Forty Two

There was a period in my 20s, where it was as if “Human-Centered Design” was my family name.

In other words, “Human-Centered Design” was a significant part of my identity. So much so that I felt an implicit sense of responsibility on my shoulders. To the degree that I took “Human-Centered Design” as if it were as serious as the continuation of my own family’s reputation & lineage.

Although… It wasn’t like “Human-Centered Design” behaved like Darth Vader who went “I am your father~” (You know?) So one could wonder why I had felt the way I had felt.

Well, after realizing empathy with my past self, I realized that one of the most important needs I had was to feel a sense of belonging. Without a sense of belonging, I had found it difficult to withstand the pain of loneliness and confusion.

To be clear, I wasn’t aware of this back then. At the time, my conscious thought kept claiming that I was merely trying to “(positively) change the world.” Given the popularity of the phrase “change the world” in the late 90s and early 2000s, this is as cliché as it can get. But I was sincere.

At the same time, what I also see now is that I valued the experience of contribution. I felt alive when I could see that I was contributing to someone’s life. I also see that I had a need to shed the seemingly less-than-worthy identity of a “student.” I had a need to belong to a seemingly more significant and meaningful tribe. A tribe which could bestow upon me a more worthy identity. A tribe to which a number of older pioneers also belonged. Pioneers who made me feel the love and validation that I needed, but couldn’t feel in relation to my own father. All of these lay underneath my subconscious.

This isn’t to say that I think I was wrong to have felt the way I did or to have pursued “Human-Centered Design.”


In fact, I cherish and take pride in my 20s.

I did the thing that brought life into my existence. That was amazing! I also did what I believed would fulfill my unconscious needs. Did it work? Unfortunately not. But I did do my best. And that’s enough for me to cherish and take pride in my 20s.

At the same time, I do find it important to admit that I had not yet attained the requisite maturity back then to confront the eventuality of our humanity. The vulnerable existence we are, once we get to know ourselves, despite how strong and stoic we may try to come across at first. Especially since today is my 42nd birthday.

Because what we do not admit stays in our subconscious. What we do admit rises up into our conscious. And it is only at that point we can design our relationship to and interaction with them.

The need to belong and to feel like we matter is a critical component of the human condition. It is as normal as gravity. There is no shame in such admission. In fact, the earlier we admit and attempt to understand it, the more we become capable of design. The design of our thoughts and behaviors. In contrast to becoming a slave to our suppressed emotions and unfulfilled needs.

In my research, I had learned that art, despite looking like a journey of creating things, is ultimately a journey of creating relationships. Relationships from which value, meaning, language, and identity emerge. Entrepreneurship is very much the same.

On the surface, entrepreneurship may seem like a journey of mere product and service innovation. But ultimately, entrepreneurship is a journey of innovating our relationships. Relationships to our customers, investors, board members, employees, co-founders, or even our so-called “self” and our family. These are all part of the same trail we are blazing.

I know many of you on this list are on your own journey of relational innovation. For some of you, I am also an explicit participant in your journey. So I want to take this time to tell you how proud I am of you all. Not for having achieved certain things or to have done great deeds. But for your willingness to admit what most would not dare admit. For your willingness to attempt to understand what most would not bother to understand.

Our humanity, that is.

Thank you.

I love you.

I’m proud of you.

August 19th 2019

Photo credit: Belinda Novika

Forty One

On Sunday, I turned 41.

I’ve been told that in “Korean age” I’m 42.

There’s something interesting about reflecting on what happened in the past after I have had a 10+year distance from it.

In my 20s, I listened to a lot of computer scientists’ inspiring lectures. They were world-famous, which gave their words that much more weight. In hindsight, it would have been one thing to learn of their views and to appreciate them for what they were (i.e. views) while quite another to be persuaded by them. For better or for worse, I leaned toward the latter.

In hindsight, there were a few critical reasons why their views had such a big impact on me.

  1. The vision they portrayed were of a revolutionary caliber with a moral framing of “saving the world.”I have a need to rebel against authority and the status quo. Their vision fulfilled that need. I could not refuse being part of the rebellion—especially if it was framed as a way to save the world.
  2. Their views also made me feel understood and accepted.Having lived my whole life as a third culture kid, I’d been looking for this feeling from mother/father figures for a long time. When I didn’t get it from my parents, I was ecstatic to get it elsewhere, even if it were from total strangers.
  3. Finally, I was under the impression that someone had the answer to life.I considered life to be a problem to be solved, and thought that if I can only find that person who has the solution to life, I’d have figured it all out. It just so happened that these computer scientists sounded so confident that I couldn’t help but assume they knew the solution to this problem called life.

All throughout my 20s, my tendency to hyper-empathize with these influential figures grew larger. As a result, I now understand my 20s as a phase of living their lives not mine. It wouldn’t be until I turn 30 that I realize how easy it is to confuse living someone else’s life with living our own.

Then at the age of 29, I received a challenge. A bewildering challenge at that. One that made no sense. An artist I met at a computer science conference challenged me to go to art school. It seemed like a crazy and irrational idea. Especially because I thought so little of art at the time. I was a man of science, engineering, and design science. Art, I thought, was fluffy, useless, bullshit. In fact, you may have noticed that I put the word “science” next to the word “design” a la Buckminster Fuller, as if to imply that the word design alone was somehow not good enough. “Why would a man of science, engineering, and design science stoop so low as to study art?” was the kind of thought I had back then. (Arrogant much?)

