Coaching From Essence

For my beloved Michèle, who won’t let me be anything less than my best self. And for the clients and coaches I have been privileged to work with, who let me coach from my essence.

Goose in a Bottle

Clients come to you because they don’t like where they are, or they don’t know how to get to some place they’d rather be. And there are good reasons for their dissatisfaction or confusion.

Okay. I don’t know the Zen answer, but here’s one answer: Break the fucking bottle. Who says you have to follow the rules? Where do the rules come from anyway? All those beliefs about who you are and what will make you happy, what success looks like, and all your fears about failure and what you have to do to avoid it—that’s your bottle. All those beliefs you have about what coaching is and who you are as a coach, and how to create a practice you love—those, too, are your bottle. Think you can only charge like a therapist, maybe a couple hundred dollars a session? Bottle. Think you can only charge by the session, not on retainer? Bottle. Think you can’t charge money if you’re a new coach? Bottle. Think you shouldn’t coach for free? Bottle. Think you need to be certified to be a coach? Bottle. Think you need a degree to be a coach? Bottle. Think you need to be older, more experienced, a white male, etc., to coach executives or be a successful coach? B-O-T-T-L-E. We help clients break their bottles. This book will show you how to break your bottle.

II Paths and Quests We must let go of the life we have planned, so as to accept the one that is waiting for us. —Joseph Campbell

Paths and Quests Let’s keep this simple. All you’re trying to do is get from A… to B.

A is where you are now. B is what you want to create.

To get to B, you first need to know what B is. That requires clarity. Getting clear about B is a better place to start than A. B is where you want to be, and where you want to be shouldn’t be limited by where you are. Once you know where you want to be, it’s helpful to know where you are. That requires honesty. You have to tell the truth about A.

What’s the most important thing you want to create in your life right now? What’s your B? Now, if you’ve thought of something that you want to create in your life, something that’s important to you, we have to ask, Where did that B come from? Have you ever had your heart broken? I’ve posed this question to numerous audiences. Everyone raises their hand. But the real question is, What did you learn from heartbreak?

We choose what to learn from our experiences. Sometimes we choose the wrong lesson. Maybe it’s the right lesson—at the time—but the lesson becomes obsolete. We have experiences, decide what they mean, and then create our future based on those choices. In other words, most of the time we’re actually creating the future from the past.

You don’t want to be on a tour. You want to be on an adventure. So, you don’t actually want to get to B. As Yogi Berra said, “If you don’t know where you’re going, you’ll probably end up somewhere else.” You want to end up somewhere else, but somewhere better than you can imagine when you set out from A. Let’s call that B-prime. Since you don’t want to get to B, B is not your goal. It’s an aim. You aim for B—the best B you can imagine—but you’re really looking not for the life you have planned but for the one that’s waiting for you. Since you can’t imagine it, you don’t really know where B-prime is.

To be on a quest, you must know how to journey into the unknown. You need to embrace uncertainty.

The faster you can learn, the faster you can create B-prime. You create B-prime by conducting experiments and by creating rapid feedback loops.

The results were better than B—I discovered B-prime. I met Michèle, my extraordinary beloved, in 2017, and we married a year later. My coaching practice is full of clients I love. I now make more money than ever (multiple six-figures), and my full practice includes only about a dozen clients (a third of whom have been pro bono because I love working with early-stage founders and entrepreneurs).

The next step is to help them become comfortable with the unknown, to embrace uncertainty. They have to have the mindset that they are embarking on an adventure. They are putting themselves in the way of serendipity, of unforeseen possibilities. Now we are creating from the future, where dreams and possibilities are not dictated by what was possible in the past. Once a client has clarified their Quest(ion), I can think of no better advice than this quote from Lewis Carroll: “If you don’t know where you are going, any road will get you there.” I encourage them to take any road.

I emphasize to my clients that there is no failure on this quest. It’s not possible. You either get your B (something you were after or something equally satisfying), or you get

B-prime (something better than you could have imagined when you set out from A—we are always helping the client optimize for this), or you get a lesson and a new road to try. It’s impossible to fail if you are paying attention.

