Roads not taken

On the risk of choosing, and the greater risk of not.

Søren Kierkegaard said: “The most painful state of being is remembering the future, particularly the one you'll never have.”

Every choice carries risk, even standing still. What we call risk often depends less on the facts than on how we choose to see them.

In this one, three paths to explore:

• Choices

• Losses

• Risks

STORY

All the ways life could go

Recently my daughter and I were watching a video from a creator she follows. At one point, they came to a very long suspension bridge. The kind that sways with every step and seems to hang forever over the drop.

She turned to me and asked, “Would you cross that?”

I paused, weighing the decision honestly. Not because the bridge was in front of me, but because I knew she was watching and this was a tiny glimpse into my appetite for risk.

This wasn’t just a random question. And it reminded me that she’s been testing and observing how people approach uncertainty for a while.

In other moments she’s told me, unprompted, about her own ambitions and her certainty in that path. She wants to be a doctor. A paediatric surgeon, in fact. But also a fashion designer. I’ve learned not to treat these as passing comments. They’re her way of charting out her own map of the world, one choice at a time. I’ve also told her two things:

• It’s great to want that, but be open to change;

• She can be both (and more).

That’s not the advice I got when, at about her age, I told my father I wanted to be a doctor. But it was a different time, and he lived a different life. His advice was shaped by the paths he had taken, and the ones he didn’t.

That’s the thing about these conversations. They’re small in the moment, but they lay ground for bigger choices ahead.

Tim Urban’s Life Paths diagram captures this perfectly. Both simple and profound, it shows a green dot on a grey line depicting the present, splitting the past and future. Behind it and stretching into the past, are one green line and countless black lines that meet the present at different points. The black lines are the many paths we didn’t take, each one leading to a different ‘today’.

It’s a visual reminder that we rarely know the full knock-on effect of a single decision, and that there are no perfectly straight paths through life.

As Tim writes in the accompanying post:

“We think a lot about those black lines, forgetting that it’s all still in our hands.”

When you focus on that green dot and all the paths in front of it, you realize that life presents you with a new junction not just at milestones, but every single day.

Every day, you are one decision away from a very different life.

When I was her age, my understanding of risk was shaped in part by watching my father. He had lived through times and circumstances that demanded caution. His decisions, while wise in context, often leaned toward safety over possibility. And without realising it, I inherited some of that caution until I found myself in situations where the bigger risk was in staying put.

I didn’t end up a doctor. But along the way, some of the many things I could have been include priest, athlete, DJ, analyst, journalist, farmer, full-time musician, model, bodybuilder. All real opportunities and decisions made.

I don’t regret the paths I didn’t take. I see opportunity in the ones ahead, standing on my grey line, with much less attachment to outcomes. Life is lived in the arena, and whatever meets you along the way is part of the journey.

Now, my daughter is growing up in a different world, with more options and more examples of people taking unconventional routes. Her version of risk is not my father’s, nor entirely mine. It’s still forming, through her questions, her observations, and yes, even through a hypothetical suspension bridge on a creator’s feed.

And I suppose that’s the point: our views around risk start forming earlier than we think, shaped by what we see others do and the futures we imagine for ourselves.

I want her to know that none of us can predict exactly where we’ll end up, so that she can focus less on being something, and more on living fully, whichever way life should go.

And that requires her to develop her own appetite for risk. Because life is risk.

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EXPLAINER

Why we’re scared to lose

Do we avoid risk because of more knowledge or the lack of it?

They say ignorance is bliss. But not with money. At least not in my opinion.

What’s more likely is that we avoid risk because of fear. Not just fear of uncertainty, but the fear of loss.

In investing (and in life) we often assume we’re making rational decisions. But in reality, we’re wired in ways that nudge us off course.

As Warren Buffett aptly put it:

“The most important quality for an investor is temperament, not intellect.”

Awareness of our cognitive biases matters more than just knowledge.

Psychologists Daniel Kahneman and Amos Tversky explored this in what’s known as loss aversion. This is the idea that we feel the pain of loss more strongly than we feel the pleasure of gain. In fact, their research found that losses feel twice as powerful as equivalent gains.

That’s why a financial loss can linger, while a gain of the exact same amount often fades quickly. You’ve probably felt this before. A slight dip in your account balance, portfolio value, or even a stock price, draws immediate concern yet a small gain is easy to ignore.

But this isn’t just about money. And it matters because these emotions can distort how we evaluate risk, reward, and opportunity. When you understand how these patterns work, you’re better positioned to respond with intention rather than instinct.

Loss aversion is why we hang on to clothes we don’t wear, apps we don’t use, and relationships we’ve long outgrown. That and the sunk cost fallacy.

It’s why people stay in unfulfilling jobs or delay important life moves, because the potential downside feels more vivid than the possibility of upside. It’s why people cling to the “safe path” even when it leads nowhere. It’s why we fear change even when it might make things better.

It’s more emotional than rational. It’s human. And it’s deeply ingrained in all of us.

When it comes to investing, this bias shows up as:

• Selling too soon after a dip

• Holding on too long after a peak

• Avoiding opportunities that “look risky” but are simply unfamiliar

Even people who “know better” fall into the trap. Because emotion tends to shout louder than logic, especially around money.

And yet, the biggest cost of loss aversion isn’t financial. It’s missed opportunity. The risk you didn’t take or the version of yourself you never explored.

Risk is where return lives, but the perception of risk and the emotional weight we assign to it is just as important as the risk itself. Loss aversion is one reason why.

Not everything is worth the risk. But not everything is worth holding onto either. Know the difference.

This 3-minute video by Quik Economics offers a great explanation if you’d like an expanded view.

“You can’t predict, [but] you can prepare.” –Howard Marks

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CURIOUS

A timeless note

There are words that don’t just visit, they find room in your mind & stay like an uninvited guest. Like this line I heard some time ago:

“The person who risks nothing, does nothing, has nothing, is nothing.”

It’s not gentle, but it holds true.

I traced the line back to a passage often credited to the late professor and speaker Leo Buscaglia, who spent much of his life helping others live more openly and more fully. The words struck a nerve then, and they still do now. And what better way to share them with you, than in an appropriate and timely context, as we’ve been exploring risk.

In my last edition, I wrote:

“Your biggest rewards, whether you see it or not, come from your biggest risks.”
–No risk, no story

This passage feels like a natural companion to that idea. Read it slowly.

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Risks
– by Leo Buscaglia

To laugh is to risk appearing the fool.
To weep is to risk appearing sentimental.
To reach out to another is to risk involvement.
To expose feelings is to risk exposing your true self.
To place your ideas and dreams before a crowd is to risk their loss.
To love is to risk not being loved in return.
To live is to risk dying.
To hope is to risk despair.
To try is to risk failure.
But risks must be taken, because the greatest hazard in life is to risk nothing.
The person who risks nothing, does nothing, has nothing, is nothing.
He may avoid suffering and sorrow, but he simply cannot learn, feel, change, grow, love, or live.
Chained by his certitudes, he is a slave.
He has forfeited his freedom.
Only a person who risks is free.

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No extra commentary is needed. The message is clear. But I’ll add just one thing:

We spend so much time managing risk, hedging, calculating, avoiding… But sometimes, the greater risk is in playing it too safe, or not playing at all. Sometimes, we just must dare to go all the way.

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The end is the beginning

Last word, ink dries.
As winds shift, so could your gaze.
Turn the page, a new chapter waits.

Onward.

AG

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Whichever path you choose, I’ll be glad you took it.