Ep #64: Navigating Holiday Grief: Tools to Empower Your Heart and Mind

The corner office doesn’t make you immune to grief. As leaders, we are experts at forecasting business trends. But what about navigating the holidays with a heavy heart? Today, I am having the conversation no business school prepared us for. Stay tuned.

Welcome to Overcoming Grief, a show for women experiencing profound grief and looking for support in healing and transforming their lives. If you are ready to heal after loss, create a new self-identity, take responsibility to do the hard things, and get massive results in your life, this show is for you. Now, here’s your host, Master Grief and Life Coach, Sandy Linda.

Hello, creative humans. Last week, a call from Sarah, one of my former clients, stopped me in my tracks. She’s a brilliant tech executive who runs meetings like a music conductor. She invited me to her office. There we were, in her detail-organized office, looking at her calendar. The color-coded blocks that read like a CEO’s playbook. Quarter four, revenue review, 9:00 a.m. Holiday party planning, 11:00 a.m. Budget forecasting, 2:00 p.m.

Then, a small purple block reads, Mom’s traditional cookie baking day. When she saw it, everything changed. The polished executive appearance toned down, and she whispered, “I can master board meetings and year-end projections, but making mom’s cookies without her, that feels impossible.”

Welcome to a special Thanksgiving episode. Whether you’re just finding us or you are a familiar friend, you landed in a space where we get it. This is a community of high-performance women who decided something powerful, that we don’t have to choose between crushing our professional goals and honoring our grief. Both can exist. Both matter.

Maybe you are listening in between meetings, your own calendar, a witness to your leadership. Or perhaps you’re here with your morning coffee, already rehearsing how you will respond to your team’s questions about your holiday plans. I see you, balancing those spreadsheets and memories, those strategic plans and sacred traditions.

Here’s what makes this community special. We see each other. The holidays are supposed to be the most wonderful time of the year. At least that’s what every commercial and store display tells us. But what happens when your heart is heavy with loss? Recent studies have shown that the holiday season is a time of intense loneliness for more than half of Americans. Women leaders are feeling this impact the most. When grief is part of your story, these festive times can feel like navigating an emotional maze.

While the rest of the world sparkles with holiday cheer, many of us are quietly struggling with the joy expected of us, with the heaviness in our hearts. Today’s conversation goes beyond typical holiday coping strategies. We’re diving into what I call executive grief intelligence. The art of transforming loss into leadership wisdom, creating new traditions that honor both our past and our presence, leading with authenticity while maintaining professional boundaries, building workplace cultures that acknowledges human experiences.

Whether you are a CEO navigating board meetings between holiday memories or a rising executive balancing team morale with personal healing, this episode is for you.

Here’s the truth. This dance between professional strength and personal grief is more common than we acknowledge. You are not alone in this dance of joy and sorrow.

Let me share something personal with you. A decade ago, Thanksgiving was a very different experience for me. My mom would launch into planning mode come October, treating our annual grocery shopping trip like a sacred ritual. She had this worn out recipe book, its pages wearing the badges of countless holiday feasts, margins filled with her handwritten notes, and as she reminded me that good food takes time

Sandy as we spent weeks perfecting every dish. Today, that recipe book sits on my shelf, a cherished time capsule. The grocery store aisles feel longer now, quieter. The kitchen that once buzzed with her energy holds different memories.

That’s the thing about grief. It doesn’t just leave an empty chair. It transformed the everyday moments we once took for granted. Leading a company through holiday festivities while struggling to maintain the spirit of your own family traditions can leave a business leader feeling a bit lost. It’s a unique challenge, maintaining your professional presence while honoring your human heart.

I know some of you are listening right now, perhaps recognizing your own story in these words. Maybe it’s not a recipe book for you. Perhaps it’s an unworn holiday sweater, an unplayed board game, or a tradition that needs reinventing. Whatever your story, know this. Your experience matters, especially during spreadsheets, strategy meetings, and seasonal celebrations.

Let’s talk about those quiet moments, the early morning walks, the drive to work, or those few minutes before your first meeting. These solitary spaces can feel overwhelming when grief hits, but they also hold incredible potential for healing.

Here’s what I’ve learned both personally and from leaders I’ve worked with. First, let’s reframe those morning walks. Instead of trying to outpace your thoughts, try this. Let each step become a conversation with yourself. When a memory surfaces, maybe it’s your dad’s holiday laugh or your sister’s infamous fruitcake, give yourself permission to pause. Take three deep breaths. Feel your feet on the ground.

