Whether humans have free will is a pretty important (and contentious) topic, but it’s super easy to argue with yourself in circles about it.
Obviously we aren’t completely free. I can’t just suddenly decide I don’t like the laws of gravity, and make them act differently. Might we be completely constrained? There’s a sense in which we are, if we constantly follow our strongest desires, and our desires are exclusively shaped by outside forces. There’s no “escaping the system”, to be influenced by something other than the universe you live in.
Although I don’t think the kind of “free will” most people believe in makes much sense, I’m something of a compatibilist according to the narrow, philosophical meaning.1 Experientially, choices are a real thing that people have to make, even if the underlying physics is just a cold set of hard-and-fast rules. Even if we can’t escape physics to make choices, physics already allows some pretty interesting things. Think of life. If you look at the physics, all you see is a bunch of lifeless rules. However, there’s clearly some way that this bunch of lifeless rules adds up to real living things. Similarly, a bunch of choiceless rules might add up to making “real” choices.
(And no, I don’t think any kind of spooky quantum mechanical indeterminacy provides a way out. How are you supposed to be controlling the nondeterminism?2)
So for the purposes of this post, let’s assume there is some kind of real thing known as free will. The question I want to ask is: do choices that involve greater levels of risk also provide greater levels of freedom?
Say I choose to get up, walk over to another chair, and sit down again. This choice has virtually zero risk of failing. However, besides that, it seems about as unconstrained as a choice could be. Nobody is coercing me into switching chairs. Clearly, this is more free than switching chairs at gunpoint. But the risklessness tells us something about the nature of the choice. There is something more independent and freeing about starting a business, or running over hot coals for the first time, or asking someone out on a date, vs. merely switching chairs. I don’t think this is a simple conflation of terms, either. The riskier choices really do demonstrate a higher level of freedom to exercise the will.
In one popular conception of freedom, it almost involves a lack of courage. In order to feel truly free to do something, you need to feel as little resistance to doing it as possible. It should take very little willpower. You’re not free to do something unless it’s easy.
However there’s another conception, occasionally touted by motivational speakers and their ilk, that real freedom involves the ability to do what you most want to do, even if you lack the willpower to want to do it in that moment. You’re most free when your will is strong enough to allow you to do virtually anything.
These views aren’t all that opposed. One view wants choices to be as easy on the will as possible, whereas the other wants you to expand your will as much as possible to make more choices seem easy. Both approaches attempt to extend your optionality, a key component of being able to freely make choices. Without options, there can’t be choices. Being open to taking on more risk is also a way to expand optionality, since it’s rare that all possible options will have the same risk level.
Now, let’s say that there’s some fixed set of options, with varying levels of risk. If you consistently only value low-risk options, you’re limiting your choices in another way, even if you sometimes do take a chance on a high-risk choice. It might be the right thing to do, given all the variables of your personality, state in life, etc., but there is something freedom-limiting about shying away from all risk. I would contend that occasionally taking risks doesn’t just make your life better in the feel-good way of “taking a chance”, but also shows that you’re actually exercising whatever amount of free will you may have.