A gumption trap is an event or mindset that can cause a person to lose enthusiasm and become discouraged from starting or continuing a project. The word "gumption" denotes a combination of commonsense, shrewdness, and a sense of initiative. Although the last of these traits is the primary victim of the "gumption trap," the first two suffer indirectly in that a reduction in initiative results in a reduction in constructive activity and therefore inhibits one's development of the first two traits. The "trap" portion of the term refers to the negative feedback loop that the event or mindset creates: That the reduction in the person's enthusiasm and initiative decreases both the person's likelihood of success in that project and the degree of success likely (thus doubly affecting the expected outcome of the person's efforts). The usual result, whether a mere lack of success or instead an outright failure complete with embarrassment and loss of the resources initially invested, further discourages the person.
The specific term "gumption trap" was coined by Robert Pirsig in Zen and the Art of Motorcycle Maintenance, and the associated concept plays an important part in the practical application of his Metaphysics of Quality. Although Pirsig's term has seen little use outside his work, the associated concept has received significant attention in mainstream psychology under the label "learned helplessness" proposed by Martin Seligman.
Pirsig refers to two types of gumption traps: setbacks, which arise from external/"exogenous" events, and hang-ups, which are the product of internal/"endogenous" factors such as a poor fit between one's psychological state and the requirements of a project.
The nature of setbacks can vary considerably. For example, a minor setback might result from a minor injury. Larger setbacks include the lack of knowledge that a certain procedural step or other condition is necessary for a project's success: If one attempts to keep working despite the lack of knowledge that this obstacle exists (let alone how to deal with it), one's lack of progress may prompt one to take long breaks from the project, to focus one's attention on other endeavors, or even to lose interest in the project altogether. Pirsig suggests preventing these kinds of gumption traps by being slow and meticulous, taking notes that might help later, and troubleshooting in advance (e.g., by laying out the requirements for one's project in logical and/or conceptual order and looking for procedural problems ranging from unaccounted-for prerequisites to gaps in one's instructions or plans).
Hang-ups stem from internal factors that can get in the way of starting or completing a project. Examples of such hang-ups include anxiety, boredom, impatience, and the failure (often borne of excessive egotism) to realize that a) one might not have all the information necessary to succeed and/or b) certain aspects of the problem might be more or less important than one believes (see Relevance paradox). Dealing with hang-ups can be as simple as reducing hyperfocus on a specific aspect of a problem by taking a short break from working on the problem or that specific aspect of it.
See also 
Philosophy of Robert Pirsig:
Related concepts in psychology and sociology: