Retiring Pointers: Transitioning from career into retirement - Creating new retirement purpose and identity - Managing retirement relationship dynamics - Reinvesting your time in retirement - Managing the retirement emotional rollercoaster – Details, episodes & analysis
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Retiring Pointers: Transitioning from career into retirement - Creating new retirement purpose and identity - Managing retirement relationship dynamics - Reinvesting your time in retirement - Managing the retirement emotional rollercoaster
Retiring Pointers is a podcast about the non-financial aspects of retirement nobody talks enough about: identity, purpose, fulfillment, connection, emotions, and creating a life you genuinely enjoy after work.
Retiring financially secure is only part of the journey. Transitioning from a successful career into retirement is a major life change that requires just as much attention.
Through thoughtful conversations and real-life stories, the show explores what it actually means to be retirement ready and retire well. From rediscovering purpose and building new routines, to relationships, hobbies, health, contribution, and reinvention, Retiring Pointers is designed to help listeners navigate the emotional and personal transition into retirement with greater confidence and clarity.
Each episode features conversations with people who are approaching retirement, living a meaningful retirement, struggling in retirement or helping others make the transition successfully - including C suite executives, partners in professional services, entrepreneurs, psychologists, health experts, community leaders, executive coaches, all with valuable perspectives to share.
Whether you’re preparing for retirement, recently retired, or simply thinking ahead to what the next chapter of life could look like, Retiring Pointers offers practical insights, inspiring stories, and thoughtful conversations to help you build a retirement that feels rewarding, purposeful, and truly your own.
Because the goal isn’t just to stop working. It’s to create a purposeful life after work, rich in meaning not just money.
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
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Preparing for retirement is about far more than just accumulating a healthy pension pot; it requires a mental shift toward how you will spend your time, energy, and wealth. Balancing the emotional realities of leaving a long career with practical financial planning ensures you do not just survive retirement, but actively thrive. Understanding both sides of this equation gives you the confidence to step away from work and build a fulfilling next chapter.
Richard Wadsworth is a financial adviser at Carbon Financial Partners who specialises in working with individuals over the age of 50. With decades of expertise, Richard goes beyond standard investment advice to help clients align their financial resources with their personal purpose and lifestyle goals. His practical, human-centered approach makes him a trusted guide for anyone navigating the transition from saving wealth to spending it meaningfully.
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Key Topics
1. The Mindset Shift in Your 50s - Turning 50 often triggers a fundamental shift from passively saving money to recognising what your wealth actually needs to achieve. As retirement nears, the focus sharpens from abstract financial figures to real-life living costs and lifestyle expectations.
2. Retiring From Work vs. Retiring To Purpose - While most professionals know exactly what job or responsibilities they want to step away from, very few have a clear vision of what they are stepping into. Exploring your personal values, health, and daily routine early on helps create a meaningful post-work identity.
3. Conquering Drawdown Anxiety and Frugality - After 30 or 40 years of building a savings habit, transitioning to spending down your nest egg can trigger unexpected financial anxiety. Establishing structured monthly drawdowns and maintaining growth assets help ease this transition and provide long-term peace of mind.
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Key Takeaways
1. Embrace Retirement as "Rewirement" or Revivement - Reframe retirement not as an ending or a slow-down, but as an opportunity to revive your energy toward new projects, interests, and passions that bring genuine fulfillment.
2. Test-Drive Your Post-Work Life Early - Don't wait until your final day at work to figure out your lifestyle; use your late 50s to trial part-time schedules, volunteering, non-executive roles, or new hobbies.
3. Know Your Finances to Build Confidence - Gaining clarity on your actual income requirements and structuring your portfolio to withstand longevity and inflation allows you to give yourself full permission to spend and enjoy your wealth.
