Anticynical #1: Being Anticynical

Being Anticynical, How Long Do You Want to Live?

Hello friend 👋,

Welcome to the first edition of my Anticynical newsletter!

To start, I’ve decided to keep it simple and minimalist. Every Thursday, one idea and one question. Both in some way “anticynical.”

But what do I even mean by anticynical? That’s the idea for today’s newsletter!

Idea: Being Anticynical

In a nutshell: the working definition of being anticynical is having a rationally optimistic mindset, with this mindset having an antifragile quality.

When I was considering online writing, I realized that it is antifragile¹: there’s little downside (worst case, no one reads anything I write) and almost infinite upside.

But my monkey brain with its self-doubt and cynicism just would not let me commit. What if my friends think my writing is dumb? Is my writing even good? By writing online, am I not just adding more noise to the Internet?

My monkey brain acts this way not just for online writing, but for just about everything. From my career², fitness routines³ to social situations at work⁴ or otherwise⁵.

A few months ago, feeling exhausted from the ever-present self-doubt, I decided that things had to change.

Instead of harboring a fearful and cynical attitude, I asked myself what kind of ideal mindset could I strive for? My response: to be anticynical.

I think of an anticynical mindset as one with antifragile rational optimism. Let’s break that down.

Naval Ravikant breaks rational optimism down eloquently:

To create things, you have to be a rational optimist. Rational in the sense that you have to see the world for what it really is. And yet you have to be optimistic about your own capabilities, and your capability to get things done.

When I’m at my best, not only am I naturally rational and optimistic, but my optimism is also antifragile. Meaning, if there are obstacles/adversities in the way, by problem-solving for them, I become even more optimistic.

But I’m rarely “at my best”, almost by definition.

I would like the anticynical mindset to permeate everything and be ever-present. I'm sure that a lot of people would also like to transcend their self-doubt in a similar way. How do you make this mindset the new default?

That’s exactly what I’m trying to explore in writing the Anticynical newsletter. I’m exploring ideas, tools, and skills for designing a fulfilling life.

Here’s the first tool.

I’ve recently made it a habit to ask myself two key questions in all kinds of scenarios:

1. What would a deeply entrenched cynic do in this situation?

2. Can I do things differently?

Often, that is enough to break out of my default mode of doubt and cynicism.

For example, last week, a friend recently told me that he was going to start a podcast. My first knee-jerk thought was a cynical one: “it’s probably going to fail, you’re not going to stick with it.”

But instead of voicing that thought or saying nothing, I flipped the anticynical switch. “Where do you record?” “What does your producer do?” “You have a theme song!?”

I learned fascinating things about him and about the logistics of setting up a podcast.

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Question: If you could choose how long you lived, what would you choose and why?

Some might choose the current natural human lifespan (80-ish years), while some transhumanists⁶ might choose immortality.

Do you think that the “limitedness” of the current lifespan is a large part of what gives life its “meaning”? Or do you believe that “limitedness” and “meaning” are unrelated and orthogonal?

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I’d love to hear from you…

Do you resonate with the anticynical mindset? Is it a cool idea, or does it seem like hacky, cobbled-up phrase?

What do you think about transhumanism?

Or anything else at all. Just hit reply.

1. An idea from Nassim Taleb’s Antifragile. If you haven’t read the book: an antifragile opportunity has asymmetric returns; high upside, low downside, with adversity and uncertainty (up to a limit) favoring the upside.

2. “ML and Software is so crowded—can I really differentiate myself?”

3. “I don’t think my current routine is working, maybe I should try this other thing.”

4. “Talking about the weather or other mundane things is so boring, and getting to deeper conversation is so much work, so let’s just not bother at all.”

5. “Why bother trying to make friends with these new people when we’re probably going to be out of touch anyway?”

6. Transhumanism, as the name implies, is a philosophy that advocates moving beyond merely human capabilities. So think cyborgs, human-AI mergers, etc.