Squiggly Careers

Latest Episodes:

CEO Shell-Shedding Moments: Purpose, Perspective and Learning from Mistakes with Nick Bent Feb 05, 2026

Show notes

This is the fourth episode in our Shell-Shedding Moments series, a series where CEOs and leaders share the vulnerable moments, the challenges, mistakes, and personal revelations that most people never see. In this episode, Nick Bent, CEO of UpReach, opens up about the moments that tested him, from handling technology mishaps to resetting organizational culture. He shares how embracing challenges, maintaining perspective, and surrounding yourself with the right people are key to navigating tough times in leadership.

🦞 Learn Like A Lobster:

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🇬🇧 Amazon UK - https://bit.ly/46lj8Av

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 the Learn Like a Lobster Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 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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CEO Shell-Shedding Moments: Kill or Continue? Making Hard Decisions with Fight Story's Georgie Holt Feb 04, 2026

Show notes

This is the third episode in our Shell-Shedding Moments series, a series where CEOs and leaders share the vulnerable moments, the challenges, mistakes, and personal revelations that most people never see. Today's episode is with Flight Story CEO Georgie Holt, who shares why great ideas are rarely obvious or easy, why comfort is the enemy of growth, and the necessity of experimentation to drive real progress.

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

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 the Learn Like a Lobster Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 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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CEO Shell-Shedding Moments: How to Fix Friction at Work Fast with Helen Tupper Feb 03, 2026

Show notes

In this special CEO Shell-Shedding Moments episode, Sarah interviews Helen, about the uncomfortable moments that help us grow. From difficult interviews to co-founder friction and communication challenges, Helen shares what happens when things feel hard at work and how to fix friction fast before it festers. If you’ve ever replayed a mistake, avoided an awkward conversation, or felt stuck in a working relationship, this episode is full of practical ideas to help you learn quickly and move forward with confidence.

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

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 the Learn Like a Lobster Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 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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CEO Shell-Shedding Moments: Opening Up about Mental Health at Work with Zaid Al-Qassab Feb 02, 2026

Show notes

Welcome to Shell-Shedding Moments, a series where CEOs share the vulnerable moments, the challenges, mistakes, and personal revelations that most people never see. Today's episode is with CEO Zaid Al-Qassab who opens up about his experiences with depression, the challenges of leading while managing mental health, and the power of vulnerability in the workplace. Zaid shares how embracing these moments can strengthen resilience, deepen connections, and create healthier work environments.

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

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 the Learn Like a Lobster Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 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

How to ask for help at work (without feeling awkward) Jan 29, 2026

Show notes

In this Squiggly Shortcut episode, Helen shares a practical, step-by-step framework for asking for help at work in a way that feels confident, clear, and effective.

Many of us struggle to ask for help because we fear looking incompetent, don’t want to burden others, or try to push through on our own. Helen breaks down how to neutralize that anxiety, identify what kind of help you need - support, solutions, or a sounding board- figure out who can give it, and frame your ask so it’s actionable and easy to respond to.

If you’ve ever felt stuck or overwhelmed at work, this episode will give you a simple, Post-It-note-sized system to get the support you need and move your squiggly career forward.

Episode 527

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

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 the Learn Like a Lobster Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 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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5 formulas for a high impact introduction Jan 27, 2026

Show notes

How do you introduce yourself in a way that turns a polite “nice to meet you” into a genuine “tell me more”? In this episode, Helen and Sarah are Borrowing brilliance from Rebecca Okamoto’s TED Talk How to Introduce Yourself and Get Hired. They unpack five simple formulas you can use to make high-impact introductions — whether you’re meeting someone new, speaking at an event, or kicking off a meeting. This episode is all about short, practical introductions that help you be heard, remembered, and taken seriously.

Episode 526

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

🎯 What You’ll Learn

- How to introduce yourself clearly and confidently

- Five practical formulas you can adapt for different situations

- Why “tell me more” is the goal of a great introduction

- How to make introductions feel natural, not scripted

- How to use questions to build connection quickly

📚 Resources Mentioned

How to Introduce Yourself and Get Hired — Rebecca Okamoto (TED Talk) https://www.youtube.com/watch?v=f_N3PGvnVKg

Impactful Introductions GPT - https://bit.ly/Impactful_Introductions

🔔S𝐮𝐛𝐬𝐜𝐫𝐢𝐛𝐞 𝐟𝐨𝐫 𝐦𝐨𝐫𝐞 𝐮𝐩𝐝𝐚𝐭𝐞𝐬:https://www.youtube.com/@SquigglyCareers?sub_confirmation=1

If you enjoyed this episode, you may also like:

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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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Skills Sprint: How to Lead Your Own Learning by Sharing It Jan 23, 2026

Show notes

In this fifth and final episode of the Learn Like a Lobster skill sprint, Helen and Sarah introduce "Helpful How-Tos" - a simple, fun way to share knowledge that helps you learn faster and helps your team too. You'll discover why sharing makes learning stick, how to overcome confidence gremlins, and a practical (and fun) format you can use immediately with your team to keep learning and growing.

