Given inequality:
\[
x + \frac{1}{x} \leq -2
\]
Multiply by \( x \) (considering sign changes):
\[
x^2 + 1 \leq -2x
\]
Rearrange:
\[
x^2 + 2x + 1 \leq 0
\]
\[
(x+1)^2 \leq 0
\]
Since a square term is always non-negative, the only solution is:
\[
x = -1
\]
Thus, the inequality holds only when \( x = -1 \).