A philosophical case study of a career changer with obsessive perfectionism

Geli Skandalis
Bootcamp
Published in
8 min readMay 26, 2023

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Embracing uncertainty, overcoming perfectionism, and discovering healing through writing & design

Comic strip meme humorously depicting philosophers complicating a simple question ‘what do I want?’ into existential queries like ‘who am I?’

Greetings, fellow wanderer.

Throughout my life, I semi-consciously stalled my successes, held hostage by the impossibly high standards I set for myself. Afraid of failure, I either pushed too hard, or didn’t try at all. Fatherhood, however, forced a reckoning — a systematic need for change to find peace in life, to find contentment. Dedicated to change while lacking clear goals, my aim became to grasp every opportunity until the “right” one appeared. As so often, that opportunity was revealed by my wife, who saw something in me that I didn’t know existed. That something was a UX Designer.

This profession seemed to materialize out of nowhere, as if it had been recently invented and specifically tailored to reflect my values and beliefs. Perhaps it had been brought into the world precisely to erase my discontent and provide a sense of purpose to the work part of my life. Technology that prioritizes human needs to help people get shit done the way they intend? Had I known the term, I probably would have called it the perfect value proposition.

In my exploration, I learned about the Center of Humane Technology and its mission to reshape the way technology is developed and used so that it enhances our well-being, strengthens society, and fosters a more trustworthy information environment.

Once I started thinking about the implications of design — how small decisions can ripple out and affect the world — I was hooked. In the process of reshaping my habits, I began to observe how artificial design choices, implemented to drive engagement, had subtly influenced my actions and shaped my behavior throughout the years.

How could I not see these patterns before? Behaviors like my impulsive buying habits that had kept me consistently broke, began to make sense. It does not have to be that way. After all, humans are not natural-born impulse shoppers; we’re shaped into them.

At that point, I knew that behavior isn’t set in stone. So, something in me wanted to stand up for life, to prevent design from dictating what we like or, more importantly, who we like or don’t like. I felt the world needed more champions, and I gave everything I had, and more, to be one of them. But my mental health, which I had struggled with since my teenage years, began to deteriorate as I was once again confronted with a major pattern: ambition and (perceived) knowledge exceeding my skills.

AI-generated image of a person trying to balance an oversized pile of books, symbolizing the challenge when ambition exceeds skill.
A hopeful learner struggling under a towering pile of books. Created with DALL·E 2

Even when we embark on journeys to help others or bring about positive change, I believe we inevitably start from a place of selfishness. In fact, it’s a necessity, essential to maintaining our well-being and sustaining our efforts in the long run. In other words, to maintain “flow” — the sense of immersion and fulfillment that comes from finding joy in taking on challenges. Knowing that these challenges can only lead to growth and learning, and that, most of the time, nothing bad will ever happen if we just go our way.

At the core of my persistent dissatisfaction with my progress and resulting unhappiness lurked an obsessive perfectionism that fed on my fears and led to a constant sense of imbalance, of feeling “off”. Ever since I realized this, I have been searching for its origins and solutions to truly embrace the belief that I am, in fact, enough.

When I embarked on my odyssey into the realm of human-centered design, I discovered that design, at its core, is deeply rooted in intentional thinking and understanding of complexity. Soon, I realized that it required far more thinking than I had initially anticipated.

Much like a computer running out of RAM or a juggler overwhelmed with too many balls, I faced the dilemma of not being able to do all the thinking in my head. Overwhelmed by thoughts, I often did not know where to start. At this time, inspired by Jorge Arango, the revelation hit me that “writing is thinking”. Motivated by this insight, I committed myself to keep writing, even when it was painful–and at times, it was quite painful indeed.

I’ve come to believe that to solve any problem, it’s essential to get our thoughts “on paper”– to save them, to dig deeper, to clear our busy minds for new ideas. Through the written word, we can contextualize our thoughts and find their intended meaning. Or, the hidden concepts behind them. In other words, to reveal a truth besides the obvious — the one that our naturally biased minds want us to believe to save us precious time and energy. Therapy also helped me a lot with finding my truth, but it was not the talking that did the healing, it was the writing afterward. The thinking.

All you have to do is write one true sentence. Write the truest sentence that you know.—Ernest Hemingway

As I’ve come to understand, part of walking my path is accepting that my truth may be true in the moment, and that it probably won’t stand the test of time, and that’s okay. No, it’s absolutely necessary to be able to move forward, to not get stuck. Whenever I think about this, I’m reminded of Hemingway’s words: “All you have to do is write one true sentence. Write the truest sentence you know.” To me, this captures perfectly the essence of embracing imperfection and the fluid nature of our understanding.

