Break the Trance of Leaderly Leadership

Who is a leader and who is a follower is becoming less and less clear, and, frankly, less and less relevant.

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My friend Nate battled cancer last year. After an abrupt diagnosis and surgery, he and his wife moved to New York City and stayed with my family during the chemo and radiation treatment. 

Nate is a leader at Community Solutions, a national non-profit organization, untangling the knot of homelessness. They have been working patiently, deftly, and joyfully, making historical progress.

He set up his office desk at our dining table, and I delighted in cooking dinners while eavesdropping on his work conversations.

During these phone calls, for the most part, he was curiously silent. He asked heartfelt questions. He re-organized conversations around what's important and unknown, and bookended each one with playfulness and care. 

 I asked him when and how he had learned to hold space like that. 

"I remember the day when I faced the decision of my career," he said, after some reflection. "I had learned the leadership ropes and had produced decent results. Then, I had to choose." 

I was all ears.

He said: "Am I going to move forward as my role? Or am I going to move forward as myself?"

One Sure Way to Move Your Career Forward

If you are in the middle of your career, you have probably come across books, workshops, and coaching programs exalting the character and skills of a great leader.

Great leaders craft a compelling vision, make difficult decisions, provide straight answers, and get others to band together and follow. They always know where they are going and how to get there. The research is clear, we are falling for this kind of leaders. And, oh, we also want our leaders to be male and tall. 

Research also shows that such charismatic leaders are more likely to leave their organizations in shambles, and that powerful leaders can go powerfully wrong.

We now see such leadership as a stereotype we want to leave behind. But we don't leave it behind. We still want it. Most people do. This is all to say that if you learn to be a leaderly leader, you are more likely to get promoted, groomed, and advanced in an organization. 

So, that's one option. Focus on practicing your leader's persona the way your particular system imagines it. If you stay with it, your career will likely advance forward and upward. 

There is another option. You begin to direct your attention to your own inner life, the lives of those around you, and the systems to which you belong. Here, you apprentice yourself to the unknown, learn like mad, and see where it takes you and who you will become.

What would that look like? 

Apprentice Yourself to Your Life

Years ago, after working in the non-profit world, I plunged into the unknown of the corporate world. That's where I could make money while making an impact in the world.

I bought three suits. One dark blue that those healthy and brilliantly happy corporate people on stock photos wore. Two gray suits to match my silver hair and give me an aura of experience. I got new ties, shoes, and a briefcase. I looked authoritative yet approachable, grand yet humble. Spot on.

I learned to speak in corporate-isms. What is the mission-critical task here, I would ask. Who are the stakeholders that we need to keep in mind, I would ask. What difference could the practice of mindfulness make here, I would ask. Asking was good. It allowed me to conceal my impostor syndrome while giving me time to find my sea legs and come up for air. 

Every week, I read one leadership book. Every month, I went to a conference where members of the human species who bear an executive presence could be found in groups.

Alone, in hotel rooms, I would replenish myself with poetry. Back at home, I would resurrect myself in my all-day kitchen retreats. 

After four years of navigating the angular world of hallways, spreadsheets, and org charts, I made a discovery. Right there, in the middle of the metal, glass, and free food--invisible to casual (or cynical) observers--were people who had apprenticed themselves to the mystery within and around them. 

They care and work for justice, relate their lives to earth, act with kindness, and seek beauty. They are giving it all joyfully, sacrificially, and systematically. And as their career progresses, they actually look forward to their final act and the art of their own disappearance.

Do you see them? No? Look again.

There is a conspiracy going on.

Make Yourself Findable

They have to dress for the role, shake hands and smile, and put on a persona of confidence at times. They have to move through their complex world, forgiving others, themselves, and God or life. Instead of following the map, their heart is wayfinding through the unknown. And growing.

Sometimes, they find themselves lonely. Sometimes they hunger for open conversations about mystical experiences and practices. Sometimes their tired ordinary selves need someone to genuinely delight in them, to appreciate what it takes for an adult to have gotten to the place they are now.

That's the price for being courageously human. If you decide to pivot like this in your mid-career, that’s the price you will pay.

You might already have questions that are summoning you. When the noise of leadership talk quiets down, you may be asking yourself, “Am I enough? Can I trust myself?” This is hard.

Fortunately, there are people like Nate everywhere. I found him, he found me, we will find you. When you choose to lead as yourself, you make yourself visible. And therefore findable.

