Squiggly Careers Live:

How You Can Keep Learning at Work (Even When It Feels Hard)
Date: February 10, 2026

Episode Overview

This special live episode of the Squiggly Careers podcast, hosted by Helen Tupper and Sarah Ellis, brings together stories and insights on how to keep learning during the tough, "shell-shedding" moments at work. Anchored by the metaphor of the lobster—creatures that never stop growing because they’re willing to shed their shells—the event features candid discussions with guest speakers Maya Richura (mental fitness and visualization expert), Tamaine Ekerell (co-host of the Making Money podcast), and Amy Conroy (Paralympian, Squad Games co-founder). Together, the group explores vulnerability, resilience, authenticity, and strategies for continuing to learn in the hardest times.

Main Discussion Themes

The Lobster Metaphor & Learning in Hard Moments

• Why Lobsters? The team uses lobsters as a growth role model:
  • Lobsters have indeterminate growth—they never stop growing.
  • To grow, they shed their hard shell, which leaves them temporarily vulnerable (jelly-like), before regrowing a bigger, stronger shell.
  • The old shell becomes fuel—they use what they leave behind to keep developing.
• Learning is Hardest—and Richest—When We’re Uncomfortable.
  • "Learning doesn't make the top of our to-do list in those moments… but it’s where we grow the most." (Helen, 06:51)
• The Importance of Staying Curious: The podcast grew out of Helen and Sarah’s own need to keep learning and remain curious together (02:30).

Key Discussions & Insights

1. Maya Richura: Mental Fitness & Visualization (09:00–22:30)

Maya’s Story

• Former elite athlete whose journey was derailed by severe ulcerative colitis at 15.
• Suffered physically & emotionally but found hope after a chance introduction to visualization while in hospital:
  • “What Helen doesn’t also know is that I knew about your work when I was at university, because… it’s okay if you don’t, you know, go into one job and spend 30 years there.” (Maya, 10:51)
  • Visualization (mentally rehearsing walking) became both a coping strategy and a new passion, ultimately helping her heal and build mental resilience.

Insight: Shell-Shedding is Hard, But Necessary

• Resisting tough moments increases pain—acceptance (“surrender”) leads to growth.
• Mental fitness—the skill of working on your mind—is as vital as physical fitness, but under-prioritized:
  • “So many people doubt their potential but they don’t doubt their limits. Why?” (Maya, 17:43)
• Visualization isn’t only for athletes; it’s about rewiring your brain to handle discomfort, setbacks, and fear.

Memorable Moment

• Maya’s pursuit of working with Nike is a prime shell-shedding journey:
  • Repeated, unreturned outreach; faced rejection and embarrassment but persisted through visualization and self-belief.
  • “My shell was broken. My ego was dead… But every day I was visualizing me at Nike somehow, whether it was doing an event with them, working with them, something. So I was wiring my brain to not give up.” (Maya, 18:50)
  • Eventually, became Nike’s first-ever Mental Fitness Trainer—a testament to grit and not waiting for opportunity, but creating it.

2. Tamaine Ekerell: Embracing Not Knowing & Learning Publicly (22:30–41:14)

Tamaine’s Career Journey

• Held a wide variety of jobs but found his most challenging “shell-shedding” moment as cohost of the Making Money podcast.
• Joined as a finance novice and initially tried to pretend expertise, but quickly realized authenticity resonated most:
  • “It was really scary because I thought, I have to be a finance expert. But then… my cohost and my director said, ‘You don’t need to be an expert, you need to be yourself.’ ... People in the YouTube comments were like, it’s really refreshing…” (Tamaine, 24:22)

Learning In the Open & Handling Feedback

• Publicly acknowledging gaps (“What is ROI?”) gave listeners permission to learn with him.
• Stresses the value of honest, constructive feedback:
  • “Asking for feedback is really valuable… but it needs to be honest.” (Tamaine, 28:50)
  • Overcoming nerves by preparing, exercising, and sleeping well.
• Encourages actively seeking critique and making note of mistakes to avoid repeating them:
  • “Write down on your notes: do not interrupt in capital letters... speak slowly in capital letters…” (Tamaine, 35:12)

