J. R. Tolkien: Famous Last Words
“A man that flies from his fear may find that he has only taken a short cut to meet it.”
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There is something you know that needs to change. You’ve known it for months. Maybe years.
But you’ve built a very intelligent life to avoid it. So have we all.
Let’s read Tolkien’s quote again:
“A man that flies from his fear may find that he has only taken a short cut to meet it.”
When I first read The Lord of the Rings, I loved it. When the movie came out in cinemas, it was the only time when, as the credits rolled, I walked straight to the box office and bought a ticket to watch it again on the next day.
I needed to go back in. And I now realise, many years later, that something in that story resonated deeply.
There’s a reason Tolkien’s work is so incredibly powerful.
The Shire is Comfortable
The Shire, the home of Bilbo and Frodo Baggins, is a super safe place. Predictable. Smug, even.
The hobbits have manicured gardens, steady routines and second breakfasts. Nothing particularly wrong. And yet, when the call to adventure comes, it terrifies them. They don’t want to leave. And neither do we.
For a lot of people, the Shire isn’t a village. It’s a version of success. The job or company that works. The income that sustains. The reputation that protects. The routine that feels stable.
But just like Bilbo, we can’t deny that nagging feeling that you’ve outgrown something. The work no longer fits who you’re becoming. The edges feel tight.
So you rationalise. You optimise instead of pivoting. You expand instead of redefining. You stay busy instead of getting honest.
And that feels like safety. But it’s not. It’s a actually the shortcut back to fear Tolkien refers to, and all fear ultimately, is existential.
Because what you’re avoiding doesn’t disappear. It compounds. And if ignored, over time, will lead to deeper regret.
I Took The Shortcut Too
There was a period in my life where my body started speaking before I did. Panic attacks. Tight chest. Shallow breath. That creeping sense of losing control.
On paper, things looked fine. I was outwardly ‘successful’ in a conventional sense. I had a family, a house, a business I had built. But I was avoiding a truth. I knew my soul was being pulled toward more purposeful work, yet I stayed in a world that no longer aligned. Part of me was dying away.
I thought I could manage it. Push through it. Adjust around it. Instead, the fear met me in my nervous system.
Tolkien was right; you can run from your fear, but you will meet it again. And when you do, it rarely feels gentle.
The 5 Why’s Exercise is attached to the bottom of this newsletter. A simple but powerful self guided exercise designed to trace your core motivations back to their root and uncover your true purpose.
The Death Beneath The Fear
Here’s what I feel most people miss. What we call fear of change is usually fear of identity death. The part of yourself that no longer serves you.
If I leave this version of my career, who am I? If I pivot the business, what happens to my status? If I slow down, what happens to my worth?
Underneath all of that is the ancient fear. Loss. Dissolution. Non-existence. Mortality.
Entrepreneurs are particularly good at avoiding this. We build. We scale. We achieve. We optimise. But sometimes growth becomes a distraction from evolution.
Why Tolkien’s Heroes Grow
The hobbits don’t leave because they’re fearless. They leave because staying becomes more dangerous than stepping out.
And when they return, they’re not the same. They’re deeper. Wiser. Connected with true purpose.
They could never have become who they were meant to be without leaving comfort.
And here’s the uncomfortable truth I have realised: midlife is the moment a lot of people realise they’re still living in the Shire. Successful on paper, having done everything ‘right’ in life, but not stretched. Respected, but not fully expressed.
You can avoid that realisation for a while. But eventually, like Gandalf, it will come knocking on your door. Sometimes as restlessness. Sometimes as burnout. Sometimes as crisis. Sometimes as panic in the chest at 3am.
Authority Is Built At The Edge
Every meaningful expansion in my life came from entering a dark cave I didn’t want to enter. Leaving the career that defined me. Writing about death in a culture that avoids that very conversation. Selling the house and leaving the Shire.
Each one felt irrational at first. Each one required letting something old die. And each one led me closer to who I actually am.
Something I am discovering in real time.
An Invitation
You really don’t have to burn down your Shire to make a shift. But notice where you’re circling something.
A conversation. A pivot. A truth about your work. A change you keep postponing.
Ask yourself: If I keep avoiding this, where will I meet it again?
Because Tolkien was right. The shortcut never leads away from fear. It leads straight back to it.
If this article resonated, please comment, like, re-stack, and share. My mission is to establish mortality awareness as a recognised wellness practise. By supporting this work, and being part of this community, you are helping this vision come true.
Live happy,
Hoppy
Tools & Updates
Visit Tools to explore 14+ self guided exercises designed to reduce anxiety, improve vitality, deepen your sleep, and bring radical clarity to your relationships, career, and health.
Reverstory: the bespoke AI tool designed to help you identify major life regrets and suggest ideas of how to course correct while you still can. Available to paying subscribers. I’m offering a special 25% off paid subscriptions until the end of this month. That’s only £6 / $8 a month to transform your life.
The Ultimate Meditation: A guided practice designed to help you slow down, reflect on mortality, and reconnect with a life of no regrets. Many people tell me it helps them discover greater calm, gratitude, and clarity.
I have been invited to perform the mediation at both Connect and Medicine Festivals this summer.
Video: Watch my conversation with author and psychotherapist Louis Weinstock, as two men discuss fear and death.
Go deeper: Return To The Womb / Socrates: Famous Last Words / The Ultimate Meditation
Full website with all content: Here
What people are saying about DTLWP: “John exactly this! In the moment when I ask ‘what is happening NOW’, fear falls apart. Only the present moment remains, in which usually nothing bad is happening.” (Sophie)
Below this paywall you will find The 5 Why’s Exercise. A simple but powerful self guided exercise designed to help you trace your motivations back to their root and uncover your true purpose.
