With increasing longevity, retirement is not a single period but a multi-stage journey. Financial plans must distinguish between the early, active "golden years" focused on travel and hobbies, and later years dominated by higher, often unpredictable medical expenses. This requires a more dynamic approach to saving and investing.

While a pension fund's ultimate goal is hitting its absolute actuarial return, this is irrelevant for short-term evaluation. In the short run, performance must be judged relative to peers or benchmarks to account for the prevailing market environment.

Institutions must manage four primary risks: failing to meet liabilities (shortfall), path-of-return volatility (drawdown), access to capital (liquidity), and the reputational risk of underperforming peers, which Matt Bank calls “embarrassment risk.” This last one is often the most delicate and hard to quantify.

Investment risk should be assessed using a 2x2 matrix plotting financial capacity against psychological risk tolerance. A high ability but low willingness is 'defensive,' while a low ability but high willingness is 'naive' and foolish, as it courts consequences the plan cannot survive.

Judging investment skill requires observing performance through both bull and bear markets. A fixed period, like 5 or 10 years, can be misleading if it only captures one type of environment, often rewarding mere risk tolerance rather than genuine ability.

Social Security is framed not just as a successful anti-poverty program, but as a system that annually moves over a trillion dollars from the younger, less wealthy working-age population to the most affluent generation in history, who are often asset-rich.

While DC plans receive huge inflows, a large portion of assets leaks out annually into rollover IRAs as employees change jobs. This dynamic means the net growth of the captive 401(k) asset pool is less explosive than top-line numbers suggest, tempering the "flood of capital" narrative for private markets.

A fund manager's fiduciary duty incentivizes them to trade potentially higher, more volatile returns for guaranteed, quicker multiples (e.g., a 3.5x over a 7x). Unlike a personal investor who can accept high dispersion (big winners, total losses), a GP must prioritize returning capital to LPs like pensions and endowments.

Investors obsess over outperforming benchmarks like the S&P 500. This is the wrong framework. It's possible to beat the index every quarter and still fail to meet your financial goals. Conversely, you can underperform the index and achieve all your goals. The only metric that matters is progress toward your personal objectives.