In 2023, my dad called to tell me he’d dropped down to four days a week at work.
He’d had a long career as an insurance underwriter, though it didn’t define him. At one point, he even left the profession to become a plasterer for a decade to better balance out his schedule. Still, it served him well enough.
“You really are getting old, then,” I joked. Dad laughed — he was only in his 50s.
We talked about his retirement and how he planned to wind down gradually over the next few years, before pulling the trigger and paying a full-time job’s worth of attention to the golf course.
That step was the first, and last dad took toward retiring. A year later, he told me he had cancer.
His diagnosis marked the beginning of a period in which I spent every day with him. He had been exceptionally fit, competing in triathlons, marathons, and Ironman races, but went from Hyrox to hospice care in just eight weeks.
Then on June 19, 2024, at the age of 56, Dad’s oesophageal cancer snatched away his future, and any prospect of a retirement.
I later realized our conversations during his illness were a textbook of the values by which he had lived his life. I’d heard him talk along similar lines in the past, but it wasn’t until I was lucky enough to spend each day for two months with him as his peer that I was able to distill them into three lessons.
Now, at the age of 32, these guide me in my career and life, and frame the way I think about retirement.
Live as if you might never make it
It may sound a morbid start, but I see this principle as both pragmatic and a call to action.
I see it as pragmatic because, of course, it is true: You might very well not make it to your retirement. And thinking about death in this way can help you take important practical steps, like ensuring you have an updated will and, at the very least, start thinking about granting powers of attorney.
And I see it as a call to action because, when loss helps you understand that life is precarious, it shines a light on how we often live without confronting the inevitability of death.
With that understanding, a more fulfilling life can emerge years earlier than it might otherwise have; one that, perhaps, you dreamed might come in retirement.
This principle led my dad to travel widely, a habit he passed to me. I’m due to visit New Zealand soon, the place he unknowingly took his final big trip. It also led him to take up the sports that piqued his interest over the years, and achieve a genuine sense of contentment.
It took me a lesson in the brutality of life, and the illuminating chaos of grief, to truly understand the importance of living it.
Build a life that gives you choices
One of the pitfalls of the first lesson is that, if taken literally, it could lead to financial ruin.
If it were a certainty I’d never make it to retirement, I’d spend everything I had now. However, in a classic catch-22, living life like I’d never make it there would delay my retirement in perpetuity.
So instead, I keep an eye on the future and try to resist the urge to part with all my money in exchange for experiences now, so that I can have some freedom of choice when I retire.
For Dad, working hard and getting an education meant having choices, and that influenced many of my decisions in life, including the one to pursue a career in corporate law.
In the end, that didn’t align with the life I wanted, but the experience gave me the skills and financial backing to choose a different legal career for myself.
Because of my job and savings I’ve built up from it, I had choices when Dad died. I was able to pause, reassess my life, and temporarily step away from my busy career.
During that time, I thought about how he used to ask me about work and I’d sometimes tell him how I wished I could just retire now to travel the world and write. He’d remind me I had a long way to go.
But now, those passions I always thought I’d save for later, like planning a trip to New Zealand or getting my master’s in creative writing, have become present pursuits.
Soon enough, though, I’ll pick up some legal work again. Why? Because unless I write a bestselling novel by the end of the year, I still want choices in retirement, should I make it there.
Find the adventure in everything
Dad took a keen interest in all aspects of life, and didn’t take much of it seriously — because of that, not in spite of it, he was still successful in much of what he did.
This lesson applies to every aspect of life, including retirement, which I’m viewing as simply another opportunity to experience a new pocket of life.
It even applies to terminal illness. When my dad was nearing the end of his life, he said something in an attempt to comfort me, which has ended up being the most transformative lesson of the three.
“Life is one series of adventures. This is just another one.”
That impacted me profoundly, and taught me to seek joy even in life’s darkest corners.
These days, I view my retirement, career, and life much differently
Losing Dad changed how I think about my life, career, and the very concept of retirement.
Most of all, it prompted me to stop deferring what I truly wanted to my final years while still setting myself up to have choices in the future.
Now that I’m taking incremental steps towards something I’d be happy to do well into my old age, the dream of retirement crosses my mind less often.
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