditation, and we explored why it can be of deep value to you as an entrepreneur. 

And that brings us to waypoint number three: An antidote to suffering and stress.

“Stress” is one of the top associations with entrepreneurship. But what many people frequently don’t realize: the real challenge is managing stress over time. You can manage the stress of the first few years. You’re like a boxer fresh into the ring, operating on adrenaline for the first few rounds. But by round four, the fatigue is starting to kick in. You’ve probably taken a few jabs, maybe even a body blow. And this is where you have to start thinking about digging deep, where the fight is as much mental as it is physical. As much with yourself as your opponent.

Cultivating clarity can help you develop the self-possession so you’re not thrown off balance during these later rounds. You’re still going to be bruised and worn, but you’ll be able to stick out the fight – and hopefully come through it triumphant.

HARRIS: Mindfulness eventually becomes an antidote to your psychological suffering. Now it’s not that negative emotions and moods no longer arise, but when they do, you can drop back and merely witness them. You can’t always do it perhaps, but you can sometimes do it. And then you can do it more and more. 

What begins to happen is that your own psychological suffering becomes a kind of mindfulness alarm, which reminds you to pay attention. And when you pay attention, it actually helps. That’s the sign that your mindfulness is becoming a useful skill. And in those moments, you no longer imagine that your suffering is coming from the outside. You’re no longer disposed to merely blame the world or other people. You recognize viscerally that that thing that made you angry or anxious wasn’t the true cause of your suffering. The true cause was internal to your mind. And you can take responsibility for noticing this process and for relaxing the apparent hold it has on you.

HOFFMAN: None of this is to say you will eliminate your negative emotions – and this is not something you should aim for. But what meditation will do is give you the ability as a leader to drop back and witness your thoughts, your emotions, your motives, and your assumptions without getting tangled up in them. Doing this is a skill and will take practice. 

And that leads to waypoint number four: Committing, over and over.

Waypoint number four: Committing, over and over

Each stage of the entrepreneurial journey demands something new from a founder. And so you’ll find yourself needing to recommit to the journey over and over again. Sam says it’s the same with meditation:

HARRIS: There’s a lot that can be said about what it means to make progress in meditation practice. In some traditions, the notion of progress can be made to seem fairly paradoxical, but there are actually a few landmarks on the path that are valid to consider as indications of whether you’re getting the intended benefit from this practice, and whether you’re recognizing important features of your own mind that are there to be recognized. 

Now, the first and most basic is whether you’re able to make a regular habit of doing the practice, and that can be hard to do. Still, you really do just have to decide to do it. And when you go too many days without following through on that decision, you have to decide to do it all over again.

Of course, any positive habit is like this: working out, changing your diet, prioritizing time with your kids. It can be very easy to let important things fall by the wayside, as you know. And then you just have to recommit all over again. So just taking some period each day to practice is already significant progress. Most people never do such a thing in their lives.

HOFFMAN: And this is where I want to take a side journey to hear how Sam decided to shift his focus from writing books to building an app – as the best way to scale his ideas on meditation.

HOFFMAN: What made you then think an app was an interesting way for helping this path forward, this direction toward mindfulness?

HARRIS: Well, I had noticed the two main meditation apps come to market and what they were doing and that there was a market for this technology. It just struck me that it was the perfect technology to deliver this instruction. It’s so much better than a book. I had taken the time to write my book Waking Up, and compared to audio, it’s just the wrong delivery system. Guided meditation and even audio instruction in lesson form is better than reading a book and then trying to go off and do it on your own. There’s something about pure audio that’s even an improvement over video.

HOFFMAN: What did you learn? Because products are always these things that are in iteration, and Waking Up is actually, in fact, a public intellectual thing of, “Look, here’s how to kind of evolve your mindfulness.” What did you learn in the iteration of the product? What was the, “Oh, do more of this, less of this. This enables scale. This kind of creates limits?”

HARRIS: Well, first let me say I am definitely still learning. I consider myself a reluctant and by no means precocious entrepreneur. So I stumbled into this. I went from writing a book on the topic to recognizing that an app would be better. And then I publicly committed on my podcast to building an app and releasing it and at that point, had no awareness, literally zero awareness, that this was going to be a fantastically complicated and expensive endeavor.

So I just didn’t understand that an app is something that’s basically never, never done. You’re continually developing it and resuscitating it. I got a fairly protracted and expensive education in app design going with the wrong shop and then going with another group that turned out also to be wrong for different reasons, but sort of got me further along and got me to an MVP that was releasable. The truth is I’m still, as you might imagine, I’m still iterating. Now, the plane is cruising at something like 30,000 feet and everything’s great, but it’s still a process of building and iterating and expanding.

HOFFMAN: Sam went out on a limb making the app. It was a lonely, unsettling, and uncertain journey – one that will be very familiar to any entrepreneur who has struggled to make their idea into a viable business. It’s a struggle that Sam crystallizes so neatly in this next excerpt from Waking Up. 

And that brings us to waypoint number five: The primate within.

Waypoint number five: The primate within

The root of the problem is what Sam calls our internal monkey – the behaviors that stem from our evolutionary origins as primates.

HARRIS: As you begin to train this capacity for merely being aware of what’s arising in consciousness, you’ll see that it’s almost like consciousness has become shackled to a monkey. But it is not the monkey. This monkey software that’s being run, of social anxiety and self-concern, all of that’s just appearing in this space of awareness.

