Podcast Summary: "STOP Doing Courses: The New Way to Learn at Work"

Jimmy’s Jobs of the Future w/ Helen Tupper
Release Date: February 11, 2026
Host: Jimmy McLoughlin (Boxlight Creative Studio)
Guest: Helen Tupper, co-founder of Amazing If, co-author of "Learn Like a Lobster" & "The Squiggly Career"

Episode Overview

This episode explores the future of learning at work, challenging the conventional wisdom of workplace courses and formal training. Host Jimmy McLoughlin chats with Helen Tupper—co-founder of Amazing If and champion of “Squiggly Careers”—about her latest book, "Learn Like a Lobster." They discuss why traditional courses are insufficient, introduce the "lobster" model for continuous learning, and share actionable strategies for embedding learning into everyday work life. The conversation is practical, insightful, and candid, moving from personal growth to business models, team culture, and even playful ways to boost learning.

Key Discussion Points & Insights

The Problem with Learning at Work

[02:01–03:20]

• Helen: It's never been more crucial to learn at work given rapid change, but it’s rarely been harder. People feel overwhelmed, don't see role models, and lack time.

“If we do not solve the problem of learning at work, then a lot of people are going to get left behind.” [02:06]

• Obstacles Identified:
  • Learning feels time-consuming
  • Lack of visibility for learning role models
  • Learning not embedded in daily work—seen as extra, not integral

The "Lobster" Metaphor for Learning

[03:20–05:50]

• Lobsters embody traits that map powerfully onto personal and workplace learning:

  1. Never Stop Growing:

     • Lobsters grow throughout life, "till the day they die."
     • Continuous learning is crucial to career resilience.

  2. Shedding the Shell (Vulnerability):

     • Growth only happens when lobsters risk vulnerability by shedding their shell.
     • People grow most when they step outside their comfort zone, even (especially) during difficult periods.

  3. Resourcefulness (Eating the Shell):

     • After molting, lobsters eat their old shell to fuel new growth.
     • Learners should use their experiences and setbacks as raw material for continued growth.

“You would never stop learning, like the lobster never stops growing... In your hardest moments when you're vulnerable, that would be the moment that you learn the most.” – Helen [04:55]

Learning Mindset & Everyday Moments

[06:54–08:14]

• Mindset: Prime people to seek learning actively.
• Moments: Recognize and utilize current activities (like meetings) as learning opportunities, rather than always adding new events or courses.

“We're already in 12 meetings this week... How do we add more moments of learning in those meetings?” – Helen [07:16]

• Practical tip: Review your calendar for learning opportunities at the start of each week.

Rethinking Meetings & Agile Work Culture

[08:36–10:40]

• Helen’s company eliminated routine 1-to-1s, focusing instead on “decision and discussion agendas.”
• Meetings are reframed to maximize clarity, purpose, and learning—preferably using agenda questions to drive energy and focus.

“It has been so helpful. Both people feel better at the end of it... It's been a bit of a game changer.” – Helen [09:42]

• Notable Stat: 70% believe less meetings would increase job satisfaction [07:44]

Where Learning Really Happens

[14:19–16:11]

• Feedback is invaluable for surfacing transferable skills and growth areas.
• Ask colleagues: “What 3 skills do I use when you see me at my best?”
• Compare data received to what you want to be known for; decide where to focus your development.

Confidence Curves & Hard Moments

[16:12–17:27]

• Career confidence isn’t linear; major changes and "squiggly" turns often result in lost confidence as well as growth.
• Normalizing vulnerability is essential for learning and innovation.

Becoming a Better Thinker: "Out Loud" vs "Quiet" Thinking

[17:49–21:55]

• People have natural problem-solving preferences:

  • Out-Loud Thinkers: Process by talking things through (Helen, Jimmy)
  • Quiet Thinkers: Reflect internally before speaking (Helen’s business partner Sarah)

• Challenge: Try out the opposite style occasionally to expand your mental toolkit and deepen your learning.

• On Boredom & Creativity:

“We're not allowing children to be bored. But in that moment of boredom is actually where creativity happens.” – Helen [21:55]

Ditching the "Course" Mindset (Practical Learning)

[23:18–26:06]

• Real learning at work comes from:
  • Experimenting
  • Failing
  • Seeking feedback
  • Sharing knowledge
• Learning is not about taking courses. Effective workplace learning is embedded, continuous, and social.

“None of them look like going on a course. It is about these practical things that we can do every day.” – Helen [23:40]

• Jimmy’s Example:
  • Did a stand-up comedy course but realized he probably learned more from simply doing it and connecting with others than from the course material itself.

The Future of Learning: Team & Social Learning

[27:45–32:17]

• Most learning initiatives focus on individuals, but Helen predicts a shift toward team-based learning.
  • Helpful How-To Exercises: Team members quickly share a practical, teachable skill with others, fostering a learning culture.

“Sharing is a really powerful way that we improve our learning as well as moving it to someone else...” – Helen [29:15]

• Teams in companies (like Kerry Dairy) already run daily "learning sprints" together—10 minutes a day as a team.

• Celebrating Learners: Companies should recognize learning (not just promotions), celebrating those who model continuous improvement.