It took me over a year since receiving this challenge of conducting my own, *ahem* scientific, experiments and to gradually build the trust & respect necessary to empathize with artists. When I finally did, it also became clear that this was a challenge I could not refuse. I had to answer the challenge. Why? Because I realized that not answering the challenge meant continuing to live someone else’s life.

Living someone else’s life of rebellion didn’t give me a sense of comfort, but it did give me a sense of safety and that ever-so-desirable feeling that what I’m doing was “important work” that “mattered.” Yet, for better or for worse, I was no longer interested in safety or mattering. I was now interested in being honest with myself in ways I had never been. I was willing to break myself wide open to find out what the hell was inside me instead of continuing to chase after something outside of me because an influential figure had persuaded me into thinking that it was the right thing to do.

For better or for worse, that’s precisely what art and my 30s offered me. It forced me to face my deepest & darkest fears. It crushed every little belief and assumption I had developed over the years. It shook me to my core and took me places I’m both horrified and grateful to have been.

To be clear, I do not recommend this to anyone. I’ll spare you the details for now as I’m not quite ready to write about them just yet. Maybe give me another 10 years.

Above all, I say all this to set myself up to say “thank you” to all those who have stuck by my side throughout my 30s. That’s it really. Because it is through your grace that I’m still alive today both psychologically and physically. I will never forget that.

You know who you are.

May you stay beautiful, always.

with warmth and curiosity,

August 19th 2018

photo credit to Sue Langford

The Irony of Care

I thought I was empathizing.

I wasn’t.

It was nearly 20 years ago.

I had a dear friend who was suffering from bipolar depression.

At the time, I had recently graduated from college with a degree in computer science. I prided myself in being an excellent problem solver. So I was determined… to solve my friend’s problem.

So What did I do? Well, I started by reading books, articles, papers, you name it, I read them all.

After gaining enough understanding of the theory of depression, I went to a local support group looking for some practical advice.

What I learned there was that the best way to help my friend was to try and empathize with her.

What this meant was that the next time my friend got depressed, I was to sit down with her and listen to her carefully. Once I could understand how she’s feeling and why, I was to express this understanding back to her. According to the people at the support group, if my understanding was correct, my friend will feel understood and that’ll make her feel better.

I was surprised.

It sounded too easy to be true.

But then I tried.

The whole time I was trying to empathize with her, she kept yelling, screaming, and bawling. Telling me that I did not understand.

What was I supposed to do? I kept changing what I said, over and over and over again, hoping… that I would eventually get through to her.

But I couldn’t.

Nearly half an hour went by and I was just sitting there with all my energy drained, exhausted and unable to figure out what I was missing.

But then… something occurred to me.

I suddenly remembered that, earlier in the day, I had said something to her, which, in hindsight, was hurtful.

So I told her that.

And like magic, she stopped yelling and screaming, as she sat there sobbing… while I finally… empathized with her.

What I realize now is that everything I’d been telling her up to that point was framed in such a way that it was all. her. fault, and I had nothing to do with it.

This was not because I had malicious intent. In fact, I had great intentions. I cared for her well-being. I wanted to help. This is the very definition of compassion!

Yet, in hindsight, I learned that despite best intentions, compassion actually lead me to frame the situation as a problem to be solved. And in doing so, 3 things happened to my mindset. 3 things… that lead me to unintentionally do more harm than good.

Now, what do I mean by this?

Distancing to Divide

First of all, I played the role of a problem solver. In doing so, I subconsciously distanced myself from my friend, to the point where I felt sufficiently divided from her.

Why did I do this? Because I was there to help her. Not the other way around. I was concerned for her wellbeing. Not mine. After all, my friend was the one with the problem, not I.

How can a problem solver possibly be a part of the problem? How can the helper be the one being helped? They can’t. It makes perfect sense for us to be divided.

But of course, in the end, I realized that I was, in fact, a part of the problem. My distancing blinded me to this.

Elevating to Judge

Second of all, in treating my friend as someone with a problem, I subconsciously elevated myself above her, to the point where I considered myself to have the superior authority to judge. Judge not only her problem as bad, but also my understanding of the problem as right.

Why? Well… Because I spent months studying depression. I may not have been the world’s expert, but I was surely a better judge than she was!

But of course, in the end, I realized that I was not a good judge at all. She was feeling the way she was, not because of depression, but because of something hurtful I had said. That’s not something I knew enough to claim authority. In other words, I didn’t know enough to elevate myself above her and judge.

So she was not wrong to reject my understanding. In fact, if anybody was wrong, it was me. I was wrong.

Focusing to Hold on

Finally, I held onto my distance and judgment. Not only that, but I also held on to a solution I had come up with even before entering the conversation.

Guess what solution I had imagined for my friend?

She. just had. to. cheer. up!

What a beautifully simple solution, right?

I held on to this solution, because I also held on to the judgment that my understanding of her was right.

But of course, in the end, I not only realized that my solution was wrong, but that the actual solution was completely new and unexpected. Yet, it was also so very obvious, simple, and even logical in hindsight. So much so that I could not understand why I hadn’t thought of in the first place. So what I had to do was actually let go of my judgment and solution, not hold on to them.

