Squiggly Careers: "Deck of Brilliance – 3 Ways to Think Differently When You’re Stuck at Work"

Hosts: Sarah Ellis & Helen Tupper
Release: February 17, 2026

Episode Overview

In this lively and practical episode, Sarah and Helen delve into the “Deck of Brilliance,” a creative online resource designed to inspire new ways of thinking and problem solving at work—especially when you feel stuck. Borrowing techniques from this deck, they share three specific idea-generating tools, apply them directly to their own business, and encourage listeners to experiment with them in their own careers and teams. The episode balances humor and vulnerability with actionable advice, making “thinking differently” feel both accessible and fun.

Key Discussion Points & Insights

1. Introduction to Deck of Brilliance

• What is it?
  • A free (or affordable) online resource created by Jumpji Ramkrishnan, containing themed “decks” of creative problem-solving techniques, each illustrated with global examples—from ads to products.
  • "If you want to get better at creative thinking, I feel like spending some time with a deck of brilliance would help you to do that." —Sarah [02:08]
• Why use it?
  • Not just for “creative” jobs; useful for anyone looking for fresh ways of thinking.
  • Examples are thoughtfully curated and illustrate practical applications.
• How it works:
  • Choose a deck (e.g., idea generation, storytelling, finding your organization’s mission).
  • Each deck gives several techniques, with explanations and global media examples.

2. Technique #1: Make a Bug a Feature

• Concept:
  • “Take the thing that you’re most self-conscious about and double down on it... Stop fixing it and start flaunting it.” —Sarah [05:12]
• Examples:
  • Ugly packaging, slow product, hard-to-pronounce names—take the “flaw” and turn it into the hook.
  • Sarah: “I've actually worked on a fashion brand before where that was true. The name was hard and people said it in lots of different ways.” [05:38]
• Applying it to Squiggly Careers/Amazing If:
  • Bugs Identified:
    • Having two coexisting brands (Squiggly Careers & Amazing If)—can be confusing.
    • Small team size compared to ambition.
    • Overwhelming amount of content, hard to navigate.
    • The “bug” in the concept of squiggly careers (e.g., career development equals less money, confusion about progress).
  • Process:
    • Instead of hiding or “fixing” these bugs, how could they be celebrated? For example, highlighting the dynamic between the two brands in their branding, or openly acknowledging abundance as a sign of plenty rather than overwhelm.
    • Helen: “So if the bug is, we have two different brand names ... How do you, how do you, so you, you turn that—?” [09:06]
  • Reflection:
    • The conversation is “uncomfortable and interesting,” pushing both hosts out of their usual improvement mindset and into curiosity and experimentation.

3. Technique #2: Switch Perspectives

• Concept:
  • “Give what you do to somebody else to describe or govern—ideally, someone who doesn’t know your work.” —Sarah [11:38]
  • As Helen puts it: “A manager could do your job. You could do the manager’s job for a day.” [12:10]
• Application:
  • The hosts asked their colleagues’ friends and families—many unfamiliar with Squiggly Careers—to explain what a “squiggly career” is. Many responses were recorded by children and adults, revealing new and unexpected perceptions.
    • Henry: “We work together and join in, even if that means stepping out of our comfort zone.” (Helen’s son) [13:45]
    • Madeline: “Even if you have butterflies in your tummy, just keep going.” (Helen’s daughter) [14:00]
    • Max (Sarah’s son): “Bad.”—“I don’t want a squiggly career. I’d want a straight career.” [14:27]
  • Key insight:
    • Responses were split: some saw “squiggly” as positive (versatility, learning), others as negative (messiness, lack of direction).
    • “By asking people outside of yourself, it stops you getting stuck in that echo chamber trap.” —Sarah [15:02]
• Reflection/Application:
  • Especially valuable for breaking out of “project bubble” mentality; fresh perspectives reveal hidden assumptions.
  • Helen recounts how a listener focus group changed her view on podcast learning: “I often think about listeners, whereas I think it made me think, 'oh, we should think about learners.' Listening is not the only way people learn.” [20:01]

4. Technique #3: Put the Audience to the Test

• Concept:
  • “Turn your audience from passive to active participants... let them judge situations or make choices, then reveal what comes next depending on what they choose.” —Sarah [21:18]
  • Illustrated with examples: choose-your-own-adventure books, video games with real consequences, or audience-propelled workshops.
• Application:
  • In a workshop, let participants choose which topics/skills are covered based on their needs, making content audience-led rather than prescriptive.
    • Helen: “You kind of, you know, we could be Helen and Sarah led to squiggly careers, which is this is what we think we should put out in the world. Or we could be audience led and we could say... the next six months of our work is going to be led by you.” [27:41]
  • In training, let participants “turn a 6 to an 8”—if they rate an idea as only useful at 6/10, challenge them to make it an 8/10 for themselves. [31:09]
• Reflection:
  • Audience-led activities drive deeper learning and engagement: “When we are involved in anything, you’re so much more engaged, you’re participating, you feel like you’re shaping something rather than having something happening to you.” —Sarah [29:25]
  • The approach can also surface assumptions and biases when participants reflect on and justify their choices.

Notable Quotes & Memorable Moments

• "Stop fixing it and start flaunting it." —Sarah, on bugs as features [05:12]
• "Even if you have butterflies in your tummy, just keep going." —Madeline (Helen’s daughter), redefining resilience [14:03]
• "No, a squiggly career is not a bad thing. It’s not a good thing." —Sarah, reflecting on her son's view and wider public perception [15:02]
• "By asking people outside of yourself, it stops you getting stuck in that echo chamber trap." —Sarah [15:02]
• "I often think about listeners, whereas I think it made me think, 'oh, we should think about learners.'" —Helen [20:01]
• "When we are involved in anything, you're so much more engaged... you feel like you’re shaping something rather than having something happening to you." —Sarah [29:25]

Timestamps for Key Segments

• 00:46 – Introduction to the episode and what Squiggly Careers/Pod Sheet is
• 01:28 – What is the Deck of Brilliance and how does it work?
• 05:12 – Technique #1: Make a Bug a Feature – explanation and examples
• 09:06 – Squiggly Careers bug: dual branding & how to play with it
• 11:38 – Technique #2: Switch Perspectives – explaining your work to outsiders
• 13:41 – Kids and family describe “squiggly careers”
• 15:02 – How external perspectives break the echo chamber
• 17:54 – Using this approach beyond branding—project and company initiatives
• 21:18 – Technique #3: Put the Audience to the Test – gamify participation
• 27:41 – What it could look like to be fully audience-led
• 29:25 – Engagement through participation and deepening self-awareness
• 31:09 – Concrete exercise: Participants co-create better solutions
• 32:41 – Where to find the Deck of Brilliance; invite to share stories and questions

Final Takeaways

• Borrowing brilliance, especially from unfamiliar sources, can unlock new perspectives and pathways when you or your team feels stuck.
• Don’t shy away from your flaws—there may be gold in the "bugs" of your brand, product, or project.
• Outsider and audience perspectives are essential. They challenge your assumptions, reveal blind spots, and spur innovation.
• Engaging your audience as co-creators, not just consumers, drives deeper learning and creativity.

For further resources, including the Deck of Brilliance and practical exercises, check the pod sheet at AmazingIf.com or in the show notes.