When Should I Retire?

Feb 253 min read

There’s a moment in life when we all start to realise a simple but brutal truth: money is replaceable, but time is not. And yet, too many people act as if the opposite is true. They work long hours, chase promotions, and stash away savings, all while their most vibrant years quietly slip away.

By the time they finally ‘retire,’ they may have a nice financial cushion—but their energy, health, and zest for life have been worn down by decades of full-time work.

So, let’s flip the script. What if, instead of squeezing every last drop of productivity out of our prime years, we started the second half of our lives sooner? Not when we’re too old and tired to enjoy it, but when we’re still healthy, curious, and capable?

What if the measuring stick or benchmark is when you realise your time is more important than your money!

The Great Illusion: Trading Time for Money

Society sells us a neat little formula: Work hard now, retire later, and enjoy life when you finally have ‘enough.’

But ‘enough’ is a moving target.

Promotions, mortgages, and the lure of a bigger nest egg keep pushing the finish line further away.

Meanwhile, your most valuable, non-renewable resource is quietly ticking away.

No matter how much money you make, you can’t buy back your 50s, your 60s, or the years where you could have been hiking mountains, learning new skills, or spending carefree afternoons with loved ones.

The Second Half of Life: A Better Plan

Instead of waiting until society tells you it’s time to ‘retire,’ why not redefine what work and life should look like?

What if we saw the traditional retirement age not as a goalpost but as a missed opportunity?

There’s a sweet spot—somewhere in midlife—when the importance of time overtakes the importance of money. That’s the moment you should take action.

Not necessarily by quitting everything, but by reshaping your life so that time takes center stage.

Real Stories, Real Choices

Take Michael. At 52, he had a thriving career in finance, but one day it hit him: his daughter would be off to college in three years. If he didn’t make a change, he’d miss the last precious moments of her teenage years. So, he stepped back from full-time work, picked up a flexible consulting role, and spent the next few years making memories instead of just making money.

Then there’s Sarah. She had always dreamed of traveling the world, but like many, she figured she’d wait until retirement. It wasn’t until she lost a close friend to illness at 60 that she realised waiting was a gamble. She sold her house, downsized, and spent her 60s exploring places she once thought were only for her retirement years.

How to Start Your Second Half of Life Sooner

Reevaluate Your Priorities: If time is your most valuable asset, are you spending it wisely? What would you do differently if you had only ten years left?
Redefine Work: Instead of ‘retiring’ in the traditional sense, consider shifting to part-time, freelancing, or consulting to give yourself more flexibility.
Test the Waters: Take a sabbatical, negotiate a four-day workweek, or try a ‘mini-retirement’ to see how it feels to prioritise time over money.
Start Saying Yes to Life: Stop deferring joy to a later date. Take that trip, learn that skill, and spend quality time with the people who matter most—now, not ‘someday.’

Final Thoughts: Don’t Let the Best Years Slip Away

It’s easy to let work consume the years when you’re healthiest, most energetic, and most capable of adventure. But one day, you’ll look back and realise that the window of opportunity for living life on your terms is smaller than you thought.

The real question isn’t “When should I retire?” but rather “How much of my time am I willing to trade for money?”

Your second half of life doesn’t begin when you finally clock out for good. It begins the moment you decide that time is more precious than another paycheck.

And the sooner you make that choice, the richer your life will be.