Empathizing and Not Empathizing

In the popular media, there is significant misunderstanding around what it means to empathize. Most confuse it with feeling what other people are feeling (That’s called emotional contagion.). Many people, like I did, also confuse techniques like active listening as being analogous to empathizing. It isn’t.

Empathizing isn’t something we do, it’s something that happens. It is an event and an experience, when we enter a state of feeling as if we’re connected or at one with an “other.” Reflecting on my mindset at the time, I now clearly see that I was entering a state that made it harder for myself to empathize with my friend. I thought I was empathizing, but I clearly wasn’t.

This isn’t to say that there’s nothing we can do. There are plenty of things we can do. Listening actively is one of them. It’s just that merely listening actively is not always enough.

Looking back, something that greatly surprised me was that once I empathized with her she thanked me.

Why was this surprising?

Because it was not what I thought was worthy of her gratitude.

It took me a significant amount of reflection before I became aware of the fact that my compassion was tied to my own need to make a contribution to her life. Reflection also helped me become aware of a belief I had, which was that to contribute to her life I had to problem solve.

Since I was unaware of how my own needs and beliefs were tied to this, I was so surprised that she didn’t appreciate this. In fact, after several trials, I started to feel indignant of how ungrateful she was of my efforts to help her. Why? Because she was not appreciating what I thought she should appreciate.

In hindsight, I am now more surprised that what I called “caring” meant little more than trying to persuade her. I wanted to get her appreciate what I appreciated. I was trying to manipulate her! Seen this way, I realized that the way I was expressing my compassion and contribution got in the way… of actually contributing to her life.

Such… is what I call the “irony of care.”

Now, let me be clear.

I do not wish to criticize the problem solving mindset.

A problem solving mindset is most certainly appropriate when faced with a problem like so:

1 + 1 = ___


  1. You cannot influence the problem, which means you cannot be a part of the problem. Thus, it makes no difference that you divide yourself from the problem.
  2. There’s no ambiguity around what is right/wrong or good/bad. Thus, assuming to have the authority to judge does not imply superiority.
  3. There is only one solution. Feel free to hold on to it.

Problem solve away if these conditions are met. It is only when these conditions are not met that you need an alternative mindset.

Now that I’m in my 40s, it’s been almost 20 years since the time of the incident with my friend. Yet, I still find this event to be a gift that keeps on giving.

In my work, I frequently work with CEOs who have no choice but to frame employee growth and engagement as a problem to be solved. I also work with employees who have no choice but to frame executive leadership as a problem to be solved. They both inevitably find out that problem solving is ill-suited for the situation. How do they find out? Usually, when the employees don’t grow much or leave and the executives start to burn-out or become even more agitated.

I recently gave a keynote at Cleveland Clinics’s Patient-Experience Summit, where I learned that doctors had framed patient-care as a problem to be solved. The patients, of course, had framed these doctors’ approach to care as a problem to be solved. As a result, not only were patients not getting any better and leaving to other hospitals, but the doctors were burning out as well. They had both learned that problem solving is ill-suited for the situation.

To judge any of these as good/bad or right/wrong misses the point. This is merely what happens naturally when we individually do not have the freedom to choose an alternative mindset to problem solving in the relationship that is giving rise to the problem solving mindset. It is also a natural byproduct of an environment that doesn’t make it any easier for people to empathize with each other.

Learning to choose an alternative mindset or designing an environment that makes it easier for people to empathize with each other is a difficult challenge. Perhaps a way to get us started is to ask ourselves and each other the following question and to answer it in an honest way.

Why do we believe the problem solving mindset is appropriate to our situation?”

• • •

Photo credit to Nicdalic

The Resentment Threshold

There are no perfect leaders, only real ones.

That might as well have been the name of the latest Dove campaign. Except, it wasn’t. It was called “There are no perfect moms, only real ones.”

Here it is.

There are no perfect moms, only real ones / Dove

As I watched it, I was reminded of all the Founders/CEOs with whom I’ve worked and continue to work. I was inspired enough to make the following remix of the transcript for them.

Although I use the words “CEO” and “Founder” in the remix, the same script can apply to middle managers or anyone who feels personal responsibility for the well-being of other humans.

Leader 1: Everybody has ideas on what it means to be a “good leader.” And most people feel like they have a license to tell you (laughs) what they think it means to be a “good leader.”

Leader 2: I’m a first time CEO and I’m just figuring it out as I go. Often times people who lead other companies, people who call themselves leadership consultants, people who used to lead companies, they all want you to do it their way. But I have to be that person that stands the ground.

Leader 3: What we do here is unconventional. Because our team is made up of people from significantly different nationalities using their second language to communicate with each other. I would say they have such a different set of challenges. They’re facing something unique.

Leader 4: We’re both our team’s CEO. You get people that are like “What do you mean you’re both CEOs?” We’re like “Yup. (laughs) We’re gonna be co-CEOs.”

Leader 5: I live to be the best version of myself, and I can be. Part of that is being a CEO. But I live to dance. I can do my art and not be any less of a CEO.

Leader 6: I found my startup without a co-founder. I’m happy where I am. I get to make business decisions on my own.

Leader 7: There are so many ways to be a leader. I don’t think I can be the leader that I want to be without climbing being in my life. It keeps me who I am and allows me to be a really good leader to my team.

Leader 4: There’s no one right way to do it all.

Leader 1: You are the only expert of your own team and organization.

