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Embracing Midlife – A Journey of Reinvention and Possibility

Midlife is perhaps the most misunderstood phase of life, often overshadowed by outdated stereotypes and misconceptions. But this phase really holds the biggest potential for growth, fulfilment, and a new beginning.

Introducing My Latest eBook

I am so happy to share my latest eBook, 10 Midlife Myths & the Truths Behind Them, with you. This eBook is more than just a guide – it’s an invitation to see midlife as a period of reinvention, recalibration, and immense possibility.

Reflecting on my midlife journey

I’ve always believed in the mantra, ‘If you leave your life to chance, you will end up living a life someone else plans for you.’ So, when I turned 50, I began reflecting on my past decade and planning for what’s next. Learning is key for me; whenever I struggle with something, I learn about it. My self-discovery led me to the work of Dr Brené Brown, her studies on vulnerability, shame, and courage, and my training as a Dare to Lead Facilitator. I realised that to make my life after the midpoint even more spectacular than the first half, I had to step out of my comfort zone and choose courage over comfort.

Lessons from the Modern Elder Academy

That same year, I attended a workshop at Chip Conley’s Modern Elder Academy, where I learned how to reframe my lifetime of experience for the second half of my life. Now, as I navigate the reality of an empty nest and recalibrate my relationship with my husband, I’ve come to understand that midlife is never a single event but a series of edits and transitions as our circumstances change.

Listening to My Inner Voice

When that little voice in my head calls on me to take action—I listen. I returned to MEA for Chip Conley’s course based on his latest book, Learning to Love Midlife and learned that we already have all the answers we need. So often, we search for answers in the world around us and neglect our inner wisdom. I made a new commitment to grow my intuition, connect with my inner wisdom, and make decisions that resonate with my soul.

This eBook is a culmination of my personal journey and the wisdom I’ve gathered from guiding clients through their midlife transitions, including insights from Dr Brené Brown and lessons from my time at the Modern Elder Academy.

What’s Inside?

10 Midlife Myths, Debunked – behind every myth lies a truth that will inspire you to embrace midlife with confidence and curiosity.
Real-life Stories of people who have redefined their paths and found meaning and purpose in their midlife years.
Actionable Insights and Reflections – practical advice and thoughtful questions designed to help you apply these truths to your own life.

This eBook reflects my belief that the second half of life should be lived with intention and purpose. It’s a time to recalibrate, to reconnect with your inner wisdom, and to plan for a future that aligns with who you truly are.

Download a copy of 10 Midlife Myths & the Truths Behind Them here

Kim

A Second Career in Midlife

Life doesn’t always go entirely to plan – and when your employer unexpectedly moves your scheduled ‘retirement’ date forward, it can leave you feeling completely unprepared. The sudden transition from being a full-time, salary-employed executive to ‘retired’ can be extremely challenging – even when you’ve proactively considered what this transition might eventually mean for you.

The Unexpected Shift

Magnus always knew he never wanted to retire in the traditional sense – to him, retirement was an outdated concept. His planning revolved around extending his work life to keep contributing to meaningful outcomes, engaging with people, and continuing to learn and grow. But, when Magnus’s planned retirement date was unexpectedly brought forward, the transition from a full-time executive role to ‘retirement’ was more challenging than he had ever anticipated.

From Theory to Reality

Although Magnus had ideas for his post-corporate life, they weren’t formulated into specific goals and objectives. The sudden shift from a structured, deadline-driven life to one of freedom and flexibility was disorienting, and he felt lost without the familiar rhythm of meetings and objectives.

Starting a New Career and finding Renewed Purpose

It wasn’t until Magnus began implementing his ideas for a second career, that things started to improve. He’d become interested in financial planning and saw firsthand how valuable it is to get the proper financial guidance at different stages in life. This also aligned well with his goal of helping people improve their lives, and he really enjoyed the process of understanding a new field and finding ways to simplify it so that it was easier for people to understand.

Magnus enrolled and completed his postgraduate diploma in financial planning at Stellenbosch University. He now combines this qualification with his experience creating digital solutions in financial services. Magnus’s been involved in some interesting new projects and feels positive about future opportunities.

Magnus’s Life and Money Lessons

Question:
In Hindsight, what would you have done differently?

Answer:
If I had to do this again, I would have started trying out aspects of my second chapter before leaving corporate life, experimenting with different work-related projects, new interests, and hobbies. I should have taken that sabbatical!

Life brings many demands and opportunities. It’s important to be goal-oriented and forward-looking, but don’t inadvertently ‘live in the future’. Constantly thinking about where you’d like to be can make your happiness dependent on future events or circumstances. Cultivate the ability to be content and happy in the moment, just as it is.

Question:
What money habits have served you well?

Answer:

  • Manage your cash flow and pay your future self, first – automated contributions to retirement funds work well.
  • Consistently invest a portion of any bonus or windfall.
  • Spend time in the market (rather than timing the market)
  • Diversify your investments – offshore is a good option.

Question:
What has been your biggest money mistakes?

