Robyn’s story may feel familiar to many of us. As our parents grow older, it’s natural to start wondering: Do they have everything in place? Are they okay financially? What would happen if they suddenly needed help?

Having these conversations with our parents can feel awkward, even intrusive. Too often, families avoid talking about money until there’s a crisis. For many of our parents, money is personal. It carries emotions like pride, fear, uncertainty, or even guilt. But these are some of the most important conversations we’ll ever have.

It’s not about taking control but gently opening space to understand what matters most to them. What are their hopes for this chapter of life? Do they feel secure? And are there plans in place for the “what ifs”?

Start with the basics

You don’t need to cover everything in one sitting. Begin with small, thoughtful questions:

• Do you have a valid, updated will?
• Where are your important documents kept, like your will, medical aid info, bank details, and passwords?
• Have you appointed someone to act on your behalf if you’re unable to?
• Have you spoken about your wishes for medical care if something happens?

Even just knowing where documents are and who to contact can make an enormous difference in a time of need.

Talk about money, gently
These conversations can also open the door to understanding how your parents feel about their financial position:

• Do you feel confident that you have enough for what you need?
• Are you comfortable with your current budget?
• Is your financial plan still suited to this stage of life?
• Do you have adequate medical aid and long-term care cover?
• Are you working with a financial planner? And would you be open to introducing them to us?

If something needs attention, starting the conversation early gives everyone time to plan rather than respond to a crisis.

This is their time too
Retirement is a significant transition and not always an easy one. For many parents, work may have provided structure and purpose for decades, and letting go can feel like a loss. These conversations are also an opportunity to talk about what brings them joy now:

• What does a good life look like today?
• What brings you happiness, meaning, and connection?
• Is there something you’ve always wanted to do?

Many of our parents have spent years putting others first. These moments are a chance to reassure them that they’ve done enough. This is their time to enjoy what they’ve built and create memories with those they love.

You don’t have to have all the answers, and you don’t need to cover it all at once. But the earlier you start, the more confident everyone will feel about the road ahead.

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

Kim

It’s not uncommon for parents to put their own lives – and their retirement savings – on hold to prioritise their children’s education. It’s a choice made with love, but one that often leaves you playing catch-up later in life. What I admire so deeply about Lyndsay and Christian is how they faced this reality with courage and intention. Instead of panicking, they took action. They made intentional choices. And most of all, they shifted their mindset.

What stands out most about their journey is the way they’ve embraced this chapter of life. Rather than seeing it as a setback, they’ve reframed it as an opportunity: to extend their timeline, re-engage with work they enjoy, and plan with clarity. They’re learning, earning, saving, and living. Here are the lessons I’ve taken from their story:

Extend your Timeline
Lyndsay and Christian have accepted that they’ll work for longer. But this gives them the time and space to plan intentionally, not reactively, for their future.

Keep growing and learning
Christian took on a new role with greater responsibility. Lyndsay embraced work she genuinely loves and is constantly looking to grow her skills to earn more, do more, and stay relevant.

Share the responsibility
This is a powerful shift. After years of leaving the finances to Christian, Lyndsay stepped in and lifted the burden. It’s a beautiful reminder of the importance of partnership – and shared accountability.

Redirect money with intention
They’re balancing the long-term with the now, saving for the future while living intentionally today. Watching them plan and save for their first overseas trip in 25 years was deeply inspiring.

Invest for future income
While you’re redirecting money to live well now, it’s just as important to redirect money into savings and investments. These grow over time while you’re still contributing and will generate an income when you need it most.

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

Kim

The first step to taking control of your financial future is valuing yourself enough to honour your dreams and priorities. What puts us most at risk is not the support we offer others – it’s when we delay the hard decisions, avoid the real conversations, and continue giving at the cost of our own future.

Lauren is an incredibly brave mother. Setting boundaries with those we love is never easy, especially when it’s our children. But it can be one of the kindest and most courageous choices we make – for them and for ourselves.

If you’re navigating a similar path, consider teaming up with an accountability partner – whether it’s your life partner, financial planner, or someone in your inner circle. These are tough, emotional decisions, and it’s hard to stay objective. An accountability partner can give you the perspective and support you need to stay true to your values and goals.

I also believe in open and honest conversations with your children. If one child receives more help, the others need to understand why. Transparency helps prevent resentment, entitlement, or feelings of being left out – and it builds a stronger foundation of mutual respect and understanding.

