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PurposeThe theoretical and practical criticality of self‐talk for leader success receives extensive multidisciplinary discussion, without a great deal of empirical research given the challenge of assessing actual self‐talk. The purpose of this paper is to advance research and theory on self‐leadership by examining leader self‐talk and its relationship to effectiveness and strain.Design/methodology/approachIn total, 189 senior executives' self‐addressed, future‐oriented letters were collected. The executives wrote these letters to themselves for their own personal development; thus, the language used represented a form of naturally occurring self‐talk. Two types of self‐talk were coded: constructive and dysfunctional. Supervisor and direct report ratings of leadership of others and creativity and self‐ratings of job strain were collected.FindingsExtensive variability among leaders in constructive self‐talk was found. Exemplars of constructive and dysfunctional self‐talk are presented. Constructive self‐talk positively related to effective leadership of others and creativity/originality as evaluated by subordinates and superiors and was negatively related to job strain. Dysfunctional self‐talk related negatively to creativity/originality.Originality/valueIn addition to illustrating the types of self‐talk used by leaders, research is extended by providing some of the first empirical evidence of how leaders' free‐flowing thoughts are related to their effectiveness and their overall well‐being, lending direct support to a principal proposition from the self‐leadership framework.