Squiggly Careers

By The Squiggly Career

Squiggly Careers is a weekly podcast that will help you take control of your career development. Hosted by the founders of Amazing If (https://www.amazingif.com/), Sarah Ellis and Helen Tupper, togeth... more

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FAQs about Squiggly Careers:

How many episodes does Squiggly Careers have?

The podcast currently has 583 episodes available.

Squiggly Careers episodes:

June 04, 2026 Compassion and why being more human is becoming a career advantage (Day 4) | Open to Work
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: [email protected]
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
...more
11min
June 03, 2026 Creativity and the human skill AI can't replicate (Day 3) | Open to Work
Creativity isn't a talent some people have and others don't, it's a skill. In day three of this special five-part series, Helen and Aneesh Rahman explore the third C, creativity, and why it's becoming one of the highest-value human skills in an age when AI can generate generic content at scale.
From Pixar's science of storytelling to the neuroscience of flow, this is a conversation that will change how you think about your own creativity, and how to bring more of it to your team.
🎯 What You'll Learn
– Why AI making generic creative content widely available actually raises the premium on human creativity
– What the neuroscience of flow tells us about when we're at our creative best (and what gets in the way)
– Why creativity is a team sport, and what that means for how you design your working week
– A simple question to ask in your team: when are you at your creative best and what contributes to it?
– One practical thing anyone can do right now to build their creative muscle, even if they don't feel creative at all
📚 Resources Mentioned
Open to Work: Aneesh Rahman and Ryan Roslansky
Creativity Inc.: Ed Catmull
Peak: Anders Ericsson
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
12min
June 02, 2026 Courage and why playing it safe in your career is becoming riskier (Day 2) | Open to Work
Even if you're not changing jobs, your job is changing. In day two of this special five-part series, Helen and Aneesh Rahman explore the second C, courage, and why it's becoming one of the most important skills you can bring to work right now.
From Polynesian wayfarers to Apollo 13 to leaving a high-profile CNN career to become an unpaid intern on a presidential campaign, courage has always been at the heart of how humans do anything worth doing. The good news? You don't have to start with a giant leap.
🎯 What You'll Learn
– Why courage is necessary for curiosity (and why being told to be compliant at work has made courage harder than it should be)
– Why if you aren't failing, you aren't doing enough in this new world of work
– How micro courage compounds over time (and why small, uncomfortable actions build to bigger leaps)
– What companies and leaders need to do to create environments where courage is actually possible
– One thing you could do tomorrow that feels uncomfortable today
📚 Resources Mentioned
Open to Work - Aneesh Rahman and Ryan Roslansky
Email Helen and Sarah to share your moment of courage and get an accountability partner: [email protected]
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
13min
June 01, 2026 The Careers Skills AI can't replace (Day 1) | Open to Work
What if the future of work isn't less human...but more human? In this special episode, Helen kicks off a brand new five-part series borrowing brilliance from Open to Work, a brilliant new book by Aneesh Rahman, Chief Economic Opportunity Officer at LinkedIn, and former Obama speechwriter.
Over the next five days, Helen and Aneesh will explore the five human skills that matter most in the age of AI: curiosity, courage, creativity, compassion and communication. Today, they start with curiosity - and why it might be the most important career advantage you can build right now.
🎯 What You'll Learn
– Why AI raises the value of human skills rather than replacing them (and what that means for your career)
– What real curiosity looks like at work (hint: it's not just reading more, it's finding a thread and pulling on it)
– Why outsourcing your curiosity to AI creates cognitive debt, and what to do instead
– How to use AI as a starting point for building curiosity, not an ending point
– How to create more curiosity in your team through debate, discussion and the willingness to say "I don't know"
📚 Resources Mentioned
Open to Work - Aneesh Rahman and Ryan Roslansky
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
14min
May 28, 2026 #564 Why Slowing Down Makes You Better at Solving Problems
Are you a fix-it-fast problem solver?
In this Squiggly Shortcut, Helen makes the case for slowing down before you jump to solutions.
🎯 What You'll Learn
– Why surface-level fixes create ping pong problems that just keep coming back
– How to use two simple questions "why is this a problem?" and "why is this an issue?" to get to the cause
– How to turn your answers into better, more targeted solutions rather than sticking plasters
– Why solving problems as a team (rather than solo) means people are more bought into what comes next
📚 Resources Mentioned
Squiggly Careers Skills Sprint Increasing Your Impact: https://www.amazingif.com/squigglysprints/
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
8min
May 26, 2026 #563 Finish Line Focus: How to Build Momentum Towards Goals That Matter
Have you ever noticed how much more you get done in the week before a holiday?

In this episode, Helen and Sarah borrow brilliance from the goal gradient effect; the research-backed finding that the closer we are to a finish line, the harder and faster we push, and turn it into something genuinely practical for your career.

Sarah introduces Finish Line Fridays: a simple way to use the psychology of progress to build momentum towards goals that matter, one week at a time. Helen tests it live with her PhD as the goal, and together they explore whether you're more of a fresh start effect person or a finish line focus person, and why pairing the two might be useful.

