Squiggly Careers Podcast: CEO Shell-Shedding Moments — How to Fix Friction at Work Fast with Helen Tupper

Episode Date: February 3, 2026
Hosts: Sarah Ellis (B), Helen Tupper (A)
Main Theme:
This special episode of the "Squiggly Careers" podcast dives into "shell shedding moments"—those uncomfortable, energy-draining experiences in the workplace that, while challenging, ultimately foster professional growth and resilience. Host Sarah Ellis interviews her co-founder and CEO of Amazing If, Helen Tupper, turning the lens inward on their unique co-founder dynamic and exploring how individuals and teams can effectively handle friction, mistakes, and discomfort at work.

Episode Overview

Helen Tupper shares personal shell-shedding moments as a CEO—times she’s encountered professional friction or discomfort, what she’s learned, and practical strategies for listeners to use when facing their own challenges. The conversation also lifts the curtain on the founders’ friendship and working relationship and offers candid, actionable advice for dealing with difficult moments with colleagues.

Key Discussion Points & Insights

1. Defining “Shell Shedding Moments”

• Shell shedding (inspired by lobsters shedding their shells to grow): Work moments that feel exposing or uncomfortable, but are necessary for development.
• Main takeaway: These moments are often energy-zapping and tough, but looking for the learning helps individuals to emerge stronger.

2. Helen’s Memorable Shell Shedding Experience

[02:07 – 05:09]

• Helen describes being a guest on a podcast where she felt interrogated and her integrity was questioned.
  • She was taken aback by the unexpected tone and intent:

    “It felt much more like I was being interrogated...almost like the integrity of Squiggly Careers was being challenged.” (A, 02:32)

• Helen admits she wanted to stop the interview but didn’t feel able to in the moment due to the live-recording setting and accompanying pressure.
• Learning Reflection:
  • In hindsight, Helen realized that listening to previous episodes of the host’s podcast could have prepared her for the style and possible provocation.
  • Despite learning this, she confesses to not having implemented this preparation in future appearances, defaulting to trust in others’ good intent.

3. Processing Uncomfortable Moments

[05:09 – 08:24]

• Helen identifies two vital supports:
  • People: Sharing uncomfortable moments quickly with her team helped stop negative rumination.

    “Sharing it pretty quickly stopped the spiral, which meant... I could move more into a learning frame of mind.” (A, 06:21)

  • Accurate reflection: Supportive teammates listened to the problematic podcast episode afterward, reassuring Helen that the reality was less dire than it felt, which allowed room for learning instead of lingering self-doubt.
• She values not only supportive but reflective conversations:

  “Supportive conversations kind of make you feel nice, but you don’t necessarily learn.” (A, 08:14)

4. Turning Mistakes into Learning

[10:16 – 11:43]

• Amazing If’s practice of “mistake moments” (a team ritual of sharing and analyzing mistakes and learnings) normalizes vulnerability and fosters collective growth.
  • The process: identify the mistake, analyze what led to it, and articulate the learning.
• Emotional challenge: Helen struggles with feelings of letting people down, which can overshadow learning. The structured process helps her move from guilt to growth.

5. Navigating Co-founder Friction

[11:43 – 19:35]

• Sarah and Helen reflect on the unique dynamic of running a company as friends turned co-founders.
• Helen notes that their rare moments of relationship friction often occur in social contexts, not at work:

  “Social situations together... just not very good...our connection is at its best when we’re working.” (A, 14:26)

• Both agree that:
  • Discussing friction openly, rather than ignoring it, is critical; this prevents negative feelings from festering into resentment.
  • Being forced to “fix friction fast” has made their partnership—and friendship—stronger.
  • Memorable quote:

    “If you just kept having those examples breed resentment, you’d never grow from it.” (B, 15:51)

Example: Writing Together Gone Wrong

[16:39 – 17:46]

• They recount a tense period co-writing a book chapter, where each rewrote the other's work rather than discussing disagreements—leading to passive-aggressive cycles.
• Lesson: Sometimes “saying the hard things”—even if just to admit something isn’t working—is essential for growth.
• Recognize when you’re stuck and consciously let go to move forward:

  “In order to grow, sometimes you do have to say the hard things. ...It might be just 'This isn’t working.’” (A, 17:49)

6. Tactics for Fixing Friction Fast

[19:35 – 21:00]

• Change the context: Move difficult conversations out of message threads or docs; switch to calls, walks, or face-to-face to avoid misinterpretation and build understanding.
• Know your audience: When others are present, be mindful that your usual back-and-forth might be misread, and adapt communication accordingly.

7. Advice for Listeners: Don’t Be Defined by the Hard Moments

[22:52 – 23:59]

• Helen’s top tip:

  “I think you want to be developed by it, but I don’t think defined by...[take] what you can and then leave it behind, because there are lots more shell-shedding moments ahead of you to come.” (A, 22:52)

• Sarah concurs, underlining that how you act after hard moments matters more than the moment itself.

8. Practical Tools to Move Forward

[24:20 – 25:28]

• For those who struggle to let go: write things down, tell your story, and avoid ruminating by repeatedly retelling the same tale—these actions help release the experience and move on.

Notable Quotes and Moments

• On what to do in uncomfortable interviews:

  “I want to stop this interview…and then feeling like I couldn’t...It felt very difficult...quite exposing.” (A, 03:02)

• On sharing quickly:

  “Sharing it pretty quickly stopped the spiral.” (A, 06:21)

• On learning vs. support:

  “Supportive conversations kind of make you feel nice, but you don’t necessarily learn.” (A, 08:14)

• On mistake sharing:

  “The process means at least I can let the learning in. And in sharing, you end up getting support from people.” (A, 11:43)

• Advice on hard moments:

  “I don’t think you want to be defined by it. So...take from it what you can and then leave it behind." (A, 22:52)

• On relationships and growth:

  “In order to grow, sometimes you do have to say the hard things. Which...might be just ‘This isn’t working.’” (A, 17:49)

Timestamps for Key Segments

• 02:07: Helen shares a shell-shedding moment (difficult podcast experience)
• 05:09: How Helen seeks support and learns from hard moments
• 10:16: Sharing and learning from mistakes at Amazing If
• 11:43: Co-founder friction and lessons from friendship at work
• 16:39: Example: Writing conflict and learning to communicate
• 19:35: Tactics: changing context and managing communication
• 22:52: Helen’s single best piece of advice for shell-shedding moments
• 24:20: Writing or telling your story to move past difficult experiences

Summary of Actionable Takeaways

• Prepare for challenging situations by researching the context and people involved.
• Seek both support and reflection—share discomfort with trusted people who’ll both listen and help you draw out learning.
• Don’t let mistakes define you; let them teach you, and then move on.
• Be open and address friction quickly in working relationships to prevent lingering resentment.
• Change the context of tense communications—sometimes, messaging isn’t enough.
• Practice letting go—write things out or talk them through to stop ruminating and create space for growth.

Final Reflection

This episode is a frank, human, and practical deep dive into the messy reality of growing at work. Helen’s candor and Sarah’s probing questions demystify the myth that leaders have it all together—growth often happens at the messy, uncomfortable edges. If you want to handle friction, mistakes, and discomfort in your own career with more resilience, this is a must-listen (or, now, a must-read summary!).