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Dealing With Despair in Day-to-Day Leadership Life

a sepia-toned photo of a rose with a bent, broken stem

Befriending the occasional dark reality that can open creative doors

Intellectually, I knew it was likely to happen. And still, I was emotionally caught off guard. My morning had gone great—teaching about ecosystems at ZingTrain’s ZingPosium. Then, later that afternoon I looked at the news. My stomach sank. My spirits went into the tank. If you’re reading this, it’s likely you know the feeling. It’s called despair. Unlike joy or sadness, it’s not a feeling I experience regularly, but in my efforts over the years to embrace and honor the full, meaningful, range of my emotions, I’ve come to accept that despair does show up in my life here and there. Two weeks ago, it hit me hard.

What triggered my emotional downturn were the four days of significant Supreme Court decisions that were released at the end of last month. As someone wrote in the wake of the news, the announcements were not really surprising, but were still shocking. I’m not suggesting that those days need to have been dark for everyone. Politics and policy demand personal points of view, and of course, some folks reading right now will have felt very differently about the Court’s decisions than I did. Diversity dictates there will be different views. I decided to share this story not to convince anyone to change their views about guns, women’s rights, reproductive freedoms, or government, but to focus on the feelings—everyone in leadership will almost certainly have experienced despairing days of their own, and we will again in the future. Despair comes quietly in our heads, hearts, and bodies, but if we don’t handle it well, it can have negative impacts on our entire organization.

One person who has spent a lifetime studying the subject of despair is existential psychiatrist and author Irwin Yalom. Yalom was born to Jewish immigrants who came from what’s now Belarus (as did my grandfather). The Yaloms arrived in Washington, D.C. during WWI, where they went on to open a grocery, above which Irwin Yalom grew up. Yalom, who turned 91 ten days before the Supreme Court’s series of decisions, has written seventeen books, many of which have helped me and millions of others to manage ourselves in more caring ways. In his 1992 book of historical fiction, When Nietzsche Wept, Yalom writes about an imagined connection between 19th century Austrian psychologist Joseph Breuer and the philosopher Friedrich Nietzsche. It includes this snippet of conversation, which, in a sense, sums up much of the struggle most all of us might have with despair:

Breuer: “… I ask you to heal me of despair.”

Nietzsche: “Despair? … What kind of despair? I see no despair.”

Breuer: “Not on the surface. There I seem to be living a satisfying life. But, underneath the surface, despair reigns …”

Nietzsche: No, no, Doctor Breuer, this is impossible. I cannot do this, I’ve no training. Consider the risks—everything might be made worse.

Breuer: “… Who is trained? … Aren’t your books entire treatises on despair?”

Nietzsche: “I can’t cure despair, Doctor Breuer. I study it. Despair is the price one pays for self-awareness. Look deeply into life and you will always find despair.”

What Yalom writes resonates with me. There is no way, I’ve come to see, to live a considered, mindful life and not experience despair many times. Denial won’t do the trick; pretending—to ourselves or others—that we don’t feel it just makes things worse. As Brené Brown reminds us, “Without understanding how our feelings, thoughts and behaviors work together, it’s almost impossible to find our way back to ourselves and each other.” There is likely no one we look up to or admire who has not dealt with despair regularly throughout their life. Despair can be caused by any number of things: deep loss, seemingly impossible financial circumstances, paths forward blocked by systemic bias, the unexpected departure of a partner or key coworker, a series of critical customer comments … Sometimes it’s a combination of all of the above. When it hits—which, even with all the advantages I have going for me, it does—despair is hard to handle.

Although it’s difficult for me to remember when I’m in the middle of it, despair, dealt with caringly, can lead to positive and creative outcomes. Psychologist Mary Pipher says:

What despair often does is crack open your heart. When your heart cracks open, it begins to feel joy again. You wake up. You start feeling pain first. You feel the pain first, but then you feel the joy. You start to experience being alive again.

My hope in writing this piece is that naming despair, owning my own, and being real about a topic that’s only rarely talked about in leadership circles, might help others to deal more effectively with their own days of despair. If we don’t know how to deal with it, we go into denial, act out in anger, launch into destructive rage, or withdraw suddenly from the world. Denial about despair can, it seems, lead to long-term depression.

Although I know the word, and I’ve grown familiar with the feeling over the years, I’m not sure I could describe despair with any degree of meaningful clarity. David Whyte writes:

Despair takes us in when we have nowhere else to go; when we feel the heart cannot break anymore, when our world or our loved ones disappear, when we feel we cannot be loved or do not deserve to be loved, when our God disappoints, or when our body is carrying profound pain in a way that does not seem to go away. We give up hope when certain particular wishes are no longer able to come true and despair is the time in which we both endure and heal, even when we have not yet found the new form of hope.