Lauren is beginning to shift her story, choosing to honour her dreams, prioritise her well-being, and find new ways to show love that doesn’t compromise her own security. These aren’t small steps. They are life-changing ones.

I encourage you to read Tiffany’s article in this newsletter: When One Child Needs More Than the Other – Rethinking Money, Fairness and Legacy. It offers practical advice on setting boundaries, having honest conversations with your children, and finding a more sustainable approach to support. True fairness isn’t about treating our children the same. It’s about showing up for each of them with thoughtfulness, love, and intention.

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

Kim

When giving brings guilt and expectations

I notice this often – how easy it is to feel guilty about spending money on ourselves when those we love are struggling. And it’s not just about who we feel we should help, but also when we choose to help. Do we step in only when someone asks, or do we offer because we see them struggling? And when we do help, do we let go, or do we quietly hold expectations about how that money should be used?

I’ve seen this play out in many of my clients’ lives – and I’ve experienced it personally. For years, I felt compelled to help whenever I noticed someone I cared about was in trouble. But I’ve learned that stepping in isn’t always as straightforward as it seems.

I remember lending money to a family member, only to find out later they’d used it to go on holiday. I was irritated. How could they use the money for something I wouldn’t have chosen? That experience taught me an important lesson: while I had offered the help, I’d also attached unspoken expectations. And when those expectations weren’t met, it left me feeling frustrated and resentful.

Here’s what that experience taught me:

1. Check your expectations: Sometimes, people haven’t even asked for help – we step in because we feel we need to. But when we do, it’s important to ask: Am I giving with strings attached? Do I expect appreciation, repayment, or for the money to be used in a certain way? If so, is that fair?
2. Pause before jumping in: It’s natural to want to rescue, but offering help before someone asks can create its own tension. Sometimes, people need the dignity of making their own decisions – or even mistakes.
3. Release the guilt: It’s easy to feel guilty for enjoying what we’ve worked hard for, especially when loved ones can’t do the same. But it’s okay to honour your own financial goals and dreams. Helping others should come from a place of love, not obligation or guilt.

These lessons aren’t always easy, but they’ve helped me approach giving with more clarity and compassion – both for myself and others. I’ve come to realise that most of my joy comes from giving as a gift, without expecting anything in return. When I let go of the outcome, I also let go of the potential for disappointment. That simple shift has allowed me to truly feel the happiness that comes with giving from the heart.

Kim

Victoria shared an incredibly brave and honest story. Borrowing from Theodore Roosevelt’s Man in the Arena – the credit belongs to Victoria, who bravely stepped into the arena with the courage to pursue victory and the resilience to face the possibility of failure.

When faced with an unexpected challenge, Victoria didn’t wait for circumstances to change, or get stuck in why is this happening to me? Instead, she stepped forward when life demanded it. It takes courage to shift from being a teacher and part-time artist to becoming the primary income earner, and Victoria did it with resilience and determination.

When life throws a curveball, how do you pick yourself up?

We are capable of more than we imagine. Have the courage to take the first step.
I always reflect on my lifeline – looking at the highs and lows of my journey reminds me of the strengths, systems, and support that carried me through past challenges.

Do you have systems or strengths you can draw on to navigate challenges?

Financial planning: It’s incredibly brave to acknowledge regret, and Victoria openly shared that she regrets not having a financial plan earlier in life. So many people believe it will never happen to me – until it does. The truth is, life is unpredictable, and having a financial plan in place gives you options when the unexpected happens. It’s about creating a safety net so you don’t have to make desperate decisions or dip into savings meant for the future. It also allows you to shift from a place of strength rather than fear.

If there’s one takeaway from Victoria’s story, it’s this: You can’t always control what happens, but you can control how you respond – and that makes all the difference.

Kim

Brandon’s story is a powerful reminder that life doesn’t always go according to plan, especially when we’re faced with a sudden change like retrenchment. But there are ways to prepare ourselves and make the transition smoother. Here are some valuable lessons we can take from his experience:

Keep building your skills

The world is changing fast, and so are the skills needed to stay relevant. We often think we’ll keep doing the same work, but that’s not always the case. Upskilling or building parallel skills is crucial – it gives you options to explore a new career path. Keep asking yourself, “How can I add value in different ways?”

