Our lives cannot but implant the knowledge in our souls that the mind is one thing and the world is another. Out of this separation arises the problem of intentionality, that our minds necesarily occupy themselves with things in the world, or that mind processes are always "about" something. In the scholastic tradition from Thomas Aquinas this "aboutness' is still seen as an immaterial or intentional direct union between the knower and the known. To know about things, e.g. a storm or a flower, implies that these things exist in the mind of the knower as intentional beings, and the nature of this kind of being is that of a relation or interface. This understanding is radically different from the cognitive theories that came to dominate in the course of the scientific revolution. According to Descartes the exterior world is grasped through the mechanical work of the senses, which then required some intermediate entity, a concept or an idea, to stand between the outside world (reality) and the mind. Henceforward the mind lost its direct access to the world, and logically enough this line of thought ended up in the conception that we can never understand the world as it is in itself. The idea of intentional being was taken up once again by Franz Brentano in 1874, who claimed that "Mental phenomena … are those phenomena which contain an object intentionally within themselves". To Brentano – and the phenomenological tradition he thus initiated – mind should be seen as real, irreducibly intentional, and inexplicable naturalistically. Philosphers of the analytic tradition rejected this whole notion claiming that whatever is real is nonintentional and explicable naturalistically. Unnoticed by most thinkers a third position was suggested by Charles Peirce, who agreed with Brentano that mind is real and irreducibly intentional but in the same time maintained, contra Brentano, that mind is explicable naturalistically. This chapter takes the semiotic realism of Charles Peirce as a starting point and discusses a biosemiotic approach to the problem of intentionality. Intentionality is seen as implicit to semiosis (sign processes) and semiosis and life is seen as co-existant. The needs of all living beings for expressing a degree of anticipatory capacity is seen as an evolutionary lever for the development of species with increased semiotic freedom. Human intentionlity is not therefore unique in the world but must be understood as a peculiar and highly sophisticated instantiation of a general semiotics of nature. Biosemiotics offers a way to explicate intentionality naturalistically.