Emails to a Young Entrepreneur: Joining the Entrepreneurial Pilgrimage

Day 136 of Self Quarantine             Covid 19 Deaths in U.S.:  149,000

Joining the Entrepreneurial Pilgrimage

Like the discussion with the young entrepreneurs at Duke’s InCube, all of us who become entrepreneurs are joining the long tradition of the entrepreneurial pilgrimage. A key part of a pilgrimage is seeing the world with new eyes. Keri Smith in her wonderfully eclectic How to be an Explorer of the World lays out our path:

As I reflect on the emails that I’ve exchanged with thousands of Mikhails and graduate students, I am reminded of David Whyte’s book of poetry Pilgrim:

“In his seventh volume of poetry, David Whyte looks at the great questions of human life through the eyes of the pilgrim: someone passing through relatively quickly, someone dependent on friendship, hospitality and help from friends and strangers alike, someone for whom the nature of the destination changes step by step as it approaches, and someone who is subject to the vagaries of wind and weather along the way.”


The way forward, the way between things,
the way already walked before you,
the path disappearing and re-appearing even
as the ground gave way beneath you,
the grief apparent only in the moment
of forgetting, then the river, the mountain,
the lifting song of the Sky Lark inviting
you over the rain filled pass when your legs
had given up, and after,
it would be dark and the half-lit villages
in evening light; other people’s homes
glimpsed through lighted windows
and inside, other people’s lives; your own home
you had left crowding your memory
as you looked to see a child playing
or a mother moving from one side of a room to another, your eyes wet
with the keen cold of Navarre.

But your loss brought you here to walk
under one name and one name only,
and to find the guise under which all loss can live;
remember, you were given that name every day
along the way, remember, you were greeted as such,
and you needed no other name, other people
seemed to know you even before you gave up
being a shadow on the road and came into the light,
even before you sat down with them,
broke bread and drank wine,
wiped the wind-tears from your eyes:
pilgrim they called you again. Pilgrim.

I was reminded of the connection between “Camino” and the effectual entrepreneuring path when I encountered Ann Patchett’s What Now? at my favorite brain candy blog “Brain Pickings.

“Echoing Steve Jobs, who in his own fantastic commencement address famously cautioned that “you can’t connect the dots looking forward; you can only connect them looking backwards,” Patchett urges these new graduates to be sure to return at some point – this, she argues, would let them reflect on the series of small choices which, as William James put it a century ago, “[spin] our own fates, good or evil, and never to be undone.” Patchett writes:

“Coming back is the thing that enables you to see how all the dots in your life are connected, how one decision leads you to another, how one twist of fate, good or bad, brings you to a door that later takes you to another door, which aided by several detours – long hallways and unforeseen stairwells – eventually puts you in the place you are now. Every choice lays down a trail of bread crumbs, so that when you look behind you there appears to be a very clear path that points straight to the place where you now stand. But when you look ahead there isn’t a bread crumb in sight – there are just a few shrubs, a bunch of trees, a handful of skittish woodland creatures. You glance from left to right and find no indication of which way you’re supposed to go. And so you stand there, sniffing at the wind, looking for directional clues in the growth patterns of moss, and you think, What now?”

Ann Patchett continues to explore What Now?:

“Nothing at all is very much out of fashion these days, as are stillness, silence, and studied consideration. Studied consideration is hard to come by with those little iPod buds stuffed in your ears and the cell phone competing with the Internet. Perhaps we avoid the quiet because we’re afraid that the answer to What now? will turn out to be I don’t know.

“It took me a long time of pulling racks of scorching hot glasses out of the dishwasher, the clouds of steam smoothing everything around me into a perfect field of gray, to understand that writing a novel and living a life are very much the same thing. The secret is finding the balance between going out to get what you want and being open to the thing that actually winds up coming your way.

“There’s a time in our lives when we all crave the answers. It seems terrifying not to know what’s coming next. But there is another time, a better time, when we see our lives as a series of choices, and What now? represents our excitement and our future, the very vitality of life. It’s up to you to choose a life that will keep expanding. It takes discipline to remain curious; it takes work to be open to the world—but oh my friends, what noble and glorious work it is.”

Many moons ago I encountered Paulo Coehlo’s Pilgrimage: A Contemporary Quest for Ancient Wisdom. The novel describes a journey on the Camino in Spain.  I inhaled this book as I realized it was the backstory behind Cursillo.  Majorcan priests created the Cursillo three day process because they were not able to walk the Camino with the young men from their villages during the war years of World War II.

The very start of the book captured me:

“’AND NOW, BEFORE THE SACRED COUNTENANCE OF RAM, you must touch with your hands the Word of Life and acquire such power as you need to become a witness to that Word throughout the world.’

“The Master raised high my new sword, still sheathed in its scabbard. The flames of the bonfire crackled—a good omen, indicating that the ritual should continue. I knelt and, with my bare hands, began to dig into the earth.