Especially in my first several sessions, I will open the session by asking the client, “What’s different? What’s different since the last session? What’s different since we first started working together?” What we pay attention to grows, and what goes unnoticed withers. If they can notice some positive change, however small, we can amplify it. That’s food for the journey. So. What’s your Quest(ion)?

Gravity

A is kind of like Earth. It has a lot of gravity. B might be the moon. The moon doesn’t have much gravity. If you’re on Earth and want to get to the moon, you need a lot of energy to escape the Earth’s gravity.

As coaches, we need to think like astronauts. There’s very little gravity in space. When we work with a client, we need to help them leave A’s gravity and find more space, the space to dream their real dream, the life that longs to live through them.

Silliness The first threshold is what I call the Silliness threshold. It’s the fear of not looking good. If you start to pursue something you want, especially something you’ve never done before, something you may not be very good at, you have to go back to being a beginner.

A true dream is not grandiose; it’s resonant. It may be big, and it may require a personal transformation, but its defining quality is that it feels authentic to the person and their essence.

To create from the future, you need to do the work of unraveling your outworn strategies for staying safe. The decisions you made to survive served you when you made them.

At the top is your essence, and then your vision or purpose.

Who are you and what do you want to create? Next is identity. Your identity is the sum of your beliefs about yourself. Do you see yourself as a visionary? A coach? A leader? An entrepreneur? Who do you need to become to be the person who does what you want to do? Become the kind of person who can create what you want to create. Examine your beliefs. To a large extent, your beliefs determine what’s possible for you. People tend to act in a way that’s congruent with their beliefs about themselves and the world—and you’re no different. But most of us don’t examine our beliefs to see if they’re helping us or hindering us. Identify your values. Your values reveal what’s important to you. Do you have the right priorities to create what you want? Know your capabilities. Do you have the knowledge, skills, and abilities required to create what you want? You can hire someone with the capabilities you’re lacking, but there are also capabilities you will need to have or develop yourself in order to reach your vision.

Many people don’t think about the inner game, which is one reason they can’t produce the results they want in the outer game. They have an identity or hold beliefs that aren’t congruent with what they say they want, or they lack…

The outer game is about the behaviors or actions you need to take—what you need to do—and the environment, or the outer world, that consists of people, places, things (i.e. resources), and time. Do you have the right people (or the right relationships), are you in the right place, have all…

You can work from the top down or the bottom up. In other words, if you commit and pursue a clear vision and purpose, it will change who you are, your beliefs, your values, and so on. But you can also change the people you hang out with, the places you go, and your behavior, which will…

It can be immensely helpful to take an inventory of your Levels of Creation: –Are your vision and purpose clear, compelling, and congruent? –Do you believe you’re the kind of person who can succeed at what you’re aspiring to do? –Do you have any untrue beliefs that are holding you back? –Do you have the necessary values and priorities, or are any of your values in conflict with one another? –Do you have the knowledge, skills, and abilities you need to accomplish your aim? If not, can you hire them? How can you acquire them yourself? –Are you taking the right action? Are you taking enough action? –Do you have…

Working on these levels is straightforward if you’re conscious and intentional about how you apply them. If you’re not, there are several gaps or conflicts within the levels that can cause problems: Integrity gaps. Integrity gaps are misalignments between your values and your behaviors. If you aren’t walking the talk, you’re unlikely to create the desired results. This is one of the most common leadership traps. Knowing-doing gaps. Some people know what they need to do, they’re capable of doing it, but they won’t take action. Why don’t they do what they know to do? There are lots of possible reasons, including holding onto an identity, beliefs, or values that are not right, enough, or aligned in a way to help them create what they want to create. Competing commitments. Competing commitments are value conflicts. For example, you might simultaneously hold both innovation and risk avoidance as values. One value may be at the forefront and the other unconscious, making it difficult to see and address this incongruity. Impostor syndrome. An impostor is someone whose identity is greater than their…

Here’s the Futurosity Continuum:

The y-axis of the continuum represents time, energy, and resources. The x-axis runs from reactive to proactive, opportunistic, strategic, and emergent. Each of these stances represents an orientation toward time, either compelling you to fix the past or pulling you to create the future.

