Squiggly Careers

Latest Episodes:

#576 Set yourself up to fail, so you're more likely to succeed Jul 16, 2026

Show notes

Want to achieve your biggest career goals this year? The answer might lie in planning exactly how you could fail first. Drawing on research from New York University on mental contrasting, Helens explore how balancing your biggest career opportunities with your realistic obstacles can significantly increase your chance of success. 🎯 What You'll Learn – What is mental contrasting and why does it build resilience? – How to identify what you want to be true in 12 months – Why optimism blindness might be holding your career back – How to honestly audit the obstacles in your way – What practical actions can reduce your risk of failure – How to take one simple step this week to move forward For questions about Squiggly Careers or to share feedback, please email: helenandsarah@squigglycareers.com Need some more squiggly career support? 1. Download our free career tools: https://www.amazingif.com/toolkit/ 2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/ 3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod 4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#575 Oracy: How to improve your speaking and listening skills Jul 14, 2026

Show notes

Do you often feel like you are just waiting for your turn to speak, rather than truly listening and learning? In this episode, we explore the power of oracy and how it can change the way you think and work.

Drawing on the work of Voice 21, Barbara Oakley, and research from More in Common, they explore what it means to develop this skill.

🎯 What You'll Learn

– Define oracy as the essential skill of speaking and listening well to build better conclusions.

– Discover why talking out loud helps you spot gaps in your reasoning and critical thinking.

– Identify the difference between a standard 121 and an oracy-first approach to problem-solving.

– Learn how to facilitate meetings that ensure equal contribution and stop interruptions.

– Practice using oracy in team settings to move away from directive leadership.

– Apply oracy techniques to your squiggly career story to articulate your value more effectively.

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

Need some more squiggly career support?

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

2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/

3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod

4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#574 How to Adapt Your Skills for Career Growth Jul 09, 2026

Show notes

Is your current way of working holding you back from your next career milestone? Sometimes, the very habits that helped you succeed in the past can become obstacles to your future progress. Drawing on Marshall Goldsmith’s concept of 'What Got You Here Won't Get You There', Helen explores what it means to develop this skill, and what your default response to it reveals about you. 🎯 What You'll Learn – Shift from giving all the answers to asking powerful questions – Implement the 'Now vs. Not For Now' list to prioritize effectively – Replace automatic 'niceness' with a strategic 'if-then' negotiation approach – Discover how to move from a 'getting things done' mentality to doing the right things – Learn how to manage your energy by saying no to unsustainable workloads – Develop the confidence to negotiate your time and resources for better impact For questions about Squiggly Careers or to share feedback, please email: helenandsarah@squigglycareers.com Need some more squiggly career support? 1. Download our free career tools: https://www.amazingif.com/toolkit/ 2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/ 3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod 4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#573 How to build a super team Jul 07, 2026

Show notes

Ever wondered what sets high-performing 'super teams' apart from those that are stalling? It's not just about talent, but a shared belief in your collective ability to learn, adapt, and succeed together.

In this episode, Helen and Sarah borrow brilliance from a feeling and dive deep into one of the most relevant topics in work and careers right now.

Drawing on the latest research into high-performing team dynamics and Helen and Sarah's own team-building frameworks, they explore how every team member can influence performance, and what your default response to collaboration reveals about you.

🎯 What You'll Learn

– Understand the critical difference between a super team and a stalling team

– Learn why collective belief is one of the strongest predictors of real-world performance

– Design simple, low-risk experiments to build on what your team already does well

– Make curiosity contagious by identifying and filling your collective knowledge gaps

– Bring the outside in to swap ideas and accelerate your team's adaptation in an AI-driven world

– Ask uncomfortable questions to uncover and remove the barriers getting in the way of progress

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

Need some more squiggly career support?

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

2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/

3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod

4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#572 The Listening Habit That Changes Every Conversation Jul 02, 2026

Show notes

Are you a conversational narcissist? In this Squiggly Shortcut, Sarah introduces a deceptively simple idea from Celeste Headlee that will change how you listen, and make you notice everyone else's conversations differently too. 🎯 What You'll Learn – What a shift response is, why we all do it, and why it matters more than you might think – What a support response sounds like in practice, and how it changes the dynamic of a conversation – Why assuming your experience is the same as someone else's can get in the way of really listening – How to notice your own patterns over the next week, and what to do with that awareness 📚 Resources Mentioned Episode 207: Celeste Headlee on the Squiggly Careers podcast: xx For questions about Squiggly Careers or to share feedback, please email: helenandsarah@squigglycareers.com Need some more squiggly career support? 1. Download our free career tools: https://www.amazingif.com/toolkit/ 2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/ 3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod 4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#571 How to Get Better at Holding Uncertainty at Work Jun 30, 2026

Show notes

Uncertainty isn't going anywhere. So what if the goal wasn't to get rid of it, but to get better at holding it?

In this episode, Helen and Sarah borrow brilliance from a feeling and dive deep into one of the most relevant topics in work and careers right now.

Drawing on Margaret Heffernan's Embracing Uncertainty, Sam Conniff and Katherine Templar-Lewis's Uncertainty Toolkit, and a brilliant HBR article, they explore what it really means to develop the capacity to hold uncertainty, and what your default response to it reveals about you.

