Status update: Finding the courageous questions

Giving uncertainty the time it requires

Part 1 of an update on our progress through the frontier

It has been about ten weeks since we withdrew from business as usual, began reconnecting to the heart of the work we want to do and exploring for the forms it might take in the world. (You can read more about that on the home page of this site)

In response to requests, this is part one of an update on how have I have been spending my time. I can only speak from my point of view, and will leave it to Hannah to report on her own progress. 


Getting under it all to find the courageous questions: notes from David Whyte

Waking up one morning to find I had no client obligations created a tremendous sense of spaciousness. And at the same time, it created a feeling that a vast future is out there just over the next ridge, tapping its toes impatiently, waiting to see what I’m going to do. But both Hannah and I have been determined to avoid making choices out of a made-up sense of urgency or fear about the future, determined to allow our next steps to grow from the questions that really matter – the roots and soil questions, the ones under our feet, down where there are no words.

But I didn’t have language for those questions. I couldn’t articulate the questions I felt pressing so strongly against my days that I felt compelled to pause my work. How to find those questions?

I have been greatly helped by the words of people who have devoted themselves to just this sort of question. Chief among them for the last few years has been the poet David Whyte. Whyte has spent decades putting poetic and mythic tradition in conversation with the experiences and challenges of people working in companies and institutions, resulting in a deep well of material.

On top of work I’ve done with his material over the past few years, this summer I have spent long mornings with his writings and recordings. In order to really “eat” this material, I made transcriptions of his recordings, Solace: the Art of Asking the Beautiful Question, Life at the Frontier: Leadership Through Courageous Conversation, and A Great Invitation: the Path of Risk and Revelation (those are links to Amazon). Then in true strategic designer style, I did some clustering of the material to gather words around the repeating themes that were resonating so strongly with me.

Here are some headline themes.

The new story becomes the old story. What was once the new story can eventually become the old confining story. We often outgrow our story long before we become aware of how much it is constraining us. And so the old stories – the stories we’ve been repeating to ourselves about what’s important in life – become a kind of prison, from which we can’t see anything beyond the house we made for ourselves.

The old story is comforting. It is home. It is the story and identity that brought us to the point where we are in life, where we feel competent and known.

In defense of the comforting old story, we close ourselves. We can refuse to join the story that is coming to fruition all around us. “It’s an art form to not just let your mind wander defensively over things you already know about your world to make sure they are still in place.”

To find the new story, we must stop the old conversation. This involves halting the defensive repetition of the old story, opening to uncertainty. Before any sort of encounter with the future, this may involve a courageous articulation of exactly the way we feel trapped or exiled. We start a new conversation by stopping the one we are having now. “You’ll never get the conversation going if you don’t go out of the house.”

The first step is realizing how far you’ve been away from yourself. It’s almost as if you are reaching a healing hand to yourself. To say you understand what you’ve been through, instead of just coercively saying it’s time to move on now, get along the way, get over yourself, and all the rest. The first step is self-healing. And it’s an admittance of how much harm you’ve done to yourself.

David Whyte

The walk into the new consists of paying open attention. Moving out from our old home is a matter of opening our attention once again to life’s invitation. Allow ourselves to be found by the world. Open our long-closed eyes, allow a meeting between “what I think is me, and what I think is not me.” To shift ourselves from insisting on a life on solid ground, and step into life as a kind of current, a stream.

…Our willingness to pay attention is always a test of our friendship with the world. And as half the world is unknown, or becoming unknown as its moving away from us, it’s really a test of our friendship with that unknowing part of the world. The world you can’t label. The world you can’t name.

David Whyte

Attention is bound to identity; attention is transforming. The way we listen to the world, the way we look at the world, these shape our identity. “Where there’s no looking, there’s no real listening. There’s very little identity.” Attention is a form of transformation. Just by paying attention, just by listening, just by seeing, just by overhearing ourselves speak what we’ve seen and learned, we are transformed.

Attention leads to beautiful questions. One of the art forms in life is to be able to ask yourself more and more beautiful questions. To leave yourself alone – stop pestering yourself to fulfill the old story, to perform, to achieve, to do what you “should” – learn how to uncover yourself, learn how to hold a conversation that actually leads you somewhere inside yourself. To think about the world in a way which is good for you, and enlarging and revelatory.

  • What story am I telling myself at the moment? Which one am I insisting on too much?
  • What if my current story wasn’t true anymore?
  • What invitation could I create for the part of myself that I want to encourage into the world?
  • How much surface area to I have to meet anything other than myself?
  • Where is my contact point: on the surface where I’m just saying this or that, hello and goodbye, or is it deeper inside me in a part that needs more silence around it?
  • What am I in conversation with?
  • What kind of circle of friendship do I have?
  • What kind of invitation am I making to life?
  • Am I actually listening for any invitations that are being made to me?
  • What is knocking on my door? Where is the door?

The whole invitation is that you don’t do the willful work of transformation. There’s no way that that part of you is coercible in that way. You don’t do the work. You put yourself in conversations, you put yourself in edges between this and that. And you crack your heart just a little bit and let the wind get behind the door.

David Whyte

Yes. That is the purpose of this season of stepping back. I’m not interested in some kind of strategy workshop or brainstorming session. I want to get into the conversations that are big enough to be called “my work.”

And by the way, while I find these points and questions tremendously helpful in my personal reflections, they are also pointedly relevant to the story and future of Fit Associates, and profoundly relevant to every single student, team, and client I’ve ever worked with. There are clues here not only for someone who has paused to consider next steps, but for any organization or community who wants to deepen its creative conversation with the world. And that, I believe, is a clue about what my future work may be.

We put ourselves in conversations in which we’ll overhear ourselves speaking the revelation. We’re going to put ourselves in places where things occur. We’re going to hang out in the great singles bar of life, and make ourselves available for seduction by the great forces of the world.

David Whyte

Resting on the edge

By | 2017-06-28T18:44:05+00:00 August 24th, 2015|Categories: From this to that|4 Comments

About the Author:

Marc’s career spans 35 years in business, design, education and technology. His work as designer, researcher, and educator has put him on the frontier of applying design methods to social and strategic questions. He is a founding faculty member of the Masters in Design for Social Innovation program at the School of Visual Arts in New York, and Distinguished Adjunct Professor of Practice at the Carnegie Mellon University Graduate School of Design. Marc’s interests include cultural immersion, language, cooking and photography.


  1. Paul Borrero August 24, 2015 at 9:28 pm - Reply

    now THAT, is a good fight. A revolution.

  2. Mark Knobil August 24, 2015 at 10:29 pm - Reply

    We have to talk.
    It’s not about you …
    It’s about me. :-)

  3. Daniel Szuc September 11, 2015 at 2:45 am - Reply

    Lovely reading.

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