Emergent If you’re on a path, being strategic may be enough. You’re clear about what you’re trying to create, and you’re intentional about taking the actions you know will produce your B. But you’re not on a path; you’re on a quest. You’re not creating from the past. Even if you’re being intentional, you don’t know how to create B-prime. You conduct experiments, try different things, and then notice how the universe responds. Being strategic means being as clear as you can be and asking for what you want. It’s a monologue. Being emergent is asking what’s possible and being in conversation with the universe. You try something, listen for a response, make adjustments, then try something else. It’s a dialogue.

The biggest trap is getting sidetracked by an opportunity that leads nowhere. Being emergent requires focus. Are you being opportunistic or emergent? Here’s how you’ll know: Have a clear vision. You must have a clear picture of what you’re trying to create. If you don’t, you’re not on a quest. You’re drifting.

Pay attention to the results you get. Don’t stubbornly persist if things don’t work out as you expected. Pay attention and see what you can learn. What is the universe trying to tell you?

Know what you’re saying NO to. It’s helpful to know what you’re creating and what you’re actively not creating. It’s addition by subtraction. Very often, the most strategic thing is subtracting or stopping an action altogether. Memorize these words from Steve Jobs: “People think focus means saying ‘yes’ to the thing you’ve got to focus on. But that’s not what it means at all. It means saying ‘no’ to the hundred other good ideas that there are.” Know your values—and your essence. When deciding what to do, make sure your actions align with your values and your essence. Ask the essential question. If you have any doubts, ask yourself, If I choose this, who will I become?

Optimize for Serendipity

Maybe you made your luck through curiosity and experimentation. You went to social events or suffered through a queue of OkCupid, Bumble, or MeetMindful dates, intentionally creating as many encounters as possible. (This is how I met my beloved.)

How to Knock Over the Empire State Building

Here’s the real question: How big does the first domino have to be? About the size of a breath mint! What does this mean for you? Most people get clear on their B, their Empire State Building, and they get excited and try to knock over the tenth domino. They push, and they push, and they can’t knock it over, and they say to themselves, “I was right all along. It’s not possible to have what I want. It’s not possible to create a form that matches my essence.” And they give up. Instead, if you start with the biggest, smallest step you can take, the step you know you can do and not fail, you will soon create so much momentum that you’re knocking over the tenth domino with ease. The critical thing to understand is that it must be the BIGGEST smallest step you can take. It has to be big enough that it matters—it will move you closer to your aim—and small enough that success is assured.

Begin Before You’re Ready

Forget ready. Begin before you’re ready. Time to knock over your next domino.

Form and Essence

To be alive is to be entangled, ensnared, engulfed in forms. We cling to forms as if they are life rafts. They save us from drowning in mystery and possibilities. But they also limit us. The aim of Coaching From Essence is to decouple people from their attachment to forms, to empower them to navigate forms, and, ultimately, to create forms that are congruent with their essence. Everyone has an essence. (Organizations do, too.)

The essence of Coaching From Essence is the conviction that everyone has a natural way of being in the world that adds value without any thought or effort on their part.

What Essence Is Natural way of being means innate, integral. Essence is not something you learn; it’s something you are. You can get better at it, but you already are it. Adds value means contribution, gift, service. Essence is always positive.

Essence is so natural and so effortless that it is often hidden from the person; it’s overlooked, under-appreciated, taken for granted. It is deep and reliable, a source of innate strength and power. Your essence is alive. Essence is palpable but elusive. It is a mistake to cling too tightly to any particular expression of your essence. You will think you understand it, and then you’ll realize you don’t. Essence is like love. You have a relationship with essence that deepens over time. Essence will unfold. Keep it simple. Keep it beautiful and mysterious.

