Retirement: Still me, just slightly better – When Is Enough?

At 51, retirement crosses my mind more than it used to. Not because I dislike my work. In truth, I wear several hats that I mostly enjoy.

I’m a Sales and Marketing Director for a software company, which pays well and strokes the ego. I run a small gardening side hustle, The Tidy Garden which scratches a different itch, and I have a sobriety club where I’m active and volunteer as a Samaritan, which reminds me daily of the struggles people face in silence, plus I’m married, have kids, a dog, and try to keep fit.

So, understand that I am not counting the days to “freedom” and I don’t feel the need to escape from work. Work is just part of who I am, and a much smaller part than it once was.

Retirement for me isn’t about stopping work, but it is about removing financial necessity from the equation.

It means reaching a point where my life does not depend on the next corporate payslip.

And so, even with that clarity, the questions gnaw away:

When is enough?
When is the right time to retire?
Will I ever feel like I’ve truly retired?
Is retirement worth looking toward too?

Retirement Isn’t What It Used to Be

For my father’s generation, retirement was a cliff edge. One day you worked, the next day you stopped. Your gold watch marked the end of one chapter. In the case of my father, it was a gold jacket, which marked the start of a quieter, slower chapter.

But for me, it’s much less about a finish line, and much more about the transition.

Work offers structure, purpose, and identity, but even the so-called “side hustles” are not about money, they’re about purpose, connection, belonging and serenity – the good stuff. I can’t imagine they’d stop when ‘work’ does?

So one thing I’ve been thinking about is this – Will I ever feel like I’ve retired?

The Dilemma

On paper at least you can plan for retirement by investing. You can fill the ISA, max the pension and make sure the mortgage is paid off. There are a plethora of calculators and tools. They allow you to make the required projections. However, life is not about spreadsheets. It’s more like rolling the dice, closing your eyes and taking that step feels like a gamble!

I hear it often through my Samaritan volunteering. People who thought they had “plenty of time” find themselves blindsided. They are caught off guard by ill health, redundancy, loneliness, or regret.

Time has a cruel habit of running out quicker than expected. Balancing it is crucial. I want to get this balance right.

Also; I note I’ve never once read of anyone regretting retiring “too early.”

What I have seen though, is a steady stream of stories about people who left it too late. People waited for one more bonus. They waited for one more promotion or one more year of saving. They found that the retirement they dreamed of slipped through their fingers.

The Balance

As a family man, it’s not just about me. It’s about providing security for my wife, setting my kids up with the right start. That’s the tug of war, isn’t it? Between wanting to give them stability and wanting to give me — time.

I’ve been “ready to slow down” for years now, but I haven’t slowed down at all. In fact, I’m doing much, much more now than ever, and it feels like there is still plenty to be done.

My fitness goals, savings plans, hobbies and side hustles — they’re not just vanity projects, they’re my retirement rehearsal.

They’re preparation for the next stage.

The danger, of course, is waiting forever to take the stage…

Should we be nervous to retire?

When Should You Retire?

If you can afford to retire, the answer has got to be yesterday? Because retirement isn’t about not working, not for people my age, it’s about working if you want to, and its about mornings that belong to you, not the work diary.

It’s about being around those that make you happy. And if you’re lucky, there will be lots of people that want to be around you also.

It’s about walks with the dog that don’t need to be squeezed in before the next Zoom call.

It’s about coffee after the jog with mates.

It’s about picking your tribe, and your tribe picking you.

And so once we’ve secured enough, the only thing standing between us and our retirement is what? Fear, trepidation nerves even?

I admit I fear retirement a little already, and I’ve probably got a few years to go?

The fear of letting go of the status, the structure and the security that comes years of repetition.

So I ask myself – what’s riskier? Retiring early and having a few less luxuries? Or is it retiring a late?