🤯Unknown Unknowns #50 - Celebration!

May 5, 2022

Welcome to the 50th Issue! Honestly, I don't think I thought we would get this far a year ago. But it's been fun for me and I hope you look forward to receiving this little note every week.

Last week was my 42nd birthday. My wife cooked an incredible meal, including my favorite dessert. It’s called Galaktoboureko, and I’ve never met anyone else who’s heard of it (who isn’t Greek). I only know about it because my childhood friend’s mom used to make it when I was a kid. I usually skip dessert because the sugar causes breathing difficulties, but Galaktoboureko is the one dessert I can’t say no to. Reply for the recipe!

Reflections:

As I’ve gotten older, I’ve questioned the reasoning behind our base assumptions. It’s the main reason why I started this newsletter. A couple of weeks ago, I talked about dealing with uncertainty. I still want to find the cause of the deep-seated fear of uncertainty for me. But in the short term, navigating and dealing with uncertainty is the key to creating action.

The way I’ve approached this in the past is by downplaying the downside in my head. Tamp down the fear and then just do it. It’s kind of like sticking your fingers in your ears and charging out.

In recent years, I’ve seen more organized approaches to lowering the downsides. One way is Daniel Vassallo’s small bet approach, starting many projects with low downside risk. Because these projects have low downside, the theory goes that they’re easier to start. Because there’s many of them, it doesn’t matter if any of them fail.

Another similar philosophy is the Silicon Valley “embrace failure” mindset. That is, don’t be afraid to start something because at least you’ll learn something even if it fails. While both of these strategies make logical sense, I wonder if they aren’t a more advanced way of convincing myself to stick my hands in my ears and start running. And is there anything wrong with that, if it does make me take action?

This essay by Nat Eliason takes an opposite approach. Instead of limiting the downside, he suggests embracing the upside. And I don’t mean the upside of completing the project, but the actual feeling that you get by attempting something hard. If there’s no fear of failure, is this project worth doing?

I’m not sure that is the case. But assuming it is, I wonder if this is also just tricking yourself.

But even if it is, does it matter? As long as we take action, and learn from it, does it matter what spurred us?

Ironically, I realize this whole discussion is another example of my desire of certainty. I want to know why and if it works before I try it.

And here’s an example of why I think understanding our attitudes towards certainty and uncertainty are so important. Our lives literally depend on it.

Tom Morgan @tom_morganKCP

The ludicrous absence of support for people pivoting careers in midlife is leading to a tragic destruction of human potential. Who is working on this?

Questions, suggestions, complaints? Email me me at chris@iswong.com. Feedback welcome.

If you enjoyed this newsletter, please share it with a friend or two. And feel free to send anything you find interesting to me!

Leaving you in peace,

Chris