Two Types of Discomfort

Kevin Yien
3 min readNov 11, 2016

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Knowing the difference between self-doubt and self-awareness

Something interesting happens when we are faced with exciting and intimidating challenges. Something instinctual. Most reference the fight-or-flight response, but I’m going to discuss a different distinction with two stories. Or you can skip to the end if you don’t feel like reading two stories :)

A story of self-doubt

As the first hire at LaunchPad Central I naturally wore a lot of hats. I didn’t really have a title, but I knew what I needed to do—anything that helped the business.

After a month on the job, we were going live with our first big customer and I was terrified. Aside from the usual concerns of launching a new product, I had a more personal concern. I was going to lead a training session on our software in front of dozens of distinguished professors and PhD’s from around the country—all experts in their fields. And here I was, a 22 year-old nobody from Illinois who stumbled into a great opportunity.

Not the actual auditorium

What qualified me to teach these people?

I was so afraid of looking like a fool that I almost let it cripple me from giving the presentation. Yet as quickly as it came, it was over, and something phenomenal happened. People came up to me afterwards. They congratulated me on a good presentation. They viewed me as the expert (on the product). They had questions. They asked me for advice. I didn’t fail.

Looking back on this experience, I felt a deep sense of self-doubt. That feeling of inadequacy we all get when faced with something we believe to be more challenging than our abilities.

A story of self-awareness

In planning my next move, I considered a few product leadership positions (e.g. VP Product). While exciting for obvious reasons, something interesting happened as I continued meeting with other companies. The hiring process exposed me to a wider spectrum of people, both in function and experience. And through those interactions, I was able uncover more things I wanted to learn. More things I needed to learn.

If you look at the entire “design stack”, I consider myself strongest at the bottom—where customer development lives—but progressively weaker as you move up.

A poor representation of the “design stack” for visual reference (apologies to all my design friends).

Now, I know that Product Managers do not need to be polished designers, but as someone who believes design will be an even greater lever in the coming age of data, this is an area I want to become much stronger in.

It was this realization—the extent to which design could affect my impact and how much I had yet to learn—that led me to halting all pursuits of product leadership roles, and focusing on individual contributor roles where I could surround myself with the most talented design and engineering minds.

Let’s quickly recap.

  • In the first scenario, I almost let irrational fear hold me back from trying.
  • In the second scenario, I made a calculated decision based on reflection.

The differences are subtle in the heat of the moment, but very real. If embarrassment is what you are avoiding, plow through the storm. If knowledge is what you will miss out on, take a moment to reflect.

Next time you face a challenge, think about what is driving your emotions and optimize for uncomfortable knowledge gains.

Could really use some feedback, so please comment on anything helpful or that you’d like to hear more about.

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Kevin Yien
Kevin Yien

Written by Kevin Yien

Product @Square. I write to think.

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