Leader 2: Believe in yourself. Believe in your ability as a human being. What you can do is what you can do.

Leader 3: Do what fits your organization. And trust yourself.

This commercial struck a chord with me because I’ve found that feeling personal responsibility for the well-being of others to be one of the most anxiety-inducing experiences ever. For many Founders/CEOs, the pressure to make payroll each month is stressful enough. It goes without saying how much stress is involved in parenthood.

A common byproduct of feeling a sense of personal responsibility for the well-being of others is feeling like we should do things for them. (An instinct often fueled by compassion.)

Now, don’t get me wrong. There is nothing intrinsically wrong or bad about doing things for others. In fact, one could argue that it is one of most noble things we could do. What I find interesting is that there are times when we cross the threshold of “doing things for others” and unknowingly enter into the realm of “expecting things from others.”

Let me take my parents as an example.

My father’s interest lies primarily in playing sports. My mother loves playing sports, too. At the same time, her primary interest lies in history and archeology, especially around the topic of musical performance. Given this difference in interests, my mother has spent her entire marriage looking for a solution to a seemingly simple challenge.

“How can I get my husband to be interested in the things I’m interested?”

She tried to get him to watch historical period dramas on TV. She tried to teach him how to sing. She tried to take him to different historical landmarks around the world. She tried to get him to read history books.

All. Failed.

Then recently, my mother came to the following realization:

I need to stop doing so much for my husband.”

When asked “What do you mean?” she said she has always wanted her husband to change because she personally felt responsible for his well-being. When probed further, she said she wanted him to change for his own good. In other words, she considered her efforts to change him as doing him a favor. So when she saw that he was unwilling to change, she associated his behavior with a lack of appreciation for the effort she was putting in to doing him a favor. This naturally lead her to feel resentment. Well… she no longer wanted to feel resentment. Thus, the need to stop doing so much for her husband.

My mother also came to accept that my father is happy staying interested in sports and sports only. As much as he may come to value acquiring other interests in the future, he did not find it sufficiently valuable now. For now, what he valued more greatly was to feel accepted and appreciated for the way he was. (Can you spot the Gordian Knot?)

I remember doing the same thing when I was an employee. As an employee, I did my best to provide value to my employer. Not only did I do this, but I did my best to do them well. Very well, in fact. Although, after a certain threshold of “well,” I started to feel resentment. Why? Because I was not appreciated or acknowledged for doing these things well.

What’s obvious in hindsight is that the things I did extra well were things I valued greatly, not things my employer valued greatly. Since my employer did not value those things enough, it was no wonder the employer was not spontaneously inspired to appreciate them. In fact, my employer was probably frustrated with me for not doing the things he valued instead.

I do not wish to judge people’s lack of appreciation for certain things as good/bad or right/wrong. What I want to highlight is that when we feel personally responsible for someone or even some thing, it’s easy to forget that there is a threshold at which we stop doing things for them and start expecting things from them. When those expectations are not met, it’s quite natural for us to feel resentment.

I’ve come to call this the “resentment threshold.”

Being a leader can often feel like a thankless job. When we lead well, people often take it for granted. When we make a mistake, people sometimes criticize us until they can see us fall to our knees. Yet we show up to work each and every day, because there’s something tugging at us. There’s someone or something we feel personally responsible for. At the same time, it’s worth noting that this same personal care can also blind us as we cross the resentment threshold.

If you’re willing, I’d like to invite you to practice noticing yourself crossing the resentment threshold. Not to judge the crossing as bad or wrong. Rather, to stay with it for a while and to be curious enough to notice it repeatedly. If it helps, you may also ask yourself the following question.

What lessons are my crossing the resentment threshold challenging me to learn?”

 • • •

Photo credit to Mark Bonica

Going Beyond Leader-Shaming

It took me about twenty five years before I started to perceive my mother as a human being.

I’m going to go out on a limb and claim that I’m not alone.

We don’t always perceive people as human beings.

“Then how do we perceive them?” you may ask.

As a means to our end.

As a teenager, I often perceived my mother as a means to permission, money, and food. She was the means to me going out with my friends, buying things I wanted, or eating breakfast, dinner, and sometimes even lunch.

Horrible, I know…

Of course, I intellectually understood that I should feel gratitude towards her for giving birth to me and for raising me. Unfortunately, those were rarely visceral experiences. So most of the times, I perceived her as mere means to my end.

The same holds true in our perception of our leaders.

I was once an employee myself. In some ways, I still am to my clients. I have also spent a significant amount of time listening to employees inside organizations as their meta-designer. In this journey, I’ve noticed at least threeinter-related lenses through which we perceive our leaders as mere means to our ends.

1. As a means to our survival: “I joined this company, because I need financial security. I keep my leader happy to meet this need.”

  • When we perceive our leaders as a means to our survival, they are an object of authority. Through that lens, we tend to latch on to every literal word they say, because it can potentially threaten our survival. A common symptom of this is when we interpret a passing and even humorous comment or suggestion they make as either an order or as a representation of our company’s values and vision.

2. As a means to achieving our goal: “I joined this company to make cool things that make an impact in the world. The leader will help me achieve that goal.”

