May 29, 2022 3 min read

David Whyte on the Set of Our Sail and the Shapes we Assume

David Whyte in his extraordinary book on life and careers, Crossing the Unknown Sea, talks about “the shapes we assume” and the “set of our sail” when it comes to our lives and work.

To awaken this inner artist, we must assume a certain shape that puts us in conversation with the elements; we must cultivate a kind of faith in the moving energies around us and the way they to come to our aid, give us lift, no matter our circumstances or difficulties.

Almost like a sail conversing with the wind, every sail will respond differently to the elements according to its shape and the vessel it propels. And the response of the sail, with a steady hand at the tiller, creates movement and direction.

As an individual, you simply need to present some surface area to life. In Woody Allen’s words: Just show up; then it is only a question of direction.

– David Whyte in Crossing the Unknown Sea

His words prompt some deep questions worth asking ourselves about our lives and work.

How is the set of our sail?

Is it helping or hindering in what we have set out to do?

What kind of shape are we assuming?

Are we expanding or contracting in the world? Are we buoying or drowning? Are we putting ourselves in a shape of possibility or in a shape of resignation? Is our shape open to receive or is it closed off? Are we looking to explore or are we playing defense? The very shape of our sail influences how we catch the wind and how much we catch.

How much surface area are we presenting to the world?

Are we emboldened and enlarged to face whatever the world throws our way, or are we cowering in fear and trepidation from the uncertainty?

Do we have any surface area we are presenting to the world?

Or have we hidden and buried those deep passions and projects that we always wanted to do but never ventured out? That big ambitious project that we have been delaying — what is the simplest thing we can do so we are “presenting some surface area to life”? If we are not willing to do even that, maybe that project is not important enough to us?

How are we “showing up”?

How do we show up for all the opportunities already in front of us? Or did we count them out without giving due attention by falling into habitual thinking patterns?

Is our sail ready to capture?

Are we ready for what the world might send our way or are we frittering away possibility? Is it setup to catch the prevailing winds or do we feel like we are going against the wind? Did you know that you can sail faster in a strong opposing wind than a weak trailing wind?

Is our sail even deployed?

Too often we become so resigned in our lot that we don’t realize that we have built over a lifetime a very effective sail but have not deployed it yet. These could be the transferable skills in our current work, the network we've built, the support of loved ones, or the more mundane but relevant aspects like savings.

It's easier in our busy, hectic lives to put our heads down and just keep going. However, every once in a while, it helps to step back and ponder over deep questions like these.

If asked from a place of genuine wonderment and enquiry, you might be surprised with the answers that can emerge.

In closing, here’s another wonderful passage from Whyte:

Once we begin to engage those elemental edges through daily courageous speech, we start to build a living picture of our own nature, exactly the same way a captain gets to know her vessel and the particular way it reacts to the elements that surround it.

As captain of our soul’s journey, we feel the angle of the sails, the creak and strain of the ropes, the lean of the tiller, and learn the particular hum and song of our conversation with the elements. It is this conversation that gives us not only our powers of survival but a music of exhilaration for our journey and arrival.

– David Whyte in Crossing the Unknown Sea

Is our journey an exhilarating one or the opposite? What are we going to do different?

Liked this post? Trymy newsletter. It's free and every edition covers essential frameworks on leadership, careers, and organizations in bite-sized form.📚 HBR 100 Best Reads: You also get a curated spreadsheet of the best articles Harvard Business Review has ever published. Spans 70 years, comes complete with categories and short summaries.

Sheril Mathews
I am an executive/leadership coach. Before LS, I worked for 20 years in corporate America in various technical & leadership roles. Have feedback? You can reach me at
Great! You’ve successfully signed up.
Welcome back! You've successfully signed in.
You've successfully subscribed to Leading Sapiens.
Your link has expired.
Success! Check your email for magic link to sign-in.
Success! Your billing info has been updated.
Your billing was not updated.