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

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

From Squiggly Careers by The Squiggly Career

June 2, 2026 · 12 min

About this episode

This episode discusses the importance of courage in the evolving job landscape and how small acts of courage can lead to significant career growth.

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: helenandsarah@squigglycareers.com For…

People in this episode

Host: Helen

Guest: Aneesh Rahman

Topics covered

  • courage
  • career development
  • micro courage
  • work environment
  • personal growth

Keywords

  • courage
  • career change
  • micro courage
  • work skills
  • personal development

Mentioned in this episode

Organizations: CNN, Open to Work

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