Unteachable Lessons and Alexander the Great.

Hi, 

This week, we have a lot to cover: 1 year of newsletter, Alexander the Great, and the lesson I am trying to learn. 

Let’s dive in. 

Today is finally the day: I have written a newsletter every week for a year. Being that I started this for no other reason than to push myself to do it, I have to say I am very happy about it.

Honestly, I have talked about that a lot, and that is all I have to say. 

This newsletter has kind of turned into the Modern Wisdom fan club, and I am cool with it. Recently, he did an episode with Ryan Holiday, who is one of my favorite authors, and when I tell you that I was listening to it with a big smile on my face, that is an understatement. 

Two of my favorite content creators talking about how they view the world, pretty cool. 

Chris Williamson has a recurring topic on his podcast that he calls “Unteachable Lessons.” These are things like: Money can’t buy you happiness, Having an attractive partner isn’t going to make you happy, achieving won’t fill the void, etc. 

Ryan Holiday offered an insight that really painted a beautiful picture in the context of these lessons. “Unteachable Lessons” are not unlearnable, they are the things that you have to learn for yourself through experience. Ryan Holiday essentially said that when it comes to each of these lessons, we all exist on a spectrum, where we have a different threshold of experience needed to learn the lessons.

He gave the example of Alexander the Great. To give you the better part of the story, I am going to use a quote from Rachel Kousser who wrote, “Alexander at the End of the World”

 Alexander had won, unexpectedly and definitively. What would he do next? His soldiers, 

who cheered and cried at the news of Darius’s death, hoped it meant their king would lead them home. Ancient biographers, and many modern scholars, have concluded that he should have. But Alexander made a different choice: instead of a triumphant return to Macedonia, he kept going east. He wanted to reach the literal ends of the earth, to see the Ocean that he believed encircled them. He wanted to conquer the known world.

The important thing to note here is that Alexander died. He never made it back home. 

Alexander conquered the known world, he had achieved all that could be understood, and there was still more that he wanted. 

On the achievement as a means to fill the void lesson, Alexander the Great is probably the furthest end of the spectrum of how far someone needs to go to learn that lesson. 

We all live on the spectrum for all of these truisms masquerading as lessons. 

This week, I was chatting with my step mom, AKA Mad Dog, and I told her I was thinking about this idea. I mentioned that when we are either at the place in our journey where we learn the lesson or are getting close, the lesson itself becomes very obvious. But, the lessons that we have a longer road to learn often elude us. 

So I asked her, what is the unteachable lesson that you think I have the longest road to learn? 

She pondered for a few moments and said, “success isn’t a destination.” She was right, I had no idea what she meant. 

Whenever I think about success, I think of the jobs I have held, the projects I have had a key part in, and the places those things have taken me. 

I think of myself as bereft of those experiences, and I am constantly asking myself why I haven’t had the opportunities I think I should have or why I don’t know the things I should know. 

I treat the timeline like a thing that is predetermined, and I am somehow falling behind schedule. 

The lesson: Success is a destination, but one that you choose. 

If you are invested in the story of Kyle, I have good news and bad news for you. 

The bad news: I don’t think I am at the end of my journey for this lesson. 

The good news: I am not at the end of the world. 

So unfortunately, 52 newsletters doesn’t feel like success in its broader sense. Writing this newsletter felt more like writing newsletter #17 then it felt like my magnum opus. 

That is okay. It’s probably more good than bad. 

I have the best news for you: I will be back in your inbox next week. 

Toodles, 

Kyle