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Timestamps
1. [00:00] Introduction and balancing financial with non-financial planning
2. [00:01] What changes emotionally and mentally when you reach your 50s
3. [00:05] Why people know what they retire from, but not what they retire to
4. [00:06] The shift away from the traditional "cliff-edge" retirement
5. [00:09] Uncovering personal purpose, values, and cold Tuesday morning routines
6. [00:13] Overcoming the tendency to deprioritise yourself in busy roles
7. [00:17] Understanding "frugality muscle" and the fear of drawing down wealth
8. [00:21] Practical ways to replace your salary and build spending confidence
9. [00:25] Three essential habits to cultivate as you prepare for retirement
10. [00:28] Where to connect with Richard Wadsworth and Carbon Financial
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Subscribe to Retiring Pointers today and take one concrete step this week toward designing a retirement that is as rich in purpose as it is in financial peace.
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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
The final 12 months countdown to retirement: Devesh Mathur, COO HSBC (India, Bangladesh, Asia Pacific)
Episode 8
Wednesday, July 29, 2026 • Duration 33:28
Devesh Mathur's Transition Into Retirement
Central topic
Transitioning into retirement isn’t just a financial event—it’s a personal identity shift that can surface as anxiety, loneliness, and uncertainty long before your “official” retirement date. Devesh Mathur shares what surprised him most: the 12–18 months leading up to retirement can feel harder than retirement itself, and planning for the non-financial side early can make all the difference.
Guest introduction
Devesh Mathur is the Chief Operating Officer for HSBC across India, Asia Pacific, and Bangladesh. As a senior executive facing mandatory retirement at age 60, he offers a grounded, high-execution perspective on how to reshape purpose, relationships, and marriage rhythms—so retirement becomes a life you step into, not a gap you fall into.
Key Topics
The hidden pressure of the “in-between” years
Devesh explains how the months before retirement come with an invisible countdown—where your role, routine, and sense of time start to feel like they’re slipping away. He describes how this anticipation can trigger more reflection than the day itself, making early preparation feel not optional but necessary.
Identity: who are you without the title?
A major theme is the question of identity when your work title disappears. Devesh challenges the idea that retirement is only about leaving a job—he points to the deeper loss of multiple identities built over decades, and the need to consciously define what you’ll be “for” next.
Designing community and connection outside work
Because so much of Devesh’s social life is work-generated, he starts building relationships that won’t collapse when he steps away. He discusses making deliberate choices about friendships, reducing reliance on workplace networks, and keeping “old connections” alive in a way that still feels relatable.
Retirement Transition Story: Graham Bleakley
Episode 7
Friday, July 3, 2026 • Duration 30:59
Retirement Transition Story : Graham Bleakley
The transition out of a high-powered career is often treated as a financial event, but it’s really a shift in identity and daily purpose. In this episode, Graham Bleakley shares how intentional preparation, especially around community and personal interests, helped him move from work to retirement in a way that felt more like starting living than “switching off.”
Graham is an ex-Systems Engineering Technical Director at the Costain Group. With a thoughtful, practical lens shaped by years of leadership, he walks through what retirement planning actually looked like for him; what he front-loaded, what got disrupted, what he missed, and how he rebuilt his sense of self as an “artist” in the making.
Key TopicsFront-loading your retirement (before you “retire”)
Instead of waiting until the walkaway date to figure things out, Graham describes the importance of starting your post-work life while you’re still employed. For him, a major gap was community, something he intentionally began building years ahead, so the landing felt steadier rather than jarring.
Managing the emotional weight of a professional exit
Leaving a senior role isn’t just logistics, it’s emotional work too, especially when you’re responsible for succession planning and continuity. Graham reflects on the strain of trying to “leave well” while also preparing himself inwardly for a complete change in purpose.
Rebuilding identity beyond the job title
Work can become a big part of who you are, so retirement may require redefining yourself in more creative and human terms. Graham shares how he found grounding through ceramics, and balance through Tai Chi, while also learning how to live without the daily rhythm of technical camaraderie.
Key TakeawaysCommunity is a stabiliser, not a “nice to have”
Graham’s story is a reminder that relationships can be the difference between a retirement that feels open and one that feels isolating. His local boat club became his most important support network, offering both belonging and a reason to get up each day.
