The Kristen Boss Podcast
Episode 240: Gratitude in the Hard
Date: November 24, 2025
Host: Kristen Boss

Episode Overview

In this Thanksgiving week solo episode, Kristen Boss explores the theme of “Gratitude in the Hard.” She candidly shares her own challenging experiences from the past year—the end of a major business, health crises, and personal loss—as she reflects on what it means to find real gratitude amidst adversity. Kristen offers listeners practical, compassionate wisdom for reframing the narrative of a difficult season, emphasizing agency and emotional honesty over toxic positivity. This episode is a compassionate reminder for entrepreneurs and anyone navigating tough times to honor the hard parts and find strength and meaning within them.

Key Discussion Points & Insights

1. Setting the Tone: Not Another Fluffy Gratitude Talk

• Kristen opens by acknowledging the difficulties many have experienced in 2025, including herself:
  • Letting go of a $20M business
  • Building something new from scratch
  • Dealing with family issues
  • Enduring a major health crisis
  • The sudden loss of her beloved dog, Hank
• She clarifies that this episode is not about “toxic positivity” or gaslighting pain but about finding honest gratitude alongside the hard.
• Quote:

  "How do we give thanks when everything is falling apart, when it’s heavy, when our dreams have not yet come to fruition, our prayers have not been answered, we’re in the messy middle, when things are still hard, when there’s no light at the end of the tunnel yet? How do we still find gratitude in those things?" — Kristen (07:45)

2. On Overstimulation and the Longing for Simplicity

• Kristen discusses the impact of information overload and chronic overstimulation on our mental health.
• She references a past episode with Sarah Boyd about how growing up in the 90s gave people natural boundaries that are missing now.
• The result: Many feel “heavy” and yearn for quieter, simpler times (06:00 – 08:00).

3. Learning from Hardship: Agency and Narrative

• Kristen reflects on how facing significant challenges made her more aware of her resilience and capability.
• She emphasizes the narrative we choose when interpreting hardship:
  • Are we telling ourselves we’re failures, or looking for growth?
  • What story do we want to tell about this season?
• Quote:

  “You can’t control your circumstances, but you can decide what you want to take from them. That’s been so much of my work this year.” — Kristen (09:30)

• She challenges listeners to consider what lesson hardship has offered them, and to be honest but gentle with themselves in framing that lesson.

4. Moving Beyond Passive Waiting

• Kristen critiques the tendency to wait for external circumstances to change (“January 1st as magical reset”) and urges listeners to embrace agency:
  • Change often doesn’t come from the outside; we must be the agents in our own stories.
  • “No one’s going to come and fix the story for you.” (16:35)
• Quote:

  “Sometimes the circumstances never change, but we change, we change in those circumstances. And suddenly what felt impossibly hard…starts to feel lighter—or we become more capable, we become stronger.” — Kristen (17:50)

5. Practical Self-Reflection

• Kristen encourages listeners to check where they’re waiting for change versus where they can act:
  • Seek therapy, set boundaries, apply for new jobs, invest in new skills
  • Take small, daily steps rather than waiting for a “magic wand” (19:00 – 20:30)
• She reminds everyone of the power of neuroplasticity—humans can rewire thoughts and habits at any age.
• Quote:

  “So much of your life is still available to you should you decide to live it differently. And there’s hope. Don’t think you’re too old or too far gone.” — Kristen (21:20)

6. Navigating the Holidays with Intention

• Kristen offers practical guidance for handling tough family dynamics over the holidays:
  • “Go in with a plan.”
  • Set boundaries, team up with a partner or loved one, and give yourself time-outs as needed
  • Be the calm and choose how you show up, even if you can’t change others (22:30 – 24:45)
• Memorable anecdote:

  “I just did the dishes a lot more…if I stay here, I’m gonna say things I later regret. So, I’m gonna just keep my hands wet and wash dishes in the sink.” — Kristen (23:40)

Notable Quotes & Moments

• On not bypassing pain:

  “It isn’t to bypass the hard in our life, and it’s not to always look for the silver lining, especially when grief demands to be felt.” (09:10)

• On agency:

  “You are the agent of change in your own life.” (17:10)

• On new beginnings not being magic fixes:

  “I think we see January 1st as like one giant Monday for all of us…Like, oh, finally going to be able to reset. But…people keep waiting for external circumstances to change so they can feel better about their life.” (15:30)

Key Timestamps

• 00:55 — Kristen introduces the episode and holiday context
• 04:45 — Personal hardships of the past year shared candidly
• 06:00 – 08:00 — Discussion of overstimulation, mental health, and nostalgia for simpler times
• 09:00 – 12:00 — Framing gratitude in hard seasons, avoiding toxic positivity
• 15:30 — Reflection on January 1st, the myth of the magical reset
• 17:10 – 18:30 — Embracing agency, becoming the agent of change
• 21:20 – 22:00 — The hope of neuroplasticity and changing your story at any age
• 22:30 – 24:45 — Practical holiday strategies for self-care and boundaries
• 25:20 — Final encouragement and closing thoughts

Takeaways for Listeners

• You can find gratitude in the hardest seasons—not by denying pain, but by choosing the most honest, constructive narrative.
• Stop waiting for the world to change; look for the small, actionable ways you can reclaim agency.
• It’s never too late to change your mindset, habits, or the story you tell about your life.
• Go into the holiday season with tools and plans for self-compassion, boundary-setting, and navigating tough interactions gracefully.

Summary Tone:
Kristen’s approach is warm, deeply honest, and pragmatic—acknowledging pain without minimizing it and guiding listeners to actionable hope. Her humor, vulnerability, and directness make this a meaningful listen, especially for those feeling the heaviness of the season.