Ohhhhh the concept of freedom is always a difficult one. What does it mean to be free? Blah blah blah.
Two things that stand in the way of freedom are character and circumstance. We often just have emotional reactions and can't do anything but follow our character. It seems like that could interfere with freedom. Also circumstance. It determines our character and much else about us.
Either way, Collingwood says that both character and circumstance are compatible with freedom. In fact, they depend on them. He claims that "man is never more free than when he acts in accordance with his character, and think[s] it absurd to maintain that an honest man shows his freedom by acting dishonestly but not by acting honestly. Indeed, character, so far from hampering freedom, confers it: or rather, confers not freedom in general but the special freedom to act in this or that way" (The Principles of History, "Reality as History," 290). Reminds me a bit of Collingwood's sense of duty. That freedom is not to be identified with capricious action, but with an individual sticking to their guns, obeying their character, following their unique path to act in the way that they must act in that moment.
Circumstance, too, therefore, is not a hindrance to freedom. It is, in fact, the only thing that can possibly enable freedom: "But essentially to be unhappy is to be in the power of circumstances, things other than oneself standing round oneself, constricting one's movements by their presence, forbidding one to do anything except what they permit.... Happiness and unhappiness are not the consciousness of freedom from passion or the force of circumstances, and of subjection to these things, respectively; they are that freedom itself and that subjection itself. As we shall see, so far from being states of consciousness they are not even first-order objects of consciousness: they are second-order objects, the terminal and initial points of desire, abstractly considered... The fundamental form of happiness is not being forced by circumstances to behave viciously, it is being forced by circumstances at all. Happiness is a condition in which the self not only rises superior to the passions which are provoked in it by circumstances, but to force of circumstances as such. The happy self is master of circumstances" (The New Leviathan, 84).
Ohhhh boy. What the hell are you talking about, bro?
What is this master image Collingwood was working towards? This fusion of history and philosophy? This overcoming of the traditional distinction between subject and object, between theory and practice.
What the hell was all this about?
How were you to lay the groundwork for the science of human affairs? Why did you die before you told me this? Why do I feel so compelled to chase your dead thoughts? To bring them back to life.
Why do I want so badly to carry Collingwood's torch?