Lessons from Life & Leadership Season 4 Episode 2: The human side of long-term planning

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The conversations across Season 4 of Life & Leadership offer a thoughtful lens on long-term decision-making and leadership. Below we continue to reflect on some key insights and consider their relevance for advisers supporting clients across different life stages.  

You can catch up on our previous reflection on Episode 1 with Mark Fennell here.    
 

Aine Kerr on purpose, sustaining energy, and knowing when to pivot 

In episode 2, tech entrepreneur and journalist, Aine Kerr reflects on a career shaped less by rigid plans and more by values, curiosity, and a willingness to adapt. From teaching and journalism to start-ups and global leadership roles, her story highlights how long-term fulfilment is a journey often built through a series of thoughtful decisions rather than a single defining moment.  
 

Why long-term fulfilment is rarely linear  

A clear takeaway from Aine’s conversation with Bobby is her belief that careers, like life, rarely follow a straight, uninterrupted path. While she had early clarity about wanting to teach, much of what followed emerged through experience, self-reflection, and a readiness to change direction when circumstances or priorities shifted.  

For advisers helping clients with retirement planning, this insight is particularly relevant. Through our work with advisers on Second Life conversations, we often hear a mix of reactions from clients approaching retirement. Some feel exasperated at the traditional view of ‘stopping work and doing nothing’. Others haven’t given retirement much thought at all, focusing instead on the numbers rather than what life might look like. As our End of Career Guidance Counsellor, Brian Mooney, often reflects, “We’re not Lego bricks, there’s no fixed way of fitting into life.” We can shape life, one step at a time.  

Aine’s story reinforces this perspective and highlights that long-term fulfilment is created by adaptability, self-reflection, and an ability to recognise that priorities and needs evolve over time.  

 

Understanding how to sustain energy over time 

Aine speaks candidly, not simply as something to be rationed or used up, but as something to be reflected on, understood, and actively replenished over time.  

This perspective resonates strongly with the Second Life approach to meaningful retirement readiness. Retirement planning isn’t about only about planning for an end to a working chapter but about shaping a life that supports ongoing financial security, social connection, and a mindset that remains open, curious, and confident.  

When clients think about how they want to use their time, skills, and energy in later life, and what helps replenish it, they’re better placed to make choices that feel balanced, meaningful, and sustainable over the long term.  
 

Takeaways and resources for advisers  

• Long-term planning rarely follows a straight, uninterrupted path. Flexibility, resilience and ongoing reflection are essential to sustainable, long-term fulfilment.  
• Energy is an important planning input. Helping clients reflect on how their energy is used and replenished today – what brings colour into their life, will help unlock more meaningful conversations about choices they can make for their second life, across financial, social, and mindset factors.  
   

Resources to support adviser conversations 

• Second Life questionnaire – a practical tool to help clients reflect on what fulfilment, connection, and balance look like in retirement.  
• Retirement chats with our End of Career Guidance counsellor, Brian Mooney and Second life Mentor, Sonya Lennon – storytelling from retirees who’ve lived the journey to, and are now purposefully leading their way through retirement.  

We hope you’re enjoying the conversations this season. You can catch up on the latest episodes here.