Why Informed Pessimists Find Discomfort Necessary

(untitled by Mr. A)

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I am an informed pessimist. I am unsure but unafraid.

This is how I operate in my daily life. I don’t pressure myself with doom or having a single way of thinking. Here’s a brief outline of what I mean.

The Upside-Down Perspective

Think Mr. A doesn’t hunt for solutions. I hunt for the questions everyone else is either ignoring or just missed altogether.

When I read something (an article, a report, a thread everyone’s sharing) I note three things:

Strengths (in one word descriptions)

Weaknesses (same)

Gaps (one sentence question)

That last one matters most. What wasn’t said? What couldn’t be said? Why did the author stop there? The gaps tell you what the groupthinkers are hiding.

The Loneliness of Seeing

When you see beyond what others see, you are automatically alone.

That means if you disagree with your circle of friends and family, you will feel discomfort. It is a necessary discomfort. Don’t fear being ten feet ahead of others or being labeled.

Try to approach memes as a starting point of questioning, not the comfortable so-called truth. The shortcuts everyone else takes start looking like trapdoors. You become fluent in a language most people never learn: the language of what’s missing.

Thinking Differently vs. Loving Trends

A public intellectual, a tech investor, gets asked: “What’s the next big thing you’re investing in?”

His answer: “I don’t chase things.

I look at small companies that are thinking differently.”

Big and world-changing overnight and thinking faster is not magic. Thinking differently is the really real.

While everyone runs toward the same glowing thing on the horizon, the real work happens in the margins. With the companies, ideas, and people who oriented themselves in a direction no one thought to look.

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The same investor said if you see 100 people leaving the room through one small door, either wait till no one is there or use the other door around the corner.

The Informed Pessimist’s Advantage

Being an informed pessimist doesn’t mean everything is bad. It means I’ve done the reading and research. Don’t shy away from those two tenets. Jump into the confusion and get a rush from the disorientation. You will emerge with something useful. Find the cracks and investigate. I understand that uncertainty isn’t a problem to solve, it’s the condition to operate in. Take your time.

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Unsure? Most of the time.

Unafraid? Aiming for most of the time.

When your need for clean answers is ignored, you understand the necessary discomfort of complexity. There is comfort in the gaps even if you are alone. You learn to flip things upside down and see what shakes out.

Think Mr. A 🫆