Simply keeping pace with peers is not a valid measure of success. If peers are taking excessive risks in a bubble, matching their performance means you were equally foolish. True skill is outperforming in bad times while keeping pace in good times.

In a world of highly skilled money managers, absolute skill becomes table stakes and luck plays a larger role in outcomes. According to Michael Mauboussin's "paradox of skill," an allocator's job is to identify managers whose *relative* skill—a specific, durable edge—still dominates results.

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.

Investors often judge investments over three to five years, a statistically meaningless timeframe. Academic research suggests it requires approximately 64 years of performance data to know with confidence whether an active manager's outperformance is due to genuine skill (alpha) or simply luck, highlighting the folly of short-term evaluation.

For a defined benefit pension plan, the ultimate measure of success is not outperforming peers or benchmarks. It is simply whether the plan can meet its financial obligations to beneficiaries. Failing to do so is a complete failure, regardless of how other plans performed.

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.

Timing is more critical than talent. An investor who beat the market by 5% annually from 1960-1980 made less than an investor who underperformed by 5% from 1980-2000. This illustrates how the macro environment and the starting point of an investment journey can have a far greater impact on absolute returns than individual stock-picking skill.

Investors rarely sell a fund for outperforming its benchmark too aggressively, but they should consider it. Research by Vanguard's John Bogle tracked the top 20 funds of each decade and found they almost always became significant underperformers in the following decade, demonstrating the danger of chasing past winners.

Even long-term winning funds will likely underperform their benchmarks in about half of all years. A Vanguard study of funds that beat the market over 15 years found 94% of them still underperformed in at least five of those years. This means selling based on a few years of poor returns is a flawed strategy.