This week on Upstream, I spoke with Katherine Boyle about building companies, families, careers, and faiths.
Fittingly, this week we’ll talk about taking leaps of faith.
Recently we’ve talked about rationality and religion, and how de-popularizing religion hasn't made us more rational. We’ve also been emphasizing the limitations of rationality/reason, namely that reason tells us everything except how to live.
We cannot derive an “ought” from “is”, as Hume would say. Or as Antonio Garcia Martinez more colorfully put it in an episode of Moment of Zen:
“Tell us what Bayes Theorem says about Israel vs Palestine. Tell us what Bayes Theorem says about how to be a good father. Tell us what Bayes Theorem says about what’s the meaning of life.”
Reason provides poor answers to these questions, and so trying to determine what you should do with your life based on reason is a dead-end. If you view life totally rationally, you start to see life as an optimization problem; And if you see life as an optimization problem, by the time you're done solving the optimization problem, you will find that what you've optimized for is a completely meaningless life.
The optimizing approach to picking life goals is like knowing the price of everything but the value of nothing. Turns out, optimizing for our own utility isn’t the most meaningful thing you could do. Indeed: When we reflect on what makes our lives meaningful, when we look back at a life well-lived, we don’t tend to focus on how we maximized utility (or pleasure) every single step of the way. We do focus on the experiences we shared with others, sure, but we also emphasize the sacrifices we made in service of something greater: A commitment, a calling.
How do you avoid getting trapped in this nihilistic process of rationalist decision making and life optimization? One answer is to not only pick a commitment rationally, but to also pick it arbitrarily.
You need to pick something bigger than yourself to believe in, but you can’t only use logic and rationality to pick it. You need to also pick the goal arbitrarily. “Goal” isn’t even the right word for it. The right word is “faith”. Faith in the sense of you believing something even when it appears to be temporarily untrue. You can rationally choose a goal, but any goal chosen rationally can also be discarded rationally. You won’t stick with the goal when things get hard. A faith, on the other hand, can’t be rationalized away. Even when times get tough, you stick to your faith no matter what. That’s why marriages have the line “til death do us part”. If you say you’re going to stay married as long as you feel like it, you’re going to likely get divorced. Because you won’t always feel like it. But if you say “til death do us part” you’ll be more likely to stick with it.
Some people think that in order to find meaning in their life they need to go on endless spiritual retreats and soul searching journeys and take psychedelics, but those will not solve for meaning in the same way that making commitments will. They might help you clarify which commitments to make, but if you don’t make commitments, you won’t have meaning. Living just for your own pleasure might make you feel good in the moment, but it won’t make you feel good when reflecting on your life, which is a deeper kind of happiness.
What leads to a deeper kind of happiness is making commitments: To family. To friends. To partner. To country. To mission. To God. To anything.
In order to make these commitments, you need to take a leap of faith that it’ll work out. But the more you understand probability, the less you’re likely to take that leap of faith. Take starting a company for example. The following phrase summarizes it in a nutshell: “We did it not because we thought it would be easy….but because we thought it would be easy.” If you knew how hard a company truly was, and how stacked the odds are against you, you might be less likely to pursue it. Most people who try to build the next SpaceX or Tesla will fail. And so on an expected value basis it doesn’t often make sense for an individual person to try. But on a societal level, we need thousands of entrepreneurs to try, since the gains of society getting a Tesla or SpaceX outweigh the costs for the individuals who try.
If the world was full of probabilistic thinkers, no one would build the next SpaceX or Tesla. The best founders put it all on the line. You want to be a probabilistic thinker as an investor, but a deterministic thinker as an entrepreneur. Because once you prioritize thinking probabilistically, you become index-minded, like an investor. Beyond a certain level, more money has diminishing returns anyway. And so if you’re optimizing for happiness, why go after anything big at all? Just enjoy life. Stay comfortable. Which is why people who do stints at VC firms usually don’t start companies afterwards. It’s just safer to index.
If thinking rationally becomes the highest goal, you become able to rationalize anything. There was a brilliant philosopher (simplifying crudely to make a point) who used her brilliant philosophy to justify leaving her husband and having a polyamorous relationship with her next. The difficulty of keeping commitments speaks to the importance of picking things for fixed and arbitrary reasons. Because if logic is your primary motivator, you’re going to convince yourself to get out of your commitments once there are more attractive options elsewhere. Commitments might be made with logic, but they’re kept by faith.
