Holidays can bring joy, celebration, and connection—but they can also awaken grief, emotional pain, and reminders of loss. Life transitions such as divorce, the death of a loved one, or family discord can make the season feel overwhelming and isolating.
In Part 2 of our Holiday Survival Guide series, we explore evidence-based strategies for managing holiday grief and navigating emotional triggers with self-compassion and reflection. These tools can help you protect your well-being and move through the season with care, clarity, and balance.
Dear Holiday Hassled,
Last time, we met Megan—a 35-year-old navigating divorce, financial strain, complicated family dynamics, and her first holiday season without her beloved father.
We identified four strategies to help her reduce stress and set self-compassionate boundaries during a challenging time:
- Name her fears and holiday stressors through a detailed Fear / Dread List
- Clarify boundary needs around money, time, conversations, and emotional energy
- Turn boundaries into action, creating practical, actionable plans
- Prepare for challenges ahead, setting herself up for success
Once Megan had set her boundaries and prepared for the external challenges of the season, it was time to look inward. The next part of her work focused on the emotional terrain of grief—the vulnerable, painful moments that surface unexpectedly. Together, we added four more strategies to her plan, each designed to bring steadiness and self-compassion to the holidays. Read on, fellow travelers.
Step 5: Name All Sources of Grief
When we think of grief, we often picture the death of someone we love—and the quiet truth that we will spend the rest of our lives missing them. That is certainly one form of grief—and an intensely painful one that consumes our emotional energy, upsets our equilibrium, and sends our thinking off-kilter. These profound losses divide our lives into before and after, forcing us to adjust to identity shifts and new versions of “normal.”
But there are other losses—quieter, less easily named—that can make the holidays feel heavier and sadder. They, too, mark the end of something that mattered deeply.
In my work with clients, I often use the word grief to describe the emotional experience that follows when something ends and life shifts from “normal” to “adjusting.” Let me give you a few examples, fellow travelers.
- The loss of a job
- The loss of health and sense of security that fade with a new diagnosis
- The loss of a home after a natural disaster or foreclosure
- The loss of professional identity after retirement
- The loss of a friendship as priorities change
- The loss of time with our children as they move toward independence
What do these losses have in common? Sadness that ebbs and flows. Helplessness. Second-guessing. Regret—with maybe a touch of shame or anger at the unfairness of it all. And the ongoing effort to keep living when our hearts feel weary.
Sounds like grief, doesn’t it?
We tend to minimize these losses and their impact, don’t we, fellow travelers? They can seem small compared to the devastating grief of losing someone we love. But they accumulate—and when they do, they push us toward the edges of our coping skills and make everyday life feel heavier and harder.
These losses may not carry the same weight as death, but they still matter—and they still hurt. And when we’re also facing the first holiday (or the second, or even the third) without someone we love, those other losses can make that absence feel exponentially harder to bear.
For Megan, this year’s grief came in many forms:
- Her father’s death
- Her divorce
- Her children’s and her mother’s losses connected to both the death and the divorce
- Not being invited to annual holiday events geared toward couples
- Not being part of a couple at holiday or school events
- The loss of ease and joy she once felt during the holidays
- The loss of identity as a married mother
- Not being able to call her father for advice and support
Despite her best efforts, Megan couldn’t change these realities or take away the ache they caused—but she could meet herself with gentleness and compassion. Naming her grief was only the beginning; her next step was learning how to live alongside it with intention, using self-compassion as her compass through the season ahead.
Step 6: Create Self-Compassion Guidelines
When we are navigating holiday grief, we must begin by acknowledging that big feelings are inevitable—and that we will manage them imperfectly. We will make careless mistakes. We will overreact. We may find ourselves dissolving into tears when we catch a whiff of a loved one’s perfume, hear the opening stanza of a particular song, or burn the hot cocoa.
Just when we most need to double down on self-compassion—and offer ourselves the same empathy and grace we would freely give anyone else—we often do the opposite. We compare. We criticize. We spiral into defeatist thinking and worst case scenario predictions.
