Most books on leadership and business strategy don’t go deep enough. They stay in the shallow waters of strategic frameworks, decision-making matrices, and hackneyed anecdotes. Rarely do they plumb the depths of our underlying psychology. Perhaps the best strategic investment we can make is not reading the latest edition of Harvard Business Review, but instead more time with a counselor exploring our own interior landscape. I say this as someone who reads many of the latest business books AND who finds himself on the plush couch in my therapist’s office, so consider me hypocritical or just hedging my bets, but my point is beneath every strategic question is a set of other questions: what is your relationship to risk? Are you actually - actually - willing to suffer that blow to ego that accompanies failure? How has your past led to a mindset of scarcity or abundance?
Courageous strategy comes from courageous humans, and often that strategy sits on the other side of doing this deep, messy, psychological work. The most important relationship a leader has is not with their team or their board or their partners. It is the relationship with themselves.