Squiggly Careers

Latest Episodes:

Learn Like a Lobster: How to Keep Growing in Your Career Sep 23, 2025

Show notes

Big news! 🎉 Pre-orders for Helen and Sarah’s brand-new book *Learn Like a Lobster* are now live. In this special episode, they share why lobsters are the perfect metaphor for modern learning, what makes the book different, and how you can start “learning like a lobster” right away. You’ll hear about the free Learn Like a Lobster Library, discover three big lobster-inspired lessons, and get practical tools you can experiment with today.

🦞 Pre-order Learn Like A Lobster below:

PRH US - https://bit.ly/3KxTeBn

Amazon UK - https://amzn.to/3KcRZaR

⏱️ Timestamps

00:00 Introduction

00:50 Big news: Learn Like a Lobster pre-orders are live

05:15 What’s in the Learn Like a Lobster Library (workshops, tools & community)

07:23 Why lobsters?

11:50 Learn as you go: experimenting with out loud vs. quiet thinking

21:15 Learning in hard moments: Fly on the wall facts

35:24 Leading your own learning: Beginner Bingo

42:43 How to join the Learn Like a Lobster Library & what’s next

🎯 What You’ll Learn

- Why lobsters are the perfect model for lifelong learning

- A technique to reframe tough moments into learning opportunities

- Ways to fuel your own growth without waiting for permission

- How to build confidence through beginner moments

📚 Resources Mentioned

- Pre-order Learn Like A Lobster: https://www.penguin.co.uk/books/463488/learn-like-a-lobster-by-ellis-helen-tupper-and-sarah/9780241718957

- The Learn Like a Lobster Library (free with pre-order)

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

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AI Skills Sprint: How To Design Your Future Career Using AI Sep 19, 2025

Show notes

This is the fifth and final episode of the Squiggly Careers x AI skills sprint series.

Today, Helen and Sarah talk about exploring Future Possibilities in your career. As careers become less linear and more unpredictable, having multiple options and directions is essential for resilience and control.

In this episode, they show how to use AI prompts to generate a mind map of career possibilities, from obvious to ambitious, pivot, and dream options. They also introduce an AI tool for practicing curious career conversations through role play, helping you build confidence and get feedback first.

With people having 10-15 different jobs on average throughout their working life, embracing a variety of possibilities actually reduces career risk and builds long-term resilience.

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

⏱️ Timestamps

00:00 Introduction

01:07 Why future possibilities matter in a squiggly career

02:48 AI prompt to explore different types of career possibilities

05:40 AI Tool: Yoodli

08:39 Team activity: who are your career role models?

🎯 What You’ll Learn

* The importance of having multiple career options

* How to use AI to generate a mind map of career possibilities

* Why creating rather than waiting for opportunities matters in modern careers

* How to practice curious career conversations

📚 Resources Mentioned

Future Possibilities Daily Summary - https://bit.ly/scss-ai-day5-summary

Yoodli - https://yoodli.ai/

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

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AI Skills Sprint: How To Make Networking Easy with AI Sep 18, 2025

Show notes

This is the fourth episode of the Squiggly Careers x AI skills sprint series. Today, Helen and Sarah are talking about Networking. Before you skip this one (we know some of you want to!), remember this squiggly stat: 70% of people's roles come through connections.

The key is reframing networking from "people knowing people" to "people helping people." This creates career karma - when you help others, good things come back to you over time.

In this episode, Helen and Sarah introduce AI tools to build your personal career board with different personas like challengers, supporters, and questioners. They also explore Crystal Knows, an AI tool that helps you communicate better with your team and network by understand their communication style.

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

⏱️ Timestamps

00:00 Introduction

00:47 70% of roles come through connections

01:15 Reframing networking & creating career karma

02:04 Building your personal career board with AI

06:20 Crystal Knows: AI personality analysis tool

09:36 Team activity: Learning goals and mutual support

🎯 What You’ll Learn

* How to reframe networking as "people helping people"

* How to use AI to create a diverse personal career board

* Team exercises for sharing learning goals and building connections

📚 Resources Mentioned

Networks Daily Summary: https://bit.ly/scss-ai-day4-summary

Crystal Knows: https://www.crystalknows.com/

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

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AI Skills Sprint: How to cage confidence gremlins that are getting in the way of your growth Sep 17, 2025

Show notes

This is the third episode of the Squiggly Careers x AI skills sprint series and today Helen and Sarah are tackling Confidence. We all have gremlins - those beliefs, doubts and fears that hold us back in our careers. They're often hidden and they can grow when we don't address them. When you learn to cage them, you get better at navigating tough moments and saying yes to opportunities that stretch you.

