$p \in \mathbb{R}^2$ is a unit-length column vector. $E=\begin{bmatrix}0 & 1 \\ -1 & 0\end{bmatrix}$ is the "$-\frac{\pi}{2}$" rotation matrix. So how to prove that \begin{equation} I-p p^T = -E p p^T E \;? \end{equation}
Of course you can let $p=[x,y]^T$ and prove this. But that is not the answer I want. I want to know how one can do some calculations and get $-E p p^T E$ just starting from $I-p p^T$?

The given unit vector $\,p\,$ spans a $1$-dimensional subspace, and $\:pp^T=p\,\langle\, p\mid\cdot\,\rangle\,$ is the associated orthogonal projector onto that subspace.
The orthogonal complement is also $1$-dimensional as we are considering $\mathbb R^2$, and it is (spanned by) "everything perpendicular to $p$", e.g. the unit vector $\,Ep\,$ or $\,-Ep$, the sign doesn't matter. The corresponding orthogonal projection is $$(\pm Ep)(\pm Ep)^T = Epp^T E^T = -Epp^TE\,.$$ Because subspace and orthogonal complement exhaust the whole vector space, the projections sum up to the identity: $$-Epp^TE\,+\,p p^T\;=\;I$$ This equality is equivalent to $\{p,\pm Ep\}\subset\mathbb R^2$ being an orthonormal basis.