Saying and Hearing “The Hard Thing”

[32:17–40:10]

• Most organizations avoid difficult feedback; unsaid truths block growth.
  • Skill 1: Saying the hard thing (with a framework for candor)
  • Skill 2: Hearing the hard thing (with openness, reflection, and feedback ‘multiplication’)
• Multiplier Effect: When receiving tough feedback, a powerful practice is to reflect, seek multiple perspectives, and then loop back with actions.

“Hearing the hard thing, like holding or ignoring it... being able to kind of hear the hard thing and hold it so that you can actually learn from it.” – Helen [33:41]

• Personal example: Helen recounts giving her co-founder feedback at the wrong time and learning to improve her delivery through follow-up discussions across her network.

The Squiggly Business Model

[41:19–47:13]

• The "flywheel" model (inspired by Jim Collins) underpins Amazing If:
  • Create useful content (books, podcasts, articles)
  • Build a community of supporters and sponsors
  • Offer products/services (workshops, toolkits)
  • Generate data, insights, and income that fuel further content
• Growth is organic, community-driven (rarely outbound sales).
• Team structure is aligned to each part of the flywheel.

Play, Fun, and Learning

[47:14–49:31]

• Play is essential for learning and team cohesion.
• Ideas to inject play:
  • Team Spotify playlists (each member explains a song that represents them)
  • "Save in a Fire" item-sharing exercise
• “The irreverent fun stuff... is important. Right. It's partly why people come to work.” – Jimmy [47:36]

Ambitions & The Next Decade

[49:56–51:23]

• Helen and Sarah are pursuing PhDs, aiming to make "Squiggly Careers" a global, credible movement, and to demonstrate that flexible, learning-driven progression is better than rigid career ladders.

“We want Squiggly to be synonymous with careers globally... I want it to be normalized and I really want it to be credible.” – Helen [50:01]

Practical Takeaway: Job Crafting

[51:30–54:58]

• "Job crafting" means evolving your role for both value creation and playing to your strengths.
• Action: Scan five LinkedIn job descriptions for roles you’d be interested in, highlight appealing responsibilities, identify commonalities, and pitch custom versions of your role to your manager close to these strengths and business goals.

Modern Hiring & Co-Creating Roles

[55:18–58:12]

• Amazing If's approach:
  • Hire people as contractors first
  • Discover their strengths and co-create a role that's both valuable to the business and fulfilling to the individual
• Result: No strict job specs; a culture embracing ambiguity and flexibility

Notable Quotes

• "If we do not solve the problem of learning at work, then a lot of people are going to get left behind."
  — Helen Tupper [02:06]

• "You would never stop learning, like the lobster never stops growing. In your hardest moments when you're vulnerable, that would be the moment that you learn the most."
  — Helen Tupper [04:55]

• "None of [these methods] look like going on a course... it is about these practical things we can do every day."
  — Helen Tupper [23:40]

• "The ability to learn is going to be absolutely paramount... It's the skill we look for more than anything."
  — Jimmy McLoughlin [22:26]

• "I would love us to put learners on a bit of a pedestal... not just promotions."
  — Helen Tupper [30:46]

• "We co-create roles... together we co-create a role that is both valuable for the business and the best use of that person's strengths."
  — Helen Tupper [57:16]

• "Curious, connected, challenging."
  — Helen Tupper describes Jimmy at his best [60:03]

Timestamps for Key Segments

| Segment | Time | |------------------------------------------|--------------| | The problem with learning at work | [02:01–03:20]| | The lobster model explained | [03:20–05:50]| | Embedding learning in meetings | [06:54–08:14]| | Banishing pointless meetings | [08:36–10:40]| | Using feedback for self-awareness | [14:19–16:11]| | Out-loud vs quiet thinkers | [17:49–21:55]| | Ditching the course mindset | [23:18–26:06]| | Future: Team-based learning | [27:45–32:17]| | Saying & hearing the hard thing | [32:17–40:10]| | Amazing If's flywheel business model | [41:19–47:13]| | Play & learning at work | [47:14–49:31]| | Ambitions for Squiggly | [49:56–51:23]| | Job crafting explained | [51:30–54:58]| | Co-creating roles & hiring | [55:18–58:12]| | Three words to describe Jimmy | [60:03–60:58]|

Memorable Moments

• Helen banishing 1:1 meetings:
  “It just felt like a nice chat... All these one-to-ones were filling my diaries with no agendas.” [08:41]

• Reframing feedback with the multiplier effect:
  “I acknowledge it... But the multiplier effect is where I take your feedback and I then go and talk about it with a couple of other people... you multiply the learning.” [34:55]

• Helen’s playlist idea for team fun:
  “Everyone in the team has to pick a track that is either meaningful to them or they think represents them... it’s fun and it's a good way of learning about each other.” [47:44]

• Co-founding patrons of a lobster hatchery “because we've gone pretty deep in the world of lobsters. Pun entirely intended.” [36:51]

Final Reflection

Helen and Jimmy present a compelling, down-to-earth vision for the workplace where learning is constant, visible, playful, and collaborative—not confined to cumbersome courses or formal training. The "lobster" is a sticky, practical metaphor: we must continually shed our shells, embrace new challenges, and consume our experiences for future growth. Their approach offers practical tools for individuals and organizations to rewire habits, boost team connectedness, and keep evolving in the world of squiggly careers.

Recommended Action:
Read "Learn Like a Lobster" and look for opportunities every week to "shed your shell"—find one real, vulnerable learning moment in your daily work and use feedback as fuel for growth.