In this episode, Helen and Sarah introduce their brand-new custom Gremlins GPT - a tool they've trained with everything they've written about confidence. This AI coach helps you identify what gremlins are getting in your way and practice difficult conversations in private. You'll discover how to create visual representations of your gremlins, role-play challenging scenarios, and build a "confidence gremlin gallery" with your team.

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

⏱️ Timestamps

00:00 Introduction

00:37 What are confidence gremlins and why do they limit us?

03:11 Introducing the custom Confidence Gremlins GPT tool

05:29 Creating visuals of your gremlins

06:36 Using AI to role-play your gremlin during challenges

08:58 Team activity: Creating a confidence gremlin gallery

🎯 What You’ll Learn

* How to identify and understand your confidence gremlins

* How to use the custom Gremlins GPT for private confidence coaching

* Tools for role-playing challenging scenarios with AI

* Creative ways to share and discuss gremlins with your team

📚 Resources Mentioned

Confidence Gremlin GPT - https://bit.ly/squigglycareerconfidencecoach

Confidence Daily Summary - https://bit.ly/scss-ai-day3-summary

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

AI Skills Sprint: How To Identify Your Values (Your Filter For Your Future) Sep 16, 2025

Show notes

This is the second episode of the Squiggly Careers x AI skills sprint series and today Helen and Sarah are diving into Values. Your values are what motivate and drive you - they're your internal compass that guides decision-making and career choices.

In this episode, Helen and Sarah share the best tool for identifying your values and how AI can accelerate the actions you take about your values, turning them into a brilliant filter for your future. They'll show you practical ways to use your values to respond to challenges at work, and share some playful approaches you can also use with your team.

When you understand what really drives you, you make better decisions for your career and become more confident as a result of having clarity about what matters most to you.

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

⏱️ Timestamps

00:38 What are values and why do they matter?

03:15 The best tool to identify your values

04:39 Using your values to respond to challenges

05:52 AI prompts to action your values

08:41 Team activity: Fun ways to talk about values with your team

🎯 What You’ll Learn

* How to identify and clarify your core values (and why it's important)

* Why values are a powerful career decision-making filter

* How to use AI prompts to turn values into actionable insights

* Fun and engaging methods to share values with your team

📚 Resources Mentioned

Values Daily Summary: https://bit.ly/scss-ai-day2-summary

Run Your Own Race Episode: https://youtu.be/cUdwIvnDpNQ

Ask the Expert: Purpose with Simon Sinek, author and speaker: https://youtu.be/DATg__SZcwE

Values Tool: https://values.institute/

Gemini: https://gemini.google.com

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

🏃‍♀️ Join our next Skills Sprint: https://bit.ly/skillssprint2024

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

AI Skills Sprint: How To Discover Your Strengths Using AI (in 10 Minutes) Sep 15, 2025

Show notes

This is the first episode of the Squiggly Careers x AI skills sprint series and today Helen and Sarah are kicking things off with Day 1: Strengths.

Our strengths are what we're known for - they shape how we show up and help us make more impact at work. And because strengths develop throughout your career, it's important to keep reflecting on them.

In this episode, Helen and Sarah share how to give AI the right prompts to help you spot your strengths in action, stretch your strengths in your team and build a clearer and more confident LinkedIn profile.

AI doesn't know you better than you know yourself, but it can act as a sparring partner - giving you new ways of looking at your experiences and surfacing patterns you might miss. By combining reflection with the power of AI, you'll walk away with practical ways to build on your strengths and accelerate your squiggly career.

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

⏱️ Timestamps

00:00 Introduction

00:48 What are strengths and why do they matter?

02:13 AI prompts to help discover you strengths

08:20 Optimising your LinkedIn profile around your strengths with AI

09:19 Team activity: 3 ways to talk about strengths with your team

🎯 What You’ll Learn

* Why strengths evolve throughout your career

* How to use AI prompts to uncover and reflect on your strengths

* How to optimise your LinkedIn profile to reflect your value

* Ways to stretch your strengths in a team setting for more impact

📚 Resources Mentioned

Strengths Daily Summary - https://bit.ly/scss-ai-day1-summary

Amy Edmondson - https://amycedmondson.com/

Claude - https://claude.ai/

Canva's AI Tool - https://www.canva.com/magic-design/

Strengths Toolkit – https://www.amazingif.com/toolkit/

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to the Squiggly Careers AI Skills Sprint 2025 🥇 Sep 14, 2025

Show notes

AI is on everyone’s minds and we’re getting curious about how it can help to develop our squiggly career skills. Join us for a 5-day sprint from the 15th September where we’ll be exploring lots of AI tools to support our 5 squiggly career skills: Strengths, Values, Confidence, Networking, and Future Possibilities. Just 10 minutes a day for lots of ideas and insights on how AI can help you to accelerate your squiggly career.

