Retirement is rarely a clean break, especially for people who have built long, demanding, and meaningful careers. In this episode, Oliver Johnston shares what it really looks like to move gradually from full-time leadership work into a retirement that feels purposeful, energising, and fully his own.

Oliver Johnston is a former business consulting leader and the founder of Stepping Out From The Top Team, an organisation focused on helping senior professionals navigate life beyond executive roles. Having made what he calls his “third attempt” at retirement, Oliver brings a refreshingly honest perspective on phased transition, identity, purpose, and creating a life that feels rich beyond work.

Key Topics

Why Retirement Can Take More Than One Attempt - Oliver explains that retirement did not happen for him in one clean step. After leaving his main career, he moved through two different encore phases before arriving at full retirement, showing that the space between work and retirement can be longer, more experimental, and more personal than many expect.

Retiring to Projects, Not Just Leisure - A central theme in the conversation is the idea that retirement works best when it includes purpose. Oliver talks about creating meaningful personal projects around health, family, home, travel, photography, and even life admin, rather than drifting into empty leisure that can leave people feeling flat or disconnected.

Creating a New Organising Principle for Life - Work often structures our days, priorities, routines, and even our sense of identity. Oliver reflects on the importance of replacing that structure intentionally in retirement, so life still feels directed and fulfilling without becoming pressured or overly rigid.

Key Takeaways

Make Retirement Planning Elastic - Oliver encourages people to avoid treating retirement like a rigid project plan. A better approach is to create space to experiment, reduce work gradually if possible, and allow your plans to evolve as you discover what gives you energy and meaning.

Don’t Retire Into Mediocrity - One of Oliver’s strongest messages is that people who pursued excellence throughout their careers should not settle for a diminished version of life in retirement. Retirement can be a time of freedom, curiosity, growth, and renewal if approached with intention.

Know Your Numbers, Then Focus on How You Want to Feel - Financial clarity matters because it helps you make informed choices about when and how to step back. But beyond money, Oliver believes the deeper question is emotional: what kind of life will help you wake up feeling purposeful, enthusiastic, and glad to begin the day?

Timestamps

[00:00] Introduction

[00:41] Why this is Oliver’s “third attempt” at retirement

[03:26] Planning for retirement and starting earlier than most

[06:10] Gradually reducing work and testing semi-retirement

[08:04] Keeping retirement plans flexible rather than rigid

[10:17] Recognising when travel and work no longer fit

[14:55] Exploring new interests: golf, reading, history, health, and family time

[19:01] Retiring to projects, not leisure

[22:23] Replacing work as life’s organising principle

[29:46] Oliver’s three recommendations for people approaching retirement

If this episode resonated, subscribe and share it with someone ready to start living well into retirement.

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Connect with Gordon : https://www.linkedin.com/in/gordon-callum-40022a4/

Take our Retirement Readiness Assessment : https://gordon-lr9eplhq.scoreapp.com

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Marcus Hurry’s conversation explores what it really takes to transition well from a long, high-level career into a new phase of retirement. For anyone approaching retirement, this episode is a reminder that leaving work is not just an ending - it is a chance to shape what comes next with intention, structure, and self-belief.

Marcus Hurry spent many years in an international senior leadership career with HSBC before choosing a new direction through self-employment. His perspective is especially valuable because he reflects honestly on the planning, mindset shifts, and practical adjustments that helped him move from corporate life into a more self-directed and purposeful retirement.

Key Topics

Planning the Transition Before the Final Day - Marcus shares how he began thinking seriously about retirement around 18 months before leaving HSBC. By watching how others retired, learning from what worked and what did not, and asking himself what would truly maximise his potential, he built a more thoughtful path into the next stage of life.

Leaving Well and Staying in Control - A central theme of the episode is Marcus’s determination to “leave well.” He reflects on the importance of controlling what you can control, maintaining your own standards in the final months of work, and making space to thank colleagues and close one chapter with real care and professionalism.

Building Structure in Early Retirement - Retirement did not mean drifting. Marcus talks about having a plan for day one, using his network more intentionally, signing up for courses before he left work, and creating a structure that gave him momentum as he moved into self-employment and a new identity beyond his former role.

Key Takeaways

Back Yourself - One of Marcus’s strongest messages is that retirement often requires a leap of belief. Whether you are moving into self-employment, study, volunteering, or something entirely new, confidence in your own experience and judgment can make the difference between hesitation and action.