Genuine kudos to anyone living philosophically and trying to innovate within the human experience. I just don’t think challenging sacred norms is the right path for most people, in the same way that most people shouldn’t try to trade stocks and time the market. The market is too complex for you to take all the factors into account. Better to just buy and hold. (Or outsource it to other people who have full context and can think rationally.) Similarly, long-term happiness is too complex to be fully modeled. It’s easy to intuit what will make you happy in the short-term, but it’s hard to know in the long term, especially when long-term happiness competes with short-run happiness, as it inevitably does. So simple rules or heuristics that have lasted a long time, even if literally false, are often more directionally accurate than false precision.
Thinking from first principles makes sense when you’re trying to innovate, but if you do it too much you don’t build upon the foundation of knowledge accumulated through the evolutionary process.
Now, one way that rationally evaluating commitments is helpful is that it helps you discard externally-imposed faiths that you don’t believe in, like certain religions or job roles or societal expectations. This is what we’ve done on a macro scale as a society. We’ve freed ourselves from commitments that were foisted upon us. But we’ve failed to pick new commitments and stick with them.
Those externally imposed commitments were also picked arbitrarily, but the difference is they were arbitrarily chosen for us, as opposed to us choosing our arbitrary commitments.
To be sure, just because you didn’t pick a commitment doesn’t mean it’s bad or not worth keeping. We have this obsession with everything needing to be intentional. Sometimes there’s a commitment that we stumbled into, that didn’t make sense at some point, that we rescripted and made our own in the process. That we intentionally chose mid-way even if we didn’t intentionally choose at the beginning. Not everything in life can be planned out from first principles. As the saying goes, we make plans and God laughs.
Stumbling into commitments is more common than we would think. After all, this is how most people had kids for most of human history. Sometimes we need a push — if we were so intentional or logical, we might not make commitments at all. Logic is good for pleasure, but not good for mustering the courage for sacrifice. And everything great takes a bit of sacrifice.
We want to thread the needle where we have enough logic to free ourselves from unwanted arbitrary commitments, but sufficient faith to make other commitments and stick with them! Because sticking with something even when it seems arbitrary is the reason why picking something arbitrarily matters. If you drop something as arbitrarily as you picked it, that’s not useful. You need to arbitrarily pick something so that your commitment is relatively impervious to reason. Because otherwise you’d reason it away. Reason is great for tearing things down, for breaking things up, but not great for mustering the courage to take on a big commitment and stick with it.
And commitments are what makes life worth living. As David Perrell put it in his essay “Hugging the X axis”:
In matters of the heart, commitment brings meaning. In matters of the mind, commitment brings knowledge. And in matters of the material world, running towards the responsibility that comes with commitment takes courage — and with courage comes achievement. People can only become world-class at things they commit to. Ultimately, the more hesitant people are about making commitments, the higher the rewards are for people who do. The alternative is empty hedonism and hard work without the rewards to show for it.
Paradoxically, optimizing for happiness doesn’t make you very happy in the end. Optimizing for meaning does, but it requires acting like you’re not optimizing for happiness at all. It requires prioritizing commitments above happiness.
Freedom has limitations, but, paradoxically, limitations are what grant you freedom. As David Brooks once said, “it’s what you chain yourself is what sets you free” Katherine Boyle wrote some great pieces about how these commitments are on the downswing.
While this may sound like cope, there’s another way to look at it: people who’ve experienced the pain of flitting from project to project or person to person are in a good position to start making commitments. Commitments become easier when you realize that, after enough wandering, the grass is unlikely to be greener, pursuing novelty has diminishing returns, and continuous optimizing comes at the cost of compounding—and nearly everything great compounds. It is easier to make and keep commitments once you've internalized the downsides of not committing—to a career, a place, a handful of people)
If you don’t have faith, there’s nothing to believe in. If there's nothing to believe in, why believe in anything? And so we don’t. And that’s why we have a commitment crisis. Because commitments don’t make sense in the abstract. The rational, logical, thing to do is always to index, or hedge, or wait until there’s something better out there and then maximize your market value. People see why this is bad, so they say, stop hedging! But they’re not addressing the chain of thinking that produces the hedging in the first place. Stop pursuing optionality, they’ll say, but hedging is the rational thing to do. So they’ll seek to hedge in some other, more subtle way.