“It was the night of January 2, 1986, and we were in Itatiaia, high on one of the peaks in the Serra do Mar, close to the formation known as the Agulhas Negras (Black Needles) in Brazil. My Master and I were accompanied by my wife, one of my disciples, a local guide, and a representative of the great fraternity that is comprised of esoteric orders from all over the world—the fraternity known as “the Tradition.” The five of us—and the guide, who had been told what was to happen—were participating in my ordination as a Master of the Order of RAM.

“I finished digging a smooth, elongated hole in the dirt. With great solemnity, I placed my hands on the earth and spoke the ritual words. My wife drew near and handed me the sword I had used for more than ten years; it had been a great help to me during hundreds of magical operations. I placed it in the hole I had dug, covered it with dirt, and smoothed the surface. As I did so, I thought of the many tests I had endured, of all I had learned, and of the strange phenomena I had been able to invoke simply because I had had that ancient and friendly sword with me. Now it was to be devoured by the earth, the iron of its blade and the wood of its hilt returning to nourish the source from which its power had come.

“The Master approached me and placed my new sword on the earth that now covered the grave of my ancient one. All of us spread our arms wide, and the Master, invoking his power, created a strange light that surrounded us; it did not illuminate, but it was clearly visible, and it caused the figures of those who were there to take on a color that was different from the yellowish tinge cast by the fire. Then, drawing his own sword, he touched it to my shoulders and my forehead as he said, “By the power and the love of RAM, I anoint you Master and Knight of the Order, now and for all the days of your life. R for rigor, A for adoration, and M for mercy; R for regnum, A for agnus, and M for mundi. Let not your sword remain for long in its scabbard, lest it rust. And when you draw your sword, it must never be replaced without having performed an act of goodness, opened a new path, or tasted the blood of an enemy.”

“With the point of his sword, he lightly cut my forehead. From then on, I was no longer required to remain silent. No longer did I have to hide my capabilities nor maintain secrecy regarding the marvels I had learned to accomplish on the road of the Tradition. From that moment on, I was a Magus.

“I reached out to take my new sword of indestructible steel and wood, with its black and red hilt and black scabbard. But as my hands touched the scabbard and as I prepared to pick it up, the Master came forward and stepped on my fingers with all his might. I screamed and let go of the sword.

“I looked at him, astonished. The strange light had disappeared, and his face had taken on a phantasmagoric appearance, heightened by the flames of the bonfire.

“He returned my gaze coldly, called to my wife, and gave her the sword, speaking a few words that I could not hear. Turning to me, he said, “Take away your hand; it had deceived you. The road of the Tradition is not for the chosen few. It is everyone’s road. And the power that you think you have is worthless, because it is a power that is shared by all. You should have refused the sword. If you had done so, it would have been given to you, because you would have shown that your heart was pure. But just as I feared, at the supreme moment you stumbled and fell. Because of your avidity, you will now have to seek again for your sword. And because of your pride, you will have to seek it among simple people. Because of your fascination with miracles, you will have to struggle to recapture what was about to be given to you so generously.”

“The world seemed to fall away from me. I knelt there unable to think about anything. Once I had returned my old sword to the earth, I could not retrieve it. And since the new one had not been given to me, I now had to begin my quest for it all over again, powerless and defenseless. On the day of my Celestial Ordination, my Master’s violence had brought me back to earth.”

The Pilgrimage continues with the author’s search for his sword along the Camino with Petrus, his new mentor. The author’s journey is one of overcoming obstacle after obstacle set before him by Petrus to provide the transformation so sought after.  Near the end of the book, the story reaches a climax as the protagonist finally transforms his yearning:

“I awoke feeling more optimistic and took to the Road early.  According to my calculations, that afternoon I would reach Galicia, the region where Santiago de Compestela was located.  It was all uphill, and I had to exert myself for almost four hours to keep to the pace I had set for myself.  Every time I reached the crest of a hill I hoped that it would mark the point of descent.  But this never seemed to happen, and I had to give up any hope of moving along more rapidly.  In the distance I could see mountains that were even higher, and I realized that sooner or later I was going to have to cross them.  My physical exertions, meanwhile, had made it impossible to think much, and I began to feel more friendly toward myself.

“Come on now, after all, how can you take seriously anyone who leaves everything behind to look for a sword?” I asked myself.  What would it really mean to my life if I couldn’t find it?  I had learned the RAM practices, I had gotten to know my messenger, fought with the dog, and seen my death, I told myself, trying to convince myself that the Road to Santiago was what was important to me.  The sword was only an outcome.  I would like to find it, but I would like even more to know what to do with it.  Because I would have to use it in some practical way, just as I used the exercises Petrus had taught me.