You are not rushing through grief. You are walking alongside it. Now, about those memories that catch you off guard, the ones that might hit during your morning coffee or between meetings. Rather than pushing them away, try this practice I call memory to meaning. When a holiday memory surfaces, ask yourself, what gift did this person or tradition give me? Maybe your mom’s obsession with perfectly wrapped presents taught you the importance of attention to detail, a skill you now use in leading your team. See how that works. We’re not just remembering, we’re recognizing how these loves continue to shape our leadership.

Here’s something powerful about creating new traditions that don’t replace the old ones. They build bridges between your past and present. One executive leader I know started a legacy project during the holidays. She takes one traditional family recipe and teaches it to her team during their holiday gathering, sharing the story behind it. Another leader transform his father’s love for holiday service by inviting a company-wide volunteer day in December.

The key isn’t to move on from grief. It’s moving forward with it, letting it inform our leadership with deeper empathy and truthfulness. When we allow ourselves this grace, something remarkable happens. We create space for others to do the same. Remember, healing isn’t linear. Some days, that morning walk will feel peaceful. Other days, it might be tough to leave your car after arriving at the office. Both experiences are valid. Both make you more human and a more relatable leader.

There’s this myth in leadership that strength means having it all together all the time. But here’s what I’ve discovered and what research actually confirms. It’s our human moments that make us most relatable as leaders. Think about it. Remember that time when a team member shared they were struggling with loss? What helped them wasn’t a perfectly crafted email or a policy quote. It was probably the moment you said, “I get it, I’ve been there.” That’s not weakness. That’s the connection. Connection, that’s leadership gold.

Let me share something that surprised me. A few years ago, during a holiday town hall, I briefly mentioned missing my mom’s holiday tradition. That small moment of authenticity opened up something remarkable. Other team members started sharing their own stories. One executive assistant created a company cookbook featuring family recipes and the stories behind them. Another manager started memory Mondays where team members could share a photo or story of someone they’re missing.

Here’s what I want you to remember. Your grief journey isn’t separate from your leadership journey. It’s part of it. When you allow yourself to be human, you give others permission to do the same.

Isn’t that the kind of workplace culture we all want to build? One where people bring their whole selves to work. You don’t have to share every detail of your personal story. But those genuine moments when you acknowledge that yes, the holidays can be complicated. Yes, it’s okay not to be okay. Those moments build trust. They create spaces where your team feels safe to express their own challenges. That kind of psychological safety, it’s what builds resilient teams and stronger organizations.

As we wrap up today, I want to speak directly to you. Yes, you. Maybe you are driving home right now or taking that morning walk we talked about. Perhaps you have been nodding along, feeling seen in ways you didn’t expect during a leadership growth podcast. Here’s what I want you to take with you.

This holiday season, you have permission to celebrate differently. You have permission to step away from the shoulds and honor what feels right for your heart. Maybe that means taking five minutes in your office to look at old photos before leading the company holiday party.

Perhaps it’s starting meetings with a moment of gratitude that includes acknowledging those who aren’t here. Perhaps it’s just about giving yourself permission to say today’s been rough and that’s okay. You’re not just surviving the holidays. You are pioneering a new way of leading through them. One that makes space for joy and sorrow to exist together. One that shows others that strength isn’t about hiding our humanity. It’s about embracing it.

Every time you honor your journey, every time you allow yourself to be both a grieving human and a capable leader, you’re creating ripples of change. You are showing everyone in your orbit that there’s no one size fits all the way to experience the holidays. Consider this not just permission but an invitation to celebrate differently, to lead truthfully, and to create spaces where others can do the same. Because sometimes the most meaningful traditions are the ones we dare to create anew.

If no one has told you lately, you are doing better than you think. Your leadership matters. Your story, all of it, makes you the leader your organization needs right now. From my heart to yours, thank you for spending this time with me. May you find moments of peace, unexpected joy, and gentle reminder you’re not walking this path alone. To all my grief warriors and everyone else, have a great week. Bye.

Thanks for listening to today’s episode of Overcoming Grief. If you’re ready to move into a new, rewarding life experience, and want more information about how to work with Sandy, visit www.sandylinda.com.