Honest Reflections on Aging & Life

The Evolution of Dreams: How Life Reshapes Our Deepest Desires

A watercolor depiction of a business vision showcasing a man gazing at a colorful urban skyline.

What’s your dream? For over twenty years, I’ve asked my English students in Japan this question, watching their eyes light up as they share visions of anything from having the next iPhone to living at Disneyland or traveling abroad. It’s a window into what matters most, cutting through life’s trivia to reveal purpose and passion.

Dreams drive us, but as time and circumstance—aging, health, family, or finances—shape our paths, they evolve. How do these aspirations change, and what do these shifts teach us about living authentically, no matter our stage of life?

Dreams in Youth: The Fuel of Ambition

As a younger person, dreams often spark ambition. They push us to take bold leaps, as I tried in my twenties (for a spell), inspired by life coach Brian Tracy’s call to chase audacious goals, a story I shared in “My Walk in the Park.” Back then, dreams were about forging a future, making something meaningful of yourself in a world full of possibilities.

Now, many seasons later, including two decades as an expat in Japan navigating “Invisible Barriers, my dreams feel gentler, shaped by new realities and tempered by experience.

One dream persists through the years: acquiring and riding my dream motorcycle across Japan’s diverse landscapes, a wish I regret not fulfilling with my ex-wife before she returned to America, yet one I still imagine for myself almost daily.

Another tugs at my heart with increasing urgency: returning to the UK to share quality time with and support my aging father, whose life has profoundly changed now with my mother in a care home – lost to dementia.

Truth be told, my desire for financial stability also stems from wanting to help my ex-wife, regardless of her choosing to live a different life – something one accepts when love transcends circumstance and remains unconditional despite separation.

Dreams in Later Years: The Search for Connection and Peace

Our dreams, whether bold or humble, reflect life’s changing seasons. In youth, they fuel adventure and risk-taking; in later years, they often center on connection, meaning, or simply finding peace amid life’s complexities.

Farming three days a week on my boss’s land, a calming rhythm I’ve embraced these past five years, has taught me to value presence over wealth at this stage of life.

Some say, “We’re rich if we have a dream, no matter our bank account,” and I appreciate the sentiment.

However, deep in my heart, I sometimes wonder if this perspective is partly self-consolation – yes, seeing the glass half-full, yet acknowledging what feels like a kind of personal shortcoming, especially still living paycheck to paycheck as I do. The narrative we tell ourselves about success shifts with time, but doesn’t always silence the questions about paths not taken.

Now in my fifties, with those around me aging too, the feeling of not having “made it” can become a persistent, frustrating itch as time marches forward, especially when we wish we could provide more support to those we care about.

As I get older, I sometimes question whether financial success has eluded me for a reason. All these years with modest financial rewards to show for my efforts. My solo online passions and creative pursuits producing little more than a welcome distraction from the regular working routine – where I serve others in what is hopefully a more meaningful, spiritual dimension of life.

Our age, circumstances, limited resources, and uncertainty about where to find support can gradually erode our confidence in reaching higher or taking risks that once seemed reasonable.

What's Your Dream? (book) by Simon Squibb, delivered via Amazon to OldDogZeroTricks

A few days ago, Simon Squibb’s book, “What’s Your Dream?” arrived at my door, its pages promising to rekindle the courage of my younger self, who would chase a goal with reckless hope and boundless energy. I will read it.

In these later years, experience prompts deeper questions: Should we temper our dreams with pragmatism, or pursue them with the same abandon we had in youth? Is wisdom found in adaptation or persistence?

Evolving Dreams: A Universal Journey

I suppose we all travel similar waters, yet experience different chapters of life’s unfolding story. In time, a youthful dream of adventure might transform into one of stability and security; a goal of wealth and achievement might shift toward quality time with loved ones or finding deeper meaning in simple moments.

What matters most is that dreams continue to animate our lives, evolving as we do through life’s inevitable changes.


How about you? What drives your dreams today? Are they wild or gentle, seemingly within reach or gloriously distant? Do you find yourself rethinking them to accommodate life’s realities, or do you let them pull you forward into unexplored territory? How have your aspirations shifted through the seasons of your life?

Share your story below—let’s explore together what keeps us moving forward when the landscape of possibility both narrows and deepens with the passage of time.


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