Find Your Fellowship in 2025
Lessons from Tolkien's Loneliness
If you’ve ever felt like you don’t belong in the place everyone thought (including yourself) was perfect for you, you’re not alone.
You need to hear this lesson about author J.R.R. Tolkien’s experience as an outsider and how Bilbo Baggins from The Hobbit shows us that even the most unlikely of heroes find strength in being different.
We’ve met…I’m
. I’m an Air Force Officer and one of the two Geeky Stoics behind this newsletter.The struggle of all naive romantics
I’m a massive J.R.R. Tolkien fan and always have been. And he didn’t just write about adventure and war — he lived it. While serving in World War I, Tolkien found himself an outsider among his fellow soldiers. His letters to his wife, Edith, reveal a man disillusioned by the brutality and bureaucracy of war. He lamented the uncouthness of certain elements of British military culture.
While training at Rugeley Camp, Staffordshire, Tolkien wrote:
"Gentlemen are rare among the superiors and even human beings rare indeed."
Maybe I’m reading into Tolkien’s commentary based on my own experience as an Air Force Officer….but this really hit home.
I joined the military with a set of values I took seriously and believed in deeply. It’s a cliche punchline at this point, but integrity, service, and excellence—I believed I’d find camaraderie among those who shared these values.
I’ll admit I’m a bit of a naive romantic.
A disconnect between ideals and reality — hurts
So yes, I imagined a fellowship of like-minded adventurers, bound by mutual respect and a shared vision of service. It would be like Band of Brothers and Saving Private Ryan, certainly not in terms of a global war, but at least in the sense of sincere belief in sacrificing for something greater. Instead, I’ve encountered a disheartening number of petty tyrants, blundering bureaucrats, and those who see military service as a steady paycheck rather than a calling.
The culture I hoped to find has always been the exception, not the rule.
This disconnect reminds me of Tolkien’s struggles—and the echoes of those struggles in his writing. Bilbo Baggins is the quintessential outsider: too Tookish for the Shire, yet too gentle and reserved for the boisterous company of dwarves. He doesn’t quite fit in anywhere. But his story reminds us that the measure of belonging isn’t conformity—it’s courage.
Bilbo’s defining moment isn’t in grand acts of strength but in his quiet decision to do what is right. When he gives up the Arkenstone to prevent a war, knowing full well it could cost him Thorin’s friendship, he embodies a different kind of bravery: the courage to uphold his values, even when it isolates him.
Tolkien’s narrative also highlights the importance of building meaningful relationships—not those dictated by proximity or convenience but forged through mutual respect and shared values. The bonds we choose matter far more than the ones we inherit. Gandalf saw something in Bilbo long before the Hobbit saw it in himself, just as we all need people in our lives who see our potential when we can’t.
Choosing integrity may make you an outsider
This realization has shaped my own path. I’m taking a bit of a left turn away from my career as an Intelligence Officer and volunteered for an assignment that isn’t necessarily the “right” career move to check the boxes. But I’ll be teaching young officers at Squadron Officer School—not because it’s a career stepping stone, but to get closer to a place where the values of the military still matter. This decision isn’t seen as career-savvy by many peers, but it feels right because I refuse to stay in environments that erode my sense of purpose.
The truth is, staying in the wrong place isn’t resilience—it’s resignation. Real courage means stepping into uncertainty and seeking out people who challenge and strengthen you. It means finding your fellow adventurers who remind you why you set out on your journey in the first place.
Thorin Oakenshield, on his deathbed, understood this truth too late:
“If more of us valued food and cheer and song above hoarded gold, it would be a merrier world.”
You must learn to value connection over conformity and integrity over ambition. And sometimes, that means being willing to walk a lonelier path until you find your fellowship.
Marcus Aurelius once said,
“If it is not right, do not do it; if it is not true, do not say it.”
This timeless wisdom echoes through Bilbo’s journey in The Hobbit, where his quiet courage meant standing by what was right, even when it risked his place within the group. Giving up the Arkenstone wasn’t a tactical maneuver—it was doing the right thing. It’s a reminder that true belonging isn’t about pleasing everyone but about living in alignment with your values. In a world that often rewards compromise over conviction, choosing integrity may make you an outsider. Yet, Tolkien teaches us, that the bravest path is the one where we stay true to ourselves.
TAKEAWAY: Don’t conform to a life of quiet disconnection. Seek out your tribe—those who share your values, who challenge you to grow, and who stand with you in the messy moments. And when the world pressures you to fit in, remember Bilbo’s quiet courage: small acts of integrity can change the course of your story.
-Riley
"staying in the wrong place isn’t resilience—it’s resignation"
This is the first post I've read on substack and it is exactly what I needed to hear. So often I feel stuck in an action just because it is easier to do nothing rather than experience the fear of trying something different. My love for The Hobbit might have something to do with the connection I feel to this post as well, either way I am a fan!
'This decision isn’t seen as career-savvy by many peers, but it feels right because I refuse to stay in environments that erode my sense of purpose.'
Exactly this. I wish I and others I knew this, and much earlier in life. Ambition is inherently a positive trait, I think (and especially needs to be encouraged in women), but is so often misdirected or misappropriated. We don't exist to fulfil others' wishes.
'I believed I’d find camaraderie among those who shared these values... I’ve encountered a disheartening number of petty tyrants, blundering bureaucrats, and those who see military service as a steady paycheck rather than a calling.'
Insert the charity sector/ third sector as it's called here in Britain, in place of 'military service', and you have my experience to a tee. You could also add 'self-congratulatory martyrs'.
Great post, Riley.