Is Living On a Sailboat like Living a Dream?

“Damn, you’re living the dream! Good on ya!”

 I often heard this phrase when I was living on a sailboat, a Columbia 29 named Tranquility, and  I sailed around as I pleased. It was usually uttered by a retired white male passing by the docks.

 It’s a distinctly North American cliché, embodied by the stereotypical characters in Jimmy Buffett’s songs: work hard all your life, retire, buy and go living on a boat to sail into the high seas chasing endless sunsets while foraging off the land and the reefs. Or, more comfortably, anchor near a white sandy beach within easy reach of booze. After all, there’s no need to chase sunsets as they show up at the same time every day anyway, so securing a good platform moored in a strategic observation point is enough.

 And if the speaker was actually “living the dream” themselves, there was always an addendum: “I wish I had done it sooner, when I was your age”—a lament directed at the deteriorating physical condition they found themselves in after a lifetime of hard work.

 This conversation always threw me off. Sailing and living aboard was never my dream in the first place, so whose dream was I actually living?

 It was accidental that at 27 I found myself living and working on a sailboat in the tropics. It didn’t stem from a carefully crafted plan, nor was it a check on a bullet point on a once-in-a-lifetime bucket list.

 My dream looked more like fixing up an old van, make it habitable, and drive the Silk Road from Italy to China.

 The original dream and the actual shape my life took shared a common core: direct contact with the elements, a nomadic existence, and a journey of discovery. Tranquility, the derelict sailboat I purchased and that became my house for many years, proved to be the perfect tool for my goals: Affordable, simple, with enough comforts to keep me alive and well yet strong enough too take offshore waves and winds.

I had no clue that sailing and living on a boat could also serve as a vehicle for personal meaning, let alone become a career and a way of life.

 Had I followed my original plans, I would likely be somewhere else, doing entirely different things. I mighthave studied Social Psychology in Buenos Aires or managed a rifugio high in the Alps. None of those dreams became reality. That doesn’t mean they never will, but that is not the point. Ending up living on a sailboat is neither a grand achievement nor a frustrated alternative to my original dreams. It’s simply what became available to express my desires and attitudes.

 The repository of daydreams I entertain myself with is packed with extravagant alternative lives. I have a collection of these internal reels that I can play non-stop for days, built around recurring themes of musical prowess, literary recognition, and financial freedom.

 Despite spending so much time lost in such mental scenarios, I doubt I will ever pull them off. And that is fine.

I find myself asking why I don’t push harder to accomplish what I once thought was the best future for myself. Is it a lack of determination, or a lack of skill? In an era that preaches you can achieve anything if you just work hard enough, why do I seem to fail at making these visions real?

Lately, I have been asking myself a different set of questions:

Do I really want to perform complex drum patterns in front of an adoring crowd? Or am I after recognition for what I do?

Do I actually want to own real estate around the world? Or am I simply desiring comfort and security for me and my family?

We all long to be valued, celebrated, and cared for. We search for connection, love, and self-realization, framing these core human needs within grand, heroic narratives where achieving extraordinary feats brings lasting happiness.

But are these internal scripts truly aligned with who we are? Or are we borrowing them from a pre-packaged shelf of socially approved ambitions?

Where do these dreams actually originate?

As nocturnal dreaming shows, the mind requires little external input to construct rich worlds. Asleep in a dark, silent room, our subconscious spontaneously scripts and directs complex narratives every single night.

In a literal sense, nocturnal dreams emerge from within, yet they borrow building block and scenarios from the reality around us.

The work of the artist is to capture this inner imagery and manifest it out of thin air, creating a novel, a sculpture, or a painting, like the uncanny symbolic imagery explored in the work of Swiss painter Peter Birkhäuser:

For most people, nocturnal dreams remain what they are: unbidden adventures in which we are merely protagonists or observers. They resist conscious control, sweeping through or quietly shadowing our waking lives.

More often, they remain locked away behind well-guarded interior doors—perhaps because attempting to externalize them can severely disrupt our hard-earned stability.

Yet not all dreams originate from within. Daydreams and life-goals have a far more cultural flavor; they circulate through stories, media, and social expectations. We absorb them from films, books, or conversations over dinner. These cultural scripts are highly contagious, attaching themselves directly to our baseline psychological needs. We inherit them from our families or adopt them wholesale from pop culture.

If that was not enough, modern culture incessantly commands us to “follow our passion,” monetizing our purpose as the sole path to self-actualization, nudging us in wanting more for ourselves and to perhaps be different.

Maybe I will eventually pick up a pair of drumsticks again and buy a second-hand kit, or set aside a few weeks to trek from hut to hut across the Alps. Or I can simply spend more time outdoors, listen to music, and play when the opportunity arises, without needing to turn these simple impulses into elaborate life projects.

While living on a sailboat, chasing sunsets, exploring remote shores, and meeting strangers is undeniably appealing, every idealized life choice carries hidden costs so substantial that keeping the dream unrealized is often a wiser path.

There is no obligation to execute our daydreams. We can lead grounded, deeply meaningful lives without transforming every fantasy into a reality. We can satisfy our core needs without putting on a spectacle. Most importantly we could stop letting borrowed, artificial dreams make us miserable.

Genuine dreams don’t disappear. They exist precisely not to be fully conquered or neatly categorized.

They exist to keep life open and fluid, to point toward a psychological True North, and to preserve our capacity for surprise and growth.

One thing is certain: when you step inside a dream and try to live it, things quickly get strange. So think twice before you demand that your life becomes one.