Loneliness has become increasingly common in society, especially for salespeople as they navigate the more remote, digital world of selling. Understanding how loneliness impacts the behaviors of salespeople – particularly as they interact with customers – is critical for firms aiming to improve sales performance and support their sales teams. Using objective self-awareness (OSA) theory as a lens, we explore the effects of loneliness and find it increases social insecurity in salespeople. Social insecurity subsequently damages salesperson outcomes by increasing sales call reluctance and conspicuous overspending on customers while inhibiting listening. As such, loneliness and social insecurity reduce sales performance, even when measured objectively from the records of a national sales firm. Results also demonstrate that rejection further exacerbates the effect of loneliness on social insecurity, and unfortunately, servant leadership does little to help. We thus offer recommendations to help managers lessen the challenges faced by lonely salespeople.