The Art of Uncomfortableness

Harry Song
2 min readAug 20, 2021

Inspired by the rule of awkward silence.

I’ve always been a person on the less awkward-tolerant end of the spectrum. I tend to fill every silence with endless talking if possible. Recently, I have became a “manager” of my intern. Naturally, that comes with the awkward getting-to-know-each-other phase and the even more awkward expectation conversations. Those simply cannot be more uncomfortable. To me, the real cringy moment is not between a question being asked and an answer being given but the silent seconds AFTER an answer has been given.

Conveniently, both my manager and I have been avoiding such conversations during our 1:1s most of the time. Today, I just got off my perf (performance) review conversations with her. The result was — not very hard to guess — disappointing.

To compare, my intern has carried similar convos more times in her 3-month tenure than me during my 2 years reporting to my manager. It got me thinking: Have I been cutting my manager slacks so much that she can just easily brush me off with vague statements that have nothing to do with my actual performances? And yet, I still thanked her for giving me these canned feedbacks. Who is the person to blame here?

It is my opinion that: A person is not a robot. Psychologically, if I were to impose massive uncomfortableness to my manager, in a respectful and an acceptable way of course, would that translate into pressure on her? Would our perf convo come out differently?

Now that I think of this, I could have not-so-subtly express my expectations, refrained myself from hiding my disappointments and insisted on keeping the meetings when she wanted to skip. Through awkward silences and emotions, I might be able to earn the care and respect I deserve … passive-aggressively.

So here I am wondering, is there an Art of Uncomfortableness?

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