When the Holidays Hurt: Grieving with Compassion, Flexibility, and Grace

When the Holidays Hurt: Grieving with Compassion, Flexibility, and Grace

The holiday season is often described as joyful, festive, and full of connection. Yet for many, it can also be one of the most emotionally challenging times of the year—especially for those navigating loss, major life transitions, or the absence of loved ones who are no longer here.

A few weeks ago, I attended a free one-hour grief session with David Kessler, a leading voice in grief education. His words were a powerful reminder that grief often becomes louder during the holidays, not quieter.

Grief Is More Than Loss

Dr. Kessler shared that grief is not only about what we have lost. It is also a process of:

• Separation

• Recreation

• Rebuilding

• Reevaluation of life

  
  

This deeply resonated with me. It echoes the reflections of spiritual writer Henri Nouwen, who wrote about his own grief after his mother’s death. He had to learn, slowly and painfully, how to celebrate holidays again without her. Grief did not erase meaning; it reshaped it.

A Gentle Framework for Holiday Grief: The “GIF” Approach

During the session, Dr. Kessler offered a compassionate framework that clinicians—and individuals—can use to support grief during the holidays. He calls it grieving with “GIF.”

G — Give Full Presence

Healing does not come from fixing grief but from being with it. Offering full presence—listening, witnessing emotions, and sitting together in pain—can be profoundly healing. You don’t need the right words. Your presence is enough.

I — Invite Choice and Curiosity

Instead of focusing on what someone should do during the holidays, invite curiosity: What might help, even a little?

Dr. Kessler recommends having both Plan A and Plan B:

• Plan A: Attend a gathering or family event

• Plan B: A comforting alternative if it becomes overwhelming

  
  

Clients are also given permission to cancel plans, pause traditions, or modify family rituals. When someone says, “I’ll never feel the holidays the same again,” a gentle reframe can be: “Not yet.”

Meaningful rituals—such as lighting a candle, writing a letter, visiting a grave, or quietly honoring a loved one—can offer grounding and connection.

F — Free Yourself from Pressure and Perfection

There is no requirement to appear cheerful, strong, or “put together.” Grief does not follow a timeline, and comparison—especially through social media—only deepens isolation. There is no “right” way to grieve.

Dr. Kessler also emphasized that when people feel “stuck” in grief, what they often need is acceptance, not encouragement to move on. Accepting where you are can create the safety needed for healing to begin.

You Don’t Have to Grieve Alone

The holidays can carry many layers of emotion, shaped by where we are in our lives and within our families. If this season feels heavy, confusing, or overwhelming, it does not mean you are doing grief wrong.

It means you are human.

Grief was never meant to be carried alone. Support—whether through therapy, community, faith, or trusted relationships—can help you make sense of your pain and find moments of steadiness again.

A Gentle Invitation

If you are struggling with grief, loss, or emotional overwhelm this holiday season, I invite you to reach out for support. Therapy can offer a safe, compassionate space to process your grief at your own pace—without pressure, judgment, or expectations.

You deserve care. You deserve support. And healing is possible, even if it doesn’t look the way you expected.

Finding Hope in the Holidays

The holiday season can feel like a paradox. On one hand, it is a time for joy and celebration. On the other, it can be a stark reminder of what we have lost. I’ve found that embracing both feelings can be liberating. It allows us to honor our grief while still finding moments of joy.

Create New Traditions

As we navigate our grief, it can be helpful to create new traditions. These can be small, simple acts that honor our loved ones while also allowing us to experience the joy of the season. For example, you might choose to bake their favorite cookies or share stories about them with family and friends.

Embrace the Power of Connection

Connection is vital during the holidays. Reach out to friends or family members who understand your journey. Share your feelings, your memories, and your hopes. You might be surprised at how comforting it is to connect with others who are also navigating their grief.

Practice Self-Compassion

Remember to be gentle with yourself. Grief can be unpredictable. Some days will feel heavier than others. That’s okay. Allow yourself to feel whatever comes up. It’s all part of the healing process.

Conclusion: A Path Forward

As we move through this holiday season, let’s remember that it’s okay to grieve. It’s okay to feel joy. It’s okay to seek help. You are not alone in this journey.

📩 If you’d like to learn more about grief support or schedule a consultation, feel free to contact me. You don’t have to walk this season alone.