Leadership grief is the sorrow of unchosen possibilities

Leaders are taught to make bold decisions. We’re trained to be decisive, to see the path ahead, to say “yes” with conviction. But we rarely talk about what is happening behind the confident face — the quiet grief that follows the yes.

A few years ago, I helped to found an academic center. When we finally settled on the mission statement, I felt relieved but also sad. Until that moment of decision, the center could have been any number of things, could have dedicated itself to a plethora of possible missions. We had talked about focusing on various issues —the ecological crisis, political polarization, burnout and post-traumatic growth; there is no shortage of challenges. And we debated the various audiences to prioritize — women clergy, queer clergy, pastors, nonprofit leaders more broadly.

Finally, we settled on a focus area, and I felt so sad about all the possibilities that we were leaving behind. Each of those areas of work is important and needed in today’s world. In leading the mission-setting conversations, I had longed for a more defined field in which we could see measurable impact. Now that it was set, I longed for a larger umbrella to be able to hold more areas of work.

Sorrow for the unchosen possibilities is a strange type of grief. It is entirely invisible. While I was smiling and confident as I accepted congratulations on what was launched, internally I was second-guessing and wondering “what if” about all the roads not taken.

This is the grief of leadership. The sorrow that comes not from loss of what was, but the loss of what never will be. Leadership grief is watching a thousand unrealized visions fade as we try to maintain focus on the one that is coming into being; it is the loss of choosing one good thing over and against a plethora of other equally, differently good things.

Every “yes” carries behind it a thousand quiet “noes.” We rarely acknowledge them, but they accumulate. The programs we don’t start, the partnerships we don’t pursue, the people we can’t hire, the projects we can’t fund; each loss leaves a minor wound. Over time, it’s death by a thousand cuts.

Leadership is an unending encounter with the finitude of our own energies and the capacities of our organizations. Leadership rewards clarity, confidence and strength — which means that our griefs must go unnamed in order to advance the chosen goal. We must choose, and choosing often means loss. Every leader I know carries a small cemetery of unchosen ideas.

Esther Greenwood, the main character in Sylvia Plath's novel “The Bell Jar,” describes the experience of seeing her life spread out before her “like the green fig tree.” From every branch hung a ripe, purple fig — each one a possible future. One fig was marriage and children; another was a famous poet; another was an Olympic athlete; another was a brilliant professor, another was a world traveler.

Greenwood “wanted each and every one of them, but choosing one meant losing all the rest.” Unable to make up her mind, she starved as figs began to wither and fall to the ground.

I often think of this passage when talking with pastors and leaders. It perfectly captures the paralysis of possibility, as well as the tragic consequences of indecision.

Like Plath’s character, leaders see an abundance of figs — but these figs are for our churches and organizations, not only for our own lives. One branch bears a new outreach initiative, another a youth program, another a meals ministry, another a community partnership. Each glows with possibility. But no leader can reach for every fig; no single organization can do it all. We reach toward one and watch the others fall.

Sometimes we let figs fall because of circumstances; a grant doesn’t come through, a key staff member moves on, the community’s needs shift. Other times, we must choose deliberately what to let go. We prune a program that’s no longer bearing fruit. We release a dream that no longer extends from the reality we live in.

As long as we refuse to decide, all the possibilities remain out before us as attainable futures. It is the feeling we see in a small child, or even a college freshman with an undecided major — so many possible paths, an abundance of pure potential. Choosing one branch, one fig, means abandoning a dozen others.

I recently consulted with an organization that had received grant funds to grow their organizational sustainability. The funds could be used toward any number of projects — succession planning, training in donor development, software for tracking clients. But they hadn’t been able to choose. When they called me, they were halfway through the grant period with the funds untouched. They stagnated, their staff frustrated, their mission increasingly unsustainable while fruit (the funds in this case) rotted just out of reach.

Certainly choosing one project and making progress on it would have been better than choosing none. But without the capacity to confront their grief, they simply refused to choose, while starving for energy and clarity.

Leadership requires pruning, but pruning is painful. It means accepting that not everything, even good things, can be attained at once. Spiritually, pruning means accepting our limitations and growing our faith. Leadership requires faith that the life of the organization doesn’t depend on our ability to do everything, but rather, to do one thing well. It requires faith that releasing one project might make energy for something else to thrive. It requires faith that other organizations, and God themselves, will step into the gaps beyond the edges of our responsibility.

The invitation of leadership is not to mask our grief with a veneer of confidence, but to practice hospitality toward it. To let grief be a guest at the table with us. To bless our grief as one more sign that we have loved our work deeply and led with all we had.

When leaders take time to grieve, they are tending to the soil of their own sustainability. They release the unchosen possibilities to the world; they give them back to God. They feel freer, opened to the work that God has given them to do.

The losses don’t disappear, but they are no longer felt as withering fruit on the branch. They fall and turn to compost. The failed projects, the endings, the “roads not taken” start to feed the roots of our wisdom.