Letter to my 18-Year-Old Self

This post is part of a collaboration that I am doing with my longtime friend, Brandon Holmes. You can find more posts like this at his blog here (link coming soon).

I promise you I will get back to financial stuff very soon, but I believe this will be an interesting read for my followers:

Dear 18-Year-Old Self,

You think you’re on top of the world, huh? I know you do. You got into college, have a nice girl friend, get to be roommates with your best childhood friend. Most importantly, you are out from under the scrutiny of your parents.

It is amazing to me how little you know.

I have the advantage of looking back and knowing all the obstacles you are going to encounter. I know what you should have done better. Hell, I wish you would have done better because then I wouldn’t have a topic for this letter to you.

The problem I am having right now is trying to understand how spitting out all my regrets to you on paper will have any impact on me now. It most certainly won’t have an impact on you since you don’t even exist.

I am not trying to say that I somehow live life now without any regrets. That is simply not true. I just want to admit to you that the person you created is not someone who will spend time putting unwarranted shame on your shoulders.

Instead, I believe writing this letter to you isn’t to help you, instead, it is meant for my children.

Before I expand on that point, understand this: When I was you, I had no idea what was in store for me, and now that you are me, that hasn’t changed.

I have no an idea what is in store for me. This fact humbles me. Of course, now that I’m older and more mature, I do things with greater conviction. I see more results for my efforts, but life is still as unpredictable as ever.

That is the main reason why this letter is better meant as a lesson for my kids.

Between you and I, we have treated numerous people wrong and felt no consequence. In that same breath, we have treated many people with kindness and respect and similar actions have not been reciprocated back to us. Nothing really makes sense.

The world seems to tangle up more as life goes on. Dealing with that confusion is now more of habit for me than a problem.

One part of being habitually confused about life is that it constantly humbles me.

I want to tell you that I have made a good life for myself. I have traveled many miles and have seen different countries. I married a girl from Europe and my kids will understand more words than me in probably 5 years. I know for a fact you would have never imagined that. I have read hundreds of financial books and became extremely knowledgeable in fields like accounting, finance and economics. I have written thousands of words and made presentations to many people. I have created businesses. I have received awards at work and fast promotion compared to my peers. The simple fact that remains is that I am confused about the world. No matter how hard I try to clear up the confusion, it just comes back thicker than the early morning fog in German vineyards.

My letter seems pessimistic, but stay with me, I am getting somewhere.

I do not have a specific path that I want to describe to you. I don’t have a singular piece of advice for you that will make you the next Bill Gates or Martin Luther King. I just want to tell you the same thing I will tell my kids. I am not your vessel to success. Only you can figure that out. Along your journey to success, accept the confusion and become friends with it. That confusion is bigger than you. It is what connects us with other people in the world.

That is all I have to say. Hmmm, wait, I do have one regret I want to share with you. Lift some wieghts before you decide to go to another toga party! Shout out to Jeremy (my college roomate I spoke of earlier and my dance partner in this picture below). We made it brother.


Grown up You