Answer:
A short-lived, painful belief in my ability to outwit the market. Luckily, this happened quite early on, and I could recover and follow a more sensible path.

Question:
What Money Advice do you have for others?

Answer:
Pay attention to your money – it brings your values to life! Money enables us to engage in memorable activities that bring us joy, live in a home we love, spend time with our kids, family, and friends, help our kids establish a sound financial footing, and the ability to help people in need.

Question:
How have you found purpose in your second chapter?

Answer:
This phase is about letting go of the ego and embracing the joy and energy of meaningful projects. I prioritise being fully present, valuing peace of mind and delighting in curiosity, humour, kindness, and beauty. Relationships with close friends and family are important to me, and I treat everyday encounters as chances to connect. I’m also more conscious of my health, focusing on physical well-being and investing in personal growth and mental health.

Always remember, when it comes to your money and your life, be inspired, be brave, and be on purpose.

Kim

Read Kim’s advice to Magnus here!

The Midlife Myths we tell ourselves, and the Truths we need to embrace

Life gets better with age. The true power of these words grows as we enter midlife; we are so much better equipped to handle life’s challenges. It’s a time when we shift from caring what others think to focusing more on personal growth. Midlife is not a crisis – it’s an opportunity, a time to unlock a whole new world of choices, challenge the myths about ageing, explore new possibilities, and step into what could be the most exciting and fulfilling chapter of our lives.

I recently returned from Chip Conley’s Learning to Love Midlife workshop at the Modern Elder Academy (MEA) in Baja. I joined a diverse group from across America and Canada, ages 33 to 70. Starting out, we discovered a midlife myth that we all shared based on this question: What percentage of your adult life is still ahead of you? How would you answer? The point is, once you dispel one Myth, a whole set of Truths opens up to you.

Here are the top 3 Midlife Myths and Truths I discovered at MEA:

Midlife Myth #1: You are not old

The fact is, we are living longer. Realising that you might live to 100 opens up a new world of possibilities. Imagine – half your life could still be ahead of you! This realisation gives you choices – to push out retirement and reconsider what it means to slow down. Why step back now if you have 15-20 good years left to work and contribute? Remember, work can be redefined not as something you do for money but as a way to serve, contribute, and add value to the world.

The Truth: You have more life left that you thought.

With this in mind, what do you want your life to look like? What do you still want to achieve?

This is your reminder to reimagine your life and make changes to ensure you don’t have any regrets. It’s time to let go of the responsibilities and commitments that no longer serve you and make space for all the things that will make this your most fulfilling chapter yet.

Midlife Myth #2: This is as good as it gets

No, it’s really not. Life is not all downhill from here. I’ve met so many people who merely bide their time in jobs, counting down the years to retirement, or define themselves solely by their work. Too often, people feel stuck or overwhelmed by regret. Why not say YES to more things. Here I am, learning to surf in Baja – something I never thought I’d do!

The only way to transform your life is with deep introspection. It’s about the hard, inner work necessary to challenge and change the habits, beliefs, and mindsets that hold you back. Understanding and being clear on your values and aligning your life with what matters most to you are the most powerful tools for deciding what to carry forward into your next chapter.

The Truth: The best years can still be ahead!

Midlife Myth #3: Spirituality is a luxury we can’t afford

We don’t often make time for spirituality. We tend to seek answers from the world around us and neglect the insights from within. I have made a commitment to myself to invest time in meditation and growing my intuition. When you make time to connect to your inner wisdom, you’re empowered to make decisions that resonate with your soul.

The Truth: You have all the answers you need.

And finally, recalibrating in midlife – whether it’s leaving your job, changing careers, starting a business, or ending a relationship – means recalibrating your time, your life and your money to support living your best life.

And this is why I designed the Transform Midlife from a Crisis to an Opportunity workshop. Because every decision we make has financial implications, and while we cannot control everything, we can plan how our money will support and enable our midlife recalibration. Make sure your transition is based on informed and rational decisions about what your money can achieve.

Always remember, when it comes to your money and your life, be inspired, be brave, and be on purpose.

Kim

Navigating Inheritance – beyond the money

Money is such an emotional topic, no matter how you look at it. When your financial status suddenly changes, for better or worse, it can be an extremely challenging transition period to navigate – not only from a financial perspective but also emotionally.

Gabriella inherited a substantial sum from her husband. They shared a beautiful and deep connection, and his death turned her entire world upside down. As a young widow, apart from navigating the overwhelming loss of her life partner, the sudden windfall left her feeling guilty, overwhelmed, and daunted by the responsibility of these funds.

How does one honour a legacy with grace and wisdom? How do you navigate this profound life transition that suddenly feels strange, unfamiliar and filled with new challenges?

Introducing Gabriella

The past few years have been profoundly challenging for Gabriella as she stood by her husband throughout his illness, caring for him and accompanying him to all his doctor’s visits. After her husband’s passing, Gabriella found herself not just mourning her life partner but also struggling with the inheritance that came with its own set of emotional weights: guilt, anxiety and fear. Apart from the guilt and feeling undeserving of the money, Gabriella felt fearful of managing it properly, worried about making poor financial decisions and dealing with the tax associated with the investment.

