Unveiling the Struggles of the Insecure Overachiever

Understanding the psychological dilemma of overachievers and nurturing intrinsic worth

image created via lexica.art

“Exceptionally capable and fiercely ambitious, yet driven by a profound sense of their own inadequacy. ”

Dose this term resonate with you? I certainly do. Throughout my academic journey, I pushed myself relentlessly to become a doctor, fueled by the desire to gain recognition from a high school teacher I had barely interacted with since graduation. It is disheartening to look back and realize that such a crucial life decision was influenced by the opinions of someone I hardly knew.

Fast forward four years after becoming a licensed clinician, I made the bold decision to switch careers and venture into the world of design, aiming to break into the tech industry. Coming from a well-paying job, I refused to settle for a position in an unknown company or an internship. Despite the challenges, I managed to secure my first role working remotely for an Australian company. From the perspective of my peers in Taiwan, my birthplace, this seemed like a remarkable achievement. Those around me were fascinated by the outcome and the path I had taken. Undoubtedly, I felt a sense of pride in myself. However, deep down, I knew that my motivation stemmed from how others perceived me. I yearned to be seen as someone capable of succeeding in any endeavor I chose, rather than as a fool who gave up a lucrative salary to pursue seemingly insignificant pursuits, becoming the subject of mockery at dinner tables.

The pursuit of achievements is an addiction. They become the measurement of our happiness. The rush of dopamine we experience upon accomplishing something reinforces our motivation, which is ultimately rooted in our own insecurities. We then seek out another ambitious goal and exhaust ourselves in a relentless pursuit, attempting to fill the void within us. This cycle continues until we look back and realize that those achievements hold no true significance. The people we tried so desperately to impress hardly give us a second thought. In the process, we sacrifice precious time with our loved ones, the enjoyment of life, and the opportunity to explore the world around us.

Furthermore, the relationships we build along this path become transactional, mere tokens in our gallery, serving to boost our ego during conversations with others. In the end, spiritually speaking, we are left feeling utterly alone. We possess the ability to envision a future beyond the reach of others, yet we have no one to share it with.

So, how can we fix this?

The first step is to acknowledge our insecurities and identify what triggers us. In my case, the fear of not being seen has been the driving force behind my relentless pursuit of high performance.

Next, we must find validation from within. External validation is nothing more than a fleeting rush, and certain companies exploit the insecurities of overachievers to meet short-term goals.

On a related note, I've noticed that remote work environments tend to exacerbate the insecurities of overachievers. The opaque decision-making processes, lack of genuine connections, and artificially scheduled interactions create an illusion that others are coping fine, while we are left alone at home, struggling and blaming our own inadequacies for being part of a company that grants us full autonomy.

I believe that companies operating remotely do not intentionally create such toxic environments. However, they should be more mindful of the potential side effects of this operational model. It is crucial for them to proactively seek out solutions to counteract these negative consequences, rather than accepting them as inherent to remote work and waiting for suffering employees to propose remedies. Dare I say, it is this very attitude that defines a toxic work environment.


We can surpass those superficial achievements that consumed our souls by building a foundation of confidence from within ourselves. It starts with each of us, acknowledging our own insecurities and recognizing our inherent worth. Once we do that, we can have a more fulfilled life and a work environment that foster genuine relationships.

Useful tool & resources

To echo today’s topic, creating a wins file can help remind us all the progress that we’ve made along the way, fostering a sense of self-worth, the internal validation for insecure overachievers.

Airtable is the tool that I use to document my growth after I quit my job. It’s easy to feel stagnated and trapped during career break, therefore I created this doc to act as a reminder of my growth. If I deserve a break, then you definitely deserved it as well. Start writing it down and be proud of how great you’ve become. This is mine, feel free to take a look and copy the format. :)

Thanks for staying with me for another week! Take care!

I am MengChi writing from my shipping container.

Join the conversation

or to participate.