🎯 What You'll Learn

– Why the goal isn't uncertainty to certainty, but uncertainty to the capacity to hold

– How to find your own uncertainty tolerance score (with an AI prompt on the podsheet to help)

– Why leaders feel more pressure than most to appear decisive, and what the research says about that

– How to use a simple matrix to plot your uncertainty by impact and duration, and respond differently depending on which quadrant you're in

– Why patience might be the most underrated skill in uncertain times, and how Helen and Sarah both score themselves on it

– What it means to reframe uncertainty as opportunity rather than threat

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

Need some more squiggly career support?

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

2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/

3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod

4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#570 The Four People Every Squiggly Career Network Needs Jun 25, 2026

Show notes

Your career doesn't need a bigger network, it needs a better one. In this Squiggly Shortcut, Helen shares the four roles that matter most for your career community, and why focusing on just these four makes building your career relationships feel a lot more doable. 🎯 What You'll Learn – What a mentor actually is (and why they don't need to be senior or long-term to be valuable) – Why a peer — someone going through what you're going through right now — can be one of the biggest accelerators for your career – How to spot a sponsor and what you need to do before they'll advocate for you – Why a coach doesn't have to be a qualified one, and what to look for instead – What to do if you're lucky enough to have one person who plays all four roles 📚 Resources Mentioned Episode 215 - How to find a career sponsor with Sylvia Ann Hewlett: https://www.amazingif.com/listen/how-to-find-a-career-sponsor/ For questions about Squiggly Careers or to share feedback, please email: helenandsarah@squigglycareers.com Need some more squiggly career support? Need some more squiggly career support? 1. Download our free career tools: https://www.amazingif.com/toolkit/ 2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/ 3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod 4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#569 Why zero distance will make you better at your job Jun 23, 2026

Show notes

How close are you to yourself, your team and the people you serve? In this episode, Helen and Sarah borrow brilliance from the concept of zero distance, a philosophy championed by brands like e.l.f. Beauty, and turn it into one of the most honest and practical self-reflection exercises they've done on the podcast.

Using Post-it® Notes and a simple scale, they plot themselves live on six different dimensions of distance, from how well they know their own strengths and feelings, to how much feedback they really get from their team, to how close they are to the people they're there to help.

This episode is brought to you in partnership with the Post-it® Brand. If today's episode sparked an idea, stick it down - find out where to buy Post-it® products at go.3M.com/squiggly

🎯 What You'll Learn

– What zero distance means and why brands like e.l.f. Beauty have made it their entire philosophy

– How to use the zero distance framework across three areas: distance from yourself, your team and your customers

– Why knowing your strengths isn't enough if you're not spending time on them

– What Helen's "I'm fine, it's fine" taxi moment reveals about emotional distance at work

– How to make feedback unmissable rather than occasional, and why rhythm matters more than quantity

– What zero distance from your customers or learners actually looks like in practice (including a story about a credit card in a glass of orange juice)

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

Need some more squiggly career support?

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

2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/

3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod

4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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

#568 Why Slowing Down Makes You a Better Learner Jun 18, 2026

Show notes

In a world that keeps telling you to learn faster, what if slowing down was actually the smarter move? In this Squiggly Shortcut, Sarah makes the case for slow learning, and shares three questions and three actions to help you get started. 🎯 What You'll Learn – Why slow learning and fast learning aren't competing, they're complementary – Three questions from the beautiful Slow Learning website to help you zoom out and reflect on how you learn – Why asking one "why" question every day is one of the simplest ways to slow down your thinking – How to take a more intentional (and less overwhelming) approach to learning AI – A slow reading idea for Learn Like a Lobster that makes one chapter feel very doable over seven weeks 📚 Resources Mentioned SlowLearning.com Episode 524 - Spaciousness: https://www.amazingif.com/listen/spaciousness-how-to-manage-your-attention-not-your-time/ For questions about Squiggly Careers or to share feedback, please email: helenandsarah@squigglycareers.com Need some more squiggly career support? 1. Download our free career tools: https://www.amazingif.com/toolkit/ 2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/ 3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod 4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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#567 How to use Tiny experiments to make progress at work | Tiny Experiments Jun 16, 2026

Show notes

What if the key to navigating uncertainty wasn't a better plan - but a better experiment?

In this episode, Sarah borrows brilliance from Anne-Laure Le Cunff, author of Tiny Experiments. Together they explore what it means to have an experimental mindset, how to design a tiny experiment using the PACT framework, and why the only experiments that fail are the ones you don't learn from. If you've ever felt stuck waiting for the perfect plan, this episode will give you possibilities you'll be energised by.

🎯 What You'll Learn

– Why a linear mindset is like climbing a ladder, and why an experimental mindset is a loop that keeps moving you forward

– What makes a tiny experiment "tiny", and why keeping the duration short is the whole point

– How to use the PACT framework (Purposeful, Actionable, Continuous, Trackable) to design experiments that actually teach you something

– Why you should only track outputs while running an experiment — and save the outcome reflection for the Plus Minus Next tool afterwards

– How to apply tiny experiments to career change, team culture, and the moments when you feel most stuck

📚 Resources Mentioned

Tiny Experiments — Anne-Laure Le Cunff

Ness Labs Newsletter

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

Need some more squiggly career support?

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

2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/

3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod

4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/

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

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