The Stories You Tell Yourself Are Keeping You Small
On Detachment, Self-Worth, and the Power to Start Anyway
To the deep thinkers,
Welcome to the Deep Thinkers Newsletter: A collection of essays dedicated to going beyond the surface.
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I was at a birthday celebration recently and overheard a conversation that I haven’t forgotten since.
A lively young woman was telling someone close to her that she wanted to start selling her baked goods. She’d been thinking about embarking on this solo venture for years, yet hadn’t pulled the trigger, because:
“What if nobody buys them? What if it turns out to be a massive waste of time? I’ve tried to get so many projects off the ground before, and none of them worked out. But someday, when things in my life are less hectic, I’ll give it another shot. Someday…”
She trailed off, and no one around her really followed up on what she’d just said.
To me, though, what I overheard was the quiet embodiment of what holds so many people (myself included) back. On the surface, her comments might not have seemed like much. Most would hear them as inauspicious banter.
You, reading this, might think I should mind my own business and stop eavesdropping on other people’s conversations.
I’d say you’re probably right.
But I was haunted by what she said because—in that moment—I saw myself in her words. I’ve said those exact things. Who hasn’t had the “someday” conversation?
We’ll get healthier… someday.
We’ll share our creative work…someday.
We’ll tell them how we really feel…someday.
None of what I’m about to share here is meant to judge her, or anyone else who keeps having that “someday” conversation…because I am her. Or at least, I have been. Often. And only recently have I begun slowly detangling myself from the need to wait for some ephemeral “someday.” But habits formed over a lifetime take more than flowery language and self-awareness to break.
I feel a tinge of sorrow for all the times I told myself that once certain conditions were met, I could finally begin to become the person I most wanted to be.
I’ve struggled to see myself as someone worthy of self-love because my achievements were lacking. I wasn’t living the life I saw in my head, so I couldn’t love myself until I was. I was clinging to a story built on past events and external milestones, and it was killing my spirit.
People do this all the time. What’s even sadder is that we keep moving the goalpost. So, even the achievements, once reached, are still not enough. And in a world that constantly reinforces the belief that our value comes from external validation, it becomes almost impossible to love ourselves as we are.
Past Narratives
It’s always easier to remain attached to our narratives, to stay a slave to the past, letting it dictate how things will unfold. It’s easier to submit to the stories we tell ourselves. To challenge them is to become vulnerable. To risk failure. To kill a version of ourselves we’ve grown comfortable with.
So I understand: detachment is not easy. That’s because it’s a process of unlearning, of standing naked before yourself without the armor of old excuses or inherited beliefs.
I’ve felt (and still feel) this resistance, especially in my creative work, right here, on this very Substack. The difference now is that I’ve built a foundation I can return to when the voice in my head tries to tell me I’m not worthy of sharing these words with you.
But it wasn’t always this way.
For the longest time, I believed that the value in pursuing my goals came from having the right conditions—some baseline level of competence or readiness. Which, of course, on its face, doesn’t make any sense. But fighting the voice that holds us back ventures beyond what “makes sense.” It's emotional. Spiritual. Existential.
Everyone has to start somewhere. Many more have to start in the thick of chaos, uncertainty, or deep personal struggle. We must till the soil—even through storms and drought. Because the world will not provide perfect conditions, and no one else can push you in the ways you truly need.
I didn’t fully grasp the weight of that truth until I read Ryan Holiday’s The Obstacle Is the Way. One line, in particular, hit me like an unexpected flying knee:
No one is coming to save you. You have to do it yourself.
That sentence broke something open in me.
Valid excuses or not, no one else would do the living, or the dying, for me. At the end of my life, all I’d have is what I chose to do... and a quiet pile of all the things I didn’t.
That realization opened my eyes to so many unconscious behaviors:
The way I placed my value in my utility, not in my humanity.
The way I chased achievements, but never peace.
The way I said “I’ll start when…” and let that become a lifelong delay.
I didn’t love myself, not truly. And so I couldn’t nurture my body. Couldn’t feed my soul. Couldn’t create without shame.
It was detachment that saved me from spiraling further—not apathy—but detachment from the narrative. The story that told me things had to look a certain way before I could begin, before I could create, before I could believe in my own capacity to bring dreams to life.
Proof Through Action
I knew I wanted to write online, but I kept putting it off, telling myself I didn’t have the right blog name, the perfect niche, or the ideal setup. I was starting from ground zero. But when I detached from the idea that I needed the latest laptop, the best software, the perfect platform, or a flawless brand, I just started writing.
I began with a WordPress blog. My writing was rough—basically a watered-down echo of the more established Stoicism blogs I was reading. I didn’t have original insights yet. Writing was hard. (Funny enough, it’s still hard.) And even though the pull to return to my old mental cage was strong, I kept going.
Eventually, I found my way to Medium.com. That’s where I began to uncover my real voice. I realized that what I wanted wasn’t to sound smart, it was to empower and encourage others through my lived experiences and personal perspective.
I spent a few months there, trying to develop a consistent writing habit. But when I found Substack, something clicked. I loved the feeling of true ownership over my work, and I stayed. I kept tinkering with my style, and only recently have I started to feel grounded in both my voice and my process.
And all of it—every word—was written with imperfect equipment, in imperfect conditions, while life kicked my ass. And still, I showed up to write.
Because I’m no longer attached to those old narratives about myself.
I’m learning to love my mind and what I have to say, without needing validation, and without waiting for perfect circumstances.
I’m still far from where I want to go with my writing. But I’ve started to taste the fruit of this labor. I’ve seen what detachment, the abandonment of excuses, and the choice to act have done for my life. All of it began when I stopped clinging to old definitions and started trusting my humanity.
It’s human to be vulnerable. To express yourself. To solve problems. To evolve.
But you can’t solve your problems from inside the cage. You have to step out. You have to love yourself enough to detach from the stories that keep you chained to a version of yourself you’re no longer proud of.
Detach—not because you don’t care. Detach because you care too much to let your own mind hold you hostage.
I hope the woman I overheard that night is somewhere selling her baked goods. Even more, I hope we can all find the freedom to be. To be human. To arrive at the end of our lives with as few regrets and excuses as possible.
Remember, the conditions will never be perfect. Live anyway.
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What I’m into this week:
Hungry for MORE by Tamara (Substack)
I’ve never trusted people who tell me they are perfectly content. Not because I think they are lying (though many are), but because contentment often sounds too much like resignation. The truth is, there is nothing inherently noble about settling. Sometimes contentment is earned after a long fight. And sometimes it’s just fear wearing monk’s robes. Don’t get me wrong, I believe in peace. But peace that arrives after a storm, not the kind that’s handed to you like a sedative when your questions get too loud. Don’t hand me mindfulness like a muzzle. I’ll take the chaos, the ache, that ache that reminds me I’m still in motion.
Much love,
—Jon ♾️
If internal validation non-existant, difficult road ahead so all for internalization of imperfection (:
Loved this & needed this thankyou!🙏✨️