1058. Q&AF: The Guilt Of Taking Time Off, Too Good For Promotion? & Feeling Behind

In this episode of Q&AF, Andy Frisella and DJ tackle three pressing questions from listeners, offering candid advice on common entrepreneurial and career challenges. From the psychological burden of taking breaks to the strategic moves required for career advancement and the pervasive feeling of inadequacy, Frisella provides a no-nonsense perspective rooted in his extensive experience.

The Guilt of Taking Time Off

The first question comes from a 24-year-old entrepreneur who has developed an "obsession" with working on his clothing brand. Despite having failed in three or four previous businesses, he refuses to give up. His struggle lies in the intense guilt he feels whenever he takes a day or two off, describing it as "mentally draining." He purposefully tries to be "mediocre" by engaging in leisure activities like having a beer or playing PS4, but finds it impossible to shake the obsession with his vision and goals. He asks if Frisella has ever experienced a similar struggle or if there's a way to avoid getting tired of the relentless pursuit.

Frisella immediately cuts to the chase, clarifying the listener's core struggle: he's trying to break his obsession with being more, doing more, and becoming better, simply to feel "normal" around other people. Frisella asserts that the listener is not programmed like everybody else. Those with a clear vision and drive to build something great will naturally view life differently from those who are merely counting down the minutes until they can go home and do nothing. This relentless drive, which the listener perceives as a problem, is actually the "product of the mindset that is required to actually build something great." Frisella suggests the listener's real struggle isn't with his obsession, but with reconciling his unique drive with the expectations of others who have never built anything substantial. He emphasizes that successful builders, creators, and innovators are "fucking obsessed" and don't want to take days off. He concludes that this obsession is a requirement for success and a blessing, ensuring that this business doesn't become his fifth or sixth failed venture. The fact that he's already failed four businesses and continues to push forward is a testament to his unique drive, which most people would quit over. Frisella advises him to let go of the idea of living like everyone else, as it's simply not going to happen if he wants to build something amazing.