Finding My Retirement Road

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Why I Started beyondWork

This blog came about as I started thinking seriously about retirement—whether that meant selling my business or stepping back from its day-to-day management. Like many, I turned to research to understand what lay ahead.

What I found was mostly focused on the financial side: estate planning, investments, and savings goals. Valuable, of course, but what I was really searching for—and what seemed far less available, at least in the South African context—were conversations about the softer side of retirement.

The psychology, the emotions, the questions of identity and purpose.
How do we shift from work to play, from structure to freedom, from constantly doing to simply being?
How do we learn to live more and stress less in this new road of life?
And where will this road lead me—and my life partner—as we move forward?

Who’s This Blog For? Well, It’s Personal…

I don’t have a particular audience in mind for this blog. I’m simply a 70-year-young guy, reasonably fit and healthy, who has spent the better part of four decades building and managing a software business.

I’m a very focused person by nature—some might say a workaholic—and I mention that because, no doubt, it influences the challenges I now face. I made the shift to semi-retirement about 2 to 3 years ago—these days I work mornings only, and Fridays are strictly off-limits. Well, that’s the plan anyway. It works… when it works. Ha, ha.

The transition from being completely absorbed in work to finding meaning and rhythm in semi-retirement – and one day, perhaps, full retirement— is, I suspect, a road full of detours.

No Manual for This…

To borrow a phrase, this road is “not for sissies.”
There’s no manual, no one-size-fits-all guide for easing into this next chapter of life.

Each of us comes at it with our own story, personality, and struggles. For some, it’s about letting go of work identity. For others, it’s about filling newly freed-up time with things that feel purposeful—or simply learning to relax without guilt ( really tough after decades of ‘work first, then maybe play later …’

These are some of the softer, more personal questions I’ll be exploring here.

How This All Started for Me

I guess my retirement journey started about five years ago. Back then, I found myself asking friends—often my ‘masters’ squash buddies—“When are you thinking of retiring?”

It became a bit of a preoccupation:

• What should I do with my future spare time?
• Should I stop working altogether?
• And, of course: can I afford to stop working?
• Do we re-locate and downsize?
• What happens to my circle of friends—will we form new bonds or drift apart?
• What kind of lifestyle do we want going forward – can we visualise it?
• Is there still life once the grandchildren turn into teenagers?
• What roles can we play in giving back to the community?

So, it’s become a constant balancing act—between time, money, and personal pursuits.

For example, if I travel too often, will my portfolio handle the expense? And can I really afford to take time away from work and from the community contributions I value?

Plans I had for my free time—write my memoirs, study AI, code some Python to automate my emails, and tackle a few other “projects”—haven’t quite played out as I’d imagined.

For now, the memoirs are on hold, and this blog has taken their place. But one thing has become clear: I need daily purpose.

Friends often ask me, “So what will you do when you stop working altogether?”

I’ve heard more than a few anecdotes of business owners who sold their companies and, just a few months later, were pulling their hair out—which, for some of us, is a struggle on more than one level.

Challenges and projects—big or small—are what weave a colourful life. One worth living, not just existing.

One of my objectives with this blog is to share some retirement planning lessons  – that are not all about Rands and cents. No doubt, the financial conundrums that this phase of our lives brings, is real,  but the latter is less than 50% related to money. After all once this aspect is planned – and managed of course – what about the quality of your days?

“This blog is my space to share the ups, downs, and lessons from this ongoing journey. I’m still finding my way out there —and maybe some of you are too…..”

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beyondWork

Work Less, Play More — Finding My Retirement Road