“I stopped short.  The thought that up until then had been only nascent exploded into clarity.  Everything became clear, and a tide of agape washed over me.  I wished with all my heart that Petrus were there so that I could tell him what he had been waiting to hear from me.  It was the only thing that he had really wanted me to understand, the crowning accomplishment of all the hours he had devoted to teaching me as we walked the Strange Road to Santiago: it was the secret of my sword!

“And the secret of my sword, like the secret of any conquest we make in our lives, was the simplest thing in the world: it was what I should do with the sword.

“I had never thought in these terms.  Throughout our time on the Strange Road to Santiago, the only thing I had wanted to know was where it was hidden.  I had never asked myself why I wanted to find it or what I needed it for.  All of my efforts had been bent on reward; I had not understood that when we want something, we have to have a clear purpose in mind for the thing that we want.  The only reason for seeking a reward is to know what to do with that reward.  And this was the secret of my sword.”

In The Alchemist, Coehlo discusses the obstacles to obtaining the courage to reach our own dream:

“All I know is that, like Santiago the shepherd boy, we all need to be aware of our personal calling. What is a personal calling? It is God’s blessing, it is the path that God chose for you here on Earth. Whenever we do something that fills us with enthusiasm, we are following our legend. However, we don’t all have the courage to confront our own dream.


“There are four obstacles. First: we are told from childhood onward that everything we want to do is impossible. We grow up with this idea, and as the years accumulate, so too do the layers of prejudice, fear, and guilt. There comes a time when our personal calling is so deeply buried in our soul as to be invisible. But it’s still there.

“If we have the courage to disinter dream, we are then faced by the second obstacle: love. We know what we want to do, but are afraid of hurting those around us by abandoning everything in order to pursue our dream. We do not realize that love is just a further impetus, not something that will prevent us going forward. We do not realize that those who genuinely wish us well want us to be happy and are prepared to accompany us on that journey.

“Once we have accepted that love is a stimulus, we come up against the third obstacle: fear of the defeats we will meet on the path. We who fight for our dream, suffer far more when it doesn’t work out, because we cannot fall back on the old excuse: “Oh, well, I didn’t really want it anyway.” We do want it and know that we have staked everything on it and that the path of the personal calling is no easier than any other path, except that our whole heart is in this journey. Then, we warriors of light must be prepared to have patience in difficult times and to know that the Universe is conspiring in our favor, even though we may not understand how.”

Coelho, Paulo (2009-10-13). The Alchemist – 10th Anniversary Edition. Harper Collins, Inc.

One of my favorite quotes that sheds light on the process of lifelong learning comes from Carlos Casteneda:

Overcoming Life’s Fears

“When a man starts to learn, he is never clear about his objectives.  His purpose is faulty; his intent is vague.  He hopes for rewards that will never materialize for he knows nothing of the hardships of learning.

“He slowly begins to learn – bit by bit at first, then in big chunks.  And his thoughts soon clash.  What he learns is never what he pictured, or imagined, and so he begins to be afraid.  Learning is never what one expects.  Every step of learning is a new task, and the fear the man is experiencing begins to mount mercilessly, unyieldingly.  His purpose becomes a battlefield.

“And thus he has stumbled upon the first of his natural enemies:  Fear!

“And thus he has encountered his second enemy:  Clarity!  That clarity of mind, which is so hard to obtain dispels fear, but also blinds.

“But he has also come across his third enemy: Power!  Power is the strongest of all enemies.  And naturally the easiest thing to do is to give in; after all, the man is truly invincible.  He commands; he begins by taking calculated risks, and ends in making rules, because he is a master.

“The man will be, by then, at the end of his journey of learning, and almost without warning he will come upon the last of his enemies: Old Age!  This enemy is the cruelest of all, the one he won’t be able to defeat completely, but only fight away.”

– Carlos Casteneda, The Teachings of Don Juan: A Yaqui Way of Knowledge, p. 83-87.

As you finish your journey through Emails to a Young Entrepreneur, David Whyte helps us finish the entrepreneurial pilgrimage:


The road in the end taking the path the sun had taken,
into the western sea, and the moon rising behind you
as you stood where ground turned to ocean: no way
to your future now but the way your shadow could take,
walking before you across water, going where shadows go,
no way to make sense of a world that wouldn’t let you pass
except to call an end to the way you had come,
to take out each frayed letter you brought
and light their illumined corners, and to read
them as they drifted through the western light;
to empty your bags; to sort this and to leave that;
to promise what you needed to promise all along,
and to abandon the shoes that had brought you here
right at the water’s edge, not because you had given up
but because now, you would find a different way to tread,
and because, through it all, part of you could still walk on,
no matter how, over the waves.

– David Whyte

Camino de Finisterre


You can find a PDF of the full Preface, Forward, and Chapters 1 – 10 here.

You can find the introduction to the Cosmos of the New Venture here.

This entry was posted in Content with Context, Emails to a Young Entrepreneur, Entrepreneuring, Flipped Perspective, Learning. Bookmark the permalink.

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