He Left Wall Street, Cycled the World for Five Years — and Came Back Believing in HumanitY

Malcolm Blair has lived several lives in one. From a childhood in New Brunswick to Princeton and Wall Street, from commercial fishing in the North Atlantic to five years travelling the world by bicycle, the 63-year-old Canadian has repeatedly walked away from conventional success to discover what comes next. Along the way, he nearly lost his life more than once. Yet perhaps the most remarkable thing about him is what all those experiences taught him about people.

There are people who think outside the box. And then there is Malcolm Blair.

That is how a mutual friend once described him to me. After spending more than 90 minutes talking to Malcolm for The Stoic Pirate, I understand exactly what he meant.

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Malcolm is 63 and comes from Saint John, New Brunswick, on Canada's Atlantic coast. He studied at Princeton, worked for Merrill Lynch in Manhattan, went into commercial fishing, built houses, travelled the world for more than five years on a bicycle and found himself in situations most of us will never experience.

But the remarkable part isn't simply what Malcolm has done. It's the way he looks at life.

“I think I've always been somebody who didn't conform,” he tells me.

One big lesson: there is always another way

Perhaps that started with his father.

Malcolm grew up as the youngest of seven children. His father had only about ten percent of normal vision and just a Grade Seven education. Yet somehow, he built a successful construction business.

His children became his eyes. They helped him read drawings and invoices and drove him where he needed to go.

Watching his father taught Malcolm something that seems to have followed him throughout his life: an obstacle does not necessarily determine the outcome.

“There’s still a workaround.”

It is difficult to listen to Malcolm's later stories without hearing that childhood lesson echoing through them.

When something doesn't work, find another way.

When everyone else accepts the obvious answer, question it.

When the road ends, keep moving.

Success — and walking away from it

Malcolm eventually entered a world almost unimaginably different from Saint John: finance.

Princeton. Merrill Lynch. Manhattan. By most conventional measures, he had made it.

And then he left.

That pattern appears repeatedly in Malcolm's life. He succeeds at something, but success itself never seems sufficient reason to continue doing it.

When I ask whether walking away required courage, he doesn't really see it that way.

“If you're confident enough that you can do something, then those obstacles are not fear. They're just stepping stones.”

And then he says something that could almost serve as a philosophy for the entire conversation:

“There's lots of people with infinite wealth that are not happy.”

For Malcolm, success is measured differently.

Happiness, he says, is waking up and being excited about the day ahead, even when you don't know exactly what that day will bring.

So after finance came something completely different: commercial fishing in the North Atlantic.

He knew finance. He understood the numbers. But he knew virtually nothing about fishing.

So naturally, he bought fishing boats.

And rather than remaining ashore as the owner, he went to sea and worked on them.

“I didn't think you could own a business you didn't know anything about.”

That meant discovering the North Atlantic in winter — including plenty of time being violently seasick.

Again: learn by doing.

A one-way ticket and no real plan

Eventually Malcolm returned to construction and became, by his own description, a workaholic.

Seven days a week. Always another project.

Then his girlfriend asked a deceptively simple question.

They were young. They had no children. No major obligations.

Were they really going to spend their lives doing this?

What if they bought bicycles and went travelling instead?

In 1992, aged 29, Malcolm boarded a one-way flight to Glasgow with his girlfriend.

They had bicycles.

They didn't have GPS — it didn't exist for travellers.

They didn't even have much of a plan.

They thought they might travel for a year.

They came home more than five years later.

What followed was an odyssey across continents and cultures that sounds at times more like fiction than somebody's actual life.

“I thought I was experiencing the last 30 seconds of my life.”

In Russia, Malcolm needed to change money. He had a single US dollar bill.. A stranger offered to help and Malcolm climbed into his car. They drove away from the road, across an enormous field and towards what appeared to be an abandoned factory.

The man barely spoke.

Malcolm wondered whether he should open the car door and roll out.

Eventually they entered the ruined factory compound. Another tough-looking man appeared.

He walked directly towards Malcolm, staring at him, and reached inside his shirt.

“I thought for sure I was experiencing the last 30 seconds of my life.”

The man pulled out a pen.

He wanted to calculate an exchange rate.

They exchanged the dollar. Malcolm got his money. And they drove him back.

It is funny in retrospect.

But it also illustrates one of the lessons Malcolm took from five years on the road: we constantly judge people and situations before we understand them.

