The 5 Biggest Regrets Before Death – A Story That Changed How I See Investing and Life [Special EP03]

Picture this. You’re ninety years old, lying in a quiet room. The air smells like disinfectant. A life-support machine hums softly beside you. Your body won’t move anymore, but your mind is unusually clear. Sunlight spills in through the window, and you can even see dust floating inside the beam.

Now imagine someone hands you a time machine—and you can return to this exact second. The moment you’re watching this video. If you could live again from here… what would you change?

Why ask something this heavy? About ten years ago, I read a book that changed the way I looked at investing and life. And it made me realise something uncomfortable: all those cash flow charts, balance sheets we analyse every day… we might be using them to answer the wrong question.

The author’s name is Bronnie Ware. She’s not a billionaire. She’s not a finance guru. She was just an ordinary hospice nurse in Australia. Her job was to sit with people who had only a few weeks left, and walk with them to the end.

Think about what that means. Day after day, she watched someone go from talking and thinking… to silence… and then to leaving. And after hearing so many final conversations, she noticed one thing: when people reach the finish line, they stop performing. The mask comes off. They tell the truth. No one cares about their title anymore. No one cares what others think of them. They care about one thing only: “Did I waste my life?”

Bronnie gathered those truths into a book called The Top Five Regrets of the Dying. When I finished it, I broke out in a cold sweat.Because I realised every single regret in that book described what I was doing at the time. And I thought—if I don’t change, then even if I hold more properties in Australia, even if my stock account looks impressive… When that moment comes, none of those numbers will buy me even a little peace.

So today, I want to talk about something different. No charts. No balance sheets. No “next big opportunity.” Let’s talk about the most valuable asset you own—and the one that leaks away the fastest: time. This might be the most important review you do all year. Because it’s not about how much you earn next quarter. It’s about how you allocate every day for the rest of your life.

Regret Number One: “I wish I’d lived my own life—not the one others expected.”

Let’s start with Bronnie’s number one regret—the most common one, almost everyone mentioned it: “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Sounds familiar, right? Even a primary school kid has heard it—teachers say it, parents say it, motivational articles repeat it nonstop. So why don’t we do it?

As an investor, I’ve seen endless examples. People buy huge homes they don’t need. A family of three insists on five bedrooms and two living rooms. Why? Because a colleague bought one. Because relatives did. People buy a car that makes no sense. Two hours of traffic every day, but they choose a two-seater sports car. Why? Because it “looks good.” Some people study a degree they don’t even like. They love art, but they force themselves into finance. Why? Because their parents say finance makes money. Under all of it is the same logic: to look successful to relatives, to get more likes on social media posts, to fit into a so-called “successful life template.”

Psychology has a fascinating concept for this: the spotlight effect. Cornell University ran a classic experiment. They asked students to wear an ugly, embarrassing T-shirt—one with a washed-up singer’s face printed huge on it—and walk into a room full of people. The students were sure at least half the room would notice and laugh. But when researchers asked the room afterwards, fewer than 20% even remembered the shirt. Most people didn’t notice at all—or they noticed and forgot instantly.

What does that tell us? We think we’re the main character on a stage, surrounded by spotlights—everyone watching our every move. “If I quit and do what I actually want, what will people think?” “If I’m in my thirties and start learning to paint, will they laugh?” “If I don’t pass that exam, will I be embarrassed?” Here’s the brutal truth—and honestly, it’s also relieving: most people aren’t thinking about you. They’re busy stressing under their own imaginary spotlight. There’s no audience judging your life choices. That audience seat is empty.

Bronnie wrote that when people finally understand this, it’s often too late—because health has an expiry date. You don’t get unlimited time. When you’re lying in a hospital bed, “other people’s expectations” won’t bring you water. They won’t reduce your pain. What’s left is your memory of all the things you could’ve done—and those memories hurt the most.

So can you start today, and do one “bad investment”? Do something others don’t approve of, but your inner voice has been telling you to do for years. It doesn’t have to be big. Maybe you don’t work overtime this weekend, and you learn an instrument. Maybe you stop replying to messages that make you uncomfortable. Maybe you say “no” once—properly, clearly, without apologising.

