Rethinking the Holidays: Less Pressure, More Presence

7 snips

Nov 19, 2025

The holiday season can be both joyful and stressful for leaders. It serves as a diagnostic tool, revealing gaps in leadership and team trust. Bill emphasizes breaking down Thanksgiving into gratitude and generosity. He suggests mapping holiday logistics for family and teams to avoid past issues. Practicing specific appreciation and acceptance enhances interactions. Leaders are encouraged to step back from control, fostering participation and inclusion. Overall, it's about embracing the season with a focus on connection and thoughtful generosity.

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INSIGHT

Holidays Are Joyful And Stressful

Holidays mix joy with added stress that leaders must acknowledge.
Bill Gallagher says personal and work pressures bleed into each other and affect teams.

ADVICE

Two-Part Thanksgiving Practice

Break 'Thanksgiving' into thanks and giving as a simple leadership practice.
Bill Gallagher advises starting with gratitude and moving to generosity and acceptance.

ADVICE

Plan Holidays With Who, What, When

Plan holidays by asking who, what, and when for family and team events.
Bill Gallagher recommends sharing those plans with your team and inviting their participation.

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Are you planning time off or avoiding the truth about your team?

In this solo episode, Bill explores how the holiday season acts as a diagnostic tool for your business. Are you building a company that thrives without you or one that collapses the second you unplug? He shares why most founders avoid taking time off and how strategically stepping away can highlight leadership gaps, capacity issues, and trust breakdowns. If you're feeling pulled in every direction heading into November or December, this episode is for you.

Topics explored in this episode:

(01:15) The Holiday Season Is a Double-Edged Sword

*The holidays are often very joyful, but they also carry a lot of stress.

*Leaders are managing business deadlines, shorter days, and personal expectations collide.

*It's important to acknowledge that stress exists alongside celebration

(02:25) Redefining “Thanksgiving”

*Break “Thanksgiving” into two core practices: Thanks (appreciation) and Giving (generosity).

*Start with gratitude for team members, family, and yourself.

*Let go of expectations, and express that through generous action.

(5:25) Build Systems That Let You Breathe

*Think through the logistics of how you will see and connect with friends and family.

*What’s gone wrong in the past? How can you prevent it from going wrong this year?

*Apply the same reflection to your team; ask how they’re feeling and what support they need

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

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Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

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