Partner with a financial planner

When retrenchment happens, emotions can run high. Fear, anxiety, and uncertainty may cloud your thinking, and making financial decisions in that state isn’t easy. A financial planner can help you stay objective and avoid making impulsive decisions, like using all your retirement savings to buy or start a business without proper planning.

Safeguard your capital

Your pension or capital is now more important than ever – keep it protected for as long as possible. Ideally, start earning as soon as you can, even if it’s just enough to cover your living expenses, while keeping your retirement savings intact and invested. Transitioning from a steady salary to marketing yourself—and potentially facing multiple rejections—is challenging, and the sooner you can generate some form of income, no matter how small, the more secure you’ll feel.

Know your Why

Finding your ‘Why’ is so important, especially when times get tough. Your ‘Why’ is the sweet spot—what you’re good at, what you love, and what the world will pay for (what the Japanese call ikigai). Keep reminding yourself of the bigger picture and why you’re pursuing this path when faced with rejection or obstacles.

Involve a mentor or coach

Find someone who can guide you through this process. A mentor or coach can provide objective, unemotional advice and help you see things clearly. They’ll give you honest feedback and help you shape your ideas into something realistic and achievable.

Explore multiple income streams

You have to be open to the idea of not relying on a single job for all your income. Explore different ways to generate revenue—what we call a ‘portfolio career.’ This might involve combining freelance work, consulting, and part-time opportunities, so you’re never dependent on just one source.

I wholeheartedly agree with Brandon that starting over after retrenchment requires a high level of motivation. But pursuing a new dream aligned with your passion makes the journey just that little bit easier.

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

Kim

One of the key lessons I love from Nicola’s journey is how important it is to keep your skills up to date, even when you’re not working full-time. This is so important for mothers who take time out to raise children. Nicola made a conscious effort to keep learning, and that decision gave her the confidence to re-enter the workforce when the time was right. It’s a valuable reminder that nurturing your skills during any career break is a long-term investment in yourself.

Another powerful lesson is how Nicola tapped into the Japanese concept of ikigai, meaning ‘a reason for being’ or a purpose that makes life worth living. It represents the intersection of four key aspects:

• What you love
• What you are good at
• What the world needs
• What you can be paid for

Nicola aligned her passion for health and mindfulness with a career that brings value to both herself and others. This is a wonderful tip for anyone looking to redefine themselves and their work in midlife. By exploring your own ikigai, you can discover a purpose that brings you joy and serves the world.

Nicola’s website (https://nicolaaylward.com/) is filled with incredible resources, from courses and programmes to dōTERRA essential oils – all focussed on the holistic balance between health and well-being.

After running the Berlin marathon, I went to bed, convinced I’d never walk again! But I used Nicola’s Deep Blue Rub, and to my amazement, I woke up feeling refreshed—my muscles felt so much better overnight.

Her Frankincense, Lavender, and Peppermint rollers have also been game-changers for me. This morning, after using them on my feet, my blisters vanished. Thank you, Nicola, for these incredible products that truly make a difference!

Magnus’s transition is a beautiful reminder of the importance of proactive planning and the willingness to adapt. When life throws unexpected changes your way, having a clear vision of what you want to achieve and staying open to new opportunities can turn a challenging transition into a fulfilling new chapter.

Magnus’s story highlights three key insights:

Embrace the Unexpected: Life often doesn’t go as planned. Magnus’s corporate retirement being brought forward unexpectedly is a prime example. It’s essential to stay flexible and open-minded when facing sudden changes – it can lead to new and exciting opportunities you might not have considered.

Ease into the Transition: Magnus’s experience of feeling disoriented without the structure of his corporate life highlights the value of a gradual transition. If possible, start experimenting with aspects of your new life before fully retiring. This parallel approach allows you to adjust more comfortably and reduces the shock of sudden change.

Integrate Your Wisdom and Skills: Magnus’s decision to pursue a post-graduate diploma in financial planning and combine it with his extensive experience is inspiring. It reminds us that by combining our lifetime of wisdom and experience with continuous learning, we can recalibrate how we stay engaged and relevant regardless of our age.

Magnus’s story resonated deeply with me, and I’m sure with many of you, too. It’s a powerful example of how integrating our past experiences with new skills can lead to a rewarding second chapter.

Remember, midlife is a time to reimagine and recalibrate your path.

What new opportunities can you explore today to create a fulfilling future – and possibly a second career?

Kim

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.