An investor's career has a finite number of deals. Calculating this number (e.g., 2 deals/year for 20 years = 40 deals) creates a sense of scarcity, encouraging more deliberate investment decisions and greater appreciation for each opportunity.

When faced with a year of unstructured time, such as a gap year, the perception of having ample time is a trap. Without immediate action on major goals like travel or personal projects, months will pass with nothing accomplished. The key is to start on day one, as the window of opportunity closes faster than expected.

Imagine you're 90, in a terrible care home, having become the worst version of yourself. Then, the best version appears, showing the life you could have had. This intense regret can generate the emotional energy needed to make significant life changes in the present.

The most meaningful achievements (building a company, raising a family) are multi-year endeavors. In an average adult life, you only have about five or six 10-year slots for these "movements." This scarcity makes the sequencing of your life's major goals a critical strategic decision.

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.

In final conversations, wealthy individuals consistently prioritize legacy, values, and family relationships over financial matters like tax savings. This highlights the need to focus on the "softer side" of estate planning from the very beginning.

To make better long-term decisions, annually ask what you will respect in 5-10 years across key life domains (work, family, health). This forward-looking self-judgment, inspired by his parents' end-of-life reflections, creates clarity and urgency to act now, rather than in the "ninth inning" of life.

We optimize for visible metrics like money but ignore hidden ones like stress or time with loved ones. These metrics are unmeasurable until they're gone—a mental breakdown occurs or time with parents runs out. Then, they become the most important metric of all.

As children become independent adults, showing vulnerability and asking for parental comfort is a profound gift. This act reaffirms a parent's purpose and sense of value in a way that material success cannot, strengthening the family bond across generations.