  • When we perceive our leaders as a means to achieving our goals, they are an object of either our aid or obstacle. Through that lens, we tend to feel entitled to judge them, because it’s clear to us whether they are aiding us well enough or downright getting in our ways. A common symptom of this is when we spend an exorbitant amount of time talking about how wonderful we are compared to how bad our leaders are. According to Dr. Goldsmith, on average, 65% of all interpersonal communications in companies involve talking about (or listening to someone talk about) how smart, special, or wonderful we are and how stupid, inept, or bad someone else is.

3. As a means to our identity: “We have such an amazing leader! The leader is my role model!” or “We have such a horrible leader! The leader is my anti-role model!”

  • When we perceive our leaders as a means to our identity, they are an object to be either copied or rebelled against. Through that lens, everything they say or do is something we aspire to replicate or differentiate ourselves from. A common symptom of this is when we side with our leaders to argue against the fresh perspective of a new team member or when we side with a new team member against our leader.

Instead of judging these lenses as good/bad or right/wrong, I want to highlight how they give rise to misunderstandings inside organizations.

1. So long as we perceive our leaders as an object of authority, we’re likely to interpret their suggestions as promoting compliance. If we end up feeling repulsed by these interpretations, we’re also likely to distance ourselves from our leaders.

  • Yet, when I mediate such conflicts, I tend to discover that the leader’s intention was to encourage autonomy and self-direction. Sometimes even to connect with their team members through said suggestions. I find this akin to my mother saying things to me casually or with the intention of connecting with me, while I would merely interpret them as coercive or offensive. I just thought an authority figure should know to do better.

2. So long as we perceive our leaders as an object of our aid or obstacle, we’re likely to interpret their decisions as short-sighted and selfish.

  • Yet, when I mediate such conflicts, I tend to discover that the leader’s intention was to make decisions for the company’s long-term sustainability and the well-being of the team. I find this akin to my mother making difficult decisions for the long-term benefit of our family and my well-being. Without having been part of the honest emotional struggles of the decision making process, I had no other choice, but to interpret her decisions as short-sighted and selfish.

3. So long as we perceive our leaders as an object to be copied or rebelled against, we’re likely to interpret their communication efforts as a form of indoctrination.

  • Yet, when I mediate such conflicts, I tend to discover that the leader’s intention was to encourage creativity and critical thinking. It’s also often the case that the communication efforts came from a place of worry. Worry of their team making a mistake or getting lost. I find this akin to my mother telling me what I should do in the future and what she thinks are the important things in life. She was saying these things because she was worried I may get hurt or lost, while I just thought she was trying to get me to think like her.

Once again, instead of judging right/wrong or good/bad, I want us to recognize that these misunderstandings are born out of the inherent difficulties of seeing through the eyes of others. It’s too simplistic to judge them as a result of poor leadership.

It’s true that some less experienced leaders try so hard to be equal that they have more trouble seeing themselves as their team members see them. At the same time, experienced leaders can also have the same blind spots. What’s important to note is that we can all develop the skills required to better prepare for and manage these blind spots by learning to realize our empathy.

Now that I’m in my 40s, I find that things have changed since I was 25. I am more likely to perceive my mother as beyond mere means to my end. I also interact with her in ways that are mutually empathic. Is it perfect? No. I’m happy that it is simply possible.

It all started with noticing myself shaming or blaming my mother, then gradually learning to choose a different set of contexts with which to interpret her words and behaviors.

Are we also willing to do the same with our leaders?

Some are. Some are not. For those willing, here’s a question you can ask yourself to get started.

“If I were unafraid of getting fired or judged, and wanted to use all the creativity and critical thinking I had to help the leader clarify and achieve the organization’s goals instead of my own, what would be the smallest next step I need to take?”

To be clear, you may say you’d rather leave the company. That is your choice. I just hope you’ll choose a better alternative than staying stuck shaming or blaming your leader. That isn’t helping anybody. As the saying goes…

“Holding on to resentment is like grasping a hot coal with the intent of throwing it at someone else.”

May you let go of the hot coal.


• • •


Photo credit to Shawn Harquail

The Perils of Hyper-Empathizing

All of the CEOs I coach are also practitioners of a craft.

Some of them are sales agents or consultants, others designers or engineers, still others researchers. This is true of myself, as well.

They are also founders of their companies.

Most of us founded our company because we wanted to keep doing what we wanted to do. Then came a time when we realized that we could no longer do it alone. We realized that we either needed people to whom we could offload what we were doing or people who could do what we ourselves could not.

What commonly happens in this process is that we get stuck in a pattern of first hyper-empathizing then not empathizing.

For example, what often happens when we hire people to do what we already know how to do? We assume they can do the job just as well as we do.

Now, of course, we intellectually recognize that they are different from us. We may also intellectually recognize that they have less experience than we do. But this does not always stop us from feeling as if they will know what we know or notice and do things the same way we do them.

This is an example of hyper-empathizing.

6 Basic Concepts of Empathy

When we hyper-empathize, despite an intellectual understanding of the difference between two people, we are either unwilling or unable to distinguish ourselves from others at a more visceral level.

When we hyper-empathize with others, only to be proven that they are not like us, we often experience emotional tension. After all, our subconscious expectation has been violated. This may then push us to the other extreme: not empathizing.

We may experience a variety of unpleasant feelings when we make this shift out of tension. At the very least unpleasant, we may feel confused why they are not like us. When more unpleasant, we may feel contempt, thinking to ourselves…

“How incompetent or stupid do they have to be to not know what I know, not notice what I notice, or not do things the way I do them?”

