Selling a business often triggers a period of depression. A founder's self-worth is deeply intertwined with the daily grind and pressures of their company. When that is removed, they experience a significant loss and must redefine their identity outside of their work.

Lasting change stems from identity-based habits, not outcome-based goals. Every small action—one meditation, one boundary set—is a 'vote' for the person you want to become. This accumulation of 'identity evidence' makes new behaviors feel natural and intrinsic rather than forced.

The common advice to 'find your purpose' can be counterproductive. It boxes you into a static self-identity, creating friction and existential crises whenever you grow or your interests change. A more flexible approach is to focus on a set of core values that guide you, rather than a single, reductive 'purpose'.

Habits must evolve with life's seasons (e.g., career changes, having children). A habit that served you well in one phase may hold you back in the next. Be willing to give up old, successful routines that no longer align with your current priorities and identity.

While psychology warns against tying your identity to your work to avoid pain from failure, high performers do exactly that. They embrace identities like "I am a writer" because this personal attachment makes excellence non-negotiable and prevents them from simply "going through the motions."

A major struggle for accomplished professionals is the internal conflict between their identity as a "stone cold high achiever" and their current lack of motivation. This cognitive dissonance—knowing you should be achieving but not feeling the "juice"—is a key psychological hurdle when past success eliminates original drivers.

Career success alone often leads to an "Is this it?" crisis. Leaders lacking an "Ironman core"—an inexhaustible purpose—eventually become empty managers of process. True leadership requires a driving mission to inspire others and sustain oneself through challenges.

When a defining career ends, the biggest struggle is often existential, not financial. Our culture fuses identity with profession ('what you do is who you are'), creating a vacuum when the job is gone. This leads to profound questions of self-worth, value, and purpose that transcend money.

People often under-plan retirement because they view it as an endpoint. A more effective approach is to reframe it as a transition 'to' something new. This encourages proactive exploration and planning for a next chapter, preventing a post-career crisis of meaning.