Suppose that I have the following integral:
$$ \int_L \frac {dz}{z^2+1} $$
I need to show that this is equal to $0$ if $L$ is any closed rectifiable simple curve in the outside of the closed unit disc. Simply put, this is where $|z| > 1$.
Initially, I thought that because "closed rectifiable simple curve" is a crucial part of the Cauchy Integral Theorem, the best way to go about this is to show that the rest of theorem must hold. That is, the domain, $|z|>1$, is a simply connected domain, and that $f(z)$ is analytic in this domain.
However, the domain does not appear to be a simply connected domain, as everything on the inside of the unit disc would prevent it from being so. By definition, a simply connected domain is one where any simple curve in that domain can be shrunk to a point that's also in the domain, so therefore, it may be possible to shrink a curve in this domain to the inside of the circle!
I must be missing a key part to this proof, because as of now, this contradicting statement has me stumped. Any thoughts/ideas?

Note that $L$ must enclose either no singularities of $f$ (read: $\pm i$), or it must contain both (with equal winding number!). In the first case, we're done by Cauchy's theorem. In the second, an application of the residue theorem shows that the integral is zero: The residues at $\pm i$ are $\pm i/2$ respectively, and hence cancel.
To make this a little more explicit: Notice that the integral is equal to
$$\int_L \frac{1}{(z + i)(z - i)} \, dz = \frac i 2 \int_L \frac{1}{z + i} - \frac{1}{z - i} \, dz$$
Up to a constant, this is the difference of the winding numbers of $L$ at $i$ and $-i$. But the assumptions on $L$ force the winding number around any point in $\overline{D}$ to be the same.