Regret Number Two: “I wish I hadn’t worked so hard.”

The second regret hits especially hard for many people: “I wish I hadn’t worked so hard.” Bronnie said every male patient she cared for mentioned this. Every one. No exceptions. Executives. Engineers. Doctors. Lawyers. They worked and climbed their whole lives. But at the end, they didn’t say, “I wish I’d earned more money.” They didn’t say, “I wish I’d reached a higher position.” They said, “I wish I hadn’t worked so hard.” Behind that one sentence are countless missed dinners. Missed school events. Weekends, they never spent with their kids.

Modern society has a strange culture—call it “worshipping busyness.” Someone says, “I’ve been insanely busy lately,” and it almost sounds like, “I’m important. I matter.” “Busy” becomes social currency. We post overtime hours. We post airport photos at midnight. A laptop next to a coffee cup—like it’s a medal. But hidden underneath is a massive trap: we tell ourselves we’re suffering now so that one day we can finally relax. “When I earn enough, I’ll take the kids to Disneyland.” “When I reach that role, I’ll take my parents travelling.” “When I’m financially free, I’ll sleep in every day.”

But it’s like a hamster wheel. The faster you run, the faster it spins. You never stop—because “enough” never arrives. Psychology calls this hedonic adaptation. You make your first million, you feel high for a while—maybe a week, maybe a month. Then your standard shifts. Now you think you need five million to feel safe. Once you have five million, the excitement fades again. You start staring at the next level—maybe a multi-million-dollar house—thinking, “When I get that, then I’ll be satisfied.” That “finish line of happiness” is something you made up. Every time you step closer, it moves further away.

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Where Is Real Value in Life?

If life isn’t mainly about work and achievement… then what is it about? A group of scientists studied this seriously for 75 years.

Harvard University ran one of the longest studies in human history: the Grant Study. It began in 1938, tracking 724 people, from adolescence into old age. Some were Harvard students. Some were children from poor neighbourhoods in Boston. For decades, researchers interviewed them, recorded their lives, health, marriages, and careers. They wanted to answer one ultimate question: What keeps people healthy and happy? Money? Fame? Working yourself to exhaustion? Living in a good suburb? The result surprised a lot of people.

What predicted happiness later in life wasn’t the number in someone’s bank account, and it wasn’t even cholesterol. It was good relationships. The people who had the most satisfying relationships at 50 were the healthiest at 80. Not the richest—those with the strongest connections. Their memory declined more slowly. They had fewer illnesses. They lived longer. The study director, Professor Robert Waldinger, summed it up in a TED talk: “Good relationships keep us happier and healthier. It’s that simple.”

And that connects directly to Bronnie’s third and fourth regrets: “I wish I’d had the courage to express my feelings.” “I wish I had stayed in touch with my friends.” When we chase external achievements, we often trade away these invisible assets.

To meet a deadline, we cut off a phone call with our parents who just wanted to chat. To protect our pride, we stop talking to our closest friend for years over something small. We give our best patience to clients—and leave our worst temper for the family.

If you think of life as a company, then family, friendship, love—these aren’t decorations. They’re your core cash flow. Once they break, it doesn’t matter how high your “market value” looks. You’re one shock away from collapse.

The Cost of Not Acting

We understand the ideas. Live as yourself. Spend time with family. So why don’t we move? Because we’re waiting. Waiting for the “perfect time.” More money. Older kids. Better conditions. A clearer market. Which brings us to the real issue: execution—our illusion about action.

I’ll use myself as an example. Before I started this channel, I wanted to do YouTube for three full years. What was I doing in those three years? “Preparing. I bought the best camera—didn’t film. I enrolled in editing courses—didn’t start learning. I wrote dozens of topics—then deleted them because they weren’t “perfect.”

