Theme for 2026

Hi, 

Do you ever have a moment where you are having a conversation or you are reading a book or listening to a podcast, and you hear someone put a word to something that you understand but never knew what to call it? 

Some call it an Aha! Moment. 

Whatever you want to call it, I had one this week, and it came from Ryan Holiday in his newest book Wisdom Takes Work. He brings up this, what seems to be a well known idea, of having a second brain. 

Your second brain is a place where your self identified best ideas live… outside of your brain. This can take the form of Marginalia (the notes in the books you read), it can be your notebooks (or in my case legal pads), or it can be voice memos. Honestly, it could probably be a lot of things. 

The point of a second brain is to be your external hard drive for all of your best thoughts. 

This was such an important moment for me because well, I have been trying to think of a concrete reason for why I write this newsletter. I know I like to noodle on thoughts each week, I like the pressure to introduce myself to new ideas each week so that I can have something moderately interesting to write about, but I didn’t have a word that summed it all up.

Until now, of course. 

This newsletter has acted as my second brain for the last 62 weeks. It has offered in moments of reflection feelings of shock that I wrote something a year ago that is helping me today, and it has offered me opportunities to disagree with myself and see the growth in my perspective. 

All of this to be said, it has been a treat. And if you have read 1, 2, or 62 I want to say thank you for coming along this ride with me. 

This brings me to my quick topic for this week. 

2026 is the year of anti-fragility. 

Let’s dive in. 

In 2020, I read the book Anti-Fragile by Nassim Taleb who is an economist. Everytime I reference this book, I need to say this: I probably missed the point. Whenever I talk about economics, just treat me like a freshman boy who is back home from their first semester of college who wants to talk about their intro to economics course. 

That’s about my understanding of economics. 

Now that we have that out of the way, I am going to tell you my take away from this book. 

Being anti-fragile is all about positive asymmetry. When you do something, make sure that there are more positive outcomes than negative, and if you do that a lot of times, you will end up on top. 

The tricky part of this advice is that asymmetry in the context that I am explaining is granular down to the individual human level. 

Your unique makeup will make something a positive asymmetry for you and a negative asymmetry for someone else. 

Let me give you an example. 

You have a fast learner and a slow learner. 

If you are someone who grasps concepts quickly, it behooves you to learn as many things as possible. As you learn more new things, you will likely find something that you are both good at and interests you. Your opportunity is in the breadth of things you can understand. 

If you are a slow learner, you are also probably a deep learner. A concept may take you more time than the latter example, but once you get it you will get it better than anyone else. Take advantage of your ability to mull over details. Your opportunity is in your depth of understanding. 

When you understand your own asymmetry, you are seeing your advantages, and thus making decisions that play well with your skillsets. 

How do you find your asymmetry? 

Ask someone close to you. BUT when you ask them, tell them, I don’t want a compliment, I am trying to understand myself better. 

I did this one time with my sales manager at my first job out of college, he said, 

“You are the only person who I have managed who has frameworks for how they make decisions and approach problems, but you are also way too nice and get walked over by the customers.” 

Being nice to customers is probably something that works well in a customer service role, probably not in a high volume outbound sales role. 

Another way you can find your asymmetry. Look for things in your life that you get an outsized return relative to your effort. I have referred to this in previous newsletters as your “easy A.” Take inventory of the things or moments in your life where you inexplicably have a better outcome than you should have… that is the beginning of finding your asymmetry. 

Conclusion

2026 is the year of anti-fragility. It is the year that I am dedicating myself to put myself in positions where I have a positive asymmetry. 

The key to positive asymmetry is understanding that the positive result can be things other than a raise at work, a new house, or whatever traditional results we look for. 

A positive result is anything that moves you forward. 

Take this second brain for example, I either write down an idea that I use for the rest of my life, or I document what I am thinking now and I have a benchmark for how my perspective has matured. No downside. 

The nice thing about this newsletter is everyone who is receiving this probably has my Linkedin or phone number.

If you want me to tell you what I think of your positive asymmetry, send me a note.

Until then.

Kyle