Notable Quotes

• On self-disqualification:
  “Most people disqualify themselves. So if you think, ‘I’m not good enough,’ then you probably won’t be.” (Tamaine, 34:42)
• On improvement: “You have to make learning part of your life… Consistency is the most important thing.” (Tamaine, 39:36)

Memorable Moment

• The “podcasting is basketball” metaphor:
  “You can’t be a podcaster and not watch your videos. Embrace the cringe. It’s like a chef: taste your food.” (Tamaine, 36:51)

3. Amy Conroy: Resilience Through Disability, Sport & Humor (41:21–59:07)

Amy’s Story

• Diagnosed with rare bone cancer at 12, resulting in leg amputation and grueling chemotherapy.
• Her relationship with her father—cheerful, endlessly supportive—anchored her through loss and change.
• Learned resilience through adversity, and found basketball as an outlet and source of self-worth and community:
  • “It’s not those ‘cushti’ success stories that distill who we are, it’s those times when our backs are against the wall and we’re having to dig really deep…” (Amy, 44:26)

Insight: Noticing, Humor & Owning Vulnerability

• Humor and kindness are key coping strategies:
  • “Sometimes just when you’re at your lowest, a bit of sense of humor… you really can change people’s day…” (Amy, 49:24)
• Admits to earlier internalizing negative perceptions about disability—had to “shed” her own self-doubt and self-censorship to join the national basketball team.
  • “I was the one getting in my own way… Sometimes whether you feel ready or not, you just have to get in the arena and go for it.” (Amy, 56:58)
• Stresses that failure (losing games) builds more learning than winning; honest post-mortems and dealing with egos helps teams improve.

Practical Wisdom

• Control your attitude if you can’t control the circumstances.
• Notice negative mental habits—what are you focusing on?
• “Don’t wait for everything to be perfect… be your own hype man and go for it.” (Amy, 58:55)

Memorable Moment

• On not letting “what ifs” and insecurities stop you:
  • “Now I’m not going to let what ifs and self-doubt and my own insecurities let me limit my own goals or dreams… Don’t be the one holding you back.” (Amy, 57:10)

Notable Quotes & Q&A Highlights

• On Authenticity:
  “All of us are born very, very unique, but most of us die a copy of someone else… Life isn’t about just having more things and copying. It’s about being more—more of who you are…” (Maya, 60:54)
• On Self-limiting Advice:
  "Never take advice from someone who hasn't done it... people will limit you based on their perspectives." (Tamaine, 62:35)
• Longest-lasting Advice:
  “Train so hard until your idols become your rivals.” (Amy, 60:53)

Timestamps for Important Segments

• 01:08 — The origin of Squiggly Careers and learning as a path through work-life's squiggles.
• 04:05 — Introduction to the lobster metaphor and why it’s central for lifelong learning.
• 09:00 — Maya Richura’s story and the power of visualization for growth.
• 22:30 — Tamaine Ekerell on embracing discomfort, authenticity, and learning in public.
• 41:21 — Amy Conroy, paralysis, sport, humor, and shell-shedding for true resilience.
• 56:45 — Amy’s advice for not letting self-doubt limit your growth.
• 59:31 — Guests share the best advice they've ever received.
• 62:55 — Closing thanks and final group encouragement.

Final Advice & Takeaways

• Keep Learning, Especially When It’s Hard: Shell-shedding moments are inevitable and are where growth happens.
• Embrace Discomfort as Data: Don’t avoid hard feelings—lean into the learning.
• Feedback Is Critical: Seek it honestly, process it bravely.
• Community Matters: Share mistakes, be honest with those around you.
• Be Your Authentic Self: Don’t let external voices or your own doubts shrink your potential.

For more resources, tools, or inspiration, sign up for the “Squiggly Careers in Action” newsletter or pick up their new book, Learn Like a Lobster.

[End of Episode Summary]