When you choose to follow the prescribed leaderly path, you live someone else’s life. And there is no you to be found.

More Human, Fewer Things Better

At this threshold, you are almost certainly trapped in the nervous system that made you successful up to here. I say trapped, because the very qualities that have led you to your current success are now your liability.

You look for problems to solve (instead of possibilities to explore). You look for certainties to protect you (instead of trust to free you). You look for explanations to fortify you (instead of experiences to transform you). The list goes on.

Instead of helping you on your way, the books, the conferences, the best practices, the life hacks are now actually in your way.

Which brings us to what seems to be the key question for leadership development in our volatile, uncertain, complex, and ambiguous times: "How can I prepare for something that does not yet exist?" 

We don't know the answer to that question. Yet. But we do know something important. Whatever comes next will involve a new kind of radical simplicity.

Jonathan Fields put it helpfully in one of his newsletters: “More human. Fewer things better.” That’s a great start.

What are, for you, those more human and fewer things that people like Nate value and practice?

You are already on your way because these values and practices are already part of your life.


 You might be part of a mastermind group or have a mentoring relationship. You might be practicing being present or learning storytelling. You might be turning to experiential retreats and coaching, or checking out TED Talks and attending conferences. Why do you do any of that? 

Is it about helping a cause, running a thriving business, launching a disruptive startup, serving your online followers, running for office, developing yourself, balancing your personal life, or raising your children?  

I bet it is about love. 

Love—anyone or anything—and you will have to take the lead at an appointed moment.  

You might love money. There is no shame here. We all have mortgages, cancers, and dreams to pay for. You might love having an influence. If you are human, it's likely you want to have control. You might be in love with freedom. You might love friends, music, sex, or earth. You might love God, gods, or dogs. It doesn't matter. If you love well, sooner or later, your love will ask you to lead. 

Leadership is a love story.  


Without faith in the future, you have no business leading. It is that simple, and you know it.

What I mean is that you already have your particular way of having faith in the future. You don't know what is about to occur the next day or the next eon, but you have developed a relationship with what you don’t know.

A story from the Jewish mystical tradition says that God is sparing humanity because, at any given time, twelve people in the world are so good, God cannot make herself end it. And—here is the kicker—we can never know who these twelve people are. They are hiding in plain sight.

That's what goes on in every corporation, every non-profit organization, every political party, and every nation. Goodness. Everywhere. 

You cannot be sure of this, of course. You cannot know. But can you believe it? And live it?

I love this passage from Simple Habits for Complex Times, by Jennifer Garvey Berger and Kieth Johnston:

"Organizations need to stop pretending they're working toward some kind of unified plan of what the future will look like (we are continually amazed at how many people know this is pretense and yet don't talk about how the emperor is naked). They need to admit that they don't actually know exactly what the future will look like but that they are going to try like mad to influence the uncertain future anyway."

Leaders of the future don't know the future. They have faith in the future. And paradoxically, faith in the future is a form of creating the future. Creating, the highest expression of leadership, is impossible to do without it.

You will get lost at times, that's for sure. But your faith will find you.

It will feel like you are free-falling at times. But who you are becoming will catch you.


That’s all that you need.

Put a finger on your wrist or your palm to your chest. Can you sense life pulsing through you?

Now, close your eyes and think of yourself being dead and buried. People are walking from the cemetery to the potluck afterward. They are going to eat potato salad there. Can you sense the life that you have now, moving through the people who will be around after you are gone?

Drop the struggle. This whole thing is not about you.

Whether you are a CEO in the center of a company or an employee on the far edge of the very same company, you both have the task of learning to lead one another. Manufacturer and supplier. Seller and customer. Professor and student. Politician and citizen. One type of artist and another type of artist. General and soldier. Parent and child.  

The era of heroics and "great-men" approaches to leadership are waning.

We are like a flock of geese flying or a herd of wild horses running together towards a shared horizon. Each one is hearing a call of what they love and responding where and when needed. You, in your own way and in your own time, I in mine, each of us as inimitable participants in something greater than ourselves.


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Who is a leader and who is a follower is becoming less and less clear, and, frankly, less and less relevant. To lead is now human.

Leading has become like listening. We are all asked to do it, everyone is capable of doing it, and everyone can learn to do it better. 

You are about to let go of something. You are about to step into the unknown. There is magic in the middle.


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