📓 Confessions of an insecure overachiever

On the quiet contradictions that shape who we are

Let me start with this: I am not insecure.

Obviously, neither are you!

There are certain things that insecure people simply cannot, and do not, do. I have it on good intel that you’re the grab-the-bull-by-the-horns type. For starters, you’re here.

If you’re the type of person that reads Substack or Medium articles in your spare time, you definitely had a high GPA in school. Your LinkedIn is probably running up against the character-count restrictions. You’ve been promoted three times in the last 2 years.

Self-doubt — what’s that? Sounds weak. We don’t do weak here.

Just look at our resumes. Insecurity can’t do that. Really, really.

I’m like 98% sure.

I am not insecure. But, I do want an agent.

If you’ve never queried a literary agent as a no-name yahoo who left their career to write their first book, allow me to set the scene:

It’s like having sixty seconds to prove your entire existence is worth knowing to the one person at a networking event that everyone’s trying to impress. Your words are locked in your chest. Your armpits are staging a small climate event. But, there’s no turning back now. You’ve spent months preparing your elevator pitch, and years chiseling your soul into the manuscript that you hope to have the opportunity to present.

Finally, you launch into your pitch.

But, halfway through your first sentence, rehearsed no less than 2,000 times in your bathroom mirror, their eyes glaze over and drift just past your left ear.

They say they’re looking for “fresh, debut voices!”

Translation: debut voices that have already had a TED Talk, at least two viral TIMES articles, and blue-verified check marks in every digital sphere.

In the absence of that, in a single email sent to a stranger — whose SUBMISSION GUIDELINES ARE TASTEFULLY COMMUNICATED IN ALL CAPS ON THEIR WEBSITE, and who truthfully couldn’t care less if you lived or spontaneously pulverized — you must perform nothing short of a small miracle.

You must prove that you are exactly what the literary world needs right now.

That you’ve uncovered a gaping hole in the cultural canon, and that you—and you alone—are fit to fill it.

In one carefully crafted pitch email, your writing must be electric, but velvety smooth. Your story must be rare, but universally resonant. You must translate professional, but also radiantly human. And, you must be passionately devoted to your writing. But, not so passionate that you might burst into tears if asked to delete — oh, I dunno — say, 80% of it?

That’s the process of querying literary agents.

Guys, it’s great. I’m loving this. I swear.

And even if you execute all of that perfectly, your fate may very well be decided by one distracted scroll. Your query email pops up on some agent’s phone, mid-diaper change or halfway through putting gas in their car. In under five seconds, they scan your carefully-worded plea for attention. Then — click.

Delete.

No “we love your voice and story!” No follow up request to see Chapter 1. No tiny glimmer of interest. Not even a polite decline. Just stone-cold silence. They escort your email out of their inbox. Most don’t dignify you with a response. And that silence merely echos the messages you’ve already been telling yourself.

You’re not Joan Didion. You’re not Steven King. Heck — you’re not even the ghostwriter of Chrissy Teigan.

Silly child, your fate has already been spoken for. Dream your dreams from a safe distance. But know this: you’re too late to actually start.

This is the lullaby that now haunts me in bed each night as I face the glow of my phone, refreshing my inbox vigorously. Eventually, I fall asleep to the soft hum of rejection. Then, the next morning, I wake up and do it again. I send out another flurry of emails.

I am powered by either tremendous optimism or complete delusion.

But this feeling—this curious tension between the sheer grit that compels me to keep going, and the rampant second-guessing that defines every step —is exactly why I wrote the book in the first place. It’s an oddly full-circle moment.

The self-doubt that I feel right now, is precisely what I felt for years in my career. This isn’t just part of my corporate history. It’s the recurring thread of my journey. This self-doubt is the truth of who I am.

It’s what I have taken years to unwind.

It’s also the working title of my story.

Owning the truth of our stories, and ourselves

Choosing a title for my memoir continues to feel high stakes. Because before anyone reads a single sentence, the title is the first pitch.

How do you name something that carries the weight of 100,000 words of your rawest truths, and doubles as bookstore clickbait? It feels like I’ve tried everything.

I toyed with rhyming couplets. I flirted with irony. Dabbled in drama. Swirled in some alliteration, just to see if it fit. I even went through a moody one-word-title phase, convinced that brevity meant literary gravitas and greatness! (I blame Cheryl Strayed and Wild for that particular phase).

Some titles felt close. But none felt like they landed spot on.

“I’m leaning towards Confessions of an Insecure Overachiever,” I announced one evening, over dinner with my parents. “What do you think?”

