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LD Breakfast Club: Career changes - Why, when and how

In our third edition of the Leadership Development Breakfast Club, we explored the topic of “Career changes - Why, when and how”. Our two speakers, female leaders Jael Chng (Co-founder and Chief Possibilities Generator, My Working Title) and Vanessa Iloste (HR VP, Sephora) shared on navigating career changes, with discussions on the why, when and how to make a successful and meaningful transition. 

Throughout the engaging conversations with speakers in small groups over the breakfast table, the speakers covered various frameworks on career transitions, several situations and considerations to be mindful of as well as personal stories on the speakers’ challenges & successes.

Our key takeaways:


First, there are four competencies when navigating career transitions:

  1. Self-insight: Knowing who you are, your strengths, likes and dislikes

  2. Decision-making: Whether you make decisions by gut or through a matrix (an analytical process)

  3. Transition capabilities: How to manage change

  4. Generating possibilities: How you can think about opportunities and new avenues

Second, some considerations and tips include:

  • Careers are very contextual, and you would need to consider trade-offs

  • Talk to more people, which could include networking and mentoring events. Tapping on internal networks could include reaching out to senior leaders within one's company, or leveraging on LinkedIn for external contacts

  • Discover yourself, your values, and motivations

  • Consider the external situation and environment 

Third, be flexible about the concept of a working identity

  • We could have multiple identities, instead of just one. It is possible to have a portfolio career instead of only one career

  • Start from thinking about the world of possibilities of what you could have become. You can conduct a series of experiments to test the waters, and start small in exploring opportunities

Other recommended resources:

YWLC’s Leadership Breakfast Club series aims to provide participants with insights from accomplished female leaders about their careers and leadership journeys, over authentic and raw conversations over the breakfast table. 

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