Exploring the Interwoven Nature of Dreams and Reality

Cate Hall is the CEO of ⁠Astera⁠, one of my favorite organizations and the new home of my friend ⁠Eli Dourado⁠, and one hell of a writer.

If you've noticed the word "agency" popping up all over the place, you have Cate to thank. Her 2024 essay, How to be More Agentic took the internet by storm and brought agency into the zeitgeist, where it has remained and grown. Now, she's even writing the Book on Agency, which you can pre-order here.

On the first episode of Hyperlegible with Tina He, when I asked who people should read more of, Tina recommended Cate. So I was excited to see Cate drop a new essay that felt like it was written at me (and I think will feel like it was written at you, too) called Crossing the Cringe Minefield:

Crossing the Cringe Minefield

When we want to improve ourselves or our station in life, she argues, we start with the things that come naturally, the easy wins. They don't work. Then, we try things we don't love but don't hate. Those don't work, either.

Finally, we're faced with a choice: give up, or do the thing that feels deeply, incredibly uncomfortable, the thing that makes us cringe. That's where the answer normally is, because the cringe is a sign that we've left that area of ourselves under-developed."

This means," Cate writes, "that existential cringe is actually a signal pointing you to where you can make the most progress quickly."

We all have something we want to get better at. And we all have something that makes us cringe to even think about.

In this conversation, I ask Cate to guide us (OK, me) through the Cringe Minefield. We sprinkle in a little agency, too, of course.

There hasn't been a Hyperlegible with more laughs or more depth. I hope you learn as much about yourself as I did, and come away as ready (as you'll ever be) to face your cringe.

At the end of our conversation, Cate makes a couple of recommendations:

Her favorite of her own essays:

How to be More Agentic

And the upcoming book on Agency

One essay everyone should read:

Dream Mashups by Malcolm Ocean

One sentence takeaway: "The places where you feel that existential cringe are actually the places you can make the most progress as a person really quickly."

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Big thanks to Jim Portela for editing!

Timestamps

• [3:37] Cate summarizes "Crossing the Cringe Minefield"

• [5:48] Why this essay resonates universally (and why your 30s aren’t too late)

• [7:20] My personal cringe around asking for help

• [8:15] Why cringe exists - the "hot stove" analogy for psychological patterns

• [10:53] How cringe distorts your sense of proportion in normal situations

• [12:19] What percentage of people actually overcome their cringe (less than 1%)

• [13:40] Whether naming your fear publicly makes it easier to face

• [15:54] How to identify your cringe using the Enneagram system

• [22:06] Why personal vulnerability in writing creates audience connection

• [23:23] How Astera's mission connects to Cate's writing on agency

• [25:57] Whether Cate kicked off the "agency trend" before it was cool

• [27:38] Coaching session: applying agency principles to Enneagram 7s

• [32:49] The "gift of desperation" - how addiction led Cate to higher agency

• [34:29] What it feels like to be high agency - seeing constraints as arbitrary

• [35:39] The challenge of figuring out what you want once you can do anything

• [37:05] Facing cringe is more agony than thrill initially

• [40:31] Final Takeaway: "The places where you feel existential cringe are where you can make the most progress as a person really quickly"