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The Question I Keep Asking
For over twenty years, I’ve asked my English students in Japan: “What’s your dream?”
Their eyes light up as they share everything from wanting the next iPhone to living at Disneyland to traveling abroad. It cuts through all the everyday stuff and shows you what they really care about.
Dreams push us forward. But here’s what I’ve noticed: as life happens—aging, health issues, family stuff, money problems—our dreams change. Sometimes they get smaller. Sometimes they get deeper. Sometimes they shift completely into something we never expected.
So how do our dreams change as we get older? And what does that say about what we actually need?
When You’re Young, Dreams Are About Making Something Happen
When you’re younger, dreams push you to take big risks. In my twenties, I chased the helicopter pilot dream—inspired by Brian Tracy’s whole “go after crazy big goals” thing. Back then, dreams were about building a future, proving yourself when everything seemed possible.
Now, two decades later as an expat in Japan, my dreams feel different. Gentler. Reality’s had its say.
One dream hasn’t changed: I still want to buy my dream motorcycle and ride it across Japan. I regret not doing that with my ex-wife before she left for America. I still picture it almost every day.
Another dream keeps getting stronger: going back to the UK to spend real time with my aging father. My mother’s in a care home now, lost to dementia. His life has completely changed, and I’m over here.
And honestly? I’d still like to help my ex-wife financially if I could, even though she chose a different life. That’s what happens when you love someone for twenty years—it doesn’t just stop because circumstances change.
What big dreams did you have when you were younger?
Later in Life, Dreams Change Shape
Our dreams shift as we age. When you’re young, dreams are about adventure and risk-taking. Later, they’re more about connection, meaning, or just finding some peace in the middle of life’s chaos.
I farm three days a week on my boss’s land. It’s become this calming rhythm over the past five years. It’s taught me to care more about being present than getting wealthy.
People say “We’re rich if we have a dream, no matter our bank account.” I get it. I do.
But deep down, I sometimes wonder if that’s just what we tell ourselves to feel better about still living paycheck to paycheck. The story we tell ourselves about success changes over time, but it doesn’t always quiet those questions about paths we didn’t take.
Now in my fifties, with everyone around me getting older too, not having “made it” financially can feel like this nagging feeling. Especially when you want to help the people you care about but can’t.
Sometimes I wonder if money has stayed out of reach for a reason. All these years of work, and I have so little to show for it financially. My online projects and creative stuff have mostly been distractions from the regular work routine—where hopefully I’m doing something more meaningful, even if it doesn’t pay much.
Getting older, dealing with limited money, not knowing where to find support—all of it chips away at your confidence about reaching higher or taking the risks that once seemed possible.
Have your dreams gotten bigger or smaller as you’ve aged?
The Book That Arrived at My Door
A few days ago, the book “What’s Your Dream?” by Simon Squibb was delivered. It promises to bring back that younger me who’d chase dreams with crazy hope and tons of energy. I’ll read it.
These days, experience makes you ask harder questions: Should we be more practical about our dreams, or chase them like we did when we were young? Does getting wiser mean accepting reality, or does it mean never giving up?
I don’t have the answer. Maybe there isn’t one.
We’re All Just Figuring It Out
We all go through this stuff, just in different ways and at different times. A youthful dream of adventure might turn into wanting stability and security. Wanting wealth and success might shift into wanting more time with people you love or finding meaning in simple moments.
The important thing is that dreams keep us going, even as they change shape.
What’s driving your dreams these days? Are they big and wild, or quiet and close? Do they feel possible, or do they feel like fantasies you’ll never reach?
Share your thoughts below. I respond to every comment, and your experience often helps others more than mine does.