🦞 Join our Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

⏱️ Timestamps

(00:00) Thank you & Well done! 00:25 How lobsters guarantee their growth

(01:00) The double win of sharing learning

(01:40) Why organisations don’t sharing learning well

(02:20) Rubber duck debugging explained

(03:30) Overcoming the "expert" barrier

(04:02) Introducing helpful how-tos

(06:51) Helpful how-to: going to events (extrovert version)

(08:06) Helpful how-to: going to events (introvert version)

(09:19) Inspiration & 24hr action

🎯 What You’ll Learn

Why "rubber duck debugging" works
Ways to make knowledge sharing fun and low-pressure in teams
How introverts and extroverts can share differently

Learn Like a Lobster Profiler – https://www.learnlikealobsterprofiler.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 Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

📮 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

Skills Sprint: How to Lead Your Own Learning with Adaptability Jan 22, 2026

Show notes

When it comes to learning at work, it’s easy to wait for permission - from managers, organisations, or “the right moment.” In this episode, Helen and Sarah explore how to lead your own learning, even when time, money, or support feel limited. This is Day 4 of the Learn Like A Lobster skill sprint, and the focus is on adaptability — the skill that helps you keep learning when things don’t go to plan. Helen and Sarah explain why relying on perfect conditions can stall your development, and how adapting your approach helps you stay resilient and relevant at work.

🦞 Join our Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

⏱️ Timestamps

(00:00) Lobsters, old shells, and self-sustaining growth

(01:04) Waiting for permission stalls learning

(02:01) Why adaptability matters at work

(03:23) Flexibility vs adaptability: the toolbox analogy

(05:08) Using AI to adapt in advance

(06:48) Live example: Learning goals & scenario planning

(09:48) Inspiration & 24hr action

🎯 What You’ll Learn

The difference between being flexible and being adaptable
How to anticipate barriers and adapt your learning approach
How AI can help you plan for obstacles and take action now

AI Prompt:

Act as a squiggly career coach. My role is: [your role]. I work in: [describe your organisation and context]. My learning goal for the next 3 months is: [what you want to learn]. Identify realistic barriers that might get in the way of this learning. For each barrier, suggest adaptive responses I could use to keep learning anyway. Present the output in a simple table.

Learn Like a Lobster Profiler – https://www.learnlikealobsterprofiler.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 Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

📮 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

Skills Sprint: How to Learn in Hard Moments (Without Spiralling) Jan 21, 2026

Show notes

This is Day 3 of the Learn Like a Lobster skill sprint, and today Helen and Sarah share a simple way of reflecting on hard moments at work so you can learn faster, avoid recency bias, and take control in tough situations.

Because when work feels messy, reflection is often the first thing we skip - or overdo. In this episode, you’ll learn practical tools, including the 5:1 formula and the WWW/EBI framework, to help you regain perspective, stay in control, and turn difficult moments into learning.

🦞 Join our Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

⏱️ Timestamps

(00:00) Lobsters grow in hard moments

(00:35) The lobster profile

(00:58) Why reflecting in hard moments needs more focus

(02:33) Thinkers vs doers: how we avoid learning

(03:45) WWW/EBI

(04:31) The 5:1 formula explained

(06:36) Fixing problems in teams

(07:39) Taking control in long haul hard moments

(09:35) Inspiration & 24hr action

🎯 What You’ll Learn

Why reflecting during hard moments leads to better learning
How to avoid overthinking or rushing past difficult experiences
A simple 5:1 approach to constructive reflection and how to use WWW / EBI individually or in teams

Learn Like a Lobster Profiler – https://www.learnlikealobsterprofiler.com/

Download our template for 5:1 reflection: https://bit.ly/llal_5to1_reflectiontemplate

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 Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

📮 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

Skills Sprint: How to Learn From Feedback (Even When It’s Uncomfortable) Jan 20, 2026

Show notes

This is Day 2 of the Learn Like a Lobster skill sprint, and today Helen and Sarah focus on one of the hardest - and most important - career skills: how to give and receive tough feedback. Learning doesn’t just happen after the difficult moment has passed - some of the most powerful development happens while things feel uncomfortable. In this episode, Helen and Sarah explore how to learn in the hard moments — particularly when feedback feels awkward, emotional, or risky.

🦞 Join our Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F

🦞 Pre-order Learn Like A Lobster:

🇺🇸PRH US - https://bit.ly/3KxTeBn

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

⏱️ Timestamps

(00:00) Lobsters grow in hard moments

(02:00) The fear of asking, giving & receiving feedback

(08:15) The “say the hard thing” framework

(05:55) Organisational silence

(06:54) A real feedback conversation

(09:12) Inspiration & 24hr action

🎯 What You’ll Learn