What Essence is Not Essence is not purpose. Purpose is about motivation and intention. I don’t believe we are born with one purpose. We can have multiple purposes, and we may be motivated to do something that may or may not have anything to do with our essence (but we’ll be happier if we choose a purpose that’s congruent with our essence).

Essence is not passion. Passion is love, enthusiasm,

You may not be passionate about your essence. It’s likely that you’re not particularly passionate about your essence simply because it comes so naturally to you. You’re likely to take it for granted. You may become passionate about a form that allows you to express your essence. Coaching is one of my passions, but it’s not my essence. It’s a form that matches my essence.

Essence is not the same as personality. You might think of it as a subset of personality. Personality refers to individual differences in characteristic patterns of thinking, feeling, and behaving. But many of those differences are learned, not innate. Essence is not the same as your values or priorities. Your priorities may be out of alignment with your essence. I’m against trying to reduce essence to an essence statement, an exact definition.

Find Your Essence

I asked her two simple questions: “What is the thread that runs through all of the things you have ever done? When you were being your best self, who were you being?”

The closest thing I could come up with was, I help purpose-driven leaders dream bigger, act bolder, and do the impossible. It would have looked good on a business card, but it wasn’t my purpose, and it wasn’t my essence.

What do your friends come to you for? What problems do they bring? What do they rely on you for? Ask them, “If I weren’t in your life, what would you miss? How am I different from the other people you know? When you think of me, what comes immediately to mind? Who am I at my best?” Make up your own questions. Become curious about their experience with you. They will have insights for you.

The Essence Questions

Here are the three Essence Questions: Will this create a life you love? Will this be of true service, in alignment with your essence? Who will you become?

Will this be of true service, in alignment with your essence? Choosing a life you love is an act of self-care. But if you only choose what is good for you, you would be coming only from self-interest. Essence wants to be of service. It’s our natural way of adding value without any thought or effort on our part.

The Red Paperclip

I did it by trading up a red paperclip. The paperclip was my pro bono coaching. Then I coached someone for $250 per month and kept increasing my fees until I landed my first CEO client, who paid $10k per month (he paid $30k in advance for three months, no refunds).

It’s easier to build your practice by attracting clients who have more at stake and are more capable of paying higher fees than by trying to raise your rates on existing clients.

You don’t want to raise your fees; you want to raise your clients.

If you are just beginning to build your practice, the most important thing is to create a full practice, even if all your clients are pro bono. Then trade them up.

Create Clients You Love

I used to hide behind professional distance. I was half-hearted. I didn’t show up fully. One of my intentions when I reinvented myself, and the way I work, was that I wanted to be wholehearted. I didn’t want to hide behind a professional persona. I didn’t want to maintain a professional distance. I wanted to be open to having a deeper, more personal connection with the people I work with. Now, I invite people into a different conversation, a different relationship. I do it intentionally, make clear agreements, and commit to creating a bigger space where more—much more—can be included in the conversation.

First, there has to be a lot at stake. What we’re working on has to be so important that failure is not an option. It has to be so aspirational that the client knows they will have to undergo a personal transformation to achieve it. Second, the quest has to be a net positive. I don’t work with clients I feel are making the world worse. Most of my clients are impact entrepreneurs or engaged in projects that will have some positive impact on the world. Third, they have to be coachable. How open are they to other points of view? How willing are they to take feedback? I will test them, asking them what I call a disturbing question, or a provocation, in the first session to see if they will engage with me. Fourth, they have to be all in. That means three things. They are willing to put everything on the table (one of my core beliefs, which I discuss with the client in the first session, is that you can’t separate who you are professionally from who you are personally). They have to make a real commitment (I don’t work with anyone for less than three months, and they pay in advance). And the fee can’t be an issue (I charge CEOs $10k per month). If it is, I go back to the first criteria and ask, “Is this important enough to you that you are willing to make a meaningful investment in yourself?” Finally, I have to like them. I think they will be fun to work with, they have a sense of humor, I might learn something. If we’re not going to enjoy working together, we’re not a good fit.