Which is why, when it comes to picking commitments, you need to prioritize faith over logic. For big decisions, like who to marry, you can look at someone’s attributes and then say, as long as these things are true, you’ll commit. Or you can just say you love the idea of a 70 year marriage with grandkids and then go all in on it when you find the right person. Making that kind of commitment is irrational if you’re optimizing for your own happiness the ways at every step of the way. How do you know what you’ll feel in 12 months, let alone 12 years? Making that arbitrary commitment risks you sticking in a relationship much longer than you should if it’s truly the wrong one. Commitments aren’t risk free after all, that’s why people try to hedge. But making that arbitrary commitment gives you a far better chance of making it work. Even great marriages have bad spells, moments where people considered ending it, but their faith and commitment is what keeps them together, and it’s often the moments where it almost ended that brought them stronger together and provided more meaning.
When I look at the things that provide me meaning, they’re the things I stuck with. I started freestyling like 15 years ago, I even started a company around it. I’ve committed to doing it as a hobby for the rest of my life. Maybe it’s dumb, maybe I suck forever. Who cares. It’s so fun for me to do it. It’s rewarding to see how much better I’ve gotten. It works for small things too. I’ve also gotten a lot of joy out of writing this weekly newsletter. I know it’s just OK, but I see progression and consistency. it’s more for me than the audience. Another thing I “just do” is watch the Knicks play. It makes no sense, I can’t justify it, but it just provides me this great source of meaning to see their growth and to discuss it with my family and friends.
“Sticking with it” also does this thing where it turns a nihilism process into a meaning making process. It's like now I’ve decided, no matter what happens to the rest of the world, I am going to make a few things true about the future: I’m going to stay freestyling, continue writing this damned newsletter, and keep watching the cursed Knicks. (I’ll also stay married whenever I get married). And then I can then redirect my powers of rationality and optimization to figuring out how to best make that leap of faith most successfully. Venkatesh Rao calls this “fixed point futurism”.
So everyone needs faith, something they can commit to even when it’s hard. That faith is built on a narrative, and that narrative is personally construed. It could be something you consciously accepted that was given to you, or it could be something that you modified to make your own. When people quote the narrative fallacy and say we should avoid narratives, they get it exactly wrong. They’re right when they say all narratives are fallacies, but they’re wrong when they suggest we don’t use narratives. We are narrative creatures. Reason is just a device to help us back into a narrative
To be clear, not all commitments are worth keeping. Sometimes you’re actually just not with the right person, not with the right company, or not living in the right city or community. Sometimes you spend a year or a decade on a person or a project and it becomes clear it’s not worth continuing. Sometimes you actually don’t believe in it anymore in a broader sense, separate from your temporary unhappiness. Something has materially changed. Sticking with your current commitment won’t make you prouder when you have full conviction it’s the wrong one. At that point you should then leave, and then make another commitment once you’re ready. If you’re having a crisis of faith, maybe sit with it until you have full conviction either way.
How do you know what leaps of faith to take? One litmus test for whether it’s a good commitment is its track record. Many people have committed themselves to, say, the absolute equality of humans, and they don’t have good things to say about it. You want to pick commitments that will serve you. Commitments that have been tried and true. There are plenty of faiths that will make you miserable. That’s why rationality is so valuable in partnership with faith, to help ensure you’ve picked the right commitment to begin with. But when you pick a good commitment, you need to take a leap of faith.
And to be clear, this advice is exclusively within an individual context. Prioritize faith when committing to marry, use logic when devising any policy or system. A good rule of thought is faith for micro, logic for macro.
To botch the serenity prayer from Reinhold Niebuhr, God grant me the discernment to use logic when evaluating commitments, the courage to use faith when making and keeping commitments, and the wisdom to know when (and how much) to prioritize each one.
Spot on. Dogs. The best commitment
Bro I am becoming a huge fan. First MoZ, then Upstream, now your Substack. Had no idea you freestyled. I’m actually originally from CT, have been rapping for a few decades, and root for the Knicks as well haha! Keep up the good work