One can of course relate to money in pathological ways. For those whose standard of value resides not in a conception of their fully-lived life (a la the builder), but in the impressions or judgments of others (be it God or society or their parents or some other “drill sergeant”), money means whatever it purportedly means to those others—status, in some circles, or wicked materialism in others, or in still others, “privilege” to be forgiven with obligate philanthropy. 

By contrast, a builder’s relationship to money is not mediated by any of these external intermediaries. She understands that money is a medium of value exchange, and what she values is set by the life she wants to build and the world she wants to live in. 

There are also simpler pathologies, such as when fear or insecurity drives founders to pursue short-term monetary gains over the longer-term health and durability of their business. But such financial anxieties can be diagnosed and remedied by re-orienting toward the overarching goal of building one’s best life, which presumably includes a healthy and durable version of one’s business (or whatever one is building) as part of it.

Quite a useful way to reframe money and its importance to a well considered life.

I think what many people really want from money is the ability to stop thinking about money. To have enough money that they can stop thinking about it and focus on other stuff.

But that ultimate goal can break down when your relationship with money becomes an ingrained part of your personality. You struggle to break away from focusing on money because the focus itself is a big part of who you are.

This, 100%, is me… and if you can relate to that yourself, give this whole article a read.

The world trends towards equilibrium. The world trends towards proof of work. It’s rare for fortunes to be created so effortlessly. Therefore, if you see easy money being made, it’s one of the strongest signals that something’s not right. Of course, some people will hit the lottery or be born into wealth. They are the lucky ones. But, most of us aren’t. Most of us have to work for it. We have to show the proof.

It’s taken me eleven years to feel like I am even close to seeing a somewhat realistic path towards wealth (and to be clear, I'm only seeing the path... I'm nowhere down it yet).

The overall message in this article is immensely helpful in dealing with my anxieties around money.

I know, I know, it’s another 10 Reasons Why list… but dang nabbit, there are some solid pieces of financial advice in here!

My personal favorite:

When someone gives you two reasons or excuses for not doing something, neither one of them is true and both are invalid. You haven’t gotten to the truth yet. Imagine asking a friend to go to a baseball game and he says “I can’t, my in-laws are coming over tonight.” Then you tell him it’s actually a day game. “Oh, I’m also sick. Not feeling well.” His in-laws aren’t coming over and he’s not sick either. There’s something else going on. If you understand this aspect of human nature, you are equipped to talk to investors.

To me, there’s no option but to give the money back. Being a tech worker is not like banking, where you know you’re not doing good for society. A lot of tech workers delude themselves into thinking they’re being “mission oriented.” I was never quite delusional enough to believe that. I was just hoping I didn’t do net harm, which in itself is hard to avoid in this industry. I want to spend and donate as much as I can in my lifetime, and if I’m able to have the money create meaning, that’d be good. I haven’t decided what I’m going to do with it yet, though.

The shortest distance between two points is reliably a straight line. If your dreams are apparent to you, pursue them. Creating optionality and buying lottery tickets are not way stations on the road to pursuing your dreamy outcomes. They are dangerous diversions that will change you.

By emphasizing optionality, these students ignore the most important life lesson from finance: the pursuit of alpha. Alpha is the macho finance shorthand for an exemplary life. It is the excess return earned beyond the return required given risks assumed. It is finance nirvana.

But what do we know about alpha? In short, it is very hard to attain in a sustainable way and the only path to alpha is hard work and a disciplined dedication to a core set of beliefs. Given the ambiguity over the correct risk-adjusted benchmark, one never even knows if one has attained alpha. It is the golden ring just beyond your reach—and, one must enjoy the pursuit of alpha, given its fleeting and distant nature.

Ultimately, finding a pursuit that can sustain that illusion of alpha is all we can ask for in a life’s work.

The end result will be a better, more resilient and richer world than ever. Yes, that will also eventually mean more money in your retirement account, but more importantly it means better and happier living conditions for every living thing on Earth.

I sure hope so.

Stewart Butterfield expanded on this idea when he discussed what he called the “Three Levels of Wealth.” My colleague, Ben Carlson, beautifully summarized the three levels of wealth as:

• Level 1. I’m not stressed out about debt: People who no longer have to worry about their credit card debt or student loans.
• Level 2. I don’t care what stuff costs in restaurants: How much you spend on a particular meal isn’t impacted by your finances.
• Level 3. I don’t care what a vacation costs: People who don’t care how expensive the hotel is or which flight they go on.

I heard Stewart Butterfield describe this idea on a podcast and was fascinated by it. Nick Maggiulli took it a step further in this article, complete with a Jay-Z reference.

Nathan Barry of ConvertKit fame shared this post on Reddit a few weeks back, and I have read it a half dozen times since then.

If you are at all interested in taking the leap into being an entrepreneur, read this. It’s more insightful and inspiring than 90% of the business books I’ve ever read.

If you are not already making $500,000 compensation in your job, there are five steps to getting you there.

Summary:

(1) Do everything you say you are going to do.

(2) Manage your boss and colleagues — don't make them spend time managing you.

(3) Proactively help the organization.

(4) Be positive (don't complain). Be a “yes, and” person.

(5) Report to someone making over $500k.

The summary is helpful for reference, but Auren Hoffman’s entire reply is quite useful if you would like to make more money doing what you do.