Second-Guessing Everything: How Imposter Syndrome Shows Up in Remote Work

A look at self-doubt, overthinking, and the quiet emotional weight of working from home.

It’s wild how fast it happens.

I’ll write something—an email, a Slack message, even a meeting agenda—and just as quickly as I hit send, the spiral begins.

Was I too direct? Too soft? Did I use too many exclamation points?
Should I have added more context? Should I have said less?
Do they think I’m capable? Or annoying? Or both?

I’ll be honest—I second-guess myself more than I’d like to admit.

Some of it is just how I’m wired. The perfectionism. The “get it right the first time” energy that was baked into so many of us coming of age during economic crashes, unpaid internships, and “just be grateful” job culture.

But some of it? Some of it is quieter.
It’s the lingering voice that asks, "Are you sure you belong here?"

And the truth is… I don’t always know.

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I wish I could tell you that I wake up every morning bursting with self-assurance and clarity. But more often than I’d like to admit, I start my day tiptoeing through my to-do list, trying to keep up without falling apart.

I reread emails five times before sending them.
I delay asking questions out of fear they’ll seem obvious.
I overthink things that no one else even notices.

There’s this part of me that’s always calculating—checking, revising, buffering.
It’s not insecurity, exactly. It’s more like… self-protection.

Because being a millennial woman in today’s workforce means carrying a lot—ambition, burnout, hope, exhaustion—all at once.

And when you work remotely? The silence is deafening.

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Remote work has changed my life, in so many good ways. But it’s also made it easier to live inside my own head.

There’s no casual feedback loop.
No reassuring smile across the table.
No whispered “you’re good” after a meeting.

Just me, my laptop, and a mind that won’t stop replaying and rewording everything after the fact.

And yet… I keep showing up.
With the second-guessing.
With the spirals.
With the soft hope that maybe this time, I won’t overthink it.

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Here’s what I’m learning, slowly and imperfectly:

💭 Second-guessing doesn’t mean I’m not capable. It means I care.
💭 Overthinking doesn’t make me weak. It means I’m paying attention.
💭 Two things can be true—I can hold self-doubt and self-worth in the same breath.

I’m still figuring things out. I probably always will be.
But there’s a certain beauty in that too—in being someone who shows up even when her hands are shaky and her voice trembles.

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To the other corporate millennials who tend to spiral and reread their own messages like they’re decoding ancient scripture:
You’re not alone. You’re doing better than you think.

📩 Tell me—what’s something you second-guessed this week that turned out just fine?