As he was completing postproduction on his short film, "Cold October," director Mikel J. Wisler had no plans to make another short film so soon. But through his freelance crew work on TV commercials, he started a conversation with digital cinematographer Kyle Bainter about possible collaboration on a short film project. Through similar connections, Mikel came into contact with an old college friend, Jennie Sophia, who expressed interest in film acting. Based on these two factors, Mikel approached fellow producer and screenwriter Andrew Gilbert with the idea of making a film with Kyle behind the camera and Jennie in one of the roles. Knowing that long time friend and filmmaking collaborator Rachel Cottom, was seeking more film acting opportunities, Mikel and Andrew crafted the story of "Always Reaching" with two female roles in mind. They now feel it is the best writing in the short film medium they have done to date.
“Always Reaching” was shot over the course of three consecutive days in May 2008. Due to the tight budget and limited availability of everyone involved in the making of this short film, the filmmakers had little room for falling behind schedule. Due to some bad weather on the first night, the first day of shooting drug on late into the night as the crew attempted to capture the shots needed for the opening of the film. Thinking quickly on his feet, director Mikel J. Wisler drafted a simpler opening for the film with fewer shots that still set the mood he wanted for the short. The rain also set up for Mikel what would eventually become the core of the sound design for the film: the storm raging outside the theatre (a metaphor for the emotional storm raging within Jacob and Angela).