The Question That Made Us Build a Yacht and Sail Away

Sailing yacht Ruffles Spray in Greece after we left our jobs to sail away.

The Question That Changed Everything

At 36, I realised something uncomfortable.

Waiting until retirement to start living felt like the wrong answer.

At the time, my life looked perfectly sensible. I worked as a Quality Engineer, and my wife Ann was a school teacher. We had stable careers, a predictable routine, and the sort of future most people aim for.

Then one lunchtime, a colleague asked me a question that, at first, seemed harmless.

“If money and responsibilities weren’t an issue, what would you really like to do?”

It was the kind of question you hear in passing and normally forget five minutes later.

But that day I didn’t have an answer.

And strangely, the question wouldn’t leave me alone.

If you’ve ever wondered whether there might be more to life than waiting for retirement, this story may resonate with you.

The Life That Looked Perfect From the Outside

From the outside, everything about our lives looked reasonable.

We had secure jobs, a comfortable home, and a future that followed a familiar path:

  • Work hard.
  • Save money.
  • Retire one day.
  • Then enjoy life.

It was the formula most people follow without questioning it too much.

But once that lunchtime question had been asked, something shifted in my thinking. I started wondering what life might look like if the usual rules didn’t apply.

Not in some wild fantasy sense, but in a practical one.

If you could redesign your life from scratch, what would you actually choose to do?

The Crazy Idea That Wouldn’t Go Away

For me, the answer that slowly emerged was to meander around the Mediterranean in the sunshine.

Not for a weekend or the occasional holiday trip, but something far more ambitious. The idea of travelling.

At first, it felt ridiculous even to think about it seriously. People like us didn’t just walk away from steady careers and start meandering around in the sunshine.

But the thought kept returning.

My work colleague gave me a book to read, Voyaging on a Small Income, written by Annie Hills. She and her husband, Pete, built a sailing yacht from scratch and sailed around the world.

The more I read it and researched this boat building stuff, the more I realised that ordinary people had done things like this before. They hadn’t all been wealthy adventurers or seasoned sailors. Many were simply people who had decided to take a different path.

That realisation was both exciting and slightly terrifying.

Because once you know something is possible, it becomes much harder to ignore.

I wrote more about the practical side of leaving conventional life in another article on how we escaped the rat race.


Our Sailing Story

Twenty years ago we built a sailing yacht and left our jobs to sail away.

The adventure eventually became a three-book memoir about chasing a dream and discovering a different way to live.

Start the journey

  1. Getting Away – A Dog Narrates Our Wild Escape to the Mediterranean
  2. Getting Back – When the Dream Meets Reality
  3. Getting On – Where the Dream, Finally becomes Real Life

Discover the books →


Building a Yacht Instead of Waiting for Retirement

Eventually, Ann and I reached a moment where the dream felt bigger than the doubts.

Instead of waiting until some distant retirement date, we decided to start building a sailing yacht ourselves.

When we told people, the reactions were mixed.

Some thought it was a wonderful idea.

Others thought we had completely lost our minds.

To be fair, there were moments when we wondered the same thing ourselves. Building a yacht is not a small undertaking. It takes time, patience, and a willingness to keep going when things get difficult.

But slowly, piece by piece, the boat began to take shape.

What had once been just an idea was gradually becoming something real.

Leaving the Safe Path

The day eventually arrived when the boat was ready, and the decision we had talked about for so long became unavoidable.

It was time to go.

Leaving behind the security of familiar routines was far more emotional than I expected. It’s easy to imagine adventure when you’re planning it, but standing on the edge of a completely different life is something else entirely.

There was excitement, of course.

But there was also uncertainty.

What we didn’t know at the time was that the journey would bring far more than just sailing adventures. It would challenge us, surprise us, and teach us lessons we could never have anticipated when the whole idea began with a casual question over lunch.

What Escaping the Rat Race Really Means

Looking back now, I realise that escaping the rat race doesn’t necessarily mean running away from responsibility or searching for some perfect life.

It means questioning assumptions.

The traditional life plan works well for many people, but it isn’t the only possible path. Sometimes the most interesting journeys begin when someone simply asks whether there might be another way to live.

For us, that question eventually led to building a yacht and setting sail.

And it changed the course of our lives completely.

The Story Behind the Adventure

Years later, I realised the entire journey, the doubts, the risks, and the unexpected moments along the way deserved to be written down.

That story became my memoir Getting Away, the first book in a three-part sailing adventure that follows our journey from the early dream of sailing away to the life we eventually found cruising the Mediterranean.

If you’ve ever wondered what might happen if you followed an idea that refused to go away, you might enjoy the story.

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