Helen Tupper: The Squiggly Career: Amazing If on Reinvention, Retention and the Leap  episode artwork

EPISODE · May 14, 2026 · 48 MIN

Helen Tupper: The Squiggly Career: Amazing If on Reinvention, Retention and the Leap

from 4-Quarter Lives · host Avivah Wittenberg-Cox

In this episode of 4-Quarter Lives, we re-visit a conversation between Avivah Wittenberg-Cox and Helen Tupper, Chief Executive of Amazing If, a company redefining careers for individuals and companies. Together they explore the intricacies of career transitions during midlife and how organizations can support these changes. The conversation also delves into personal experience, highlighting the essential balance between work and life.Helen Tupper is co-founder and CEO of Amazing If, a company with an ambition to make careers better for everyone. Together with her business partner Sarah Ellis, she is the author of three books: The Squiggly Career, You Coach You and, most recently, Learn Like a Lobster: Confidence boosting tools to help you get unstuck at work and reignite your career. Sarah and Helen are also hosts of the podcast Squiggly Careers which has had 4m downloads and their TED talk, The best career isn’t always a straight line, has been watched by almost 2m people. In 2023 Helen was awarded a place on EYs International Winning Women programme. Prior to founding Amazing If, Helen held leadership roles for Microsoft, Virgin and BP and was awarded the FT & 30% Club’s Women in Leadership MBA Scholarship.Some Useful Links:* Amazing If website.* Book: The Squiggly Career, by Helen Tupper and Sarah Ellis* Book: Learn Like a Lobster, by Helen Tupper and Sarah Ellis* The Squiggly Careers podcast.* Helen Tupper’s LinkedIn Get full access to 4-Quarter Lives | Elderberries at elderberries.substack.com/subscribe

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Helen Tupper: The Squiggly Career: Amazing If on Reinvention, Retention and the Leap

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This episode was published on May 14, 2026.

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In this episode of 4-Quarter Lives, we re-visit a conversation between Avivah Wittenberg-Cox and Helen Tupper, Chief Executive of Amazing If, a company redefining careers for individuals and companies. Together they explore the intricacies of career...

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