They paused, choosing their next words with care. No parent wants to crush their wee-child’s creative spark, even when it’s a lopsided macaroni sculpture.

“Are you sure ‘insecurity’ really speaks to your audience?” They offered gently, in response. “I just think it might turn some people off. How about just Confessions of an Overachiever, and drop the insecure part?”

I winced, but I also understood.

“Insecurity” gives people the ick. Maybe for high-performers, most of all.

It doesn’t translate bold and biased for action! It translates messy. You can’t trust them with the bottom line of the business. Worst of all, it reads: self-pity.

Gross.

We “overachievers” don’t tolerate self-pity in ourselves or other people. We simply don’t have the patience for it.

We’re too high-agency. Too resilient. Too gritty to wallow on insecurities. And sometimes, too certain we don’t have it. Heck — the self-doubt can’t be that bad if we racked up all of these achievements!

“Overachievers” want answers and strategies and outcomes. We’re highly effective people. Which is why we march towards the bookstore aisles that offer seven tidy-steps towards self-improvement. Self-doubt isn’t sexy. It simply won’t sell.

But, I also don’t know if I can sell anything other than the truth.

I am an insecure overachiever — gone too long misdiagnosed.

There’s a tension deep within me. A tension that defined my career. A dance I did each day.

I charged full-steam ahead, delivering repeated acts of heroism. All while battling demons within. I drowned out my bone-deep exhaustion with more work. I ignored the gnawing sense that my career success was fueled by self-doubt I refused to admit.

That tension is my truth.

It’s the beating heart of the book. It’s the uncomfortable core of my identity. It’s the thread that I’ve been tugging on since page one.

We’re overachievers. There’s greatness sewn within us. But, there are also contradictions we don’t like to contemplate. There are also darker truths.

This is the story of how excellence is sometimes stitched from our very worst parts.

The shadows and the superpowers of “insecure overachievers”

I’ve been thinking a lot about this potential title, and all of the conflicting feelings that come with it.

I know I can fix a critical breakage at midnight, and deliver a flawless readout on remediations to the C-suite. I also know that in order to that, I’ll need to slay a dragon spewing fiery hot self-doubt for 72 hours straight. I’ll be drenched in sweat with a crippling migraine.

But, my cool smile will say —Wow, she really has executive presence!

It took me a long time to really understand myself. To know these two parts of me, and to hold them side by side. And if I’m going to stamp the summary of this contradiction next to my name on the cover of a book, I better be clear about what it means to me. What it means to feel like an “insecure overachiever.”

The good, the bad, the whole twisted beauty, that many of us carry inside.

First, the bad and the ugly of “insecure overachievers”

1. We only chase what we can win

You and me — we possess an odd duality: both a hunger to achieve at the highest levels, and a deep-rooted fear of risk to what we’ve established.

That’s a bit wordy. What I really mean is this: we effing hate uncertainty.

We hate work that’s slow to offer results. We hate the prospect of failure and wasted effort. And we self-rationalize our way out of starting new things that don’t promise money and guaranteed results.

Because of that, we’re prone to an awful trap. We don’t choose what we pursue based on what we truly want. We don’t follow what excites our soul. Instead, we pursue what feels reliable and familiar. The things with the highest probability of coming out on top.

And, we will come out on top.

But, it will come at a cost.

We warp our internal compass. We mistake what’s achievable for what’s meaningful. We convince ourselves we want the goal because we have confidence we can reach it. Meanwhile, the quieter wants—the risky uncertain pursuits beyond our comfort zones of expertise—get buried beneath our actuarial assessment of achievement. Maybe we secretly want to open up our own pottery studio, or get a PhD in Physics, or — dare I say — write a book! But, we convince ourselves it’s too late. We secretly think we’re not good enough.

So, we stick to what we know. We’ll like what we do. But, we’ll never love it. We’ll follow. We’ll be diligent. But, we’ll never know what it’s like to feel pulled by something. To be genuinely inspired.

If we’re lucky, something shakes us out of this sleeping-walking state.

Sometimes, it takes burnout, to remind us we’re not dead yet. To light a fire under our soul, to think long and hard, about what we really want for our life.

2. We ignore the body until it breaks

Overachievers know precisely how to wield their mind. Their sheer mental willpower delivers a work ethic like none other. But, ask us how our bodies are doing, and we might look confused. Or, worse. Annoyed.

Yes, we go to the gym. Obviously, we track our steps. We’re disciplined with our diet. We stay in tip-top shape. But, we’re quick to roll our eyes at anything that sounds like “woo-woo” wellness talk.

