We show theoretically that the usual estimated investment strategies will not achieve the optimal Sharpe ratio when the dimensionality is high relative to sample size, and the $ 1/N $ rule is optimal in a 1-factor model with diversifiable risks as dimensionality increases, which explains why it is difficult to beat the $ 1/N $ rule in practice. We also explore conditions under which it can be beaten, and find that we can outperform it by combining it with the estimated rules when $ N $ is small, and by combining it with anomalies or machine learning portfolios, conditional on the profitability of the latter, when $ N $ is large.