In Hindsight

This year has been all about recalibration and embracing the messy middle of midlife. At 56, I ran the Berlin Marathon, became a granny, and adjusted to life as an empty nester. Some changes were planned, others weren’t, but every experience taught me this: the only way to navigate this life stage is to be kind to yourself and brave enough to follow your heart.

When life throws a curveball at 53, it can feel like the ground has shifted beneath you. For Brandon, that curveball was retrenchment—a moment that brought shock, panic, and an overwhelming sense of uncertainty. The news left him with a racing mind, a cold sweat, and a burning question: What now?

Midlife is often marked by profound change—a phase where the roles we’ve played and the lives we’ve led shift completely. For Nicola, this came in the form of moving cities, empty nesting with her children going to boarding school, and re-entering the workforce after years as a stay-at-home mom.

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.

Midlife often arrives quietly, slipping into our lives amidst the chaos of daily routines, career pressures, and family responsibilities. It’s a life phase that leaves us with mixed emotions – nostalgia for our youthful past, anxiety about the future, fear about what’s to come, regret, and, very often, a profound search for meaning and fulfilment.

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.

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.

What if you find yourself in midlife, living a life that you carefully planned – emotionally and financially – only to find yourself merely existing. Not connecting with people who truly matter, not having a sense of community and belonging, and not living according to your authentic self.

Midlife is reflection time. It’s not only a time to makeover your money, but also a time for reinvention and growth. A time to pause and edit your life going forward. It’s the time of life when we ask ourselves: Where to from here? And the answer always holds both a money and a life perspective.

Every now and then, life has a way of surprising us with unexpected moments that lead to meeting truly inspirational people. Imagine my surprise when, during a night’s stay at Game View Lodge in Vryburg, I met Tersia and her husband, Theo, and learned about their retirement philosophy. Here was a couple with a thriving business who viewed retirement as a series of chapters. I love meeting people with big dreams and the passion to make it happen! Tersia and Theo wholeheartedly embraced Chapter 2: Act 1 as their chance to live their unfulfilled dreams on their own terms … and there’s more to come.

This has been a wonderful year filled with stories of inspirational midlife transitions, lessons learnt and wisdom shared. I have learnt that behind every financial plan lies a story brimming with hopes and dreams, courage, and the desire to live life to the fullest … not only in retirement, but right now. I have seen so many clients determined to live fuller, happier lives and put plans in place to make it happen – regardless of their phase of life.

You may not know this about me, but way before I became a financial planner, I owned my own catering business. Although I absolutely loved my business, I sold it 22 years ago to be a stay-at-home mom when my second child, Josh, was born. It took eight years and many hours of reflection, personal growth and studying to re-enter the working world. From catering to financial planning – who would have thought!

Ever wondered if it’s possible to ignite a fresh business venture in your 60s? And uplift others at the same time? Meet Gys, who, instead of dreaming of retirement, found a compelling project that leveraged his lifelong wisdom, experience and business acumen to transform a business idea into a remarkable new venture.

If you could rewrite your life story at 50 – what would it look like? Is it possible to turn curveballs into a compelling new direction, especially when you’re halfway through the game? Meet Lynda, a remarkable woman who faced multiple challenges in midlife: transitioning to a rediscovered purpose, a new career, the silence of an empty nest and confronting the financial realities of retirement.

Have you ever reflected on living your life differently? Do you have dreams and a longing to make changes? Thoughts about getting off the rat race? Having a more balanced life? Finding more joy and not wanting to wait to retire before enjoying life?

Nikki was faced with a choice in midlife – doing the same thing for another 10 years, or starting something new altogether. “My biggest fear was stepping away from my not insignificant corporate salary and annual meaty bonuses and share allocations…” says Nikki.

Have you ever felt that you are simply settling for more of the same?

Last month, I shared David’s story with you. As an entrepreneur restarting his business after bankruptcy, David shared some of his biggest regrets and mistakes. I love that David is excited to start afresh but willing to do things differently. Business-wise, David learnt to be fierce with reality, take control of his finances and get expert help. So many entrepreneurs make the mistake of seeing their business as the only income stream, while it is a good idea to have additional income streams (savings and investments) separate from the business.

In my previous blog, I shared Lily Mason’s story with you. The top money tip that stands out for me from Lily’s advice to her younger self is that she retired too hastily, without taking the time to reflect and plan her next chapter. She also did not have a trusted relationship with a financial planner and no one to mentor or guide her to have done things differently. The good news is that Lily is now taking time to think about her life going forward and ways to find renewed meaning and purpose. I am positive Lily will transition from a successful career to enjoying a significant life.

In my previous blog, I shared the top money tip I live with – paying yourself first. This month I’ll introduce you to Lily Mason, a midlife client with sage advice for her younger self – and lessons that we hope everyone in midlife (and younger) will benefit from and learn from. These lessons come from a place of experience, of having made real mistakes that we’ll all be able to resonate with; and represent the wisdom of having lived and learnt.

I am always inspired by how much generations can learn and grow from each other and how the flow of wisdom, insight and knowledge can add value to our lives. I speak to people about money every day, and one of the things I am most grateful for in my work is how much I learn from my clients.