DeDe Esque
In the United States, the season between Halloween and the New Year brings with it expectations of joy, celebration, and togetherness. Yet for many, this time of year can carry a profound weight. Whether mourning the loss of a loved one, processing a major life or career transition, or feeling the absence of what once was, grief and loss do not pause for the holidays—they often intensify.
Leaders often feel they must compartmentalize their grief to maintain their professional presence. They worry that showing vulnerability will undermine their leadership and/or their standing within the organization; however, acknowledging grief doesn’t diminish their capacity to lead. In fact, it deepens it.
Why the Holidays Hit Harder
There are many logical reasons why the holidays hit harder when it comes to grief and loss, and some of them could be:- Sensory overload: Holiday music, scents, traditions, and even the quality of the light during the winter can trigger powerful memories
- Cultural pressure: Expectations to be cheerful and grateful can intensify feelings of isolation
- Performance anxiety: Leaders often feel they must hide vulnerability and “perform happiness” to maintain credibility
Understanding Ambiguous Grief
Not all losses are clear-cut. “Ambiguous grief” occurs when loss lacks closure, is unclear, or remains unresolved according to psychologist Pauline Boss. In professional contexts, this might include:- A mentor with dementia who no longer recognizes previous team members
- Team dynamics that dissolved or shifted significantly after organizational restructuring
- A career identity fervently pursued for perfection and now must be released, but still feels present
- The colleague who left the organization without a proper goodbye
- Strained relationships where someone is physically present but emotionally absent (which is prevalent in family situations, as well)
The Five Stages: A Map, Not a Mandate
A familiar and long-standing grief framework was identified by Elisabeth Kübler-Ross as the five stages of grief—denial, anger, bargaining, depression, and acceptance—while these stages have become culturally accepted, they are not a linear checklist according to Kübler-Ross. They can be experienced simultaneously, with skipped stages entirely, and/or in a sequence that is completely “out of order.” Grief doesn’t follow rules, and there’s no “correct” way to move through it. For more on the five stages, discover the Kübler-Ross Foundation here: Dr. Elisabeth Kübler-Ross and the Five Stages of GriefSupporting Yourself This Season
According to grief experts, there are a few practical ways that leaders can support themselves during the holidays and into the darker days of winter:- Permission to opt out: There is no obligation of cheerfulness or attendance to events. Say no to gatherings that feel like too much
- Create new rituals: Light a candle, write a letter, or donate to a meaningful cause. Small acts can honor a loss without erasing the pain
- Communicate clearly: Tell needs with colleagues, teammates, or family. “I’m keeping things low-key this year” gives others permission to provide support
- Protect energy supplies: Grief is exhausting. Rest more, commit to less, and release the pressure to maintain a usual pace
- Seek support: Therapy, coaching, or grief counseling provides a container for feelings too large to process alone.