meta_pixel
Tapesearch Logo
Log in
Squiggly Careers

Courage and why playing it safe in your career is becoming riskier (Day 2) | Open to Work

Squiggly Careers

AmazingIf

Management, Careers, Business

4.9 โ€ข 838 Ratings

๐Ÿ—“๏ธ 2 June 2026

โฑ๏ธ 12 minutes

๐Ÿงพ๏ธ Download transcript

Summary

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. ๐ŸŽฏ What You'll Learn โ€“ Why courage is necessary for curiosity (and why being told to be compliant at work has made courage harder than it should be) โ€“ Why if you aren't failing, you aren't doing enough in this new world of work โ€“ How micro courage compounds over time (and why small, uncomfortable actions build to bigger leaps) โ€“ What companies and leaders need to do to create environments where courage is actually possible โ€“ One thing you could do tomorrow that feels uncomfortable today ๐Ÿ“š 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: helenandsarah@squigglycareers.com 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

Transcript

Click on a timestamp to play from that location

0:00.0

Anish, welcome back to day two of our series on Open to Work.

0:04.0

Your New York Times bestselling book, how did you feel when it was on the best sell? Relief, I think, because we weren't sure how it was going to land and if anyone wanted to read it and if the message would resonate. So I think it was, oh, this was worth it, is what it felt like. Well, I think it's a brilliant book. think for all of the Squiggly Career listeners

0:20.2

is a real companion to Squiggly careers

0:22.4

because this is why you have to develop the skills because

0:25.0

this is what's happening at work. Well, this is partly why we wrote it and you're called out

0:28.8

in this book and so many sort of early thinkers about how we should change work and careers

0:33.8

are in the book. We wanted to take all of that and all that you've been doing for years now

0:38.1

and give it this bigger frame, this complete disruption to work. I think the greatest disruption

0:43.3

to work in human history backed by LinkedIn as a point of view that people will believe

0:47.6

that feels credible because we've got more than a billion members. We're in 200 countries and

0:51.7

territories. So we're so thankful and grateful for the work that so many of you have done to tee up how we should approach this and felt like our role was to sum all that up into this big moment so that people could like pull from it. Actually, it's a super quotable book. I was like highlighting and like, that's a great point. That's a great point. We've got so many points in it. I really like there's a quote in here that says, even if you're not changing jobs, your job is

1:14.9

changing. And that's such an important point because I think some people might think, oh, well,

1:19.6

I'm in my job. I'm happy. It's like, no, that this change is happening to you.

1:23.5

I mean, what's interesting, I hadn't thought about it till now, is that you might be in a squiggly line career in ways you don't realize in the job that you're in without changing

1:30.9

that job title. Takes software engineers right now. Their job is fundamentally changing from largely

1:36.8

coding to now things like talking to customers, thinking about ethical implications of what they build.

1:42.4

That's like changing your job, even if you're not

1:45.0

changing jobs, into a new job. So there's going to be squiggly line careers happening even for

1:49.7

people who don't change jobs or job titles. It's constant. So that links to me to the skill that we're

1:55.7

going to focus on today, which is all about courage, which I think of the five, I was like,

1:59.7

oh, this is the hard one. And I was

2:01.5

like, there's a whole context that sits around courage. So tell me why you felt that this

...

Transcript will be available on the free plan in 25 days. Upgrade to see the full transcript now.

Disclaimer: The podcast and artwork embedded on this page are from AmazingIf, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of AmazingIf and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright ยฉ Tapesearch 2026.