You may need rest before you go after the next thing
He emphasises that relief and euphoria can arrive alongside real fatigue. Graham’s experience suggests that slowing down (and letting energy return) is part of doing retirement well, not something to rush past.
Plan with intention, but let life evolve
Am I really ready to retire in my 50s?-Neil Osmond shares his experiences
Episode 6
Friday, June 19, 2026 • Duration 33:00
Deciding to walk away from a successful career, especially for an entrepreneur, is rarely as simple as just stepping off the treadmill. This episode explores the complex transition from business ownership to a new life rhythm, tackling the often-unspoken psychological challenges of losing one's professional identity and the search for purpose that follows.
Today’s guest is Neil Osmond, who founded and built a company over 17 years before orchestrating a successful sale. His journey, stepping away in his early 50s, provides a raw, honest perspective on navigating the "wilderness" of early retirement and finding fulfillment beyond the boardroom.
Key Topics
The Entrepreneur’s Identity Crisis
Neil discusses the immediate shock of selling his business, describing a period of feeling lost as his role shifted from owner to employee, and eventually, to someone navigating life after work. He highlights the jarring reality that while everything changes regarding one's position in the world, the external markers of life often remain the same, creating a unique dissonance.
Replacing Mission and Purpose
The transition away from work is not just about filling time; it is about replacing the mission and purpose that a career previously provided. Neil reflects on the importance of creating new structures and finding meaningful pursuits, whether through volunteering, mentoring, or simply being present for family, to stay engaged and satisfied.
Navigating the Expectations of Others
There is often immense pressure from peers and society to immediately start a "second act." Neil shares his experience in overcoming the internal cognitive dissonance of feeling like he’d been given a "golden ticket" and the societal pressure to justify why he wasn't immediately rushing back into building a new business or seeking a new role.
Key Takeaways
The Seasonality of Retirement
Retirement is not a uniform, static state. Neil emphasizes the difference between the seasons of the year and the seasons of life, noting that activities that are fulfilling in the summer may not be possible in the winter. Recognising these rhythms is crucial for maintaining a sense of well-being throughout the year.
Timestamps
Retirement Transition Experiences - Oliver Johnston
Episode 5
Monday, May 25, 2026 • Duration 34:14
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.
Retirement Transition Experiences - Marcus Hurry
Episode 4
Monday, April 13, 2026 • Duration 30:14
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.
- 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.
Retirement Transition Experiences - Liz Preston
Episode 3
Tuesday, March 31, 2026 • Duration 32:46
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.
- 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.
Retiring Pointers Taster
Episode 1
Tuesday, March 31, 2026 • Duration 02:34
Retirement can look straightforward on paper, but for senior leaders it often brings deeper questions about identity, purpose, rhythm, and what a meaningful life looks like after the role ends. This opening episode introduces Retiring Pointers as a space for honest conversations about that transition — helping listeners move beyond the idea of simply stopping work and toward building a life that feels fulfilling and well-lived.
In this introductory episode, host Gordon Callum, founder of Retiring Point, sets out the purpose behind the podcast and who it is for. His perspective is especially valuable because he speaks directly to the realities executive level professionals face when stepping away from senior leadership and into a new phase that calls for just as much intention as a career once did.
Key Topics
What Really Changes in Retirement - This episode highlights that retirement is not just a diary change or a job title disappearing. For many senior leaders, it affects identity, influence, legacy, health, relationships, finances, and the structure of everyday life in ways that are often underestimated.
Learning from Those Who’ve Lived It - Retiring Pointers is built around real conversations with former CEOs, C-suite executives, senior partners, non-executive directors, and other experienced leaders. The focus is on the decisions, doubts, and discoveries that rarely appear in public announcements but shape the reality of retirement.
Designing a Meaningful Next Chapter - Rather than offering vague ideas about slowing down, the podcast promises grounded insight and practical examples. It is about helping listeners think ahead, learn from others, and create a version of retirement that feels purposeful, sustainable, and true to who they are now.
