Regrets aren't about specific failures, but about consistently choosing the safe, logical path (the 'big boy/girl') over the intuitive, risk-taking inner voice (the 'little boy/girl'). A life without regret requires letting your inner child 'come out and play' at critical forks in the road.

Regret traps you in a cycle of reliving past mistakes without changing the outcome, similar to how worry focuses on an uncontrollable future. Reflection, however, is an objective debrief of the past to extract lessons, gain clarity, and inform future actions for growth.

The habit of emotional withholding isn't selective. When you consistently suppress feelings like sadness or anger, you also unintentionally stifle your ability to experience and express joy. Emotional health requires being open to the full spectrum of feelings, not just the negative ones.

A significant trauma often triggers an automatic, reflexive response of guilt and shame. This emotional reflex drives individuals to bury or avoid the trauma, which is the exact opposite of the communication and confrontation needed for healing.

Contrary to pop psychology, guilt can be a powerful motivator. Guilt makes you feel "I did a bad thing," prompting amends. Shame, however, makes you feel "I am a bad person," leading to withdrawal or aggression. A healthy dose of guilt can fuel moral ambition.

The fear of loss is stronger than the attraction to gain. This "loss aversion" explains why people hesitate to initiate positive gestures, like smiling at a stranger in an elevator. They are willing to sacrifice an almost certain positive reciprocal outcome (98% chance) to protect against a tiny risk of looking foolish (2% chance).

End-of-life regrets often stem from things left undone or unsaid. To avoid this, one can regularly use a simple 'final checklist'—a set of powerful questions about one's life, relationships, and priorities. This isn't about cleaning up at the end, but about actively building a life so full that there's nothing left to fix.

A founder's retrospective analysis often reveals that delayed decisions were the correct ones, and the only regret is not acting sooner. Recognizing this pattern—that you rarely regret moving too fast—can serve as a powerful heuristic to trust your gut and accelerate decision-making, as inaction is often the biggest risk.

We procrastinate not from laziness, but from a fear that our best effort won't be good enough. Delaying a task creates a private, deniable failure ("I could have done it if I'd tried"), which feels safer than risking a public failure that could harm our identity.