There are a couple of ideas that tug on me with a force I haven’t felt before my experience in the last 2 years.
Regarding my career
It’s become more of a priority to sustain a living in a way that feels deeply tied to others. There are a lot of ways to make money, but finding a way that doesn’t feel alienating, finding a way that feels like I’m lifting others is harder to pull off. To be clear, any constraint limits your options. Expectancy-wise I’m paying for this preference the same way a remote worker might be taking a pay cut compared to the counterfactual. But this is only a concern if I measure expectancy only in dollars. That’s falling into a trap of letting legible accounting dictate all of what matters. You know what’s more baller — giving your soul a bank account and finding a way to stack it. That means more energy for everyone else around you.
Look, if you have the luxury of reading a Substack at your desk, then simply making money is easy. You just have to be good at something. By definition, mediocrity is everywhere. It’s a low bar for ambition. Making enough money on your terms takes either top 1% talent or being good at something plus courage. If you stop at just being above average at something, some overlord will always stand ready to make you part of their portfolio. But you’ll just be another asset to be rebalanced on their schedule.
You don’t become irreplaceable until you display how you are different (I’m obviously talking about the differences that are helpful while remaining aware that many strengths are weaknesses in other contexts). You cannot do this from a place of fear. You can’t maximize opportunities if you can’t afford to say no. So it stands to reason that you don’t want to build your life in a way that makes you unable to say no. That’s the real trap of conformity. Conformity isn’t clothing. It’s not even what you say necessarily. It’s relegating your agency for comfort to someone with a different mix of values because you were too lazy to identify your own. And the irony is they probably did the same.
[It’s out of scope for this post, but this idea is deeply intertwined with learning which I believe is really about agency and freedom from conformity. And I don’t mean that in some truther way which is just conformity sold as alternative. Like what “grunge” became. And I say this as someone with all the albums.]
Spending Money Strategically
I mentioned that emotionally moving was expensive. It’s expensive to transact real estate and travel. But the costs were worth the information. That’s a concept that exists in poker or even trading. For example, you can “fish” mid-market by dangling a one-lot to see where the bots live (and to defend yourself against such tactics, in a dark pool for example, you can define a minimum trade size).
In The Art and Science Of Spending Money, Morgan Housel offers a menu of ways to spend money that you may not have considered. #10 explains why:
Not knowing what kind of spending will make you happy because you haven’t tried enough new and strange forms of spending.
Evolution is the most powerful force in the world, capable of transforming single-cell organisms into modern humans.
But evolution has no idea what it’s doing. There’s no guide, no manual, no rulebook. It’s not even necessarily good at selecting traits that work.
Its power is that it “tries” trillions upon trillions of different mutations and is ruthless about killing off the ones that don’t work. What’s left – the winners – stick around.
There’s a theory in evolutionary biology called Fisher’s Fundamental Theorem of Natural Selection. It’s the idea that variance equals strength, because the more diverse a population is the more chances it has to come up with new traits that can be selected for. No one can know what traits will be useful; that’s not how evolution works. But if you create a lot of traits, the useful one – whatever it is – will be in there somewhere.
There’s an important analogy here about spending money.
A lot of people have no idea what kind of spending will make them happy. What should you buy? Where should you travel? How much should you save? There is no single answer to these questions because everyone’s different. People default to what society tells them – whatever is most expensive will bring the most joy.
But that’s not how it works. You have to try spending money on tons of different oddball things before you find what works for you. For some people it’s travel; others can’t stand being away from home. For others it’s nice restaurants; others don’t get the hype and prefer cheap pizza. I know people who think spending money on first-class plane tickets is a borderline scam. Others would not dare sit behind row four. To each their own.
The more different kinds of spending you test out, the closer you’ll likely get to a system that works for you. The trials don’t have to be big: a $10 new food here, a $75 treat there, slightly nice shoes, etc.
Here’s Ramit Sethi again: “Frugality, quite simply, is about choosing the things you love enough to spend extravagantly on—and then cutting costs mercilessly on the things you don’t love.”
There is no guide on what will make you happy – you have to try a million different things and figure out what fits your personality.
Recently, I’ve seen a wild example of this.
My wife has a close friend that was in the rat race grind. After joining Yinh on the board of OrFA, the friend has been regularly visiting the orphanage in Vietnam. She’s a tall blond, as American as apple pie. A stranger in a strange land in the Vietnamese countryside. But she found herself deeply moved by not only the children but the local culture and all its people. She has dramatically re-arranged her entire life to prioritize her involvement and presence in Vietnam. Witnessing the impact on an otherwise familiar, professional life that started with a donation and some curiosity has been a powerful frame shake. (My family, 13 of us in total, are going to Vietnam for a few weeks this year and have already planned a soccer match between all the kids at the orphanage. If my kids moan about what’s for dinner after that trip, they’re getting lit the f up).
This is a reminder. You can just do things. You can’t introspect your way to knowing what you want. It’s too much projection of your current self into a different reality. It doesn’t recognize that the feedback changes you.
Spending money in a new way is just another method to try on different versions of yourself. To explore personal frontiers on the not-so-crazy lark that there are deeply rewarding modes to explore the world that you are completely ignoring. Your fixation on the crowded paths your surroundings have directed you towards might frustrating, not because of any personal failings, but because those paths are overbid (look no further than the college admission Hunger Games).
If you can’t be happy unless you get that house or that wedding or that title, it’s not because they are your destiny — it’s because you haven’t taken your imagination off-leash.