Squiggly Careers

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/
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Most people wait until they're ready to make a career move before having career conversations.
In this Squiggly Shortcut, Helen shares the only script you need to make curious career conversations feel less daunting and a lot more useful.

🎯 What You'll Learn

– What a curious career conversation actually is, and why having them regularly (not just when you're ready to move) makes a real difference
– How to make the ask in a way that's low pressure and easy to say yes to
– Three questions to structure the conversation: one to get people talking, one about strengths, and one about future-proofing your skills
– What to listen out for in each answer, and how to use it to work out whether an opportunity is actually a good fit for you

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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Emma Grede has some strong opinions about careers, and not everyone will agree with all of them. In this episode, Helen and Sarah borrow brilliance from Start With Yourself, Emma's new book, picking out six of her most provocative statements and asking the question: do we agree?

Emma Grede, co-founder of Skims and Good American, is refreshingly unfiltered about what it takes to build a career on your own terms. Helen has curated the statements most relevant to squiggly careers, and Sarah hasn't seen them in advance. What follows is honest, at times uncomfortable, and occasionally results in a rewrite.

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

– Why guilt might actually be a useful signal (and when it isn't)

– What "you can do all things, just not all at the same time" really means for how you prioritise at work

– Whether an extraordinary career always requires extraordinary effort, and why the word "extraordinary" is more personal than you think

– Why pushing off difficult conversations is costing you more than you realise

– The difference between networking and actually building a network

– Why you can't build anything of value by yourself (and where Helen respectfully disagrees)

📚 Resources Mentioned

Start With Yourself: Emma Grede

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

In a world full of words, the people who communicate with clarity, humanity and story will stand out.

In the fifth and final episode of this special series, Helen and Aneesh Rahman close out Open to Work with the last of the five Cs, communication, and why it might be the skill that ties everything together.

From Martin Luther King to Pixar to the pressure of a TED Talk, this is a conversation about why great communication has never been more human, and what you can do to make yours more so.

🎯 What You'll Learn

– Why AI making generic communication universally available raises (not lowers) the value of human storytelling
– Why the most important story you'll ever tell is the story of yourself
– How clarity fits into communication, and why speaking simply doesn't mean thinking simply
– Two practical things you can do right now to make your next presentation more human: add a story or make an analogy
– Why the future of communication comes down to four words: speak human, be human

📚 Resources Mentioned

Open to Work: Aneesh Rahman and Ryan Roslansky

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

What if compassion isn't just a nice-to-have, but one of the most important skills for the future of work?

In day four of this special five-part series, Helen and Aneesh Rahman explore the fourth C, compassion, and why the new world of work demands something the industrial age actively discouraged.

From quietening your inner critic to really listening to a colleague, this is a conversation about what it means to be more human at work, starting with yourself.

🎯 What You'll Learn

– Why compassion wasn't valued in the industrial age (and why that's changing fast)
– Why compassion for yourself has to come first, and what that looks like in practice
– How to show genuine (not performative) compassion for the people you work with
– Why phone calls and walk-and-talks might be better than video calls for building real connection
– One simple exercise to anchor yourself in your own strengths, without listing a single job title or degree

📚 Resources Mentioned

Open to Work: Aneesh Rahman and Ryan Roslansky

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