Jack asked me what he should do.

I think this is interesting, because I’m trying to work that out too. I’ll share what I said, and I’ll try to explain my advice too.

I told him he could do anything, but he just had to figure out what he wanted.

Turns out, that’s the hard part.

A little about him: he’s never gone too far into it, but he claims to have come from a place of financial risk. He’s not a Rockefeller or anything now, but he works hard, sometimes 6 days a week, he has been living below his means, and is trying to create a comfortable cushion for his life.

Here’s the thing, and I think this kind of goes to the heart of the matter: money is more than just a number. It’s emotional too. Whether Jack gets to ten thousand, a hundred thousand, or even a million, he will never feel like he has enough until he starts feeling like he has enough.

Yes, I know that if you don’t have enough money for food or rent, or are going through bankruptcy, this conversation is not for you, but for the large majority of people, if you don’t have legal judgments against you, you are actually probably pretty ok.

The question of what you should do is un-answerable without first figuring out what you want to do. I don’t, personally, believe in ‘shoulds.’ The only thing I truly know as a should is the biological imperative given to us by evolution: you should continue breathing. You should eat food in order to live to the next day. But, beyond that, if it’s not the laws of physics, most of existence is pretty negotiable.

Let’s dig in here

Why is it so hard to answer that question: What should I do?

I think part of the problem is that we all think we have perfect windows into our own minds. I mean, for me, I live here, in my thoughts. How could I not know myself? I am myself. The assertion that I don’t know the thing I am seems almost laughably absurd.

But it shows up again and again through philosophy, that idea that the unexamined life is not worth living. Know thyself, be true to yourself. I think, therefore I am.

It’s all about the very weird difficulty of knowing what is going on in your head.

There is something I learned about from podcasts that has really revolutionized my thoughts about all of this.

Memetic desire
We don’t want the things that we want. We want the things that we see other people wanting. And, more insidious (or more fascinating, depending on whether or not you’re charmed by the world around you) is that we don’t even realize it’s happening.

Restaurants have this all the time. What is the best restaurant in town? It’s usually a toss up between the small boutique, artisanal, incredibly high quality place that has focused obsessively on their food, and then the old tried and true favorite. Every town has their own, or couple if it’s a larger city. Burger Joints, Steakhouses, Fish places: places that people like because they are popular. We go there to see other people, people go there because they are busy and thus they continue to attract more and more people. Quality is a way to break into the echo chamber that is social proof and memetic desire, but sometimes random chance and luck generate self propelling popularity. It just is what it is.

We don’t want money to have money. If everyone died tomorrow except for you, you wouldn’t look to amass money. Going around collecting $20’s off the ground in a world where only you exist would be meaningless. We collect money because people want money. Money is valuable because money is what people want. We want the thing that other people want.

We want social connections because other people want social connections, in this dizzying, self-autolytic explosion, desire creates desire, and our wants are the misappropriated wants of our neighbors, the mirror image of those around us, holding mirrors to others, and like two mirrors facing one another, there is an infinite chain of connections.

It’s all turtles all the way down.

I know I want money. I also want social connections, and power, and a car, and an iphone, and also a six pack (when cheesecake isn’t in front of me) and cheesecake (when I can’t see my abs). But I rarely stop to think: why do I want these things? Do I want these things in and of themselves, or do I want these things because other people want these things?

What do you want to want? What are the desires that you chose to have?

And that brings me back to my friend Jack. He asked me what he should do.

He was asking about career advice. He is working on getting his Court of Master Sommeliers Certified Sommelier Certification (a very fancy way to signal to the world, his employers and to guests in restaurants that he knows about alcoholic beverages). He asked me because I have actually done that certification.

He wanted to know if there was a path in front of him as a manager, or a distributor or liquor rep. He’s at an inflection point. He just had a kid. Trying to map out his future. Does he want to work late nights when his child is 5 years old? 15? He thinks not. My big regret, as I think back on the conversation is that I didn’t challenge him on something he said: “I don’t want to be working nights when my kid is older.”

I think he wanted me to tell him directly to do xyz.

I want to know why he thinks to be an ideal dad that he shouldn’t work nights. Is that what he really thinks, or is that what he believes society thinks? Would he not have a chance to be with the kid throughout the day? Is there something magical at nighttime that makes them more family appropriate?

I digress. I didn’t tell him what to do. I just asked him to think about what he wanted to do. Truly, deeply, by himself.

I couldn’t tell him to do anything in any sincerity. Any more than I could tell you what you should do or you could tell me.

Everyone is unique. We are, all of us, our own unique snowflake of broken, and we all must provide our own paths forward.

Any advice you get will be distorted in one way or another. I can tell you how I organized my life, but if you don’t like not having things listed out in a calendar, you’d fail at my system. I list tasks by day, not by time. I’m fairly busy, and without flexibility, my schedule will blow up.

I used to drink too much. I know that, and I’ve largely put that behind me. I’m incredibly anxious and stressed, just in general. My path wouldn’t make sense to someone that hadn’t made mistakes like mine in the past. Someone that was calmer and more centered…

I enjoy solitude. To an extrovert, my life looks like a prison, whereas I see a sanctuary….

What do you want? It’s a cliche, but they say that you can do anything, but you can’t do everything. You just have to pick.

Financial independence? It’s in your grasp. Mental peace and stability. Those can be yours too. Sobriety. Done. Weight lifter? Jazz musician? Podcaster? Writer? Speaker…

What do you want?

That’s the question. The rallying cry. And I have no answers for you, just for me.