To be clear, I do not wish to judge this good/bad or right/wrong. I simply want to highlight the fact that hyper-empathizing is very common. It happens to all of us. Wives do this when the husband doesn’t put the dish in the dishwasher. Husbands do this when the wife hangs the toilet paper under (or behind) the roll instead of over (or in front of) the roll.

At the same time, this is a slippery slope to micro-management. Micro-management is a source of tremendous stress for both the CEO and their staff. Sustained for the long-term, CEOs will burn out and staff will become passive and disengaged.

Hyper-empathizing also plays a role when the person we hired has skills we ourselves do not, but we still have an opinion on their skills.

And boy, do we have opinions.

For example, we may not be a software engineer ourselves, but we’ve heard that pair programming is an effective way to build software. So we hire a bunch of programmers and demand that they do pair programming. Oh, and to make sure they don’t misunderstand our intentions, we show them proof why pair programming is great. After all, we’re good leaders. We don’t make irrational demands. So we share research findings, success stories from our past lives, or things we’ve heard from our trusted sources of information.

When we do this, we often assume that since we are convinced of the value of something, the others will also be convinced. Now, of course, we intellectually recognize that they are different from us. We may also intellectually recognize that they have more experience than we do in their field of expertise. But this does not always stop us from feeling as if they will think or feel like we do.

To our surprise, we may hear our newly hired engineers express their concern about pair programming. Here, we, once again, experience emotional tension and we are often moved to not empathize. This time, we may feel contempt, thinking to ourselves…

“How closed-minded and fearful do they have to be to not accept data, facts, or science?”

Once again, I do not wish to judge this good/bad or right/wrong. I simply want to highlight that this is very common.

At the same time, if you demand they follow without questioning your authority, the approach can merely give rise to resentment and begrudging commitment. When people are carrying out a change initiative not only without a genuine sense of commitment, but also filled with resentment, chances are good that it will have a negative impact on the potential for the change initiative to succeed.

Moving from hyper-empathizing to not empathizing and getting stuck there is one of the most basic patterns of struggle I see in leadership.

The alternative is simple, but not easy. You have to have greater mastery over realizing your empathy so you can start by empathizing without hyper-empathizing. This can be difficult. At the same time, if you’re willing and motivated, you can learn it through deliberate practice.

Afterwards, you can also engage others in an empathic conversation so that you develop a sense of unity not merely a hierarchy of command. When we carry out a change initiative from a place of unity, there is a far greater chance that the initiative will succeed — despite disagreements. This is not magic. It’s simply because when a united group of committed individuals come across an obstacle, they are more likely to figure out a way to make things work. On the other hand, when a divided group of uncommitted individuals encounter the first sign of an obstacle, they are more likely to either give up or stay stuck blaming the people who gave the order. As the famous saying goes “See? I told you it won’t work.”

Once again, I know this is easier said than done. At the same time, if you’re willing and motivated, you can learn to do this through deliberate practice.

Heres a question you can ask yourself to get started.

“How can I involve others in the decision making process in a way that sufficiently fulfills their need to be heard and understood even if the ultimate decision may not be to their liking?”

May you get unstuck from the pattern of first hyper-empathizing then not empathizing.

• • •

Photo credit to U.S. Army

The Cost of Withholding Gratitude

One of the most clear patterns I see when coaching CEOs is this.

They all had one or more people who have significantly and positively changed the trajectory of their lives.

When I hear them talk about these people, I see their eyes light up with admiration and exuberance. It’s clear to me how much of an impact these people have had on their lives.

What’s interesting is that alongside these expressions of admiration and exuberance, I sometimes hear their expressions of shame or regret as well.

For example, one CEO told me that his mentor went through a major bankruptcy and has since become impossible to locate. He regrets that he never had the chance to fully pay him back for the help he has received. Another CEO told me that he is making steady progress toward paying his mentor back. At the same time, he feels ashamed to admit that he’s yet to achieve enough success to do so.

These are painfully familiar feelings for me.

In college, I studied under a professor named Dr. Randy Pasuch. You may have heard of his famous talk titled “The Last Lecture.”

Dr. Pausch was a computer science professor and a virtual reality researcher. He once gave an inspiring and uplifting talk titled “The Last Lecture: Really Achieving Your Childhood Dreams.” The talk was remarkable not only for its positive message, but also for being delivered while he was suffering from pancreatic cancer with 3 to 6 months left to live. The talk went on to become a viral sensation on Youtube.

In college, Dr. Pausch significantly and positively changed the trajectory of my life by giving me a reason to study computer science. Some may find it strange to think that one needs a reason to study. But to be completely honest, without a clear reason, or a sense of purpose, retaining interest in computer science was a struggle. All that kept me going was a sense of pride and duty. The school I was attending was best known for its computer science program and I had promised my parents I would be studying computer science.

That was, until I took Dr. Pausch’s class.

What I learned from Dr. Pausch’s was that I didn’t have to be interested in computers to learn computer science. According to him, all I had to be interested in was connecting with other people through shared experiences. Experiences that may include such feelings as joy, sorrow, surprise, or even fear. For him, the computer was nothing more than a means to that end. It was a medium to facilitate the realization of our empathy.

And that resonated with me. Profoundly.

And just like that, I had finally found a reason to study computer science.