Key Takeaways
Retirement Needs Intention - One of the clearest messages in this introduction is that retirement deserves the same level of thought and care that leaders gave to their careers. A fulfilling next chapter does not happen by accident; it is something to be shaped consciously.
Retirement Transition Experiences - Stephen Du Toit
Episode 2
Tuesday, March 31, 2026 • Duration 30:48
This episode explores the emotional reality of stepping away from a high-powered leadership role and into retirement — especially when your identity, routine, and sense of value have long been tied to your work. For anyone approaching retirement, it’s a deeply relevant reminder that leaving the job is only one part of the transition; working out who you are afterwards can be the harder part.
Stephen Du Toit joins Gordon Callum to reflect on his transition from President of Coca-Cola Canada into retirement after a 27-year career with the company. His perspective is especially valuable because he speaks with honesty about the fear, uncertainty, loss of structure, and gradual rebuilding that can come after a successful executive career ends.
Key Topics
When retirement becomes real - Stephen shares the moment retirement first felt real to him, sparked unexpectedly by hearing Jürgen Klopp talk about leadership energy and knowing when it is time to step away. That reflection led him to ask not just whether he could keep going, but whether it was fair to himself and the business to begin another major cycle without full commitment.
The emotional shock of stepping away - Although the decision to retire was carefully considered, Stephen describes the final year as an emotional roller coaster. He worked intensely right up to the end, which helped him stay focused in the moment, but meant the true impact of retirement only hit on day one — and it hit hard.
Rebuilding identity, routine, and purpose - In the months after leaving Coca-Cola, Stephen found himself navigating fear, restlessness, and a loss of clarity around who he was without the title. He talks about the importance of routine, reconnecting with people, investing in personal “hygiene” tasks like finances and planning, and slowly shaping a new identity around contribution, entrepreneurship, mentoring, and family.
Key Takeaways
Don’t stay in denial about the transition - One of Stephen’s clearest reflections is that many people underestimate the psychological side of retirement. It’s easy to stay busy finishing well at work, but if you avoid preparing emotionally for what comes next, the sudden absence of structure, status, and daily purpose can feel deeply unsettling.
Key Takeaways
Plan your next chapter while you still have momentum
Waiting until after retirement can make the transition sharper and more painful. Devesh recommends designing what comes next during the final runway—using that same drive and structure to test purpose-aligned directions.
Create an identity separate from work—early
To protect your emotional landing, start defining who you are beyond your role before you retire. Devesh emphasizes that the earlier you can create “anchors” for purpose, the smoother the shift becomes.
Protect your relationship with clear, shared agreements
Retirement changes daily life at home, not just professional life. Devesh highlights the importance of explicit conversations with a spouse about shared spaces, responsibilities, and decision-making—so retirement doesn’t become an unspoken mismatch.
Timestamps
\[00:00\] Introduction and why transition matters
\[00:01\] Guest background: Devesh Mathur and his retirement timeline
\[00:03\] The surprising difficulty of the 12–18 months before retirement
\[00:05\] Identity shock: “Who am I without the title?”
\[00:09\] Finding personal anchors: mentorship and advisory roles
\[00:12\] Designing the next chapter before you retire
\[00:15\] Social life shift: moving beyond work-generated relationships
\[00:19\] Avoiding the “chorus of critics” trap
\[00:22\] Work relationships and the evolving retirement “energy”
\[00:24\] Retirement excitement—and the realistic “honeymoon” question
\[00:28\] Purpose in pro bono work and what still motivates
\[00:30\] Three tips: plan early, build identity, and protect marriage transition
If retirement is a doorway, let this episode help you plan the life on the other side.
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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
Although he’s a planner, Graham doesn’t treat retirement like a fixed project. He describes taking “one step further” the way training works, allowing new interests to grow naturally into something deeper, rather than trying to recreate work in a new costume.