I fell into a trap: I believed I had to be completely ready—confident, expert-level—before I could start. Then reality slapped me. When I finally uploaded my first video… you know what happened? Nobody watched. I was stiff on camera like a robot. The lighting looked like a horror film. But something surprising happened: even though it was terrible, I felt a kind of joy I’d never felt before. Because I wasn’t just watching life anymore. I was in the arena. After that, I stopped focusing on “becoming famous overnight.” I focused on one thing: Am I a little better than yesterday? Maybe someone leaves a comment saying, “Alex, that helped me.” Maybe one day I finally understand colour grading. Those tiny bits of feedback—that’s the fuel.

Here’s the truth: clarity comes from action, not thinking. If you stand on the shore, you’ll never learn to swim. You’ll never understand what buoyancy feels like. You have to jump in, swallow some water, choke a little—then you learn. Investing is the same. You keep waiting to buy the bottom and sell the top, trying to make the perfect trade… and you end up missing the whole bull market. Life works the same way. The most expensive price you pay in this world is the cost of inaction.

Amazon founder Jeff Bezos has a famous decision method called the Regret Minimisation Framework. When he was deciding whether to quit his high-paying Wall Street job to start Amazon, he thought like this: “If I’m 80 and looking back, will I regret trying and failing? Probably not. But I know I would regret it if I never even tried. That regret would haunt me.”

So stop waiting. You think you’re avoiding risk—but you’re quietly building the biggest risk of all: reaching the end with nothing but “almost.” Not even a failure story worth remembering.

Regret Number Five: “I wish I’d let myself be happier.”

This brings us to Bronnie’s fifth regret—the one that hit me the hardest: “I wish I had let myself be happier.” Notice the wording: let myself. Happiness isn’t luck. It’s not something you bump into by accident. It’s a choice—and in many ways, it’s a skill.

Many people told Bronnie they only realised at the very end that they’d been trapped in old patterns and habits. They feared change, feared stepping outside their comfort zone, so they convinced themselves they were satisfied.We often park happiness in the future: “If I buy that house, I’ll be happy.” “If Bitcoin hits USD 200,000, I’ll be happy.” But that points to a simple fact: the future doesn’t exist.

It sounds abstract, but think about it. The past is a cheque that’s already expired. The future is a promissory note that hasn’t been cashed. The only cash you actually hold is this moment.

My father once told me a simple story that stayed with me. A child asked his mum, “Mum, what’s the best day of your life? Your wedding day? The day I was born?” She smiled and shook her head. She looked her child in the eyes and said, “Today.” The child didn’t understand. “Today? Today is ordinary. Nothing happened.” The mum said, “Because today is all we have. Yesterday is gone. Tomorrow isn’t here yet. If I don’t like today, then I’m wasting my whole life.”

If you’re unhappy right now, giving you ten million won’t magically fix it. You’d just become an unhappy rich person. Because the ability to be happy is like a muscle—you have to train it. It’s noticing the smell of coffee even on a terrible day. It’s being grateful your family is still healthy beside you—even when the stock or housing market is crashing.

Let Me Ask You to Do One Thing

Let Me Ask You to Do One Thing. Turn off your phone screen for a second—or look out the window—and ask yourself: If today were the last day of my life, is what I’m doing right now what I want to be doing? If the answer is “no”… and it’s been “no” for many days in a row, you need to wake up.

Don’t wait until the alarm on a life-support machine is beeping to start regretting. Don’t wait until you no longer have the strength to hug someone before you remember to love. Don’t wait until every door is closed before you decide you want to go far away. That phone call you’ve been wanting to make—make it now. That application you’ve been delaying—fill it out now. That side project you keep thinking about—write a plan tonight. That sentence you’ve kept in your heart—say it to him or her now.

In this world, the only person you truly have to answer to is yourself. One day you’ll be older, sitting in a chair, looking back. What determines the height of your life isn’t how many zeros are in your bank account balance. It isn’t how many properties you own. It’s whether—even once—you listened to your inner voice, and had the courage to step forward. The biggest risk in life isn’t failure. It’s living an average life, then comforting yourself with, “Being ordinary is fine,” while quietly knowing you didn’t really live.

I hope this video becomes a turning point for you.

Watch the video version of the blog on YouTube.

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