Show, Don’t Tell Show, don’t tell. Coach, don’t sell. You will not get coaching clients by telling them what you do or what they will get by working with you. You only get coaching clients by coaching them.

Instead of telling her about coaching, I say, “Would you be open to doing some work now?” “What do you mean? Like right now?” “Yeah,” I say. “We have a few minutes. Would you like to do some coaching right now?” “Okay,” she says. So I started coaching. I coached her for literally five minutes.

Dream Together Many coaches think of the first session as a “teaser” session, “fit conversation,” “needs assessment,” or “discovery” session. I don’t think of it that way. It’s important to understand what your goals are for the first session. One goal is to establish rapport and build trust. Before the coronavirus, I liked meeting clients in cafes (now I coach clients all over the world via Zoom).

The second goal is to hear their story. I’m listening for their Levels of Creation, especially their identity (their beliefs about themselves), their beliefs about what they’re trying to create, and their values. Third, and most importantly, I’m also listening for their essence, their way of being in the world that adds value without any thought or effort. My role as their coach is to help them create a form in the world that’s congruent with their essence so they can be more successful and fulfilled.

If I’m talking to the CEO of a well-funded company, I say, “The fee is $10,000 per month retainer. We meet twice a

month for two hours, or weekly for an hour, but you have virtually unlimited access to me. You can call me or ping me anytime, within reason. I trust both of us to know what’s reasonable. You’re not on the clock. I’m here for you. I usually respond within twenty-four hours, rarely forty-eight hours if I’m traveling or at a client offsite. If you need to hop on a quick call, ping me first, and I’ll call you back.”

I have never had anyone take advantage of this, but leaders love to know they have virtually unlimited access to you. Less than half of my clients have contacted me for a coaching session outside our scheduled sessions.

There are four commitments that I ask all of my clients to make: Be all in. We already talked about this when I presented my ideal client criteria to them. They’re responsible for the agenda. They need to show up for our sessions knowing what they want from coaching. As we work together, I’ll have ideas that might be helpful and bring those to the table, but I can’t tell them where they want to go. Keep all agreements. If they say they will do something, I expect them to keep their word. A client will sometimes agree to take on homework. If they do, I trust that they will do it. One of the agreements I ask of all my clients is to send me their notes, insights, and actions within a couple of days of a session. Some of them won’t agree to this, but if they do, I expect them to do it. For most of my clients, I create a Google Drive folder, and they keep their notes in a Google Doc or, if they take handwritten notes, they will often take pictures and upload their notes after our sessions. Feedback and responsiveness. A coaching relationship should be one relationship in your life where you never have to guess where you stand. We give each other feedback. I will ask the client for feedback at the beginning or end of almost every session, and I will be liberal with mine. Responsiveness is about avoiding stories. I commit to responding to my clients within twenty-four to forty-eight hours. We close the loop. For example, if someone sends me their notes, I always acknowledge them, whether or not I comment on them. I don’t want a client wondering what I thought about their notes if they’ve shared something vulnerable, and I didn’t respond.

If they don’t keep them, I don’t beat them up; I remind them of their commitment. I’m not an accountability partner; that’s babysitting. If someone wants to work with me, they have to show up powerfully. And they do.

Boundaries For decades, I hid behind my professional persona, keeping a professional distance. Then I realized that doing so made me very unhappy. My work wasn’t satisfying. It got in the way of deep work. People don’t trust you if they don’t know you. If you don’t let them see you as a human being, it’s tough for them to be open with you. How do you balance being the coach and holding space for your clients while being a human being and showing up with some personal vulnerability? When is it okay to tell your story to the client?

There is only one criterion for talking about yourself with a client: Is this the most helpful thing I can say right now?

Coach Above Your Level

Whenever a client asks you if you can do something, say yes. Then figure out how to do it.

