An Australian nurse named Bronnie Ware once wrote a book that struck a chord around the world.
She had spent years caring for people in their final days, and through those many bedside conversations, one truth kept emerging: the deepest regrets people had weren’t about what they did, but what they didn’t do.
Now, I’m not a nurse.
But I’ve spent over 20 years having deep, often emotional, conversations with successful families around the world, people nearing retirement, people already retired, and those still grinding through their careers.
And over time, I’ve noticed many of the same regrets come up again and again.
Because here’s the thing: time always wins.
And it’s the one thing you can’t buy more of.
This blog explores two powerful sets of insights: the five biggest regrets Bronnie heard from people at the end of their lives, and the five I hear most often from those in or near retirement.
More importantly, I’ll also share how to avoid these regrets becoming part of your own story.
Life isn’t a rehearsal.
But too many of us live as if it is, putting off joy, delaying decisions, chasing perfection, and waking up one day wondering how we ended up with a life we never really chose.
Bronnie Ware’s work captures this beautifully.
These were the top five regrets of the dying, according to her:
“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
This was the most common regret. So many people lived on autopilot, following paths mapped out by society, family, or culture. They didn’t pause to ask, “What do I actually want?”
“I wish I hadn’t worked so hard.”
They equated busyness with worth, thinking their long hours proved something. But in the end, all that time lost can’t be reclaimed.
“I wish I’d had the courage to express my feelings.”
Avoiding uncomfortable conversations led to broken relationships and unresolved emotions. They bottled things up, even with those they loved most.
“I wish I’d stayed in touch with my friends.”
People assume friendships will survive long absences. But connection requires intention.
“I wish I’d let myself be happier.”
Many treated happiness like a guilty pleasure rather than a priority. Joy was postponed, as if it needed permission.
It’s heartbreaking, but it doesn’t have to be your story.
What retirees regret most
When we shift the focus to those already in retirement or approaching it, some of the regrets echo Bronnie’s list.
But others are more specific to this stage of life.
Here are the five I hear most often from retirees.
By the way, I also published a YouTube video on this very topic, which you can watch here if you prefer:
Many people wait for perfect timing, the ideal market, the perfect pension pot, that elusive “just right” moment.
But it rarely comes.
Meanwhile, their window of health, curiosity, and freedom quietly begins to close.
One client of mine in his mid-50s was financially set.
But he kept saying, “Just one more year.”
When he finally stepped back, his partner had been diagnosed with a serious illness.
Their travel plans were cancelled.
The sabbatical? Too late.
He did retire well, but with regrets.
Modern retirement doesn’t need to be all or nothing.
Treating it like a cliff edge leads many to work longer than they need to.
If you have the means, you may already have the permission, you just need to recognise it.
Try this: Explore phased retirement. Reduce your hours. Take a year off. You don’t have to vanish overnight, but you can start living more freely sooner than you think.
Oddly enough, many retirees underspend.
Even those with solid financial plans often act like their funds are fragile.
Fear of running out keeps them from enjoying what they’ve earned.
I once worked with a man who had saved millions, but in retirement still lived like he was in his 30s - cutting corners, skipping holidays, always anxious.
It wasn’t until his mid-70s, after a health scare, that he finally let go.
He told me, “I could have afforded the memories. Instead, I banked the money and lost the time.”
Your early retirement years are your golden window.
That’s when energy, mobility and appetite for adventure are highest.
Don’t waste it waiting for a feeling of “safety” that may never come.
Try this: Set aside a “spendable” bucket, money earmarked for joy, memories, and living well early in retirement. Build a plan with clear guardrails so you know when to spend more, and when to scale back.
Many people save the big trips for later.
But later doesn’t always cooperate.
A friend of mine always talked about doing South America after retirement.
Two years later, a health condition changed everything.
Long-haul travel was off the table. “We always thought we’d do it next year,” he said. “Now it’s not even an option.”
Travel takes energy, stamina and spontaneity.
It’s about timing, not just budget.
And that window for meaningful, active travel? It closes faster than people expect.
Try this: Make a list of your travel goals. Prioritise the ones that are more physically demanding, long-haul or adventurous. Front-load the big ones while you still can.
Too often, we assume passions and hobbies will emerge naturally once we retire.
But if you don’t explore them early, you may struggle to even know what excites you outside of work.
One retired lawyer I knew had no plan beyond “more golf”. Six months in, he was bored stiff, not for lack of time, but because he’d never practised curiosity.
After decades focused on one profession, he didn’t know how to be a beginner again.
Purpose in retirement doesn’t show up by itself. You build it through exploration. Without it, retirement can feel empty, even with all the freedom in the world.
Try this: Start now. Take a class, learn something new, volunteer, pick up an instrument. It’s not about being good at it, it’s about laying the groundwork for a meaningful life beyond work.
This one’s brutally simple.
People pour effort into building wealth but neglect the one thing that makes it enjoyable: their health.
You could retire early, mortgage-free, financially bulletproof.
But if your health fails, your dream of hiking the Amalfi Coast might turn into sitting on a tour bus watching others live it.
Health isn’t a “nice-to-have” in retirement, it’s the foundation.
Without it, everything else starts to fall away.
Try this: Build your health strategy like your financial plan. Schedule movement. Prioritise strength. Optimise your sleep and nutrition. Don’t wait for retirement, your habits today determine your quality of life tomorrow.
So, how do you make sure you don’t end up with these regrets?
I use a simple tool with clients, something called the Accountability Document.
It’s not about numbers or strategy, it’s about perspective, and having no regrets.
It forces you to zoom out and ask the big questions before crisis hits.
Not “how much do I need?” but “what do I want my life to mean?”
It’s helped me walk the Inca Trail, climb Kilimanjaro (twice with my son), hike to Everest Base Camp, and, most importantly, create real memories with the people I love.
And I believe it can help you too.
If you'd like to know more, you can download an example here.
Retirement isn’t just a financial milestone, it’s a life transition.
And like all big transitions, it’s full of potential and risk.
You could use this time to finally live on your terms, or let it slip by while waiting for the “right” moment.
Don’t wait.
Start now.
Even small shifts today can lead to a retirement you’ll be proud of, not one you’ll look back on with regret.