Ivy Sea Online: Navigating the entrepreneurial "dark night"

Sooner or later, it happens to everyone — the proverbial "dark night of the soul". Though, while all (or most) are called, few elect to take up the call and reap the wisdom therein. At its heart, the "dark night" has traditionally been seen as a call for us to take a quantum leap in spiritual growth, authenticity, and potential.

Distinct from the inevitable daily challenges of entrepreneurship, and different from the mental-health condition of clinical depression, the entrepreneurial "dark night" arrives with a seemingly brutal and all-encompassing effect that seems to deteriorate confidence and directional-surety with a swift blow, and block old pathways and trusted sources of light and guidance.

The "dark night" seems to rip asunder much or all we've taken for granted, whether that means accolades, relationships, attachments, accounts, revenues, net worth, connections — all of the things we hang our sense of worth on are challenged by the "dark night." It makes us question whether it's possible to do what we are attempting, and whether we're even up to the challenge of fulfilling our vision that once lit our way and energized us to our core. It may even seem (or it might be true) that everything is teetering on the brink of complete disintegration.

When the "dark night" arrives, as it will once — or possibly several times — during the entrepreneurial journey experience, it gives us new insight into the line of the 23rd Psalm that states "Yea, though I walk through the valley of darkness…". But in the thickest parts of that darkened path, we do fear, we do doubt, we do feel lost and unsure. And we haven't yet found or seen that light that will lead us out of the valley. We're there, vulnerable, in the darkness of unknowing.

For entrepreneurs, who are often by our nature optimistic, visionary, motivated, action-oriented, creative, problem-solving, and relatively confident (at least enough to take the leap and make the attempt), the "dark night" can be quite the change of perspective, pace, and experience.

After all, what makes it a "dark night" is that things are beyond our control, beyond our ability to "do something about them," beyond our ability to understand or even see our way out of the darkness.

What is there to do, then — to whom or what can you turn — during the "dark night", when one of the most fearsome traits of its darkness is not knowing? How do we accept the invitation to "desire truth in the inward being" and "find the wisdom of the inner heart," as Psalm 51.6 suggests?

Understanding and navigating the dark night

The "dark night" must be experienced, just as we must experience night before the arrival of day, or winter before the warmth and new growth of spring. It must be looked at, because it is a bringer of wisdom, insight, authenticity, and truthfulness. If we have the courage to look into the dark night, and the fortitude to navigate and journey it, it can lead us to an unveiling of greater understanding and insight.

Among other things, we can always find comfort and wisdom from those who've walked what Irish vision-poet Fiona MacLeod called "the dark and starless road."

The phrase "dark night of the soul" originated with 16th century mystic, San Juan de la Cruz, more commonly known, perhaps, as St. John of the Cross. A supporter and protégé of the maverick, deeply faithful Christian mystic Teresa of Avila, Father John was imprisoned by the Inquisition and tortured, as were all who questioned and threatened doctrine or who experienced or spoke of true faith, true Jesus teachings, true love for the Divine.

St. Juan de la Cruz escaped his torturers, and found welcome and safety among St. Teresa's nuns. He wrote a poem about his dark night of the soul, and his re-emergence into Light, and the Sisters of the order asked him for wisdom teachings so that they might use the poem and his insight for their own spiritual practice.

He had spoken the experience of many who had come before him, many who were his contemporaries traveling the darkened path, and many who would come after him.

Aside from the direct honesty with which it arrives, the "dark night" has a habit of calling into question all that might be false, and shaking to the core all that might be Ego-oriented rather than rooted in the authenticity of heart and soul.

The "dark night" calls for nothing less than complete and utter surrender into a state of true faithfulness. Whether we consider ourselves religious or not is incidental.

From the dark night into daylight

We usually have to keep up with the day to day requirements of our business, but there is also a call to look more deeply, to challenge our assumptions about what we're in business for and how we do business and what business we do.

As is the case with the Chinese character that means both "crisis" and "opportunity," the "dark night" is an opportunity for us to get clear about what really matters, to get clean about what's really authentic. And from that place, a truly powerful cycle of entrepreneurship can emerge — one that feels heart-felt and right to us, and one that's all the more distinguished and of service because of its truthfulness.

Two things are crucial for entrepreneurs experiencing the "dark night": The first is allowing "down time" or open space for meditation, prayer, reflection, reading that nourishes the soul and catalyzes insight. The "dark night" can't be navigated by the action or "busy work" that is tolerated by day.

And second, the entrepreneur in the "dark night" needs to reach out for support from people who've been there, who can offer insight, who can listen deeply, who can reflect back key questions, and who can just be compassionate and empathetic witnesses to another's walk through the dark night. Just as journeying into deep wilderness might require a guide to help us navigate unfamiliar and seemingly unfriendly terrain, so does a "dark night of the soul."

Guides might include other entrepreneurs who've navigated the "dark night" and lived to tell about it (no doubt the wiser for it), or true spiritual guides or teachers (which differs from religious guides, though some religious guides might also be a spiritual guide, not all are). Guides might be found in person, online, or via books they've written. Maybe all three. Some dark-night navigators may feel depressed, and also elect to find a trusted and skillful therapist for additional support and guidance.

Though we live in a culture that has forgotten the blessings hidden in the dark night, much less how to navigate the dark night with wisdom and courage, the blessings are real and other courageous navigators have made their wisdom available to those who seek it. What we've forgotten can be recalled. There is light on the other side of the "valley of darkness," just as surely as day follows night.

* Reference to Psalm 51:6 is from the book Celtic Benediction: Morning and Night Prayer, by J. Philip Newell.

Why wait to reconnect with your vision and act upon these and other "conscious, big-vision entrepreneur" tips? Contact us at Ivy Sea for a telephone-consultation or "tailored to you" E/Tele-Workshop to focus in on your strengths and opportunities. Find out more about your Ivy Sea "E-and-Tel" Consultation.