Insecure overachievers are made, not born.

Insecure overachievers are dangerous.

They are smart, articulate and well-read. They can be charismatic, arrogant and narcissistic. They push themselves to their limit, obsess over self-development and frequently burn out.

Because of their smarts, they can intellectualize their own flaws, outwit others during intense debate and charm even their most ardent critics.

Combined this with a capitalistic system that rewards this behavior and you’ve got a recipe for potential disaster.

How do I know all of this?

Because I am one of them.

I became a CEO at the age of 21. I have won numerous awards and accolades. Now at 26, I hold a senior position at work and manage people years or even decades older than me.

I have been appointed to professional boards and committee positions that most people wait until their late 30s or 40s to get on. I make a six-figure packaged salary, co-host a podcast and am currently waiting to build a house.

And I got most of this because I am deeply insecure.

“Sometimes society can reward your mental illness” — Russell Brand

My biggest fear is: dying having not achieved anything.

Fear of not being remembered. Fear of being left behind. Fear of not having had a positive impact on the world. It sounds ridiculous when I think about it and even more ridiculous as I write it out now.

But that’s how insecurities work. They aren’t rational. They don’t abide by any logic. And they can hijack the emotional center of your brain like a parasite. Controlling how you feel, how you act and what you do.

I know I’ve inherited this insecurity. It is a connection I share with my dad and probably his dad as well. That side of the family is constantly obsessed with being rich. Focused on their status and what other people think of them.

One of my grandfather’s prized possession was his Rolex watch. Not that he can wear that in the temple he is currently buried in.

I’ve taken steps to get better. But the insecurity is still there. It might never leave me. I am writing this article as part of my own therapy as well as bringing awareness to an important topic.

We all know an insecure overachiever. They could be a family member or a friend or a friend of a friend. It might even be that handsome (I mentioned the narcissism right?) but insecure person looking back at you in the mirror.

A Harvard Business Review article by Professor Laura Empson describes insecure overachievers as:

“Exceptionally capable and fiercely ambitious, yet driven by a profound sense of their own inadequacy. This typically stems from childhood, and may result from various factors, such as experience of financial or physical deprivation, or a belief that their parents’ love was contingent upon their behaving and performing well.”

Reading that definition hit me like a ton of bricks.

Like it was pulled straight from my therapist’s notes. Being a first-generation migrant of loving but working-class Chinese-Singaporean parents, you can bet I’ve internalized one or more of these behaviors in my programming.

But maybe I’ll outgrow it? “I could start to lose that insecurity once I’ve proven myself professionally,” I say to try to reassure myself.

Unfortunately, insecurity does not end with seniority.

Read this:

“It feels like a constant need to prove you should be where you are, and a constant concern, before every meeting that I go to… am I going to make an idiot of myself here and are people going to see through a façade and think actually there’s no real substance to this?”

Does this sound familiar?

Who do you think wrote this?

Well, it wasn’t me or a recent graduate or an early career professional.

This is a reflection of Jeremy Newman.

“Until recently, Jeremy was the global CEO of BDO, one of the world’s largest accounting firms. He currently chairs important government bodies and a range of other institutions. By any measure he is hugely successful in his professional life, and yet here he is, telling me that he privately worries constantly that he is not good enough,” writes Laura Empson

Still not sure if you’re an insecure overachiever?

Here are 5 more signs to look out for.

1. Achievements define your happiness

You have an unhealthy attachment to achievement. You want it at all costs. Even if it means sacrificing time with your family, friends and doing things you really like. You often surrender companionship for the sake of your goals.

Having goals and wanting to achieve big things in life is not inherently bad. But there is a balance. Your intention for wanting to achieve a goal is almost more important than what goal you want to achieve.

If you achieve this goal will you get the love you crave? Will you feel admired? Will you finally make your parents proud of you? Will it feel that void you feel at night when silence takes over?

Achievement can be like a drug. Numbing any sort of pain or insecurity you might have. How can you feel bad about yourself when you’re kicking ass and taking names?

