In this episode of The Impostor Syndrome Files, we explore why the success we work so hard to achieve can still leave us feeling like something’s missing. My guest this week is Jason Connell, a licensed therapist whose own experience chasing bigger opportunities led him to question why each accomplishment left him wanting more. He shares how recognizing that pattern changed his career and the way he helps other high achievers navigate their relationships with themselves. Together, we explore how we learn to connect our worth to what we accomplish and why that belief can keep us searching for reassurance in the next achievement or someone else’s approval. That search often shows up as perfectionism, people-pleasing or a fear of making mistakes, even when we have plenty of evidence that we’re capable. Jason offers a thoughtful perspective on why feeling good enough can remain so elusive and what it takes to begin changing that experience. Our conversation also explores how these patterns affect our relationships, particularly when we assume everyone around us feels more confident and secure than we do. Jason shares practical ways to work with self-doubt and become more intentional about whose opinions we allow to shape how we see ourselves. We close by discussing how greater self-compassion and more honest conversations can help us feel more connected to ourselves and the people who matter most. About My Guest Jason Connell is a Denver-based licensed therapist and author of When Success Isn’t Enough: Why High Achievers Feel Empty — And What to Do About It. His work focuses on high achievers navigating the gap between outward success and how life actually feels. Before becoming a therapist, Jason built a successful career as a professional speaker and executive coach. He consulted with senior executives at Fortune 500 companies, members of the Bush and Obama White Houses, and professional athletes. On paper, he had built the kind of career he thought would make him feel successful. Privately, he was struggling in relationships, becoming disconnected from friends, and realizing that achievement, validation, and overwork were not changing what was happening underneath. That realization led Jason into therapy. He later closed his speaking business, went to graduate school, and became a licensed therapist. Today, Jason works with high achievers, including founders, executives, surgeons, hedge fund managers, professional athletes, Division 1 coaches, Marine Corps officers, and clients who are leaders at organizations including Google, Tesla, Stanford, Wharton, and Harvard. Jason’s work explores the psychology beneath relentless achievement, including why the traits that help people succeed can sometimes make it difficult to rest, feel fulfilled, or know who they are outside of performance. ~ Connect with Jason: Website: https://jasonconnell.co Book: When Success Isn’t Enough: Why High Achievers Feel Empty — And What to Do About It https://a.co/d/0egpZMhL Online Consult: https://jasonconnell.co/contact/ ~ Connect with Kim and The Impostor Syndrome Files: Join the free Impostor Syndrome Challenge: https://www.kimmeninger.com/challenge Learn more about the Leading Humans discussion group: https://www.kimmeninger.com/leadinghumansgroup Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6 Join the Facebook group: https://www.facebook.com/groups/leadinghumans Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session Connect on LinkedIn: https://www.linkedin.com/in/kimmeninger/ Website: https://www.kimmeninger.com