Inheriting from someone you’ve loved deeply has a profound emotional impact.

While Gabriella’s experiences are uniquely challenging, they resonate deeply with others navigating similar transitions. It’s not uncommon for people in these situations to struggle with feelings of isolation, disconnection, and anxiety about financial decisions.

Gabriella’s journey through a devastating transition

Question
What have been your biggest challenges with the inheritance?

Answer
The hardest part was trusting myself. I was daunted by the thought of managing the money and setting realistic expectations about my capabilities. Initially, I blamed the inheritance as the source of my stress and worry, but it was really a catalyst for uncovering deeper emotions like grief, fear and anger. Life and financial planning have helped me see that my stress was less about money and more about underlying emotions that I hadn’t addressed.

Question
Have you experienced guilt, pressure, isolation, or an identity crisis since receiving the inheritance? How have you coped with these feelings?

Answer
The responsibility felt overwhelming – I felt guilty stressing about wealth when others struggle – and guilt over the freedom it gives me to pursue my dreams due to such a devastating event.

People don’t regularly talk about money, and I felt isolated, afraid to seek help for fear of being judged incompetent or unworthy. As a young widow, I felt alone and unequipped with the life skills to tackle this responsibility on my own.

Reflecting on these emotions, I realised they were self-imposed and untrue – they were stories I created based on my own insecurities. The reality is that my husband trusted and believed in me to manage this transition, be the guardian of the inheritance, and, most importantly, live a fulfilling life. This realisation inspired me to honour his belief in me and embrace the gift he has given me.

Question
How will you honour that legacy that your late husband left behind?

Answer
I’ve learned that honouring his legacy is also about honouring mine. His wish was to be a part of my growth and happiness for the rest of our lives, and through this inheritance, he supports me in living my legacy now, not waiting until after I’m gone.

Question
A significant life-changing event often demands we pause, reflect, and start a new chapter. How will you navigate your life from now on? What will you do differently?

Answer
I will continue to pause, breathe, and check in with myself. I will remind myself to separate perceptions from reality, to be authentic, and to live life meaningfully and purposefully.

Question
What prompted you to reach out to a financial planner? Has it been helpful?

Answer
I knew that I needed help working on my complicated relationship with the inherited money and recalibrating and planning for a new chapter with a new identity. I cannot imagine navigating this process without the team at Chartered, from estate settlement to taxes, life and financial planning. I learned how to move forward without feeling overwhelmed. Chartered provided a sense of security, allowing me to take a breath, sit with uncertainty, and confidently explore my new identity. It’s reassuring to know that ‘it’s going to be ok, we’ve got this.’

Question
What new money habits are you embracing?

Answer
I’ve learned that it’s ok to ask for help, trust myself, and let go of the need to control everything. I am starting to understand that money should support and enhance my life, and it’s not something I need to hoard, feel guilty about, or be afraid of. My new money habits are to:

  • Remind myself that money is my friend – not a foe.
  • Take control of my money – this means checking in on it, not obsessing or ignoring it.
  • Staying thoughtful (sometimes conservative) but not hoarding it or limiting myself.
  • Check in with the ‘stories’ I am creating around money and assessing whether they’re true.
  • Learn more each day about how I can grow and support money while it grows and supports me.

Question
Do you have advice for others who may be going through significant transitions?

Answer
Pause. Breathe. Ask for help. Allow yourself to experience all the emotions – the grief, the fear, the pain… allow it to come and allow it to go. And the most important piece of advice – stay open.

Question
Do you have any advice for others regarding a sudden windfall?

Answer
Find specialist support that you trust. You don’t have to know it all, and you don’t have to do it all alone. My financial planners aren’t just that; they are my life advisors, sounding board, support system and team.

Kim’s Advice to Gabriella

Honouring a legacy and moving forward

Nothing can really prepare you for the emotional turmoil of losing a loved one. Life suddenly feels unsafe and unpredictable, and you need to find deep resilience to pull through. Although Gabriella’s husband had carefully planned for her future, entrusting her completely to manage the inheritance and use it to take care of herself and pursue her dreams, the responsibility felt overwhelming. The guilt and daunting sense of duty left her fearful of mismanaging the funds, anxious about making mistakes and terrified of wasting the gift left to her.

I am incredibly proud of Gabriella – reaching out for help, especially when it comes to money – is a courageous thing to do. She has embraced a planning team to help guide and support her through this transition. Gabriella needs to be patient and kind to herself. Learning to accept money (whether earned or inherited) and then formulating and implementing a financial plan is a process that takes time. You don’t have to have all the answers from the start. She is also learning to improve her relationship with this money. In truth, this money is not meant to be feared or cause guilt. Gabriella needs to become friends with this inheritance and accept that its purpose, as her friend, is to enable her to live her life purposefully and pursue her dreams – just as her husband intended.

Always remember, when it comes to your money and your life, be inspired, be brave, and be on purpose.

Kim