Podcast Summary:

Squiggly Careers
Episode: CEO Shell-Shedding Moments: Kill or Continue? Making Hard Decisions with Fight Story’s Georgie Holt
Date: February 4, 2026
Guests: Sarah Ellis (host), Helen Tupper (host, off-mic), Georgie Holt (CEO of Flight Story)

Episode Overview

This special edition of the Squiggly Careers podcast explores the concept of “shell-shedding moments”—transformative, uncomfortable periods leaders face while growing, likened to a lobster shedding its shell to grow bigger and stronger. Host Sarah Ellis interviews Georgie Holt, CEO of Fight Story, about her hard-won lessons making tough decisions, balancing when to give up or persevere, and how she supports herself through vulnerable leadership moments.

Key Discussion Points & Insights

1. Introducing Flight Story and the Creator Economy (03:00–05:05)

• Georgie Holt introduces Flight Story as a media and investment company co-founded by Stephen Bartlett, with a mission to build the future of creator-led media.
  • “We really believe that the future of media is creator led.” (03:00, Georgie Holt)
  • Creators are replacing legacy media institutions by leveraging their personal brands as major intellectual property (IP).
• Example: Stephen Bartlett has built a blueprint for successful, human-centric media brands.

2. The Difference between Good and Easy Ideas (05:35–08:21)

• Georgie discusses a fundamental leadership insight:
  • There’s a significant difference between “good ideas” (which are inherently hard) and “easy ideas” (which tend to feel flowy or obstacle-free).
  • Hard does not mean bad—hard often means it’s a good, worthwhile idea.
• Quote:
  • “A big difference between a good idea and an easy idea...what I talk to my team about a lot is that a good idea is really hard because there aren’t that many. The good things are very hard, and it is what makes them good.” (05:35–08:21, Georgie Holt)
• Holds two truths: good = hard, and these tensions are part of growth.

3. Kill or Continue – Making Hard Calls (09:21–13:39)

• Georgie explains Flight Story’s philosophy of “Kill or Continue” decisions:
  • The goal is to discern—using data and evidence—whether to persist or let go of projects or ideas.
  • Fast, deliberate decision-making is vital for a fast-moving company.
  • Clear goals, vision, and metrics act as the filter for these decisions.
• Quote:
  • “The kills or the losses feel like wins, because the faster you kill something, the more you can focus on your primary goals and drivers...failure is intrinsic to our results and our ability to succeed.” (09:23–12:15, Georgie Holt)
• Emphasizes decision frameworks, first principles, and conscious alignment with desired outcomes.
• Key reflective question: “Who am I when no one is looking?...What would the most courageous version of me do?” (12:15–13:39, Georgie Holt)

4. Creating Structure for Vulnerable Moments (13:40–15:07)

• Discussed importance of building structures that allow for difficult, objective conversations:
  • “You’ve worked really hard to create a lot of clarity, both for yourself and for other people…what do we use as a filter for our decision making that isn’t just how I happen to feel about something?” (13:40–15:07, Sarah Ellis)
• Encourages leaders to be transparent and use frameworks rather than gut feelings, reducing ambiguity and anxiety.

5. How CEOs Support Themselves During Shell-Shedding Moments (15:08–19:05)

• Georgie shares her support strategies:
  • Primarily turns inward—reflects on her own first principles and self-knowledge before seeking external advice.
    • “Can I be really honest? I go to myself…there are people in my cell phone that I call…but I like to understand how I think about something before I even go and ask someone else.” (15:07–16:00, Georgie Holt)
  • Acknowledges that turning inward is rare, especially among women leaders, and reflects on building healthy self-worth and self-reliance.
  • Reminds herself: “It's on you to get you to where you want to be.” (17:57, Georgie Holt)
  • Stresses the need to welcome discomfort as a sign of growth and opportunity rather than something to avoid.
  • Encourages being open to insights—sometimes answers or inspirations come unexpectedly when you’re alert to them.

6. Reframing Discomfort and the Growth Mindset (19:05–20:39)

• The hosts discuss research showing people often equate discomfort at work (“I feel bad, therefore I must be failing”) with a need to seek safety or ease, when in fact discomfort can signal a valuable stretch or growth moment.
• Personal anecdote from Sarah Ellis: steep learning curves can feel overwhelming but are necessary precursors to real development.
  • “Actually, don’t give up now because then you’re not going to get the rewards of all that learning.” (20:38, Sarah Ellis)

7. Parting Advice – Learning and Self-Compassion (21:04–22:36)

• Georgie offers two key pieces for listeners:
  1. Distinguish good ideas from easy ideas and welcome hard, growthful challenges.
  2. Embrace “love notes to yourself”—capture moments of self-appreciation, insights, and affirmations along the journey.
     • Inspired by creator Maggie Sellers (Riam on Hot Smart Rich).
     • “You’re writing this extended love letter through the rest of your professional and personal life.” (22:18, Georgie Holt)
• Celebrate and document self-progress and moments of courage to fuel long-term leadership development.

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 05:35 | Georgie Holt | “A good idea is really hard because there aren’t that many…hard is what makes it good.” | | 09:23 | Georgie Holt | “The kills or the losses feel like wins, because the faster you kill something, the more you can focus on your primary goals…” | | 12:15 | Georgie Holt | “Who am I when no one is looking? Who would I be if I was the very best version, the most courageous version of myself in this moment?” | | 15:10 | Georgie Holt | “I go to myself…and I don’t hear many women say this. It feels like an unusual thing for a woman to say.” | | 17:57 | Georgie Holt | “It's on you to get you to where you want to be.” | | 22:18 | Georgie Holt | “All of these notes and ideas are going to start to be constructed into a sort of a sense of appreciation and gratitude of how far you are progressing…and be the most courageous version of yourself.” |

Timestamps for Key Segments

• 00:00–01:10: Book pre-order and episode context
• 02:01–05:09: Introduction to Georgie Holt and Flight Story’s vision
• 05:10–08:21: Good versus easy ideas, embracing hard problems
• 09:21–13:39: Kill or continue decisions and strategic frameworks
• 13:40–15:07: Creating clarity and support systems
• 15:08–19:05: CEO self-support through vulnerable moments
• 19:05–20:39: The value of discomfort and growth curves
• 21:04–22:36: Final advice and the power of self-affirmation

Episode Tone & Refreshing Openness

The conversation is reflective, practical, and candid, with Georgie offering warm encouragement and unguarded self-insight. Throughout, there’s a focus on actionable frameworks, self-awareness, and embracing both the vulnerability and excitement of stepping beyond comfort.

Key Takeaways

• Good ideas are often challenging; discomfort is a sign of learning.
• Build frameworks (like “kill or continue”) to make difficult decisions less subjective and more mission-driven.
• Know and trust yourself first, but also stay open to unexpected insights from others and the world around you.
• Celebrate progress by documenting moments of growth and self-appreciation (“love notes” to yourself).
• Reframe discomfort as a positive signal—a shell-shedding step towards becoming bigger, braver, and better.