I believe that the greatest obstacle to learning new skills is the fear that our minds produce about what may lie ahead. The future is cloaked in complexity and uncertainty, but if we recognize that we are on a journey of growth through learning, with nothing to lose, we can boldly face the challenges that lie right in front of us. Not only that, we can embrace setbacks, and even deviate from what we initially thought our future had to look like (or, in a business sense, the future of our services and products).

That essentially means that we become more flexible to life’s challenges, which by definition is what intelligence is. The ability to make the right decisions at the right time.

Simple image of quote: “We may never know what we don’t know unless we try to know something.”

We will probably never fully comprehend the vastness of what we don’t know. And we may never know what we don’t know unless we try to know something. If we simply put down what is already there, without judgment, we can slowly begin to understand and to feel joy in our actions. To heal.

Writing, or deep thinking, I think, is a form of self-understanding — or perhaps even understanding that there is no self to begin with. And after all, if we lack self-understanding, how can we hope to understand others on an emotional level, let alone the complexities of the world at large? How can we offer solutions that do more than heal the symptoms of a problem if we can’t see what causes them?

By understanding our universal human values, fears, and their origins, and by accepting a measure of selfishness, we can gain the perspective necessary to truly help others. The key is to ground our every decision in sound self-knowledge, kindness, and compassion.

The similarities between writing and design became apparent in this process of self-understanding. A whopping 99% of what we jot down (or design, develop, produce, etc.) is probably nonsense — even if it seems logical at the moment.

The real magic lies in realizing that this seemingly chaotic 99% is not something to be avoided, but warmly embraced. It’s by navigating this vast, disordered sea of ideas that we eventually find and connect the rare and precious 1% — the truly insightful, meaningful gems. So, it’s not just okay that 99% seems like “noise,” it’s absolutely necessary, in my opinion. Because it’s from that noise that our “signal,” our meaningful contribution, emerges.

The breadth of thought that goes into any endeavor may be hidden from those who consume its outcome, but the final message is not. This is why it must be crafted with care and consideration. I fundamentally believe that our thoughts — our personal truths — if not handled with care, have the potential to cause harm not only to ourselves, but also to the world around us.

As a writer, you should not judge. You should understand.— Ernest Hemingway

As I’ve developed my design and writing skills, I’ve disciplined myself not to rush through my ideas. Rather, I record them, revisit them, take intentional pauses to spark creativity, and reevaluate them with an unclouded mind to discern what clicks and what doesn’t. In essence, writing, design, and even life itself require surrender to present imperfections, a conscious effort to withhold judgment, and a commitment to pursue understanding instead. It is about accepting and wholeheartedly embracing the ebb and flow inherent in the creative process.

Or in the more straight-forward words of Ernest Hemingway, “As a writer, you should not judge. You should understand.” To extend Hemingway’s wisdom, regardless of the roles or titles with which we identify, our key to nurturing meaningful connections with life, lies in cultivating systems of consciousness that nudge us out of judgment and into empathy and understanding. To me, this is the essence of creation, and what helps me navigate the vastness of the unknown.

By refraining from judging and instead seeking to understand, we create a space for our ideas to flourish. When we approach life with curiosity and compassion, we unlock the potential for more profound insights, more meaningful connections, and ultimately healing.

Animated GIF showing Joey from the TV show ‘Friends’ humorously claiming ‘I am pretty wisdomous.
Classic Joe, confidently stating, ‘I am pretty wisdomous.’ Courtesy: Giphy.

Here are some of my favorite books that have been a constant source of inspiration:

Other resources:

I’d long felt the urge to share my thoughts with the world, but I’d held back, shackled by the illusion that I wasn’t ready, or even worthy — whatever that meant. Wondering why anyone would invest their precious time in the musings of some insignificant random dude — surely an imposter — I challenged my ways of thinking with the vague goal of getting shit done and finally being happy.

I’ve decided that my dry spell is ending now.

So, what are some of the questions I grappled with?

  • How could I find balance in life? And what does balance even mean?
  • How could I recognize my successes and see past my failures?
  • How could I start trusting my decisions?
  • How could I accept and embrace feedback?
  • How could I get shit “done”?
  • How could I increase my focus and feel more productive?
  • What is productivity even?
  • How could I pursue my passions? And most importantly, what was I even passionate about?
  • And many more…

Thank you for reading, I deeply appreciate your investment and I hope there was something in my words for you. I can only try to convey my truth. However, my truth is not the truth. It is a truth — and it is open to discussion.

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Ethics-driven Systems Thinker | Productivity & Well-being G(r)eek | Philosopher | Human