Control What You Can Control - Not everything about retirement will unfold exactly as planned, but some parts can be shaped with intention. Marcus shows how focusing on what you can influence - timing, preparation, conversations, and first steps -creates a more grounded and positive transition.

Create New Habits for the Life Ahead - Retirement is not only about stopping old routines; it is about building new ones. From reading more widely and studying again to finding personal ways to stay motivated and measure progress, Marcus highlights the value of creating habits that support purpose, growth, and enjoyment.

Timestamps

[00:00] Introduction

[01:11] Reaching the fork in the road: stay in corporate life or try self-employment

[02:18] What Marcus learned from watching other people retire

[06:03] The 18-month planning phase and the question of maximising potential

[07:50] Why leaving well and controlling what you can matters

[10:01] The final week, day one planning, and using your network wisely

[12:15] The first month of retirement and building a credible new story

[16:33] Early surprises: energy, admin, and working alone

[19:00] Study, new habits, and the mindset shift retirement requires

[28:56] Marcus’s three key pieces of advice for approaching retirement

If this episode resonated, subscribe and share it with someone who is ready to start living well into retirement.

--

Connect with Gordon : https://www.linkedin.com/in/gordon-callum-40022a4/

Take our Retirement Readiness Assessment : https://gordon-lr9eplhq.scoreapp.com

Visit Retiring Point online : https://retiringpoint.com

Retirement can arrive more like a cliff edge than a gentle transition, especially when your identity has been deeply tied to work for decades. In this episode, we explore what happens when structure, purpose, and professional status suddenly fall away - and why preparing emotionally for retirement matters just as much as preparing financially.

Liz Preston joins Gordon to share her honest experience of leaving a successful career in healthcare leadership and stepping into an unexpected period of loss, uncertainty, and self-doubt. A former senior NHS leader in Scotland and founding director of Synaptic, Liz brings a thoughtful and hard-earned perspective on rebuilding confidence, rediscovering purpose, and creating a more balanced retirement.

Key Topics

When Retirement Doesn’t Feel Like Freedom Yet - Liz reflects on the difficult final months after the sale of Synaptic, when the transition she expected never really happened. Instead of a gradual handover, she found herself in limbo - no longer fully involved, but not yet emotionally or practically prepared for what came next.

The Loss of Identity, Value, and Routine - One of the strongest themes in this conversation is how retirement can affect self-worth. Liz speaks openly about missing structure, contribution, and the feeling of being needed, highlighting how the emotional side of retirement can be far more challenging than many people expect.

Finding Purpose Again in New Ways - Over time, Liz began to rebuild a sense of meaning through third-sector non-executive and trustee roles, coaching, and a wider mix of personal interests. She shares how shifting from “what job can I get?” to “what kind of life do I want?” changed her experience of retirement completely.

Key Takeaways

Prepare for More Than the Finances - Financial planning matters, but it is only one part of retirement readiness. Liz makes a powerful case for thinking earlier about the personal, emotional, and professional shifts that retirement brings, so the transition feels less like a shock.

Don’t Wait Until the Cliff Edge - Putting off retirement thinking is easy when work is busy and rewarding, but it can leave you exposed when change comes quickly. Liz encourages listeners to start exploring possibilities sooner, so they have something meaningful to move toward, not just something they are leaving behind.

A Good Retirement Includes Both Purpose and Pleasure - Work-like activity can still play an important role in retirement, but it does not need to dominate life. Liz’s story shows the value of creating a broader rhythm that includes contribution, friendship, learning, hobbies, travel, and space to enjoy a more flexible life.

Timestamps

[00:00] Introduction

[00:19] Liz Preston’s career background and transition from Synaptic

[01:24] The unexpected limbo before retirement officially began

[03:08] Loss of purpose, self-worth, and the emotional impact of stopping work

[05:12] Applying for non-executive roles and dealing with rejection

[06:29] Discovering third-sector opportunities and regaining direction

[12:17] Why retirement preparation should start earlier

[15:03] Finding purpose through trustee and non-executive work

[19:35] Redefining identity after a long professional career

[25:42] Building a fuller retirement with hobbies, friendships, and flexibility

If this conversation resonated, share it with someone who needs a reminder that retirement is a beginning worth preparing for.

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Connect with Gordon : https://www.linkedin.com/in/gordon-callum-40022a4/

Take our Retirement Readiness Assessment : https://gordon-lr9eplhq.scoreapp.com

Visit Retiring Point online : https://retiringpoint.com