While not the worst thing to be addicted to, you can see a long road of loneliness ahead. You might get to a point in your life when you realize what you sacrificed for isn’t what you actually wanted.

Achievements are fickle. There will always be a bigger prize. Much like a rat wheel, the hedonic treadmill of achievement is designed to keep you running. A bigger platform. A more prestigious award. It never ends.

Research in positive psychology shows that the pursuit of goals produces longer-term happiness than the momentary happiness that comes from actually achieving that goal. So it really is all about the journey.

My grandfather didn’t teach me much. But the one thing I learned from him is that you can’t bring your achievements to your grave. And after 1–2 generations, not many people will remember them anyway.

Remember this:

“There will never be an end to the to-do list, future goals, and plans, the things we want to achieve and see. But the fact that we don’t have everything we want is exactly what makes life so fulfilling,” writes Olivia Goldhill

2. You hunger for other people’s admiration

Hunger for admiration begins with a void and ends with a void.

Building your life around receiving admiration is building a life directed by other people’s expectations, external criteria, and definitions of success that don’t actually fit you.

When you play stupid games, you win stupid rewards.

3. You sacrifice commitments in favor of status and success

Write down your priorities in life.

Where does time with family and friends sit? What about exercise and connecting with nature? How do you prioritize your commitment to your partner or kids? How about your commitment to your own health?

Sacrificing for the long term is a normal part of life. But how much sacrifice is too much? There are just some things in life that just aren’t worth sacrificing. No matter the potential upside.

For instance,

• Health

• Reputation

• Relationships

Once broken, they are hard to fix. And even when fixed, they might never be the same again.

You are great at sacrificing for your goals, but do you know what you’re not willing to sacrifice?

4. Your relationships are more like transactions

Most of your relationships are defined by one characteristic: competition.

Your colleagues compete with you for promotions, raises, and projects. You might work as a team but you think as an individual. You connect with your colleagues at arms-length. Keeping them at a safe and manageable distance.

You sometimes refer to your friends as your networks. The dynamic of your friendships is one-sided. You tend to dominate the conversation with how well you’re doing or subtly hint at how important you are.

5. Your view of the world is from a high pedestal

The view from the pedestal is nice. You can admire the great landscape and see the path you are on. The wind is blowing on your face and the journey is beckoning.

But you are lonely. Many insecure overachievers have an undercurrent of loneliness. An unwavering feeling that no one truly understands them. The lonely quest for greatness you might think to yourself. A bargain you’ve made.

To compensate, you use your achievements to attempt to replicate the love and glory from strangers that you want from your friends and family. But it flows in only one direction. Much like an Olympian receiving a medal.

But it doesn’t have to be that way. You still have a choice to get off the pedestal without hindering your ability to achieve your goals. Humble yourself. You are not the most important thing in the world.

Summary:

“Your insecurities may have helped to get you where you are today, but are they still working for you? Is it time to acknowledge that you have “made it” and to start enjoying the experience a little bit more?” — Laura Empson

Intelligence is knowing ahead of time when you need to start. Wisdom is having the awareness of when it is time to quit.

You might think that your insecurities are good. By definition, they have gotten everything you enjoy in life so far. A great career, money and status. But what is the limit? When do they stop being useful?

Sooner or later, your insecurities will cease to be an asset and start being a liability. One day there might not be anything else to aim for. No more achievements, no more goals. What would give your life meaning then?

What can you do about it?

• Notice your triggers — What conversations or topics trigger your insecurity? Which people tend to bring that side of you out? Are there certain environments you should avoid?

• Create a new definition of success — Success is subjective. You get to decide how you measure your life. Create a definition of success that doesn’t produce its own opposite. Time with family, connection with nature, and impact on your local community.

• Compile evidence — Create a folder of ‘wins’. This will help to remind you that you’re doing great when that voice comes out that you’re worthless.

• See a trained professional — You are not alone. And sometimes it is hard to see the label when you’re inside the bottle. A trained professional can help you manage and develop personalized strategies.

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