🎯 What You'll Learn
– What the goal gradient effect is and why it explains so much about how we work (and why rats are involved)
– The difference between the fresh start effect and finish line focus (and which one you're more naturally wired for)
– How to run your own Finish Line Fridays: from picking your goal to setting your first action before you've even finished the current week
– Why knowing the "when" matters as much as the "what", and how to actually protect time in your diary
– How shared finish lines might be even more motivating than solo ones

📚 Resources Mentioned
Farnam Street, Goal Gradient Effect: https://fs.blog/goal-gradient-hypothesis/
Sketchplanations: https://sketchplanations.com/

For questions about Squiggly Careers or to share feedback, please email: [email protected]

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
...more
35min
May 21, 2026 #562 The 24 Hour Rule: Why Waiting Makes You Better at Work
Ever sent a reply you immediately regretted, or said something in the heat of the moment you wish you hadn't?
In this Squiggly Shortcut, Sarah makes the case for the 24 hour rule, and shares the research that backs up why waiting is almost always worth it.
🎯 What You'll Learn
– Why giving yourself 24 hours moves you beyond fight, flight or freeze (and why sleep is doing more work than you think)
– 3 things to do in that 24 hours while you're processing: name it to tame it, separate facts from feelings, and ask whether you'll still care about this in 12 months
– Why it's okay to say "I'll come back to you tomorrow" (and why people actually find it reassuring when leaders do this)
– What to do when you don't have 24 hours and an hour is the best you can get
📚 Resources Mentioned
Episode 364: How to improve your judgement: https://www.amazingif.com/listen/how-to-improve-your-judgement/
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
8min
May 19, 2026 #561 How to Spend More Time in Your Zone of Genius at Work
How much of your working week are you spending on things you're genuinely great at, and how much is quietly draining you?

In this episode, Helen and Sarah borrow brilliance from Gay Hendricks' Zone of Genius framework, sparked by Emma Grede's book Start With Yourself, and turn it into one of the most practically useful exercises they've tried in a while.

They work through all 4 zones live, competence, incompetence, excellence, and genius, sharing their own honest examples (including payroll, passive meetings, and branding). Then Helen shares a surprisingly simple way to use AI to analyse your diary and find out exactly how your time is really being spent.

This episode is brought to you in partnership with 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 the four zones actually mean, and why spending too much time in your zone of excellence can be just as much of a trap as your zone of incompetence
– How to map your own work across the four zones using Post-it® Notes
– A simple diary audit method and how to use AI to turn your ticks into percentages (and real insight)
– Why this is one of the best team exercises Helen and Sarah have come across for making strengths visible and actionable

📚 Resources Mentioned
Start With Yourself — Emma Grede
Zone of Genius — Gay Hendricks

For questions about Squiggly Careers or to share feedback, please email: [email protected]

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
...more
34min
May 14, 2026 #560 4 Ways to Stop Self-Sabotage at Work
Does your inner critic get loudest exactly when you need it to be quiet? In this Squiggly Shortcut, Helen unpacks what self-sabotage actually looks and feels like at work, and shares four simple things you can do to start turning the volume down.
🎯 What You'll Learn
– Why self-sabotage tends to show up hardest in the moments that matter most (and what that costs you over time)
– How to spot the specific situations where your inner critic is having the biggest impact
– Why "name it to tame it" is one of the most useful things you can do with a worry
– One simple language swap, from "I can't" to "I don't", that shifts you from feeling stuck to feeling in control
📚 Resources Mentioned
Episode 283 - How to stop self-sabotage: https://www.amazingif.com/listen/how-to-stop-self-sabotage/
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
9min
May 12, 2026 #559 What to Do When Your Work Feels Pointless
Have you ever finished a week at work and wondered what you actually did that mattered? In this episode, Helen and Sarah borrow brilliance from David Graeber's book Bulls*it Jobs...and find it uncomfortably relatable.
Helen and Sarah explore what pointless work actually looks like, why it's more common than most of us admit, and, crucially, what you can do if you find yourself in it.
🎯 What You'll Learn
– What makes a job "pointless" according to Graeber's definition (and why it's more about your own assessment than anyone else's)
– Why high-paid pointless jobs are often more draining than they sound
– Five practical strategies for surviving and escaping a job that doesn't feel real (from scanning sideways to pitching yourself a new role)
– Why treating your career as a series of experiences rather than an identity makes these moments easier to navigate
– When to leave (and why calling it fast is increasingly the right move)
📚 Resources Mentioned
Bullsh*it Jobs — David Graeber
I Don't Want a Job (Not a Real Job) — Amy McNeese, The Pony Project
For questions about Squiggly Careers or to share feedback, please email: [email protected]
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
...more
38min

FAQs about Squiggly Careers:

How many episodes does Squiggly Careers have?

The podcast currently has 583 episodes available.

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