Research suggests that high-achieving leaders are at higher risk for lower levels of life satisfaction, given their proclivity for relationship fatigue, ambition addiction, and issues with self-trust. Given these challenges, it is worth examining their inner speech for reframes that improve happiness. A small convenience sample of the researcher-practitioner's active coaching clients (N=10) was surveyed, responding to a revised achievement motives scale (AMS), a satisfaction with life (SWL) measure, and other relevant information. This preliminary study found that clients surveyed could be characterized as high achievers. They also engaged in the researcher-practitioner's S.I.L.L.Y. coaching model – focusing on stillness (S), introspection (I), limberness (L), loving self-talk (L), and authenticity in the form of learning to “be you” (Y). Lastly, the average SWL score among clients proved higher at the time of survey than before engaging in the coaching process, suggesting a worthwhile line for further inquiry.