Hi. My name is Greg and I’m an Insecure Overachiever.
Since I can remember, I've always tried to be perfect.
Hmm... that's not quite right. Let me try again.
Since I can remember, I've always tried to appear perfect.
That's more like it.
I earned good grades in school, then followed a 'so-called' successful path in life—career, marriage, house, kids, minivan... sigh, minivan.
For so long, I loved appearing successful and 'perfect.' But it's time to admit that, for most of that time, I've felt like a total fraud. I wouldn’t call this Imposter Syndrome per se. Instead, I’d label it like this:
I am an insecure overachiever.
Shit. Did I just say that out loud?
The thought of labeling myself with the word insecure has me literally squirming in my chair and choking on my coffee. But there it is. Because it’s true.
In the 12-step AA recovery model, the first step is honesty—accepting and stating what you are and acknowledging that you need support to overcome your addiction. While being an insecure overachiever is not at all the same as being an alcoholic or addict, the parallel is undeniable.
I've admitted to myself (and now to you) what I am. And now, I can put myself on a path to recovery.
What Is an Insecure Overachiever?
The term "Insecure Overachiever" describes anyone who never stopped thinking of life like school. We are strivers—people who get great jobs, live beautiful lives, own beautiful things—but deep down, we know we’ve missed the point.
We’ve spent our lives meeting other people’s expectations, collecting accolades for our outward achievements, yet never truly asking ourselves: "What do I actually want, value, and desire?"
Western culture thrives on insecure overachievers. We buy things we don’t need to impress people we shouldn’t care about, and we work tireless hours for companies that, frankly, don’t care about us.
But I’ve met people who don’t fall into this trap—people who are deeply happy and secure in who they are and what they’re doing. They could be working in a coffee shop, leading an organization, or volunteering at a local charity. What they do matters far less than the fact that they are living intentionally, in alignment with who they truly are.
These people are authentic. They’re driven. And they’re awesome.
Odds are, you know people like this. In fact, you might even be one of them.
The Path to Change
Sadly, outside of brief glimpses in time, I haven't been one of those people. But... I'm starting my journey to become one.
It's terrifying. It's exhausting. It challenges everything I thought I knew about myself.
And it’s the best thing I’ve ever done.
David Brooks' book, The Second Mountain has been making the rounds lately—and for good reason. It's REALLY good. In it, he dedicates a WHOLE CHAPTER to defining what an insecure overachiever is. When I read it, it felt like someone turned on a light and revealed the room I'd been sitting in for years.
I wanted to share it with you.
I think many more of us are insecure overachievers than we care to admit. We bury ourselves in busyness and achievement to avoid facing the real questions about who we are and what we truly value. Tragically, many of us will die without ever answering those questions—because there are mortgages to pay, bosses to keep happy, and never-ending to-do lists.
But... there’s a way out.
Rather than letting life pass us by while we're on autopilot, we can choose to live with intention.
I get it—"living with intention" sounds abstract and overwhelming. So let’s start small.
If you think you might be an insecure overachiever, here’s where to start:
Admit it.
Acknowledge it.
Know you’re not alone.
There’s at least one more insecure overachiever out there—me—figuring this out alongside you. And once we’re honest with ourselves and each other, the journey toward living with intention can begin.
“We like to think of ourselves as consistent, rational beings, possessing certain attributes and not others. Yet a person who is completely consistent, who possesses no contradictions, comes across as less real. Wooden. Plastic.”