And when we meditate, whether we’re formally meditating or we’re just paying attention clearly even in the midst of our living, those can be moments where we cut the connection to all of these evolved tendencies merely by paying close attention and recognizing the space in which everything is appearing in each moment. And that can be a profound relief. So, whatever happened yesterday and whatever may yet happen today, take this moment and with clear attention to a sound or a sensation or an arise in thought, simply cease to be a monkey.

HOFFMAN: And now for our final waypoint, number six: Eternal failure.

Waypoint number six: Eternal failure

Founding a company can be very lonely – even when you have co-founders. In the rare instances that you can catch your breath, you will often find yourself dwelling on worries about decisions made, or decisions not yet taken. It’s all too easy for these brief moments of darkness to turn into an all-engulfing fog that will cloud your judgment and therefore your chances of success.

Establishing a mindfulness practice is one way to build the mental resilience to move through that fog. There’s a catch-phrase in Silicon Valley that entrepreneurs need to “fail fast.” What that means is that you have to try risky things, accept that some will fail, learn quickly, and then move on to the next risky thing. It sounds simple, but it requires mental resilience and self-awareness. And for this, meditation is uniquely helpful.

HARRIS: When we practice meditation, one of the things we learn is how to begin again in each moment. You notice that you’re distracted. You’ve been lost in thought for who knows how long and then suddenly you return to a clear witnessing of the contents of consciousness.

You notice a sound, or the breath, or some other sensations in your body. Or you see the present thought itself unraveling, and in this clear noticing of this next appearance in consciousness, we’re training our minds. We’re practicing a willingness to simply return to the present moment without judgment, without disappointment, without contraction, with a mind that is standing truly free of the past. And it’s always possible to recover this freedom, no matter what happens.

HOFFMAN: There is no entrepreneurship without learning. And there’s no entrepreneurship without a lot of adversity and failure along the path. The key is to learn from that failure and move on, not dwell on it and become stuck.

This is why the ability to recommit and to do so passionately is important. Recognize your failures in the positive context of moving forward. Self-criticism that impedes your learning will impede your ability to iterate and grow.

Some of my biggest learnings as an entrepreneur have come from saying, “Oh, I really sucked at that. I didn’t do that well.” And then incorporating what I learned into my future game play.

Making the time investment to clarify your thinking and master your own emotions will help you go through this process more rapidly, learn more, and scale faster. 

The importance of being honest with yourself

And that brings us to the end of this masterclass. But it by no means brings us to the end of the fascinating topics Sam and I covered in our interview. One I wanted to share with you in particular was our discussion about the importance of being honest with yourself.

It’s a first principle that both Sam and I see as foundational in scaling our ideas

HOFFMAN: I wish we had a lot more of a society being reflective about who we are as individuals and as society and who we should be, who we should become. How did you get into the public intellectual path?

Because part of the thing that I think is interesting, especially as we get to Waking Up and the app, is you start playing a scale public intellectual role. 

HARRIS: Intellectual honesty really has to be the ground truth of our conversation with one another. And so, I think public intellectuals are the people who try to do that most deliberately and try to stand outside of any institutional pressure that would make it harder to do that. 

HOFFMAN: The way that I think about that is, I think public intellectuals are individual and collective truth-seekers, and then the question, when you ask yourself, are you a truth-seeker? Well, how good of a case can you make for yourself being a truth-seeker? 

Most people just say, “Oh, I am. I mean, I do.” And you’re like, “Well, no, no, no.” If you’re actually a truth-seeker, you’re going to be able to make a very philosophical, like, a detailed case of, “This is actually in fact how I am seeking truth. This is my openness to having my mind changed. These are the ways in which I am testing my beliefs to see if they are right or, matter of fact, they’re almost always partially wrong, how I should be improving them, how I should be refining them.”

And most people can’t make that case, and so my hope for the public intellectual evolution in society is that truth-seeking becomes more of an aspirational and cultural norm which, obviously, today, we are very far away from.

HARRIS: I think one heuristic there is to notice what your incentives are and to notice those times where what is true or acknowledging what is true or what you have every reason to believe is true is going against the grain of those incentives, and to just notice what you do at those moments. I mean, is that a moment where you decide to just prioritize some other topic in some way that you can’t really argue for — apart from the fact that it is convenient, whether financially or reputationally, to not be standing where you actually think the truth is?

And I, just as a point of pride that is very close to the core of my ethical worldview, I have just decided that I’m going to – whenever I can notice that I’m getting pushed by something other than intellectual honesty, an alarm goes off in me, and I want to reset. And it’s not to say that I’m perfect at it. And it’s true that I will occasionally, I’ve learned to pick my battles in the sense that you have to be aware that not every single fact that you could defend is worth defending at the first possible opportunity to defend it. Right? And so, there’s been some learning for me there. But I definitely err on the side of putting both feet in my mouth when it matters.

HOFFMAN: Being honest about your endeavor is vital for you as a founder. It will save you wrong turns and wasted effort. But you will need trusted companions who will help you stay close to this guiding truth. You will need to be open to having your truth challenged and your mind changed.

Similarly, for meditation to work you need to commit to the process involved. Both journeys have a lot in common, not least of all that they constantly humble you.

I’m Reid Hoffman. Thank you for listening.