Reflecting on the Bittersweet

Although the self-reflection so integral to leadership development may be one of the worthiest endeavours we will ever undertake, it is not a simple journey. As leaders and coaches, we cannot grow in others what we have not first explored in ourselves. Examining what lies at the core, pulling back the curtain on our shadow selves and removing the bindings that tie us to our own limitations is a bittersweet endeavour. How might delving into this contradiction help us to evolve truer iterations of ourselves?

In her recent book Bittersweet: How Sorrow and Longing Make Us Whole, author and thought leader Susan Cain explores this term describing that which is both painful and pleasurable, an overlapping paradox of joy and sorrow.


As an emotional space, bittersweet assures us that we have the capacity to hold complexity. It is liminal and beguiling, resonant with the tension between extremes.


It may be that the moments we spend in the bittersweet are the ones in which we are most fully human. In savouring the bittersweet, we are aware of our impermanence and recognize the beauty in what is fleeting.

True to the contradictory nature of its name, the bittersweet plant (solanum dulcamara) has the capacity to harm or heal. While the leaves and berries are poisonous, the stem has been used as medicine. In 1908, folklorist Clara Kern Bayliss wrote that bittersweet nightshade was once thought to protect against evil magic.

For full potency, it had to be gathered in silence.

“Character, like a photograph, develops in darkness.”
• Yousaf Karsh

In 2021, a woman in a Montreal hospital posted a heartfelt tweet.

“Today Is the day I tell my son that I’m dying from cancer. It’s reached a point where he has to hear it from me. Let all my tears flow now so that I can be brave this afternoon. Let me howl with grief now so that I can comfort him.” Dr. Nadia Chaudri wrote.

The tweet went viral. As Chaudri continued to chronicle her experience with ovarian cancer and bidding goodbye to her “Sun and Moon,” she unexpectedly amassed a following of 146,000 Twitter followers. In her final days, she took advantage of her newfound celebrity to raise half a million dollars toward minority student fellowships.

We are drawn to bittersweet stories like this one, which transcend simple definitions and honour the space between one reality and the next.


“Ring the bells which can still ring
Forget your perfect offering
There is a crack in everything
That’s how the light gets in.

Leonard Cohen

In an interview on The Tim Ferriss Show, Susan Cain elaborates on the meaning behind Canadian poet Leonard Cohen’s famous words. His reflection on brokenness and beauty draws on an idea from the mystical side of Judaism, suggesting that all of creation was once a single vessel of divine light. We now live in a world where shattered slivers of that vessel are buried all around us, hidden treasure waiting to be revealed.

We ourselves are both broken and beautiful.

In the days of the ancient philosophers, Plato’s Symposium floated the idea that humans were once extraordinary creatures with two faces, four arms and four limbs. When they grew arrogant and tried to confront the gods, Zeus grew angry and split them in two. Since then, our yearning has compelled us to search for the missing half of our full selves in the hope of reconciliation.

To take it a step further – perhaps that missing half is not embodied in another person, but lies in our shadow selves.


“We need only to think of the people whom we judge or dislike or against whom we hold secret prejudices to find ourselves in the grip of our [own] darker nature.”
• Zweig and Abrams


A bittersweet exploration of our full selves moves us away from simplification and dichotomy to ask the Buddhist question – who knows what is good or bad?

We are not creatures of pure light or darkness, but something in between. We cast a shadow.

Your shadow hides in those parts of yourself that you reject. It is reflected in what you disparage. Look again at something or someone you loathe, and you will find your shadow loitering there.

Yet any quality which we may name as weakness – from pride and anger to meekness and fear – has a purpose and a place in the right context. We all contain these qualities, and choose how to focus them.

While it is easier to deny a difficult truth than to look it in the eye, suppressing parts of ourselves takes tremendous energy. In becoming aware of and acknowledging our shadow, we see ourselves in all of our complexity.

Just like the bittersweet plant, shadow qualities have the potential to help or hinder us. Accepting the shadow is a bittersweet reconciliation.


“The identification of a hidden superpower that our culture doesn’t normally talk about …. the superpower of being in touch with the simultaneous joy and sorrow of life – I believe it’s one of the deepest superpowers we have.”
• Susan Cain


Containing contradictions, bittersweet invites us to move beyond either/or limitations. In exploring the richer both/and concept, we stretch ourselves to hold nuance, shades of gray and contradictory truths. Moving beyond limiting assumptions supports us to create a change mindset capable of leading powerful transformation.

The journey of self-reflection is a vertical development which will arouse your curiosity, stretch your abilities, challenge and provoke.

Exploring the bittersweet has a messy, magnetic quality to it – the adult equivalent of wiggling a loose tooth. Bittersweet enfolds us at milestone moments as we look back at where we have been and advance to the next stage. It is there in the threshold of transitions, as we close one door and open another. It resides in  familiar rituals reminding us of those who are no longer with us.


“For each of us, there comes a time when we must awaken and become what we were born to become.”
• Seth Adam Smith


Bittersweet recognizes the release of what we once were, as we step more fully into who we are capable of being.

In our fascination with bittersweet lies a full acceptance of life as it is – a betwixt and between space containing intersecting realities. Developing the capacity to appreciate the bittersweet expands our ability to lead through complexity and multiple truths. As we dance with the bittersweet, we play at the edges where ambiguity lives.

WRITTEN BY: Kerry Woodcock, who as director of Novalda develops core, collective and change leadership capacity in leaders, teams and organizations,, andJillian Millar Drysdale, a professional communicator who delights in making important ideas accessible.

Question | Do you savour the bittersweet?

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