Welcome entrepreneurs. I’m so glad you’re here.

Longtime readers know that meditation plays a critical role in how I coach founders, albeit in a less obvious way than my experience building and scaling tech companies. (Incidentally, I’ve recently embarked on a year-long journey with NLP Marin, so my leadership influences are becoming more eclectic, not less).

One of the most powerful tools for leadership in my experience, meditation is misunderstood by most founders and leaders, and their misunderstanding prevents them from seeing its potential.

In this week’s essay, we’ll explore how meditation supports rapid growth in “inner game” of entrepreneurship, and set leaders on the right path to getting the most out of their time on the cushion.

The Misconceptions of Meditation

For many leaders just getting started with meditation, there’s an idea that meditation should be  “Zen.” They picture a serene person with a shaved head and maroon robes inside a little bubble of serenity even as hurricanes swirl all around. During meditation, thoughts should cease, or at the very least slow down, and one should be able to float in peaceful darkness. 

These are misconceptions, and they stand directly in the way of leaders benefiting from a meditation practice. 

When I first went to study in Michigan with Sokuzan, a meditation master of both the Chogyam Trungpa and Kobun Chino Roshi lineages, I arrived at the monastery with my questions and ideas about meditation. I’d already been meditating for seven years, so I figured I knew some things. He was just going to help me get to the next level. After we’d greeted each other and I told him about my quest to deepen my practice, he said, “you’re very intelligent.” I must have smiled or otherwise reacted because then he said, “it’s not a compliment. It’s just an observation. It’ll get in your way here.”

Understanding Shikantaza Meditation

I didn’t understand until much later (frankly my reaction at that moment was entirely emotional, despite my seven years of sitting), but that response was him helping to deepen my practice. 

Foundational to Shikantaza (“just sitting”) meditation, he explained, is the recognition that in meditation as in life we tend to react to thoughts or experiences in one of three ways. “We either embrace them,” he said, pulling an imaginary something toward his chest. “We reject them,” he pushed his palm toward me. “Or we look away,” he turned his head. The key, Sokuzan said, was to not do any of those things. 

“What else do you do if you aren’t doing those things?” I asked. 

“Notice what you notice,” he said. Zen masters speak obliquely, I’ve found.

After nearly 2,000 hours on the cushion, those are still the most useful meditation instructions I’ve heard, along with “hold everything still, and watch what moves.” What I’ve noticed as I meditate is that when I’m holding everything still, my leg might start to itch, and when in response I do one of those three, very natural things, the itch steadily gets worse and worse until I cave and scratch. On the other hand, if I simply notice the itch, leaning into it and trying to experience its texture, it itches. And that itching feels a bit like tingles and heat and anxiety, and then I realize it actually stopped itching a while ago. Thoughts and emotions work like this, too. Look directly at an unpleasant thought, not to get rid of it but to really see it for what it is, and quite often it just unravels.

This isn’t always the case, of course. Beginners expect meditation to feel Zen, whatever impression that vague word gives them, and then when they’re beset by thoughts, feelings, sensations -- when they have an experience of any kind, in other words -- they think they’re doing it wrong. For the record, the only way to do meditation wrong is to not do it. Once you’re sitting down to meditate, you’ve won. All you have to do from there is to hold everything still and to watch what moves. Watch your reactions to those moving things, how automatically you embrace, reject, and look away. And instead of reacting, just notice the urge to react and, look more closely at it. Notice how little control you, the one who is trying to hold everything still, have over any of this movement. 

If what you notice is a lot of thinking about golf (me, sometimes), or an itchy knee, or immense anger at something that happened the night before, or the insufferable need to swallow a mouthful of saliva, whatever you’re noticing IS the meditation. It doesn’t need to be more (yes, this is what meditation should be like, more of this please), less (this isn’t right, I should be Zen goddamn it, thinking about sex isn’t Zen), or different (I should be watching my breath). Just be where you are, and look as closely as you can. Curiously. As if whatever you’re noticing has something to teach you, if only you can see it truly. 

Doing this, the first lesson you learn is the foundational temporality of everything. No matter how intense, every thought or feeling or sensation has a beginning and an end. Even the overwhelming need to swallow, if you simply stay with it, it’s just tightness, tingliness, and an urge, and then before you know it it’s gone. The second lesson you learn is how unnecessary most of your reactions are, really. How silly all your yelling and scratching and swallowing and box checking seems, the moment the triggering sensation has passed. You learn that you don’t have to react all the time. 

Applying Meditation to Leadership

Why does meditation matter for leaders? It makes them better leaders.