“Listen” to my body?

Sure. Absolutely.

Right after I finish this 12-hour sprint on three iced coffees and crank out a Board presentation from scratch.

Our answer to any problem—emotional, physical, existential—is usually more output. More grind. We don’t pause to investigate what it says about ourselves. We just plow ahead instead.

Head pounding? Neck tight? Sleep shot? Gut screaming — hey, this doesn’t feel right? We tune it all out. We’ve trained ourselves to ignore even the loudest signals. We’ve forgotten what it feels like not to hurt. We logically know that life is sacred, but we treat our own vessel like crap. We refuse to believe the long-term damage to our physical health.

Eventually, that numbness spreads. First to your limbs, then to your relationships, and finally to your sense of self. Real embodiment isn’t about pushing your body to the breaking point.

It’s about being unafraid to trust your body, and pause. And to maybe, take a step back and ask yourself:

Is this what I really want?

Now, the superpowers of overachievers

Despite the unsavory parts of our nature, there are also some remarkable strengths that deserve to be named. Truths that go beyond “blind grind” and point towards some genuine gifts. These are the things we need to lean into, balance with rest, and redirect towards our deepest wants.

1. We can laser-focus like no one else

Give an overachiever a mission, and we’ll zero in like a heat-seeking missile. “Focus” is a conscious effort for regular folks. But for us, we don’t need to consciously focus. We’re automatic. We lock in.

Food? No need. Sleep? Optional. All distractions. Unregistered.

Whether it's building a strategy deck, mastering how to deadlift, organizing the world’s best bachelorette party for a friend, or learning a new language, the ability to go deep isn’t limited by domain. It’s something we bring to every realm we invest in. We go full-throttle, once we decide what we want.

It’s that ability that makes us capable of achieving mastery in many realms. Not because we’re naturally gifted, but because we’re willing to stay in the weeds longer than most without realizing it. It’s easier for us to get into “flow.” We run laps while others rest, without it feeling like hard work.

Our resilience is truly a gift. The key is pointing that gift, even in the direction that self-doubt sometimes tries to talk us out of it.

If we hone in on what we actually want, and ignore the uncertainty that scares us, no one can get it done like us. We truly can achieve anything.

2. We know what excellence actually looks like

Some people are just trying to “finish” the assignment. Overachievers are mentally comparing it to the gold standard from 2003 that won first place in an international competition.

We don’t just work hard, baby-cakes. We study what great looks like.

And once we see it, can’t un-see it. We’re physically incapable of accepting anything less. Excellence isn’t abstract to us. It’s specific, and we know it when we hit it.

That makes us relentless improvers. Detail obsessors. Tireless iterators. And, yes, occasionally annoying group project partners.

We’re not merely chasing a finish line. We’re chasing the feeling. That deep sense of something finally being just right. Not “good enough.” Excellent.

In fact, we don’t understand how other people can’t see that some output is still only good, and not yet extraordinary. Oftentimes, for us, mastery isn’t a milestone that we’re consciously shooting for. It’s just a byproduct of our attention to detail, and our visceral sense of what “best-in-class” looks like.

We may struggle to trust our ability to reach our own high standards. But, seeing those standards is hard to teach. We have the rare capacity for true vision.

Owning the whole title: the insecure overachiever within me

I’m still not sure if this will be the title of my book. It’s just a possibility.

It’s not like people even call you an “overachiever” once you’re grown up. It’s just called, succeeding. But I was called it plenty as a kid. For some reason, it still haunts me.

It contains sweet, sweet praise. And a connotation, an aftertaste, that stings.

It captures the whole truth, in all its twisted beauty.

It captures the parts of me that still quietly crave status. It captures the parts that still struggle to rest without guilt. It captures the parts that still long for deeper meaning, but in the meantime, pad my resume with more fluff.

But, I also know that it captures some of my greatest strengths. I know the superpowers that can kick in, even when I’m feeling most terrified. I know that when I move through my fear of falling short, I’m capable of charging towards any pursuit. I know I come out feeling soul-aligned.

One step, in front of the other. One day at a time. That is, after all, how I wrote a 300-page book. Beside all the self-doubting bits of me, a heart found the strength to start.

And, even if no agent asks to read the manuscript—

Even if I’m still refreshing my inbox at midnight for another 2 years—

I’ll sleep easy knowing one thing.

There’s nothing I ran away from. Nothing I wanted to try and didn’t. I may still be an “insecure overachiever.” But, I’ll be living in my whole truth.

In every page of my book, every day of my life, I’ll forever feel good about this:

Fear never got the final word.