Timestamps
[00:00] Introduction
[01:10] The 2019 Catalyst: Recognizing the Need for Change
[03:40] Balancing Professional Succession with Personal Exit
[05:40] Why Community Connection Must Come Before Retirement
[09:50] The Evolution of Purpose: From IBM to Costain
[12:30] Managing the Exhaustion of the Final Months
[15:15] Finding Joy in New Interests: Ceramics and Tai Chi
[19:15] Navigating the Loss of Work Camaraderie
[23:05] Redefining Your Identity Beyond an Official Title
[28:40] Three Top Tips for a Successful Transition
If you’re approaching retirement, take one small step this week toward community and a life that feels like yours—then press play.
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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
Financial Clarity as a De-stressor
The shift from earning a steady income to managing a capital lump sum can be a source of significant anxiety. Using tools like financial modeling or seeking professional advice can help transition from a state of uncertainty to one of confidence, allowing you to focus on living rather than worrying.
The Power of Structured Flexibility
For those used to high-octane professional lives, complete freedom can feel overwhelming. Neil recommends implementing just enough structure - like a personal Kanban board or daily habits - to provide a sense of achievement and purpose without stifling the freedom that retirement is meant to offer.
[00:00] Introduction
[01:07] Neil’s journey from business owner to early retiree
[03:28] The emotional stages of selling a business
[06:12] Dealing with the loss of professional identity
[10:43] Facing the "What's next?" question in your early 50s
[14:10] The value of professional coaching and structured thinking
[16:21] Creating a new, fulfilling rhythm of life
[21:12] Looking ahead and the joy of intentional family time
[23:25] Using a personal filter for choices and opportunities
[30:24] Advice for others stepping out of business ownership
Your retirement should be tailored to your life—take the first step toward defining your own path by subscribing today and sharing this episode with someone currently navigating their own transition.
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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 :retiringpoint.com
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
Visit Retiring Point online : https://retiringpoint.com
Control What You Can Control
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.
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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
Don’t Wait Until the Cliff Edge
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
Shared Experience Can Be Reassuring - Hearing how other leaders have navigated the move away from senior roles can make the transition feel less isolating. The podcast creates room for honest reflection and practical guidance from people who understand the complexity of this stage.
This Is About More Than Leaving Work - The show frames retirement as a chance to redefine success, contribution, and daily life. It encourages listeners to see this period not as a winding down, but as an opportunity to build a life that is both enjoyable and meaningful.
Timestamps
[00:00] Introduction
[00:08] Meet Gordon Callum and the purpose of the podcast
[00:12] Who Retiring Pointers is for
[00:30] The real issues retirement brings into focus
[00:47] What guests will share in each episode
[01:06] Why this matters for pre-retirees and recent retirees
[01:15] Practical insight for approaching transition with intention
[01:37] The kinds of leaders featured on the show
[01:47] Episode formats: conversations, panels, and reflections
[02:03] How the podcast helps listeners shape their next chapter
Subscribe and take one small step toward 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
Visit Retiring Point online : https://retiringpoint.com
Create structure before you need it - Retirement can quickly feel disorienting when every day loses its shape. Stephen found that maintaining a morning routine, reflecting weekly, and setting small personal goals gave him a much-needed sense of control and helped him bridge the gap between corporate life and whatever comes next.
Your next identity needs intention - Losing a title is one thing; losing the language you use to describe yourself is another. Stephen’s story is a powerful reminder that retirement is not just about stopping work, but about actively building a new sense of self — one grounded in values, relationships, contribution, and possibility.
Timestamps
[00:00] Introduction
[00:51] The moment retirement started to feel real
[03:19] Announcing the decision and the emotional reaction at work
[05:30] The final 12 months: intensity, doubt, and neglecting self
[08:17] Day one of retirement and the shock of it becoming real
[10:34] The first few months: holidays, family focus, and underlying anxiety
[13:18] Loss of people, routine, and a sense of direction
[16:38] Feeling out of control and the struggle to find meaning
[21:18] Identity after executive life: who am I now?
[29:18] Stephen’s advice for preparing earlier and avoiding denial
Take one step now to shape the retirement you want - and share this episode with someone else who needs to hear it.
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