All those experiences on the cushion, you carry them around with you wherever you go. One of the primary opportunities of meditation is to see your mental machinery for what it is (thought patterns, nothing much to do with you) so that you recognize that machinery at play throughout your waking life, whether it’s with your family, in the boardroom, or in pitch meetings. Once you recognize the machinery steering your actions and your life, you for the first time have the option of choosing another path. A path not driven by a pervasive-and-yet-for-most-people-unconscious need to feel good feelings and avoid feeling bad ones. 

If you see that you tend to think about how badly the meditation is going and how you don’t know what you’re doing, trust that you’ll question your performance in other areas, too. If you find yourself forcing focus on the breath, berating yourself when your mind wanders, rest assured that you’re beating yourself up like a drill sergeant the other 23 hours as well. 

Notice the pattern, and then notice your reaction to the pattern. Notice how automatically you want to embrace it (fuck yeah I’m a drill sergeant, that’s what gets results!), reject it (man I feel like such an imposter, I wish this would go away), or look away (that’s enough meditation, I have work I should do). The pattern is machinery, but so is your reaction to it. Notice all of it, and practice looking closely.

By practicing in this way while meditating, you’re training yourself to sit with uncomfortable thoughts, emotions, and sensations when they show up in the boardroom as well. Feel like an imposter about to enter an investor pitch? Fantastic. Don’t embrace that feeling, don’t reject it, and don’t look away. Just notice. See if you can let the feeling be there as just a feeling, sensations and thoughts, without telling yourself the story that it’s significant or true. 

And then if you reject it because it’s natural to hate feeling like an imposter and want it to stop, notice your rejection of the feeling as, itself, simply another feeling. Feel like you shouldn’t be rejecting feelings so severely, like you should know better? Notice that judgement as yet another feeling. Watch your mind create layers and layers of feelings and judgements and thoughts, stacked atop one another like turtles all the way down.

Notice all this. Don’t embrace it, don’t reject it, and don’t look away. Then watch what happens to the whole stack of sensations.

Embracing Imperfection: When it feels like you’re doing it wrong, in meditation as in life

Being present with whatever is, what you practice in meditation, is a muscle like so many things. With practice, it becomes easier. Your feelings and thoughts become less significant, stay less long. But even after a decade of meditation, sometimes discomfort still sticks with me longer than I’d like. It doesn’t unravel on my timeline, even though I’ve learned that all thoughts/feelings eventually do. In this case I remind myself again not to default to the automatic reactions Sokuzan warned me about. Instead, I look closer. I try to see the texture of the feelings. For example, I might try to see “imposter syndrome” as its phenomenological parts: 

• Fluttery stomach

• Heat in chest

• Tightness behind eyes

Or whatever. My fear signature is mine, and yours will be unique to you. Whatever the signature, the dissolution of something that feels overwhelming in the moment into its parts can help you to see a ravaging emotion for what it really is: simple sensations in your body, and insignificant thoughts in your head. And you can sit with bodily sensations and insignificant thoughts, right?

Stay with the sensations, and take care to notice when you don’t notice them anymore. Even the shittiest feeling, at some point you’ll realize it’s gone. 

Harnessing Meditation for Leadership

The goal of meditation is not to eliminate these shitty feelings. Feelings are a part of being human, and our emotional range is a feature, not a bug. The goal is to work with shitty feelings more skillfully. Entrepreneurs spend a lot of time pushing. We strive, we create, and we put ourselves in crazy, uncomfortable situations we’ve never been in before. Then, we demand performance. Sometimes the programs that are running in our mind support that performance, and we raise money, hire the best talent, and build successful companies. But sometimes the programs running in the background get in the way. 

A feeling comes when you notice one of these programs, when you notice that you’re feeling shitty or like an imposter. It shouldn’t be that way, you might tell yourself. You’re at a pitch meeting, for crying out loud. You shouldn’t feel like an imposter. You should just have your shit together and be crushing it like everyone else is doing. Then there’s another thought that crushing it is what leadership, or entrepreneurship, really is. And that because of your chaotic feelings and self-talk you must be somehow doing it wrong. At another time you might even know this is bullshit, but the thought, and the accompanying unpleasant feeling, comes nonetheless. 

The feeling comes that your experience should be somehow different than it is. Said differently, the feeling comes that your meditation should be somehow Zen.

All just more thoughts. Just your brain’s machinery keeping itself busy. 

In the immortal, oblique, yet in my experience universally applicable instructions of Zen master Sokuzan: Hold everything still, and watch what moves. Don’t embrace, don’t reject, don’t look away. 

Then watch what happens.