The Woman Who Reinvented Her Career 5 Times (And Why Your 'Messy' Path Might Be Perfect) - with Career Transition Expert Jane Jackson

The Woman Who Reinvented Her Career 5 Times (And Why Your 'Messy' Path Might Be Perfect) - with Career Transition Expert Jane Jackson

Career GrowthInterviewConfidenceWellbeing
Published: 8/10/2025

Show Notes

Feeling stuck in your career? Think it's too late to make a change? Meet Jane Jackson, who proves that career reinvention is not only possible but can lead to extraordinary success.

From flight attendant at 17 to Nike-sponsored athlete to successful career coach at 40, Jane's journey through 5 career changes and 5 country moves will completely shift how you think about career progression. After moving countries with teenage daughters, and rebuilding her entire professional life from scratch, Jane discovered the frameworks that help thousands of professionals navigate successful career transitions.

In this episode, you'll discover why your "messy" career path might actually be your greatest asset, how to identify your transferable skills, and the exact steps to reinvent yourself at any age. If you've ever felt like your career journey doesn't follow the traditional playbook, this conversation will be your roadmap to freedom.

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Connect with me

🔹LinkedIn: https://www.linkedin.com/in/georgiehubbard/

🔺 Instagram: http://instagram.com/georgielhubbard

🔸 Website: https://www.georgiehubbard.com

📚 Early access to Pivotr (AI Career Mentor): https://www.pivotr.com

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Connect with Jane Jackson

🔹LinkedIn: https://www.linkedin.com/in/janejackson/

🔸 Website: https://janejacksoncoach.com/

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💡 What You'll Learn About Career Transition:

- How to successfully reinvent your career at any age (Jane's 5 career changes prove it's possible)

- The career anchor method: discover what truly drives your career decisions

- Why non-linear career paths are actually an advantage in today's job market

- How to identify and leverage your transferable skills across industries

- The values assessment technique that reveals why you feel unsatisfied at work

- Jane's framework for navigating major life transitions while building career success

- How to turn crisis moments into career opportunities and growth

- The self-belief strategies that overcome imposter syndrome and career doubt

- Why resilience and adaptability are the most valuable career skills for the future

- Practical steps for career pivoting when you feel completely lost

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⏱️ Career Transition Timeline:

05:00 - Jane's incredible career journey: from flight attendant to career coach

08:00 - The pivotal moment at 40: how personal crisis led to career breakthrough

12:00 - From Korean Airlines cabin crew to Nike-sponsored fitness champion

15:00 - The ultimate career reinvention: moving countries, divorce, and starting over

18:00 - The childhood experience that built Jane's resilience and adaptability

23:00 - How tough times create the skills needed for successful career transitions

25:00 - The career anchor framework: finding what truly drives your decisions

28:00 - Georgie's struggle: balancing ambitious career goals with personal fulfillment

32:00 - Jane's advice for managing the "two sides" of professional ambition

35:00 - Why values alignment is crucial for career satisfaction and success

40:00 - The reality of career transitions for women: timing, family, and financial independence

44:00 - How to stay relevant in an AI-driven job market through continuous learning

48:00 - The transferable skills framework: identifying what makes you valuable anywhere

52:00 - Overcoming self-limiting beliefs and building unshakeable career confidence

56:00 - The power of accomplishment-based resumes and personal branding

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📝 The Bottom Line:

Your career doesn't have to follow a linear path to be successful. Jane Jackson's story proves that career reinvention is not only possible at any age, but that the skills you develop through life's challenges become your greatest professional assets. Whether you're feeling stuck, facing redundancy, or simply questioning your career direction, the key is gaining clarity on your values and career anchor, then taking strategic action to move toward work that truly fulfills you.

Stop waiting for the "perfect" time or the "right" opportunity. Your messy, non-linear career path might be exactly what prepares you for extraordinary success. The most important step is the first one – and it's never too late to take it.

Watch on YouTube

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