The recovering know-it-all.

How trading "rightness" for empathy has improved my life and my career.

I wouldn’t claim to be “cured” of my know it all-ism, even now, I often catch myself thinking I know more about a subject than I actually do. But the difference today is the awareness. I feel I’ve reached a point where I can see my own “bullshitting” in real-time. I’ve learned to zoom out and realize that while I know what I know, in the universal scheme of things, I actually know very little.

The journey from being a “know-it-all” to a “Knows-some-stuff-that-might-not-work-for-you” person hasn’t been a straight line. It’s been a series of ego-crushing revelations that reshaped not just how I design, but how I exist.

The portfolio and the professor.

When I started university, I arrived with an already inflated ego. I had spent two years at a specialized design high school; I already had a portfolio. I was way ahead of the game compared to other students starting from ground zero.

Then I met my professor. He looked at my work and told me, quite simply, that it was “not as great as you think is.” He called out my heavy use of filters, my lack of alignments with my copy, my overall repetitivness and lack of personal perceptive in my work.

It hurt. I thought I was good; he showed me I wasn’t seeing the full picture yet. Paradoxically, I gravitated toward him. He revealed the “invisible” world of design to me: the nuance of typography, the intentionality of alignment, and the profound power of white space, concepts I hadn’t considered, or even heard of in high school.

I grew. I did better projects. I regained confidence. But this time, that confidence started to morph into something more dangerous: a renewed sense of “knowingness” that felt greater than those around me.

The arrogance of success.

In my late 20s, I landed at a large ad agency working with brands like Whirlpool and Maytag. I was surrounded by directors who helped me become exactly who I wanted to be. My work was being praised. I was “successful.”

And that’s when the know-it-all in me really peaked.

I looked at clients as “idiots” who knew nothing about design. I would walk into meetings ready to go to war over the smallest details. I felt that if they would just listen to me—the “knower”—they would finally have great design, and my true genius would also shine through. People would see me the way I saw myself, the guy with all the best ideas. I was the giver of insight; they were merely the receivers.

I see this in a lot of young designers all the time now, shit, I see it in a lot of people everywhere all the time now. Especially now that information and knowledge is so freely available. Everyone is the knower. But the know-it-all stage is just that, a stage. And for me, the exit from that stage began with a book I didn’t even want to read.

The empathy catalyst.

A boss I respected gave me The Seven Habits of Highly Effective People. At the time, I thought it was the most boring book imaginable. I never would have chosen to read the book of my own will. I read it, but disregarded almost the entire book…… except for one chapter: Empathy.

It was the first time I seriously contemplated the “other.” I started to realize that my clients had bosses, too. They had pressures, KPIs, and corporate stresses that had nothing to do with “cool design.” My “rightness” started to seem somewhat irrelevant if I didn’t understand their reality because I was mostly trapped in my own.

The door to my ego cracked open, just a tiny bit. I started going into meetings not just to defend my work, but to consider the human across the table. I wont claim any massive transformation overnight, but it did start to happen.

The world is bigger than my perspective.

The real shift happened in 2009. I quit the agency, sold everything, and spent a year backpacking through India, Southeast Asia, and China.

When you see how vast and diverse the world is, your own perspective stops feeling like the “standard.” You realize that your “right” ways of doing things is just one way among billions. Later, moving to Taipei and diving deep into yoga philosophy cemented this.

I started to see that knowledge is subjective. What I know is based on my own experience, my books, and my exposure. It is relevant to me, but it is never guaranteed to be true or relevant for anyone else. That doesn’t mean Im lesser than, it just means I’m not more than. We are all the knower, and the not knower. We are all actually on the same level, just with peaks and valleys in different places. So to speak.

The Asterisk

Today, I still have strong opinions. I’ve spent my life gathering experience in branding and design, and I believe that experience can benefit people. But I’ve replaced the “guarantee” with an “asterisk.”

Now, when I give advice, I try to frame it like this:

“Here is my experience. Here is what I believe in. I think it will work for you, but I could be wrong. Take what serves you, and leave the rest.”

This shift doesn’t change my expertise; it changes my impact. When you remove the “know-it-all-ness,” you remove the red flags. You realize that there is no hierarchy of knowing. A scientist knows things I don’t; I know things they don’t. We aren’t on different levels; we’re just in different valleys.

I’m still recovering. I still catch myself trying to be the “holder of total rightness” occasionally. But I’m much happier living in the “maybe.” The world is a better place when we share our light without insisting it’s the only sun in the sky.