Give Yourself Away

I believe very strongly that it’s important to do pro bono work, even if you’re a very experienced coach. I believe this for several reasons. First, you have to get good. And to get good, you have to practice. Second, you have to start building a network, and the more people you talk to, the more people you work with, the more you optimize for serendipity. When people have powerful experiences, they tend to talk about them. That’s how you create a practice that is one hundred percent referral. Third, you have to become a coach. You have to change your identity. A coach is someone who coaches.

Finally, pro bono coaching is big heart practice. Pay the universe in advance, come from abundance, be generous with your being, and you will be surprised how quickly opportunities begin to show up for you.

Six Coaching Questions

Here are the Six Coaching Questions: How can I help? What’s the current situation? What’s the ideal scenario? Why don’t you have it right now? What could you do? What will you do?

1. How can I help? This question is about setting the agenda. What should we focus on? What’s the most valuable thing we can talk about?

2. What’s the current situation? This is about understanding context. It’s also an invitation for the client to tell their story. This question is all about curiosity.

3. What’s the ideal scenario? What would it look like if you found the perfect solution to this problem and the situation was exactly the way you wanted?

4. Why don’t you have that right now? This is a critical question. We have to look at what’s in their way. Invite them to think of all the things that are missing or would have to be different in order to reach B.

“How do you keep yourself from having what you say you want?” There is always something they’re doing or not doing that, if they stopped or started doing it, would help them create their ideal scenario.

5. What could you do? This is about getting creative and generating options. Ask the client what they’ve already tried. (You don’t want to offer something and have them respond, “I tried that. It didn’t work.”)

6. What will you do? Of the options you’ve discussed, what actions will they take? What’s the first domino? Invite them to commit to taking action, however small, but don’t be attached to having the client take action—it isn’t always about the do loop. Sometimes the step they need to take is to reflect on everything you’ve talked about.

The Wayfinding Question

If you were to distill all of this down to a single question that you most wanted an answer to, what would the question be?

VI The Dark Ally Hell is not punishment, it’s training. —Shunryu Suzuki

The demon—the problem—is not the problem. There will always be problems in your life. The response to the problem is the problem. And how you respond depends on what you think you’re responding to.

Fear Fear is panic or anxiety. What are you afraid of? Write it down. What’s the antidote to fear? It’s courage. Courage comes from a word that means heart. The antidote to fear is heart. When you love what you’re doing enough, you won’t be afraid. If you’re hesitant, remind yourself how much you love what you’re creating. Some people become afraid, even when things are going well. They feel they don’t deserve to be successful.

Do you deserve to be successful? Why do you deserve to be successful? (Pause for a moment and feel your answer to this question.) If you don’t feel you deserve to be successful, there’s a simple cure. Deserve means serve. The word deserve literally means to serve well. If you don’t feel you deserve your success, serve more. Find a way to create more value. Most big problems are the result of avoiding small problems. Are there small problems you’ve been avoiding that might turn into bigger ones? How can you keep small problems from becoming bigger problems in the first place? Face your fears by doing a premortem. A postmortem looks at everything that went wrong after the fact and tries to figure out how to do better next time. A premortem looks at all the things that could go wrong and figures out what to do about them before they happen.

Remember Milarepa? He tried to chase his demons away, but they became more entrenched. He tried to teach them, and they just sat and stared. He opened himself up to what they could teach him, and all but one disappeared. But how did he get rid of the last demon? He said, “Eat me if you wish,” and put his head in the demon’s mouth. At that moment, the biggest demon bowed and dissolved into space. What do you make of that? Whenever you let yourself fully feel your feelings, they always change into something else. What we resist persists. When you face your demons head-on, when you face the worst thing that can happen to you, you’re free. Don’t turn away. Turn toward everything.

Our Work as Human Beings Back in the mid-80s, I led personal growth workshops and retreats. I was in my mid-twenties. My father had died a few years before, and while I didn’t know it at the time, I was doing everything I could to make sense of my loss, my unfinished business, and to find my way.

One of the posters I used to promote my workshops was roughly painted with a coarse, fat brush. It read: OUR WORK AS HUMAN BEINGS IS TO TRANSFORM OUR PAIN INTO SOMETHING BEAUTIFUL.