Nearing thirty, Doug Collins (Brian Geraghty) is dating a woman he no longer loves and doing a job he hates. Doug's long-term girlfriend Clare (Alexia Rasmussen) despairs of the relationship and decides to move out of their Brooklyn apartment. For the first time in years, he sees new possibilities in life beyond his current situation, and decides he will seek out new adventures he will strive to get the most out of life. As a start, he will climb Kilimanjaro. Doug recruits his strong-willed, well-paid friend Mitch (Chris Marquette) to join him on the trek. He starts training and, at a running track, he meets an athletic, extrovert Yvonne (Abigail Spencer). Doug begins pushing himself to become the man he wants to be. Life begins pushing back. Expenses and troubles pile up. Ultimately, Doug faces a difficult decision of whether to set his new goal aside -- maybe forever -- or to push ahead to the mountaintop.