For me, despair comes when hope is blocked; if “hope” in the organizational ecosystem is the sun, maybe despair is like an eclipse—the sun is completely blocked out. Unlike in nature, that eclipse can last a lot longer than just a few minutes. Despair, as I’ve experienced it, is a loss of belief in the future. It’s the sense that all the existential exits have been blocked, making a path to a more positive future impossible. At best, despair is difficult. At an extreme, the depths of despair is a place in which we wish that our lives would end. It would be disingenuous to say I’ve never had that feeling. Søren Kierkegaard says that in dark times, “Despair is the disconsolateness of not being able to die.”

In damaged, unhealthy, organizational ecosystems, Charles Blow reminds us, indignity and inequity can reach unmanageable levels of despair. Writing a week after the killing of George Floyd, Blow says:

Despair has an incredible power to initiate destruction. It is exceedingly dangerous to assume that oppression and pain can be inflicted without consequence, to believe that the victim will silently absorb the injury and the wound will fade. No, the injuries compound, particularly when there is no effort to alter the system doing the wounding, no avenue by which the aggrieved can seek justice. This all breeds despair, simmering below the surface, a building up in need of release, to be let out, to lash out, to explode.

What Blow describes isn’t just what makes the national news—you can see these small explosions in badly run businesses where pressure, sadness, abuse, and frustration build up over the years. Eventually, things blow up. By contrast, if we deal with despair well when it happens by owning it and moving through it with some modicum of authentic effectiveness, we can probably keep those explosions from happening.

We need to honor despair to create the kind of healthy lives we want to lead—individually and collectively. Here are some ways that have helped me, and I hope, will help you and yours as well:

Feel it – This may sound obvious, but it’s not the norm. So many of us have learned to respond to despair with distraction, drama, blaming, aggressive anger, drinking, or drugs. Raging at others, of course, simply makes things worse. As Ukrainian writer, lawyer, and women’s rights activist Larysa Denysenko reminds us, “It is always easier to bully and tyrannize someone who is smaller in order to feel that you are bigger.” Others (like me) might try denial or shutting down, but that doesn’t work well either. Nor does shaming ourselves for what we are going through. Uncomfortable as it is, learning to feel the feeling is, I’ve learned, the right thing to do. As Sam Keen says, “Despair is a primal emotion that is rooted in the honest awareness of our true helplessness to change the cosmic drama.”

Embrace that despair will eventually end – Despair is in great part what it is because, when we’re in it, it feels as if there’s no way forward. But if we work with it, despair does eventually depart. In the spirit of this, Anzia Yezierska arrived in New York as a young girl with her parents in 1893. They came from a region of Poland that was then part of the Russian Empire, leaving behind a time and place in which Jews dealt with a great deal of discrimination and despair. Yezierska became a chronicler of the Jewish American immigrant experience—sharing the story of people, very much like her parents, who came here with hope but found out quickly that America was not the panacea they had imagined. Yezierska became quite successful—Hollywood sought her out to make films of her books, but she was so uncomfortable with its inauthentic culture that she moved back to New York. Her 1925 book The Bread Givers is a great book, but working on it, it turns out, was not easy: “It took all morning to write one page—sometimes only a paragraph or a sentence. Many times the morning passed with nothing but despair for my labors.” Still, Yezierska saw, as so many of us have, that her period of despair would pass, and better things would follow. It was “in my darkest moments of despair,” she wrote, that “hope clamored loudest.”

Actively work at increasing hope – Despair comes when hope goes dark. Which means that one antidote is to gently work at growing hope. There’s a lot in Secret #45 about how to use the “Six-Pointed Hope Star” to make this happen—for others around us, and, importantly, even for ourselves.

Get curious – Writer Joe Cardillo says, “Curiosity is an antidote to despair. … curiosity disrupts despair, insisting that tomorrow will not be a repeat of today. Curiosity whispers to you, ‘You’re just getting started.’” One way to get curious is to explore the feeling. Studying the facts of the situation can help as well. Reading about Ukraine in the last four months has been one of the most interesting, inspiring, and insight-providing parts of my life. My studies have given me great understanding and a much deeper appreciation of the diversity, complexity, and creativity of Ukrainian culture. In the last week I’ve learned more about the history of the Supreme Court than I had learned in my whole life. From that learning, I’ve already had half a dozen realizations that can help us to be more caring and constructively run our organization (one good reminder—use Bottom Line Change when you want to make a big organizational change).

Work with dignity – If dignity is the way we show up in our ecosystems, then the frequency of despair will be diminished. Certainly, the destruction that Charles Blow described will be far less likely to happen. And when despair does happen, we can work together in dignified ways to deal with it. For more on dignity check out this post, or look at the current print issue of Zingerman’s News.