And fear is not always a reliable interpreter of reality.

When the gun really was a gun

There were other moments when the danger was very real.

During an encounter in Africa, an argument with a drunken man escalated. Malcolm hit him with a bar stool. The man collapsed.

Then another man approached Malcolm.

This time, what came out was not a pen.

It was a pistol.

He put the barrel against Malcolm's temple and pulled the trigger.

Nothing.

The chamber was empty.

“And so I'm here today.”

Malcolm can still remember the warmth of the gun barrel against his head.

What fascinates me is what comes next in his telling of the story.

He doesn't turn himself into the hero.

Instead, he asks what he could have done differently. He recognises that he helped escalate the confrontation.

Those experiences, he says, teach you to treat things differently next time.

The best places were people

After hearing stories like these, I expected Malcolm's strongest memories to be landscapes, countries or extraordinary places.

They aren't.

When people ask him for the best place he visited, he almost dislikes the question.

Because the best places were made special by the people he encountered there.

“The best place involved somebody that I met.”

And again and again, strangers surprised him with their generosity.

One of the most beautiful examples happened on the Bolivian Altiplano.

A poor family allowed Malcolm and his girlfriend to sleep in their barn. Later, a little girl named Maria appeared carrying potatoes for them.

Not leftovers.

Not potatoes the family didn't need.

Their best potatoes.

“We picked our very best potatoes for you.”

A family with almost nothing had given strangers the best of what they possessed.

That stays with you.

So does another experience in Central Africa, where Malcolm found himself among hundreds of thousands of displaced people. After not eating all day, he and his partner sat down to share a single boiled egg.

Nearby lay the body of an elderly woman.

People stopped and stared at them.

Malcolm realised what they were seeing: two foreigners who somehow still had food.

“I never felt so guilty in my life.”

Minutes later, behind the walls of a mission, they were offered imported cheeses and other food.

They couldn't eat.

Outside, people were starving.

More than thirty years later, Malcolm becomes emotional remembering it.

Coming home was another journey

After more than five years, Malcolm finally returned to Canada.

But you don't simply switch off an experience like that.

Normality itself had become strange.

After years of sleeping wherever the road allowed, even sleeping in a bed felt uncomfortable. For a while Malcolm preferred the floor.

The journey also changed his relationship.

He and his girlfriend had married during the trip, after carrying a five-dollar wedding dress bought in Russia in a bicycle pannier all the way to southern Africa.

Back in Canada, they had two children.

But ordinary life after years of extraordinary intensity proved difficult.

Malcolm speaks about that without pretending everything worked out perfectly. Looking back, he acknowledges his own failures.

That honesty matters.

Adventure has a price too.

Yet when I ask whether there are experiences he wishes he had never had, his answer is clear.

“I don't have that sort of regret at all.”

He would do it again.

“Go and see for yourself.”

Perhaps this is what makes Malcolm Blair so fascinating.

He has every reason to be cynical.

He has seen violence. Extreme poverty. Death. Corruption. Fear.

He has had a gun pressed against his head.

And yet after travelling through radically different societies and depending repeatedly upon strangers, his conclusion about humanity is remarkably optimistic:

“There's just as much good in the world as there ever was.”

That sentence stayed with me.

Because our picture of humanity today is increasingly constructed through screens, headlines, algorithms and other people's interpretations of reality.

Malcolm's picture was built differently.

He met people.

He slept in their homes.

He ate their food.

He needed their help.

Sometimes he was afraid of them.

And very often they surprised him.

Maybe that's why one of his simplest pieces of advice is also one of his best:

“Go and see for yourself.”

Talk to the stranger.

Try something you haven't done before.

Don't allow other people to decide what you should fear.

And don't become so certain about how the world works that you stop being curious.

Malcolm describes it beautifully: try to remain “a child in mind.”

Because if we keep looking at problems in exactly the same way, we will keep finding exactly the same answers.

“If you want a different outcome, then you have to be willing to look at things a little different way and try something different.”

At 63, Malcolm Blair is still doing exactly that.

After Princeton, Wall Street, the North Atlantic, five years on a bicycle and enough adventures for several lifetimes, perhaps his greatest achievement isn't that he survived all of it.

It's that he remained curious.

And that after seeing both the best and the worst of humanity, he still chooses to believe in the good.

Maybe that is what a successful life looks like.