Introduction: The Weight of Holiday Expectations

The holiday season often arrives wrapped in layers of expectation. Family traditions, cultural norms, social media snapshots, and even our own inner voices whisper what the season “should” look like. We imagine perfect gatherings, flawless meals, joyful reunions, and a sense of peace that somehow emerges from the chaos. Yet for many, the reality is far different: strained relationships, financial stress, grief, or simply exhaustion.

As a coach and pastor, I’ve seen how expectations can quietly erode joy. They create pressure to perform rather than freedom to experience. They turn the season into a checklist instead of a celebration. And when reality doesn’t match the picture we’ve painted, disappointment follows.

This blog is an invitation to let go of those expectations—not by abandoning meaning, but by designing a holiday season that feels right for you. One rooted in authenticity, aligned with your values, and spacious enough to breathe.

Naming the Expectations

The first step in letting go is naming what weighs on us. Expectations come in many forms:

• Family traditions: “We’ve always done it this way.”
• Cultural scripts: “The holidays are about big gatherings, gifts, and decorations.”
• Social media comparisons: “Everyone else looks so happy—why don’t I?”
• Internal voices: “I should be more cheerful, more generous, more spiritual.”

When we pause to name these, we begin to see which ones serve us and which ones drain us. Scripture reminds us of this discernment: “Everything is permissible, but not everything is beneficial” (1 Corinthians 10:23). Not every tradition or expectation is life-giving.

The Cost of Carrying Expectations

Expectations aren’t neutral. They carry costs:

• Emotional cost: Anxiety, guilt, or resentment when we can’t meet them.
• Relational cost: Tension with loved ones when traditions clash.
• Financial cost: Overspending to keep up appearances.
• Spiritual cost: Losing sight of the deeper meaning of the season.

When we cling to expectations, we risk missing the very joy we’re chasing. Jesus himself challenged cultural expectations of his day, reminding people that the Sabbath was made for humanity, not humanity for the Sabbath (Mark 2:27). The holiday season, too, is meant to serve us—not enslave us.

Designing a Season That Feels Right

So what does it mean to design a holiday season that feels right for you? It means shifting from performance to presence, from obligation to intention. Here are guiding principles:

• Clarity of values: Identify what matters most—connection, rest, generosity, faith.
• Permission to adapt: Traditions can evolve. You can say no. You can simplify.
• Space for authenticity: Choose practices that reflect who you are, not who others expect you to be.
• Attention to wellbeing: Protect your emotional, physical, and spiritual health.

This is not about rejecting the holidays. It’s about reclaiming them.

Practical Steps for Letting Go

Here are some coaching steps to help you move from expectation to intention:

1. Reflect on past seasons: What drained you? What gave you life?
2. Name your non-negotiables: A quiet morning, a faith practice, a family ritual.
3. Release the rest: Give yourself permission to let go of what doesn’t serve you.
4. Communicate clearly: Share your intentions with loved ones. Invite collaboration.
5. Create new rhythms: Experiment with practices that align with your values.

Think of this as designing a holiday blueprint. You’re not erasing traditions—you’re curating them.

Personal Side: My Own Journey

I’ll share personally: there have been seasons where I carried too much expectation. I wanted every gathering to be harmonious, every service to be inspiring, every family moment to be picture-perfect. The weight of that left me drained.

It wasn’t until I began asking, “What feels right for me this year?” that things shifted. Some years, that meant smaller gatherings. Other years, it meant focusing on rest. Sometimes, it meant embracing grief instead of pretending it wasn’t there.

The freedom came not from lowering the bar, but from changing the bar altogether.

Scripture as a Guide

Scripture offers wisdom for this journey:

• “Come to me, all you who are weary and burdened, and I will give you rest” (Matthew 11:28).
• “Better a dry crust with peace and quiet than a house full of feasting, with strife” (Proverbs 17:1).
• “Do not conform to the pattern of this world, but be transformed by the renewing of your mind” (Romans 12:2).

These verses remind us that peace, rest, and renewal are more valuable than performance.

Questions for Reflection

Here are some questions to ask yourself and reflect on:

• What expectations are weighing on me this season?
• Which traditions bring me joy, and which bring me stress?
• How do I want to feel during the holidays?
• What practices will help me embody that feeling?
• What conversations do I need to have with loved ones to set boundaries?

Designing Your Own Holiday Framework

Consider creating a simple framework for your season:

• Theme: Choose a word (peace, joy, simplicity, connection).
• Practices: Identify 3–5 activities that embody that theme.
• Boundaries: Decide what you will say no to.
• Support: Identify who can encourage you in this journey.

This framework becomes your compass, guiding you through the noise of expectation.

The Gift of Letting Go

Letting go of expectations is itself a gift. It opens space for:

• Joy: Found in small, authentic moments.
• Connection: Built on presence, not performance.
• Peace: Rooted in alignment with values.
• Freedom: To design a season that feels right for you.

It’s a gift you give yourself, and by extension, those around you.

Conclusion: A Season That Feels Right

The holidays don’t have to be perfect to be meaningful. They don’t have to meet every expectation to be holy. They simply need to be authentic, aligned, and spacious enough to breathe.

As you step into this season, may you find the courage to let go of what doesn’t serve you, and the freedom to design a holiday that feels right for you.

And may you hear the gentle invitation of Christ: “Peace I leave with you; my peace I give you. I do not give to you as the world gives” (John 14:27).

Thanks for stopping by the fire,

Coach Dennis