the case for oversharing
reflections from one year of writing my newsletter
On February 12, 2024, I shared my first essay on Substack.
At approximately 5pm, my imported list of friends and family received a short story in their inbox—one most had already read in a zine I created with a friend months prior.
Despite the oozing levels of contextual familiarity, I was still nervous to my core in the moments leading up to hitting publish. I remember the build up and ecstasy as if I felt them yesterday.
Forty essays later, here I am, celebrating leap years’ one-year anniversary. It also happens to be my first newsletter post since turning 241.
Through writing, I’ve gained a level of mental clarity, self-honesty, and emotional maturity that—even to myself—feels surprising at times. Give yourself room to grow and watch how thoroughly you can fill the space. It may not always happen as quickly as you’d like, but it's the volume of progress, not rate, which matters in the long run.
I’ve always been a decent writer. Never exceptional enough to consider studying literature or pursuing something like journalism, but good enough to feel satisfied with my ability to express my thoughts on paper and earn As in my high school English classes.
I say this to emphasize that, for me, the hardest part of running this newsletter hasn’t been the writing itself. In fact, sitting down in the morning and typing away, free from distractions, is the most therapeutic part of my day.
The hardest part of this newsletter, unequivocally, has been overcoming posting anxiety.
Even though I’ve published for a year, each and every Monday essay has been preceded by a cortisol-fueled weekend of pounding away at my keyboard, trying to make sense of my words while already dreading the underwhelming reveal I will have to make once it’s time to share this week’s yap with the world.
I’ve found that posting anxiety manifests in two ways.
The "Not Ready Yet" Anxiety
The first, common among creators, leads one to believe that their work isn’t ready yet. Despite all the pieces being in place, the looming pressure of publishing convinces you that you’re just a few more edits short.
Let me just rework this paragraph, then it will be ready, then it will be perfect.
At best, this creates burnout and apathy toward the work you once loved, yielding something marginally better.
At worst, your work is relegated to an ever-growing pile of drafts and half-baked ideas that will never see the light of day—lost opportunities to share genuinely impressive ideas with the world.
I used to feel not ready yet anxiety all the time, but not as much anymore. What helped me overcome this was realizing how delusional it is to believe that a few extra sentences or hours of editing would somehow elevate my random Monday newsletter into the upper echelons of literary greatness.
No amount of editing can fix a shit essay, so might as well publish it, learn from the process, and move on to the next one.
The Fear of Oversharing
The second form of posting anxiety is more subtle, pervasive, and toxic.
At its core, it stems from a fear of oversharing—a byproduct of how social media has evolved in recent years. We find ourselves in this weird era of the internet where it’s become not cool to post, and sharing too much feels desperate.
This shift in social norms has been hard to digest. As a result, many hide behind claims of being private or “above” the need for validation—when in reality, they’re masking embarrassment and a fear of looking vulnerable.
I’m just not the type to put my life out there on the internet like that.
I’ve muttered those exact words, pretending self-censorship was self-control, as if holding back signaled mystery or strength.
And in doing so, we’ve all played a part in shaping a world where passively consuming influencer content is a consensus better alternative to sharing our own thoughts with the people closest to us.
We’ve been handed the keys to a Ferrari but insist on driving it like a Corolla. And we justify this trade-off because the dopamine hits keep coming. It’s easier to cruise in comfort than risk looking foolish behind the wheel.
But a Ferrari isn’t meant to be driven like a Corolla. You don’t buy it just to keep it in the garage.
At some point, you have to hit the gas and see what happens.
Do I overshare on this newsletter?
I ask myself that question from time to time.
Maybe I share more than you’d be comfortable with sharing yourself. But while I’ve been candid about my struggles, I’ve never once trauma dumped, nor gotten into the intimate details meant for myself and those closest to me.
Despite publishing nearly every week, only a handful of people know the full picture that is my life—how suffocated I feel at my current job, the frustration of repeated knee surgeries, the loneliness that lingers daily. I’ve touched on these topics once or twice, but only at the surface level. What I share here is just the tip of the iceberg.
What you don’t see behind these curated words are pages of unfiltered thoughts—hundreds of journal entries, scattered Post-it notes shoved into my desk drawer, poems that will never be published, doodles filling my sketchbooks. That’s the reality of self-expression: what we show to the world is just a sliver of what exists within.
We vastly underestimate how much depth we actually hold. Give yourself more credit. You’re far more complex than an Instagram post of curated highlights or a Substack essay summarizing a controversial take. Sharing your life online a bit more isn’t going to put a target on your back—people are too caught up in their own lives to scrutinize yours the way you imagine.
But the first step to sharing openly isn’t posting online. It starts with oversharing with yourself.
When I first started journaling, I struggled to be fully honest. I held the irrational fear that someone would find my journal, read my thoughts, and know me too intimately. In reality, I think I was just afraid to open up to myself. I wouldn’t even curse in my own journal, as if censoring my thoughts somehow kept them contained.
That’s why I believe the first step is to over-express yourself to yourself. Write down what you love, what you hate, what you think about when you’re alone. Track your favorite books, keep a journal of how you’re progressing in your hobbies, and most importantly, get to know yourself, without the filter of an audience.2
And once you do—once you feel comfortable in your own skin—share the parts you want to share with the world.
What I’m trying to say is this: while oversharing is real and subjective, most of us err too far on the side of restraint. We hold back when we don’t need to.
I’d love to see a return to carefree sharing—where creativity and authenticity outweigh fear and algorithmic pressure.
Not everyone needs to start a Substack. Writing isn’t for everyone, but self-expression is.
So whatever your medium, share something. Share thoughtfully, share bravely, and share more than you think you should.
We all want to hear you more.
Kobe!
I recently read this essay on non-performative ways to track hobbies, which I think is a great way to test the waters.
"At worst, your work is relegated to an ever-growing pile of drafts and half-baked ideas that will never see the light of day—lost opportunities to share genuinely impressive ideas with the world." I think at some point, this concept of drafts and half-baked ideas became a best-case-scenario for the way my mind works and processes things. Instead of viewing it as a dumpster, I view it as a garden where I plant things and then am forced to nurture them or discard them as seasons change.
Congrats on writing for a year!
Write on, Raymond! As Marianne Williamson once wrote, "Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won't feel insecure around you. We are all meant to shine, as children do"