Megan was no exception. She predicted that her inner critic would take center stage at inopportune times, delivering long monologues of self-recrimination and regret. So we created a plan to lower the volume on her inner critic’s ramblings.
Megan’s Mantra
Double down.
When the holidays test your inner strength, double down on self-compassion.
When the holidays test your self-acceptance, double down on grace.
When the holidays test your resilience, double down on courage.
Double down. Double down. Double down.
Because when life feels heaviest, fellow travelers, our work isn’t to be perfect or to distract ourselves from emotion—it’s to return, again and again, to compassion, grace, and courage.
Megan’s Self-Compassion Guidelines
- I will honor that I am vulnerable this year and avoid shaming self-talk.
- I will decline invitations that fuel stress.
- I will take breaks when I need to collect myself and recenter.
- I will protect my boundaries and not worry about others’ opinions of them.
- I will be intentional about my social media use.
These guidelines weren’t rigid rules—they were anchors, designed to help her notice familiar thought patterns, pause, and choose intentional action over autopilot existence.
They were also lighthouses—steady beacons reminding her to keep looking forward and to hold close the parts of herself she most wanted in view when she felt lost or off-course.
Step 7: Prepare for Triggers and Unfinished Decisions
Navigating the holidays while coping with loss often brings two types of challenges:
Predictable triggers: moments we can anticipate will stir our grief.
For me, it might be missing one grandmother’s Estée Lauder Youth Dew perfume and the other’s sweet potatoes at Thanksgiving (a recipe none of us have ever quite managed to replicate). For you, it might be an empty chair, a favorite song, or a family tradition that has changed.
Unfinished decisions: the “I’ll get to it later” matters we haven’t had the emotional bandwidth to face while surviving acute grief. These linger quietly in the background, consuming our energy until we bring them into the light.
Megan identified both types. Some surfaced immediately; others emerged over time as she gave herself space to reflect.
Predictable triggers
- Her dad’s empty chair at the Thanksgiving table
- Putting together her kids’ Christmas gifts alone
- Hearing Silent Night (her dad’s favorite carol)
- Addressing the Christmas card to “Mom” instead of “Mom & Dad”
- No gift exchange with her ex-husband on Christmas Eve after the kids’ gifts were wrapped
Unfinished decisions
- Does she take over her dad’s tradition of driving the kids to see Christmas lights—or create a new one?
- Does she give her ex-husband the tie she bought him last January before he asked for the divorce?
- Does she take the kids shopping for a gift for their dad? Could they give him the tie?
- Does she help her mom decorate her Christmas tree?
- What should she do with the Christmas ornaments that were souvenirs from special trips with her husband?
Together, we created a menu of options to guide her through these emotionally charged moments—times when it’s hard to make clear decisions or access calm problem-solving. Each option was realistic and flexible, giving her permission to choose what felt most supportive in the moment—without pressure or guilt.
Predictable Trigger Example & Menu Options
“I will put together my kids’ Christmas gifts alone instead of with their dad.”
- Megan could set up small comforts—a favorite movie, a warm cup of cocoa—to bring emotional balance to a situation she knew might feel lonely.
- She could allow her emotions to surface and meet them with acceptance: “I won’t always feel this sad, but right now I do—and that’s okay.”
- She could simplify by avoiding gifts that required assembly.
- She could invite a trusted friend for support and laughter, clarifying in advance what kind of help would feel most comforting.
Unfinished Decision Example & Menu Options
“I’m not sure what to do with the Christmas ornaments from special trips.”
- Megan could choose to hang them, honoring those trips as joyful and meaningful experiences that could now be held with both gratitude and emotional complexity.*
- She could pack them away for now, giving herself permission to revisit the decision later when she had more clarity about her course of action.
- She could offer them to her ex-husband.
- She could donate them.
Giving ourselves a moment to name predictable triggers, unfinished decisions, and a menu of options for handling them brings a kind of deep exhale—the kind a child releases after drawing a picture of the monster from their nightmares.
On paper, it never looks quite as scary as it did when it was swirling in the dark corners of the mind, gathering energy and speed as it ran unchecked. This practice helps us externalize our fears and worries, giving them shape and boundaries so they stop fueling the difficult emotions that pull us away from the present moment.