But then I lost touch with Dr. Pausch.

For 8 years.

As a matter of fact, a month before “The Last Lecture,” I sent him the following e-mail:

I don’t know if you remember me. My name is Slim from your BVW class from way back in 1999. I worked on the Van Gogh project. I’ve been working at MAYA design for the past eight years!

I now serve as the assistant director of engineering here, and we’re looking to hire some hardcore thinkers who are also genius makers.

I thought ETC would be full of such people! Are you the right person to talk to if I want to figure out how to lure that talent over? Are there protocols for doing such a thing? (i.e., hold an informal info session at ETC)

Any advice would be awesome.



To which he responded:

Slim, Good to hear from you, and *of course* I remember you — things like the Van Gogh world leave long memories!

I’m sure the ETC would love to have MAYA come and recruit — and there are definitely venues for that. Unfortunately, I’m no longer involved in the day-to-day of the ETC, so I’ve CC’d Drew Davidson, who can help you out with things.

Best wishes,


I don’t know if it’s obvious, but I had no idea he was ill. In fact, the subtext of my e-mail was me showing off to him that I had made significant advancements in my career since graduation.

Why was I showing off to Dr. Pausch? Because I wanted him to be proud of me.

I’ve come to learn that this is one of those silly things we do to those whom we love and admire.

Instead of just telling them that we love them or that they mean a great deal to us, we try to gain their recognition by bragging to them about something that is utterly meaningless in the grand scheme of things like status, fame, or fortune. And because we get so blinded by our desires to be recognized by the other person, we fail to tell them what it is that we really mean to tell them, which is that we are grateful.

A couple weeks after “The Last Lecture,” I found out that he was terminally ill.

Guess how I found out?

By watching “The Last Lecture” on Youtube.

On Youtube.

A talk held just a few miles from where I worked.

How could have I been so poor at keeping in touch with someone I considered my hero? I tried blaming it on my shyness. I tried blaming it on my busy life. I tried all sorts of excuses before giving up, and quickly writing him a long e-mail pouring my heart out.

But upon hitting the “send” button, I realized that his inbox was probably overflowing with e-mails in response to “The Last Lecture.” It was unlikely that he would ever read my e-mail. He may never know how he changed my life.

Staring into the computer screen, I couldn’t help but ask “Why?” Why couldn’t I have told him sooner? How stupid does one have to be, to wait so long to say something so simple?

If your life was significantly and positively changed by someone, the question need not start with “How can I pay them back?” The question can start with something much simpler. “How can I communicate my gratitude?” You do not have to wait until you achieve “success” to do this. Let them know what it is they did or said that you appreciated. Let them know how that made you feel. Let them know why this was significant to you. Do it for them. Do it for yourself.

Thank you Randy. I cannot say enough how much I appreciated your honesty. When I heard you say that your interest in computer lies not in the computer itself, but in its ability to facilitate empathy among people, I felt a profound sense of resonance. You made me realize that I’m not the only person who feels that way. You gave me the permission to be who I am. To realize that it is ok to feel the way I felt. Once I felt comfortable being who I am, it completely reframed my relationship to my subject matter of study. To this day, my interest in computer science is strong. All because it helps me facilitate empathy among people.

• • •


Photo credit: Gabriel Robins

A Blindspot of User-Centricity

There was a time in my life, when I had a hyper-focus on user-centricity.

I met with users in person. I spent hours listening to their concerns. I genuinely felt for them.

When I returned to the office to transcribe every word they had said, it all came rushing back to me. I remembered some of them tearing up with gratitude simply because I was willing to listen. Empathizing with these users… That was probably one of the most fulfilling part of my job.

But then… Upper management entered the scene, and messed things up. They would come up with all sorts of excuses to either cancel the product we were designing for these users or kill the feature that these users most needed!

“How dare they?!” I proclaimed with great indignation. “Can’t they see how much goodness this project could bring to the world? How evil and greedy do they have to be to do such horrible things?”

I was furious.

So furious that I was determined to solve this problem called ‘upper-management.’ It was clear to me that it was the thing getting in the way of bringing about a better world.


I never solved the problem.

I eventually ended up leaving the world of design, thinking to myself “There’s got to be a better model of innovation.”

This question lead me to research how artists innovate differently from designers.

One day, during the course of this research, I found myself in a woodshop. I had come into the shop with a beautiful vision of a chair I wanted to build.

My vision of the chair was not only aesthetically pleasing, but also highly ergonomic and comfortable for the potential user of the chair. I could not wait to finish it!

But then… The wood started to mess up my vision. It resisted, no, refused to bend in the exact way I wanted it to bend so I can make it feel comfortable for people to sit on it!

“What a piece of crap?!” I proclaimed with great indignation. “What good is a material if it can’t bring value to its users?”

I was furious.

So furious that I was determined to solve this problem called ‘wood.’ It was clear to me that it was the thing getting in the way of realizing my vision of a better chair.


I never solved the problem.

But this time, I did not leave wood behind in search of a “better” material. I thanked it for teaching me a valuable lesson.

What the wood had taught me was that I had a tendency to think of anything or anyone who got in the way of achieving my goal as a “problem.” This realization forced me to take a good look at all my relationships. Sure enough, I was treating my parents as problems. I was treating my friends as problems. I was even treating myself as a problem from time to time. The pattern was everywhere.