🥇 Sign up for the sprint here: https://bit.ly/3UC3jPy

👥 Join our Squiggly Community: https://www.linkedin.com/company/amazing-if/

⏱️ Timestamps

00:00 Welcome to the Squiggly Careers AI Skills Sprint 2025

00:43 What is a Squiggly Career?

01:10 What is a Sprint?

01:40 Supporting you while you sprint

02:13 FAQs

03:12 Learning with thousands in our community

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

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#496 4 Team Habits That Are Holding You Back (and What to Do Instead) Sep 09, 2025

Show notes

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

This week, Helen and Sarah shine a light on the unhelpful habits that teams often slip into without even realising it. From meetings that drag on autopilot to one-to-ones that don’t deliver what you need, these routines can waste time, reduce energy, and stop people from working at their best. In this episode, they share the four most common team traps and practical alternatives to try instead. You’ll hear how to spot unhelpful routines, reset them without blame, and create new habits that help your team feel more energised, inclusive, and effective.

⏱️ Timestamps

00:00 Announcement

01:02 Introduction

05:15 Why teams get stuck in autopilot

08:20 Trap #1: Repeating the same roles in meetings

15:40 Trap #2: Defaulting to recurring meetings

21:58 Trap #3: One-to-ones that lack focus

29:45 Trap #4: Unhelpful communication and collaboration

38:37 How to experiment and reset as a team

42:30 PodSheet and next steps

🎯 What You’ll Learn

4 common team habits that hold people back
Why recurring meetings and default roles reduce effectiveness
Alternatives to traditional 1:1s that create more value
How to reset team communication for clarity and collaboration
Simple experiments you can try together to build better ways of working

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

🏃‍♀️ Join our next Skills Sprint: https://bit.ly/skillssprint2024

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

#495 The September Reset: Stop Old Habits, Start New Wins Sep 02, 2025

Show notes

🥇 Sign up for the sprint here: https://bit.ly/41jasYO

Are old habits holding you back from the progress you want to make? September often feels like a natural reset point—a chance to stop what’s no longer serving you and start building new wins. In this episode, Helen and Sarah share their own September “starts” and “stops” to inspire you to reflect, reset, and refocus. You’ll hear how small, intentional changes can help you create space for growth, protect your future self, and build habits that last beyond the September spark.

⏱️ Timestamps

00:00 Announcement

01:02 Introduction

03:45 Why September feels like a reset moment

07:18 The power of starts and stops

10:35 Weekly Borrowed Brilliance

15:40 Building from scratch with AI

21:58 Parallel learning (habit stacking with podcasts)

26:45 Monthly mentor moments

32:30 Responding quicker instead of waiting

36:55 Leaving the phone behind in the evenings

41:48 No more post-it actions

44:55 Stop moaning about Mondays

48:20 How to use this as a team activity

52:00 Wrapping up & accountability

🎯 What You’ll Learn

Why September is such a powerful time to reset and refocus
How to identify habits that are helping—or holding—you back
Practical ways to design new starts that spark motivation
How to stop habits that drain your energy and confidence
Why sharing starts and stops as a team builds connection and support

📚 Resources Mentioned

How to Change by Katy Milkman (for the “fresh start effect”)

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

🏃‍♀️ Join our next Skills Sprint: https://bit.ly/skillssprint2024

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

#494 Be yourself more with skill Aug 26, 2025

Show notes

This is the fourth and final episode in the Squiggly Careers Quote Series, and today Sarah shares the quote that has shaped her approach to leadership: “Be yourself more with skill.” Inspired by the book and article Why Should Anyone Be Led by You?, this episode explores how true leadership comes from leaning into your strengths and embracing uncomfortable situations that spark growth. There’s no blueprint for being brilliant, and whether you're in a leadership role or not, you don’t need to become someone you’re not—it’s about being a better version of yourself.

⏱️ Timestamps

00:00 Introduction & Announcement

02:33 The quote: "Be yourself more with skill"

07:44 Action 1: Job Crafting – Be the architect of your career

10:30 Action 2: Ask for feedback on blindspots

13:03 Action 3: Have a squiggly stretch

🎯 What You’ll Learn

- How to lead authentically by leaning into your strengths

- How to be the architects of your own work life

- How to take intentional control of your job description

- Smart ways to ask for feedback on blindspots

- The value of stepping into uncomfortable situations

📚 Resources Mentioned

Why Should Anyone Be Led by You?: What It Takes To Be An Authentic Leader Hardcover

by Robert Goffee and Gareth Jones https://www.amazon.co.uk/Why-Should-Anyone-Led-You/dp/1578519713

HBR Article 'Why Should Anyone Be Led by You?: https://hbr.org/2000/09/why-should-anyone-be-led-by-you

Job Crafting Article by Dan Cable https://dan-cable.com/linkedin-article/job-crafting/

For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com

More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

🏃‍♀️ Join our next Skills Sprint: https://bit.ly/skillssprint2024

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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