The first element of the revolution of dignity work is to “Honor the essential humanity of every person we interact with.” In the context of despair, it’s particularly important to help those around us to be seen and heard for who they are. Michigan State professor of English Kathleen Fitzpatrick writes in Generous Thinking; A Radical Approach to Saving the University about her struggles earlier in the 21st century to respond to the state of society and in her work in education. She was hit hard emotionally, much as I was a few weeks ago. Kathleen, who I met in one of the ZingTrain Master Classes, shares, “It’s hard to imagine paths forward at a moment of such profound despair.” Supporting her students, showing them positive paths forward, in turn helped her to gain purpose, reminding herself in the process, “… certainty that even in the midst of despair there was work to be done, and that it was my job to do some small part of it.”

Getting stuck down in despair will do nothing good; feeling it, honoring it, and working through it can quietly help change the world. This is the work, in a way, of the “Three and Out Exercise”—by authentically appreciating three individuals, one at a time. I started the practice to improve my energy, but it’s well suited to dealing with despair as well. In that same vein, listening to Briony Greenhill’s beautiful music while working on this piece reminds me that when I’m down in despair, pushing myself to honor others helps them, and also me at the same time. In Greenhill’s lovely song, “I see you, I love you,” she sings:

Is there a dream in your heart that wants to live but it doesn’t live yet?
What seed do you have in there that wants to grow, but it hasn’t been sown yet?
What would it be like to take that seed in the palm of your hand and say
“I see you, I love you, I believe in you, and I’m gonna give you some time”?

Watch for joy – While it’s true that joy can appear on its own, I’ve learned the hard way that no matter how deeply I feel despair, the reality is that there are joyous things happening all around me—the “butterflies” of joy are there, we just have to be mindful enough to notice them. I see coworkers do amazing things every hour. As you can probably tell, it’s a rare week that I don’t stumble on some new music or read a few pages of a great book. And, I am fortunate to work with fantastic food and drink every day. And later in the same week in which I felt like I was hitting bottom, Lisa Schultz from the Roadhouse taught the “No Drama” session for ZingTrain that I wrote about last month. Both the content and her presentation were terrific!

Get going – Most often, we take action in our lives because we’re motivated to move forward. There are times though—like when we’re experiencing despair in which the inverse is true: getting moving can help us get motivated. Even small steps in a good direction can help me make my way through despair. This isn’t about running away, it’s about moving one mental foot in front of the other to do something. Joan Baez is the daughter of an immigrant—her father, Albert Baez, was born in Mexico, came to New York, and went on to be a physicist who invented the x-ray microscope. Joan, who gained global acclaim for her music and her activism, once famously said: “Action is the antidote to despair.” (Baez, I’ve been told, once played a house concert in the living room where Tammie and I spend a lot of our time, perhaps in the fall of 1961 when Baez was in town doing a show at what was then called Ann Arbor High School.) Small positive actions (like the “Three and Out” exercise, taking on some small thing on an action list, reaching out to a long-lost friend, studying the history of Joan Baez’s appearances in Ann Arbor, etc.) can help move me—and maybe you—into a better mental space.

Make art – In “The Roots and Impact of African American Blues Music,” published through Whitworth University, Emily Weiler writes, “The earliest forms of blues reflected feelings of despair, sorrow and many other moods of the singers.” Listen to Son House’s “Death Letter Blues” to get a taste of what that despairing resolve sounds like in action. For me, art helps me deal with despair through writing; the appropriately titled “Working Through Hard Times” pamphlet is all about it. Throughout human history people have painted, written poetry, played music, etc. as a way to work through pain and despair. Rather than doom-scrolling or other routes of avoidance, it’s productive to engage with our emotions in creative ways.

Be actively grateful – Paying attention to the positives even when—or maybe, especially when—the problems feel overwhelming makes a difference. As Sam Keen writes,

Make a ritual of pausing frequently to appreciate and be thankful. … Notice that the more you become a connoisseur of gratitude, the less you are the victim of resentment, depression and despair. Gratitude will act as an elixir that will gradually dissolve the hard shell of your ego—your need to possess and control—transform you into a generous being. The sense of gratitude produces true spiritual alchemy, makes us magnanimous—large souled. … For no particular reason you can detect, depression lifts, despair is replaced with an undefinable sense of hope, and enthusiasm returns.

It’s always a good time for gratitude. I’m grateful to you for reading, I feel fortunate to be around so many great people and so much amazing artisan food and drink every day, and I’m appreciative of being part of an organization in which writing about despair is considered a healthy act of leadership. I’m grateful for my girlfriend, her big heart, and good work to farm and to rescue dogs, and all our own loving pups. Though I’ve never met her, I am very grateful for Boston College historian Heather Cox Richardson. Her nearly nightly enews, “Letters from an American,” gives me insight, understanding, and great historical perspective on an array of issues, including the situation with the Supreme Court. Once a week or thereabouts Richardson takes a “night off”—even then she sends a short note to say so. Far more often than not, her writing brings me hope. This one from last week felt right for what I was writing here:

It’s been a long, hard week. Going to call an early night.

Before I do, though. … Thank you all for being here. I have heard people this week despair of this country, but I look around at you all and I have faith.

And so … I’ll be back at it tomorrow.

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