It’s not about erasing the monsters entirely—that’s beyond our power, fellow travelers.
It’s about seeing them clearly enough to remember that we still hold the crayon—and choose how we fill the paper.
*With permission to move or remove them later if they began to draw her focus away from the beauty of the whole tree.
Step 8: Set Holiday Self-Care Goals
Remember, fellow travelers, managing stress requires a mind-body plan. Our emotions are processed not just in the mind but through the body—through muscle tension, fatigue, pain, and shifts in sleep, appetite, and energy. That’s why no holiday survival guide would be complete without tending to the body that carries us through emotionally complex waters.
Megan knew the weeks between Thanksgiving and New Year’s would be especially challenging. Her father had loved the holidays and had always been a steady source of support for her and her children. She felt confident he would have helped her navigate the grief of her divorce.
Now, in her first post-divorce holiday season, familiar traditions carried both comfort and pain—each one a reminder of what once was and what no longer is.
Together, we designed manageable, specific well-being goals to protect her energy and stamina.
- Issue: Difficulty sleeping or skipping meals when stressed.
- Goal: Maintain healthy sleep hygiene (bedtime by 10 p.m., reduced screen time, Insight Timer meditations) and aim to eat at least two nourishing meals each day. Keep healthy grab-and-go options available to reduce reliance on sugar for comfort and snacks.
- Issue: Skipping her daily walk—a major stress reliever.
- Goal: Walk two miles and aim for 8,000–10,000 steps at least five days per week.
- Issue: Feeling too tired for journaling or therapy.
- Goal: Journal briefly before bed (“5 gratitudes,” “best and hardest moment,” “something that made me smile”). Protect downtime. Commit to biweekly therapy appointments through mid-January.
- Issue: Rumination about divorce or missing her father.
- Goal: Pause after brief reflection; choose an “emotional balance” activity (movies, journaling, games, reading, volunteering).
- Issue: Self-blame or regret.
- Goal: Ask, “What does self-compassion look like right now?”—then choose kindness in thought or action or both.
By setting small, realistic goals rooted in compassion and awareness, Megan refocused on what remained within her control: caring for her body so it could better sustain the emotional work of grief and healing.
Looking Ahead
It’s important to remember, fellow travelers, that Megan isn’t walking through this season of grief alone. Her young children are grieving too—facing their first holiday without their grandfather and their first with divorced parents.
In Part 3 of our Holiday Survival Guide, we’ll explore how to support grieving children while caring for your own tender heart. Even if you don’t have children to care for this season, I invite you to read along. We were all children once, and those younger versions of ourselves still live within us—parts that long for comfort, reassurance, and understanding. You may find that the same strategies can bring healing to the child within you, too.
Still River Counseling’s 8-Step Holiday Coping Plan
A self-compassion framework for navigating stress, loss, and change.
- Identify Your Fears & Stressors
- Clarify Your Boundaries
- Turn Boundaries into Action
- Prepare for Challenges Ahead
- Name Your Sources of Grief
- Create Self-Compassion Guidelines
- Prepare for Triggers & Unfinished Decisions
- Set Holiday Self-Care Goals
Closing Reflection: “Good Enough” Holidays
Grief, in whatever form it appears, is the other side of love and caring—proof that we’ve invested our hearts in relationships and pursuits that matter to us.
When grief joins us for the holidays, self-compassion may look like adjusting expectations to match the truth that our emotional (and mental) energy is already working overtime. It’s okay to say, “This wasn’t the year for that,” or to settle for “good enough.” Some holidays will look less like a Hallmark movie and more like a treasure hunt for small polka dots of joy and moments of respite amid the waves of sadness and anger—with stress levels in the okayish range.
Hopefully, fellow travelers, those holidays will be rare compared to the many filled with comfort, connection, and genuine joy—through old traditions and the new ones we create along the way.
With each self-compassionate step we take, we learn to move with our pain instead of against it.
We’ll meet again soon in Part 3. In the meantime, return to Megan’s mantra:
Double down. Double down. Double down.
Ubuntu.
— Jennifer
