Squiggly Careers: Skills Sprint – How to Lead Your Own Learning by Sharing It

Hosts: Helen Tupper & Sarah Ellis
Date: January 23, 2026
Episode Theme:
How to unlock deeper, lasting personal and team learning by proactively sharing what you know—a fun, effective and confidence-building approach to career development.

Episode Overview

The final day of the Squiggly Skills Sprint centers on the powerful idea that sharing your learning is a proven, practical strategy for cementing new skills and knowledge—while fostering collective growth. Helen and Sarah dig into why people hesitate to share, how you can make learning contagious in your team culture, actionable ways to start (including the “helpful how to”), and why overcoming confidence barriers matters. The episode wraps with inspiring career advice and a hands-on community challenge.

Key Discussion Points & Insights

1. The Double Win of Sharing Learning

• Why Sharing Matters:

  • When you share what you’ve learned, you deepen your own understanding and help others grow.
  • Reflection and articulation—required when sharing—help you spot gaps in your knowledge.
  • Helen: “Not only when you share does your learning last longer because you have to reflect on what you know. … but also you’re sharing that with someone else, so it helps them too.” [01:00]

• Cultural Impact:

  • Sharing learning frequently as a team makes learning part of your culture, not just an individual activity.

2. What Gets in the Way – and Why It Doesn’t Have To

• Barriers:

  • Most organizations don’t share learning effectively, but it’s usually less about being competitive and more about lacking natural opportunities.
  • We often wait for the “when” rather than making sharing a habit.
  • Sarah: “People keep a lot of what they’re learning to themselves… not because it’s a competitive advantage, but because there’s just not the opportunity, there’s not the when.” [01:40]

• Rubber Duck Debugging Analogy:

  • Describes how explaining something aloud (even to an inanimate object) forces clearer thinking and reveals what you don’t fully grasp.
  • This “sense-making process” works for everyone, not just coders.
  • Sarah: "We want a lobster to kind of talk to the lobster. ...You’re just having to explain… it’s like a sense making process.” [02:31]

• Confidence “Gremlins”:

  • Fear of not being “expert enough” can block people from sharing. Don’t let perfectionism or imposter syndrome get in the way.
  • Helen: “We don't want that fear of expertise to get in the way… find fun ways to share and it becomes easier.” [03:29]

3. How to Share: “Helpful How To’s” and the Power of Play

• The ‘Helpful How To’:

  • A fun, low-pressure team exercise where everyone preps and shares a quick “how to” on anything—work or non-work related.
  • Examples from the team included “how to make pour-over coffee,” “how to poach an egg,” “how to learn a language,” and “how to get better at writing copy.”
  • Sarah: “It was fun, it was fast… everyone was laughing… it felt universally like something everyone could just have a go at.” [05:06]

• Easing In:

  • Start with any topic, then progress to work-related or process-based “how to’s.”
  • Team members may request how-to’s from others based on perceived strengths. This surfaces skills we might undervalue in ourselves.
  • Helen: “Once everyone starts practicing it, you’ll just get a bit more confident giving it a go.” [06:49]

4. LIVE DEMO: Helpful How-To’s (Extrovert vs Introvert Approaches)

Situation: How to go to an event if you feel nervous

• Helen’s Extrovert Tips: [07:11]

  1. Research who’ll be there—makes it easier to connect quickly.
  2. Enter the room with energy—attracts others and reduces nerves.
  3. Take control—introduce people to each other and give yourself a constructive “role.”
  • Quote: “If you can be the person that gives energy, I think you…become a bit of a magnet. Energy attracts other people.” [07:11]

• Sarah’s Introvert Tips: [08:02]

  1. Go with someone—don’t feel you have to go alone.
  2. One meaningful connection is a win—don’t pressure yourself to network with everyone.
  3. Follow-up thoughtfully—often an introvert’s strength is building the relationship after the event.
  • Quote: "Meeting one new person is a win...if I have made one meaningful connection, then that's actually really useful." [08:02]
  • Self-awareness: Don’t let introversion become an excuse to avoid events—stretch yourself.

5. Final Wisdom and Community Action

• Inspiring Advice from Dr. Carly Daniels (25-year lobster expert): [09:35]

  • “Dive into everything you can at work, even those jobs you think will be hard or you’re not sure if you know how to do it. Don’t be afraid to ask questions and have confidence in yourself as learning often hides in the places we least expect.” [09:49]
  • “I discovered my strengths and passions not by knowing, but by doing, volunteering, and giving it all a go. Remember that everyone started somewhere and had to learn to get where they are in life.” [10:24]

• Action Challenge: [10:31]

  • Share your own “helpful how to”—on any topic, for work or life—on LinkedIn, tagging the Squiggly Sprint and Amazing If. If enough are contributed, they’ll compile a community “helpful how to” handbook.

Notable Quotes & Memorable Moments

• "We're really trying to help you to be lobster-like with your learning." — Sarah [00:26]
• "The more generous we are with our learning, the better it is for us, and obviously the better it is for everybody’s growth." — Sarah [03:29]
• "Don’t let that fear of expertise get in the way of sharing. The more fun ways you can find, the easier this gets.” — Helen [03:29]
• “Playing is a really good way to learn.” — Helen [05:40]
• “Everyone started somewhere and had to learn to get where they are in life.” — Dr. Carly Daniels [10:24]

Timestamps for Important Segments

• 00:01 – Gratitude for participation, lobster learning metaphor
• 01:00 – Why sharing cements learning ("double win" explained)
• 01:40 – Barriers to sharing and the rubber duck analogy
• 03:29 – Confidence gremlins and making sharing fun
• 04:20 – “Helpful how to” exercise explained
• 07:11 – Helpful how to: Extrovert vs introvert event strategies
• 09:35 – Career wisdom from Dr. Carly Daniels
• 10:31 – Community action: Share your own helpful how to

Conclusion

This episode champions “leading your own learning” by sharing your journey, ideas, and practical skills with others—for the benefit of yourself and your wider community. Power through barriers like expertise anxiety, start with small, playful steps, and watch as learning becomes contagious. See sharing as both your gift to others and a fast track to your own growth.

Next Steps: Share a “helpful how to” in your team or online, and keep the squiggly learning spirit alive.