Users are important. Yes, they are.

At the same time, they are a part of a larger whole. There are many kinds of people involved in what we call the “design process.” Unless we think of all of them as human beings with equal dignity, it becomes exceedingly easy to treat any one of them as mere problems to be solved. This is a natural blindspot that develops when we hyper-focus on a single group of individuals.

Please don’t get me wrong… Doing this is easier said than done. It takes great energy, not to mention skills to do it. Skills that fall under the umbrella of realizing empathy.

In fact, even after having learned my lesson, I still notice myself treating people as problems to be solved.

So what I now do is pause to ask myself this question. “What is it that I’m having difficulty appreciating about the other person that makes it so easy for me to resort to treating them as mere problems to be solved?”

I have a feeling I’ll do this until the day I die.


• • •


Photo credit to Seattle Roamer


Embodying and Understanding

Some people seem to think that if we can merely understand someone we can empathize with them.

This is not true.

In Korean, we often say “이해는 되는데 납득은 안돼.” Literally translated, this means I can understand, but I cannot let the understanding in. Figurately translated, this means “I can understand, but I cannot empathize.”

To explore what this means, we need to talk about the difference between understanding and embodying.

Understanding something implies that we have a model, which we can use to articulate the underlying structures and relations of that thing.1

Embodying does not automatically connote understanding.

Take walking as an example. Most of us have never bothered to understand walking, but it’s something we have embodied nonetheless. Although, if you spent a few minutes right now, you could probably arrive at an understanding—regardless of how inaccurate, imprecise, or limited it may be.2  And once you do, you will be able to articulate your model in some way, be it using words, images, or physical demonstrations.

Understanding does not connote embodying, either.

Let’s say you spent a whole year reading a book that articulates a model of how snowboarding works. Even if you have become a master at articulating this model, when you actually get on a snowboard, chances are good that you’ll fall flat on your ass. That’s because you have yet to embody it.

Given this, one can say that even if you understand, if you are unable to augment it with an embodied experience you can have a difficult time empathizing or letting the understanding in [to your body].

Say you’re engaged in an empathic conversation with another person through words. Chances are good that you’ll start developing an understanding based solely on what you can directly perceive from them—their words, tone of voice, facial expressions, gestures, etc.

But an understanding of the other is not all you’ve got.

You also have embodied experiences from your own past. If you’re able to appropriately use these past experiences as references, you will be able to augment the understanding you are developing. In other words, by relating an experience you have embodied in the past with what the other is articulating, you can start to appreciate and resonate with the qualitative aspect of what the other is articulating. This can help you empathize, even if you do not understand.

The catch, however, is that you have to relate it to an experience that is qualitative similar enough instead of superficially similar enough. For example, if you try to empathize with someone’s experience of going to school you may fail to empathize simply by relating it to your own experience of going to school. That’s because while the experience may be superficially similar enough they are not necessarily qualitative similar enough. In other words, to empathize you may have to augment your understanding with an experience that has nothing to do with going to school, but nonetheless qualitative similar enough.


Wiggins, Grant P., and Jay McTighe. Understanding by design. Alexandria, VA: Association for Supervision and Curriculum Development, 2005.

It’s tempting to define understanding as being intrinsically accurate and complete, but this is overly ambitious given that understandings often prove to be inaccurate/imprecise/limited only in hindsight. For example, geocentricity was a model proven to be inaccurate and Newton’s theory of gravity was proven to be accurate and precise only within a certain range of scale, and therefore limited. By allowing room for error or incompleteness, we can more precisely refer to these understandings as inaccurate/ imprecise/ or incomplete in hindsight instead of having to retroactively refer to them as not understandings.

3 For a related discussion surrounding various kinds of understandings, check out Dr. John Bigg’s research on the SOLO taxonomy.

Subjective Model of Self and Other

When we empathize, we feel as if we are connected or at one. To capture this subjective quality of the event, the traditional model of a static self in relation to an other is inadequate. A more useful model will be one that accommodates a dynamic way of thinking about the relationship.

One way to model this is as follows.

Say we represented our conscious and sub-conscious processing of stimuli as the center of an arbitrary plane. We can then arrange the various sources of stimuli as dots surrounding this center, and place them near or far depending on how much we can empathize with them at any particular moment in time. In other words, the closer to the center the dot is, the more we perceive them as being connected with the self. The farther out from the center the dot is, the less we perceive them as being connected with the self.

In this model, if we’re experiencing flow playing a musical instrument, the instrument would be placed close to the center. Same would happen if we’re up on the mountain immersed in nature feeling at one with it.

On the other hand, if we cannot understand the thoughts we’re having, those thoughts will be placed far away from the center.

Thus, an implication of this model is that much of what we traditionally consider to be intrinsically connected with the “self,” can, at times, be an “other” with which we cannot empathize. Moreover, what we traditionally consider to be an “other”, can, at times, be connected with the “self.”

In other words, what constitutes the self and the other can change from moment to moment across time, as our relationship to the various sources of stimuli changes from moment to moment.

In light of this, I will now modify the definition of empathizing as follows:

Empathizing is a state of feeling as if we are connected or at one. Not empathizing is a state of feeling as if we are disconnected or at odds with an “other.” These feelings may last a brief moment or a prolonged duration of time and the “other” may be anything we can perceive as an object, be it a human being, an art object, or an idea.